# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ate226
_database_code_depnum_ccdc_archive 'CCDC 2036677'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2020-10-12 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2020-09-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
''
aurelien.crochet@unifr.ch
katharina.fromm@unifr.ch
olimpia.mamulasteiner@hefr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_absolute_configuration syn
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   25.3513(5)
_cell_length_b                   13.4380(7)
_cell_length_c                   9.4134(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3206.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18946
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      1.52
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.7608
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, , Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method 
'The material was recrystallised from diisopropyl ether by slow evaporation'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1844
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            48181
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.870
_diffrn_reflns_theta_min         1.607
_diffrn_ambient_temperature      250(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'STOE IPDS2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Stoe IPDS2'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4236
_reflns_number_total             6844
_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       'X-Area (Stoe & Cie, 2009)'
_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6844
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.026
_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)+(0.1002P)²+0.4523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.2001
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3) = Uanis(O3A) = Uanis(O4) = Uanis(O4A)
3. Others
 Sof(O3A)=Sof(O4A)=Sof(H4A)=1-FVAR(1)
 Sof(O3)=Sof(O4)=Sof(H4)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C31(H31), C33(H33)
4.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C32(H32A,H32B), C34(H34A,H34B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4B), C5(H5), C6(H6), C9(H9), C10(H10), C22(H22), C23(H23),
 C24(H24), C25(H25), C28(H28), C29(H29)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O4A(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23243(13) 0.2520(3) 0.8373(4) 0.0653(9) Uani 1 1 d . . . . .
H1 H 0.202873 0.240941 0.802764 0.098 Uiso 1 1 calc R U . . .
O2 O 0.20108(18) 0.4065(3) 0.8508(5) 0.0865(13) Uani 1 1 d . . . . .
N1 N 0.34041(15) 0.2642(3) 0.7371(4) 0.0534(9) Uani 1 1 d . . . . .
C1 C 0.2351(2) 0.3462(4) 0.8791(6) 0.0606(12) Uani 1 1 d . . . . .
C2 C 0.28043(19) 0.3688(4) 0.9737(5) 0.0551(11) Uani 1 1 d . . . . .
C3 C 0.2728(2) 0.4468(4) 1.0690(6) 0.0670(13) Uani 1 1 d . . . . .
H3 H 0.242177 0.485833 1.062738 0.080 Uiso 1 1 calc R U . . .
C4 C 0.3098(3) 0.4674(5) 1.1726(7) 0.0749(16) Uani 1 1 d . . . . .
H4B H 0.304109 0.520067 1.236476 0.090 Uiso 1 1 calc R U . . .
C5 C 0.3547(2) 0.4114(5) 1.1827(6) 0.0748(16) Uani 1 1 d . . . . .
H5 H 0.379547 0.424234 1.254583 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3631(2) 0.3362(4) 1.0863(6) 0.0638(13) Uani 1 1 d . . . . .
H6 H 0.394458 0.299011 1.092504 0.077 Uiso 1 1 calc R U . . .
C7 C 0.32724(19) 0.3132(4) 0.9804(5) 0.0545(11) Uani 1 1 d . . . . .
C8 C 0.34053(18) 0.2352(4) 0.8747(5) 0.0547(11) Uani 1 1 d . . . . .
C9 C 0.3532(2) 0.1389(4) 0.9134(6) 0.0607(12) Uani 1 1 d . . . . .
H9 H 0.353905 0.120379 1.009632 0.073 Uiso 1 1 calc R U . . .
C10 C 0.3650(2) 0.0697(4) 0.8082(6) 0.0634(13) Uani 1 1 d . . . . .
H10 H 0.374178 0.004133 0.832827 0.076 Uiso 1 1 calc R U . . .
C11 C 0.36311(19) 0.0979(4) 0.6673(6) 0.0557(11) Uani 1 1 d . . . . .
C12 C 0.3691(2) 0.0303(4) 0.5414(6) 0.0629(13) Uani 1 1 d . . . . .
H12 H 0.376745 -0.040466 0.562490 0.075 Uiso 1 1 calc R U . . .
C13 C 0.3204(2) 0.0508(4) 0.4468(7) 0.0670(14) Uani 1 1 d . . . . .
H13A H 0.312669 -0.001932 0.377982 0.080 Uiso 1 1 calc R U . . .
H13B H 0.288764 0.070609 0.499384 0.080 Uiso 1 1 calc R U . . .
C14 C 0.3523(2) 0.1380(4) 0.3861(6) 0.0664(13) Uani 1 1 d . . . . .
H14 H 0.346591 0.151538 0.283913 0.080 Uiso 1 1 calc R U . . .
C15 C 0.3462(2) 0.2282(4) 0.4844(5) 0.0667(13) Uani 1 1 d . . . . .
H15A H 0.373776 0.277068 0.462882 0.080 Uiso 1 1 calc R U . . .
H15B H 0.311907 0.259613 0.468020 0.080 Uiso 1 1 calc R U . . .
C16 C 0.35045(19) 0.1971(4) 0.6366(5) 0.0537(11) Uani 1 1 d . . . . .
C17 C 0.4028(2) 0.0790(4) 0.4217(6) 0.0663(13) Uani 1 1 d . . . . .
C18 C 0.4523(2) 0.1354(6) 0.4638(8) 0.091(2) Uani 1 1 d . . . . .
H18A H 0.443640 0.184730 0.535189 0.137 Uiso 1 1 calc R U . . .
H18B H 0.466959 0.168210 0.380868 0.137 Uiso 1 1 calc R U . . .
H18C H 0.478071 0.089148 0.502034 0.137 Uiso 1 1 calc R U . . .
C19 C 0.4168(3) 0.0043(5) 0.3049(8) 0.0852(19) Uani 1 1 d . . . . .
H19A H 0.442840 -0.042313 0.340492 0.128 Uiso 1 1 calc R U . . .
H19B H 0.431056 0.039529 0.223624 0.128 Uiso 1 1 calc R U . . .
H19C H 0.385314 -0.031685 0.276588 0.128 Uiso 1 1 calc R U . . .
O3 O 0.1133(4) -0.0271(6) 0.4572(11) 0.087(2) Uani 0.589(8) 1 d . . P A 1
O3A O 0.1434(6) -0.0287(9) 0.5055(16) 0.087(2) Uani 0.411(8) 1 d . . P A 2
O4 O 0.1873(4) -0.0533(6) 0.3315(12) 0.087(2) Uani 0.589(8) 1 d . . P A 1
H4 H 0.171663 -0.106453 0.315692 0.131 Uiso 0.589(8) 1 calc R U P A 1
O4A O 0.1605(6) -0.0345(9) 0.2785(17) 0.087(2) Uani 0.411(8) 1 d . . P A 2
H4A H 0.147766 -0.091299 0.282451 0.131 Uiso 0.411(8) 1 calc R U P A 2
N2 N 0.13543(15) 0.1931(3) 0.7448(4) 0.0543(9) Uani 1 1 d . . . . .
C20 C 0.1554(2) 0.0082(4) 0.3993(5) 0.0589(12) Uani 1 1 d . . . . .
C21 C 0.1719(2) 0.1142(4) 0.3946(5) 0.0549(11) Uani 1 1 d . . . . .
C22 C 0.2067(2) 0.1420(4) 0.2884(5) 0.0591(12) Uani 1 1 d . . . . .
H22 H 0.217554 0.094708 0.220995 0.071 Uiso 1 1 calc R U . . .
C23 C 0.2257(2) 0.2380(4) 0.2799(6) 0.0688(14) Uani 1 1 d . . . . .
H23 H 0.248802 0.255956 0.206140 0.083 Uiso 1 1 calc R U . . .
C24 C 0.2108(2) 0.3074(4) 0.3797(7) 0.0736(15) Uani 1 1 d . . . . .
H24 H 0.223518 0.373019 0.374192 0.088 Uiso 1 1 calc R U . . .
C25 C 0.1771(2) 0.2800(4) 0.4877(6) 0.0656(13) Uani 1 1 d . . . . .
H25 H 0.167889 0.327233 0.557148 0.079 Uiso 1 1 calc R U . . .
C26 C 0.15625(19) 0.1844(3) 0.4967(5) 0.0541(11) Uani 1 1 d . . . . .
C27 C 0.11786(19) 0.1665(4) 0.6148(5) 0.0536(11) Uani 1 1 d . . . . .
C28 C 0.0672(2) 0.1344(4) 0.5936(6) 0.0661(13) Uani 1 1 d . . . . .
H28 H 0.055278 0.119577 0.501479 0.079 Uiso 1 1 calc R U . . .
C29 C 0.0338(2) 0.1238(4) 0.7089(6) 0.0671(14) Uani 1 1 d . . . . .
H29 H -0.000989 0.101339 0.695743 0.080 Uiso 1 1 calc R U . . .
C30 C 0.05197(19) 0.1466(4) 0.8438(6) 0.0613(12) Uani 1 1 d . . . . .
C31 C 0.0217(2) 0.1349(5) 0.9804(7) 0.0741(15) Uani 1 1 d . . . . .
H31 H -0.013859 0.104950 0.972827 0.089 Uiso 1 1 calc R U . . .
C32 C 0.0597(2) 0.0867(6) 1.0882(7) 0.0836(18) Uani 1 1 d . . . . .
H32A H 0.042264 0.057118 1.170854 0.100 Uiso 1 1 calc R U . . .
H32B H 0.085277 0.040732 1.045860 0.100 Uiso 1 1 calc R U . . .
C33 C 0.0813(2) 0.1925(6) 1.1136(6) 0.0777(17) Uani 1 1 d . . . . .
H33 H 0.092216 0.207225 1.212361 0.093 Uiso 1 1 calc R U . . .
C34 C 0.1224(2) 0.2129(5) 1.0005(6) 0.0685(14) Uani 1 1 d . . . . .
H34A H 0.130998 0.283964 0.999891 0.082 Uiso 1 1 calc R U . . .
H34B H 0.154700 0.175904 1.022793 0.082 Uiso 1 1 calc R U . . .
C35 C 0.10270(18) 0.1825(4) 0.8566(6) 0.0583(12) Uani 1 1 d . . . . .
C36 C 0.0261(2) 0.2325(6) 1.0704(7) 0.0790(17) Uani 1 1 d . . . . .
C37 C 0.0223(3) 0.3325(6) 0.9951(9) 0.095(2) Uani 1 1 d . . . . .
H37A H 0.031090 0.385357 1.061112 0.142 Uiso 1 1 calc R U . . .
H37B H -0.013393 0.342052 0.960404 0.142 Uiso 1 1 calc R U . . .
H37C H 0.046689 0.333792 0.915745 0.142 Uiso 1 1 calc R U . . .
C38 C -0.0114(3) 0.2316(9) 1.1993(8) 0.116(3) Uani 1 1 d . . . . .
H38A H -0.012477 0.165235 1.239772 0.175 Uiso 1 1 calc R U . . .
H38B H -0.046565 0.250688 1.169019 0.175 Uiso 1 1 calc R U . . .
H38C H 0.001163 0.278271 1.270227 0.175 Uiso 1 1 calc R U . . .


_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 H1 0.8300 . ?
O1 C1 1.328(7) . ?
O2 C1 1.214(6) . ?
N1 C8 1.353(6) . ?
N1 C16 1.331(6) . ?
C1 C2 1.485(7) . ?
C2 C3 1.392(7) . ?
C2 C7 1.404(7) . ?
C3 H3 0.9400 . ?
C3 C4 1.381(9) . ?
C4 H4B 0.9400 . ?
C4 C5 1.368(9) . ?
C5 H5 0.9400 . ?
C5 C6 1.375(8) . ?
C6 H6 0.9400 . ?
C6 C7 1.385(7) . ?
C7 C8 1.484(7) . ?
C8 C9 1.382(7) . ?
C9 H9 0.9400 . ?
C9 C10 1.391(8) . ?
C10 H10 0.9400 . ?
C10 C11 1.380(7) . ?
C11 C12 1.502(7) . ?
C11 C16 1.402(7) . ?
C12 H12 0.9900 . ?
C12 C13 1.547(7) . ?
C12 C17 1.557(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C14 1.533(8) . ?
C14 H14 0.9900 . ?
C14 C15 1.533(8) . ?
C14 C17 1.542(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 C16 1.495(7) . ?
C17 C18 1.520(8) . ?
C17 C19 1.530(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
O3 C20 1.290(10) . ?
O3A C20 1.157(14) . ?
O4 H4 0.8300 . ?
O4 C20 1.321(10) . ?
O4A H4A 0.8300 . ?
O4A C20 1.280(14) . ?
N2 C27 1.351(6) . ?
N2 C35 1.348(6) . ?
C20 C21 1.485(7) . ?
C21 C22 1.385(7) . ?
C21 C26 1.404(7) . ?
C22 H22 0.9400 . ?
C22 C23 1.379(8) . ?
C23 H23 0.9400 . ?
C23 C24 1.377(8) . ?
C24 H24 0.9400 . ?
C24 C25 1.378(8) . ?
C25 H25 0.9400 . ?
C25 C26 1.392(7) . ?
C26 C27 1.497(7) . ?
C27 C28 1.368(7) . ?
C28 H28 0.9400 . ?
C28 C29 1.385(8) . ?
C29 H29 0.9400 . ?
C29 C30 1.385(8) . ?
C30 C31 1.505(8) . ?
C30 C35 1.379(7) . ?
C31 H31 0.9900 . ?
C31 C32 1.542(9) . ?
C31 C36 1.565(10) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 C33 1.541(10) . ?
C33 H33 0.9900 . ?
C33 C34 1.516(8) . ?
C33 C36 1.552(8) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 C35 1.500(7) . ?
C36 C37 1.522(10) . ?
C36 C38 1.543(9) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 H37C 0.9700 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 H38C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C16 N1 C8 119.0(4) . . ?
O1 C1 C2 114.4(4) . . ?
O2 C1 O1 122.3(5) . . ?
O2 C1 C2 123.0(5) . . ?
C3 C2 C1 115.7(5) . . ?
C3 C2 C7 119.2(5) . . ?
C7 C2 C1 124.9(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4B 119.9 . . ?
C5 C4 C3 120.2(6) . . ?
C5 C4 H4B 119.9 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(6) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 118.7 . . ?
C5 C6 C7 122.5(5) . . ?
C7 C6 H6 118.7 . . ?
C2 C7 C8 122.6(4) . . ?
C6 C7 C2 118.0(5) . . ?
C6 C7 C8 119.4(5) . . ?
N1 C8 C7 116.0(4) . . ?
N1 C8 C9 121.5(5) . . ?
C9 C8 C7 122.6(4) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(5) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 126.1(5) . . ?
C10 C11 C16 117.9(5) . . ?
C16 C11 C12 115.8(4) . . ?
C11 C12 H12 116.2 . . ?
C11 C12 C13 105.4(4) . . ?
C11 C12 C17 111.9(4) . . ?
C13 C12 H12 116.2 . . ?
C13 C12 C17 86.9(4) . . ?
C17 C12 H12 116.2 . . ?
C12 C13 H13A 114.3 . . ?
C12 C13 H13B 114.3 . . ?
H13A C13 H13B 111.5 . . ?
C14 C13 C12 86.0(4) . . ?
C14 C13 H13A 114.3 . . ?
C14 C13 H13B 114.3 . . ?
C13 C14 H14 115.2 . . ?
C13 C14 C17 87.9(4) . . ?
C15 C14 C13 109.1(5) . . ?
C15 C14 H14 115.2 . . ?
C15 C14 C17 111.0(5) . . ?
C17 C14 H14 115.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C14 110.5(4) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
N1 C16 C11 122.7(4) . . ?
N1 C16 C15 118.6(4) . . ?
C11 C16 C15 118.6(5) . . ?
C14 C17 C12 85.3(4) . . ?
C18 C17 C12 118.3(5) . . ?
C18 C17 C14 119.1(5) . . ?
C18 C17 C19 108.8(5) . . ?
C19 C17 C12 111.8(5) . . ?
C19 C17 C14 111.9(5) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O4 H4 109.5 . . ?
C20 O4A H4A 109.5 . . ?
C35 N2 C27 118.5(4) . . ?
O3 C20 O4 118.8(6) . . ?
O3 C20 C21 126.8(5) . . ?
O3A C20 O4A 127.0(9) . . ?
O3A C20 C21 120.7(7) . . ?
O4 C20 C21 114.4(5) . . ?
O4A C20 C21 112.0(7) . . ?
C22 C21 C20 117.4(4) . . ?
C22 C21 C26 119.5(5) . . ?
C26 C21 C20 123.0(4) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(5) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(5) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.5(5) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.1 . . ?
C24 C25 C26 121.8(5) . . ?
C26 C25 H25 119.1 . . ?
C21 C26 C27 125.7(4) . . ?
C25 C26 C21 118.1(5) . . ?
C25 C26 C27 116.1(4) . . ?
N2 C27 C26 114.5(4) . . ?
N2 C27 C28 121.7(5) . . ?
C28 C27 C26 123.5(5) . . ?
C27 C28 H28 120.2 . . ?
C27 C28 C29 119.5(5) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 120.3 . . ?
C28 C29 C30 119.5(5) . . ?
C30 C29 H29 120.3 . . ?
C29 C30 C31 126.2(5) . . ?
C35 C30 C29 117.9(5) . . ?
C35 C30 C31 115.9(5) . . ?
C30 C31 H31 116.4 . . ?
C30 C31 C32 106.7(5) . . ?
C30 C31 C36 109.8(5) . . ?
C32 C31 H31 116.4 . . ?
C32 C31 C36 87.2(5) . . ?
C36 C31 H31 116.4 . . ?
C31 C32 H32A 114.3 . . ?
C31 C32 H32B 114.3 . . ?
H32A C32 H32B 111.4 . . ?
C33 C32 C31 86.4(5) . . ?
C33 C32 H32A 114.3 . . ?
C33 C32 H32B 114.3 . . ?
C32 C33 H33 115.5 . . ?
C32 C33 C36 87.7(5) . . ?
C34 C33 C32 107.5(5) . . ?
C34 C33 H33 115.5 . . ?
C34 C33 C36 111.9(5) . . ?
C36 C33 H33 115.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
C35 C34 C33 110.8(5) . . ?
C35 C34 H34A 109.5 . . ?
C35 C34 H34B 109.5 . . ?
N2 C35 C30 122.9(5) . . ?
N2 C35 C34 118.1(4) . . ?
C30 C35 C34 119.0(5) . . ?
C33 C36 C31 85.2(5) . . ?
C37 C36 C31 118.9(5) . . ?
C37 C36 C33 119.1(6) . . ?
C37 C36 C38 109.5(6) . . ?
C38 C36 C31 112.0(6) . . ?
C38 C36 C33 110.3(5) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N2 0.83 1.91 2.726(5) 169.1 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -151.6(5) . . . . ?
O1 C1 C2 C7 23.1(7) . . . . ?
O2 C1 C2 C3 23.0(7) . . . . ?
O2 C1 C2 C7 -162.2(5) . . . . ?
N1 C8 C9 C10 -1.5(7) . . . . ?
C1 C2 C3 C4 172.7(5) . . . . ?
C1 C2 C7 C6 -172.1(5) . . . . ?
C1 C2 C7 C8 11.1(7) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C2 C7 C8 N1 55.1(6) . . . . ?
C2 C7 C8 C9 -126.0(5) . . . . ?
C3 C2 C7 C6 2.5(7) . . . . ?
C3 C2 C7 C8 -174.3(4) . . . . ?
C3 C4 C5 C6 1.6(9) . . . . ?
C4 C5 C6 C7 -1.4(8) . . . . ?
C5 C6 C7 C2 -0.7(8) . . . . ?
C5 C6 C7 C8 176.2(5) . . . . ?
C6 C7 C8 N1 -121.7(5) . . . . ?
C6 C7 C8 C9 57.2(7) . . . . ?
C7 C2 C3 C4 -2.4(7) . . . . ?
C7 C8 C9 C10 179.7(5) . . . . ?
C8 N1 C16 C11 -2.4(7) . . . . ?
C8 N1 C16 C15 175.5(5) . . . . ?
C8 C9 C10 C11 -0.9(8) . . . . ?
C9 C10 C11 C12 -173.3(5) . . . . ?
C9 C10 C11 C16 1.5(7) . . . . ?
C10 C11 C12 C13 127.4(5) . . . . ?
C10 C11 C12 C17 -139.7(5) . . . . ?
C10 C11 C16 N1 0.1(7) . . . . ?
C10 C11 C16 C15 -177.8(5) . . . . ?
C11 C12 C13 C14 84.3(5) . . . . ?
C11 C12 C17 C14 -77.9(5) . . . . ?
C11 C12 C17 C18 42.8(7) . . . . ?
C11 C12 C17 C19 170.3(4) . . . . ?
C12 C11 C16 N1 175.4(4) . . . . ?
C12 C11 C16 C15 -2.5(7) . . . . ?
C12 C13 C14 C15 -83.7(5) . . . . ?
C12 C13 C14 C17 27.8(4) . . . . ?
C13 C12 C17 C14 27.4(4) . . . . ?
C13 C12 C17 C18 148.1(6) . . . . ?
C13 C12 C17 C19 -84.4(5) . . . . ?
C13 C14 C15 C16 43.0(6) . . . . ?
C13 C14 C17 C12 -27.7(4) . . . . ?
C13 C14 C17 C18 -147.6(6) . . . . ?
C13 C14 C17 C19 84.0(5) . . . . ?
C14 C15 C16 N1 -172.8(4) . . . . ?
C14 C15 C16 C11 5.2(7) . . . . ?
C15 C14 C17 C12 82.0(5) . . . . ?
C15 C14 C17 C18 -37.9(7) . . . . ?
C15 C14 C17 C19 -166.4(5) . . . . ?
C16 N1 C8 C7 -178.0(4) . . . . ?
C16 N1 C8 C9 3.1(7) . . . . ?
C16 C11 C12 C13 -47.4(6) . . . . ?
C16 C11 C12 C17 45.4(6) . . . . ?
C17 C12 C13 C14 -27.6(4) . . . . ?
C17 C14 C15 C16 -52.2(6) . . . . ?
O3 C20 C21 C22 -157.5(8) . . . . ?
O3 C20 C21 C26 26.3(11) . . . . ?
O3A C20 C21 C22 151.7(10) . . . . ?
O3A C20 C21 C26 -24.6(12) . . . . ?
O4 C20 C21 C22 20.0(9) . . . . ?
O4 C20 C21 C26 -156.3(7) . . . . ?
O4A C20 C21 C22 -23.1(11) . . . . ?
O4A C20 C21 C26 160.7(9) . . . . ?
N2 C27 C28 C29 -3.4(8) . . . . ?
C20 C21 C22 C23 -177.3(5) . . . . ?
C20 C21 C26 C25 175.5(5) . . . . ?
C20 C21 C26 C27 -5.7(8) . . . . ?
C21 C22 C23 C24 1.2(8) . . . . ?
C21 C26 C27 N2 128.8(5) . . . . ?
C21 C26 C27 C28 -57.0(7) . . . . ?
C22 C21 C26 C25 -0.7(7) . . . . ?
C22 C21 C26 C27 178.1(5) . . . . ?
C22 C23 C24 C25 0.3(9) . . . . ?
C23 C24 C25 C26 -1.9(9) . . . . ?
C24 C25 C26 C21 2.1(8) . . . . ?
C24 C25 C26 C27 -176.8(5) . . . . ?
C25 C26 C27 N2 -52.4(6) . . . . ?
C25 C26 C27 C28 121.8(6) . . . . ?
C26 C21 C22 C23 -1.0(8) . . . . ?
C26 C27 C28 C29 -177.3(5) . . . . ?
C27 N2 C35 C30 -0.7(7) . . . . ?
C27 N2 C35 C34 -179.6(5) . . . . ?
C27 C28 C29 C30 0.5(9) . . . . ?
C28 C29 C30 C31 -177.1(6) . . . . ?
C28 C29 C30 C35 2.2(9) . . . . ?
C29 C30 C31 C32 135.2(6) . . . . ?
C29 C30 C31 C36 -131.7(6) . . . . ?
C29 C30 C35 N2 -2.2(8) . . . . ?
C29 C30 C35 C34 176.8(5) . . . . ?
C30 C31 C32 C33 82.5(5) . . . . ?
C30 C31 C36 C33 -79.5(5) . . . . ?
C30 C31 C36 C37 41.2(7) . . . . ?
C30 C31 C36 C38 170.6(5) . . . . ?
C31 C30 C35 N2 177.2(5) . . . . ?
C31 C30 C35 C34 -3.8(8) . . . . ?
C31 C32 C33 C34 -84.7(5) . . . . ?
C31 C32 C33 C36 27.6(4) . . . . ?
C32 C31 C36 C33 27.2(4) . . . . ?
C32 C31 C36 C37 147.9(5) . . . . ?
C32 C31 C36 C38 -82.7(6) . . . . ?
C32 C33 C34 C35 46.3(7) . . . . ?
C32 C33 C36 C31 -27.2(4) . . . . ?
C32 C33 C36 C37 -147.7(6) . . . . ?
C32 C33 C36 C38 84.5(7) . . . . ?
C33 C34 C35 N2 -178.0(5) . . . . ?
C33 C34 C35 C30 2.9(8) . . . . ?
C34 C33 C36 C31 80.8(6) . . . . ?
C34 C33 C36 C37 -39.8(8) . . . . ?
C34 C33 C36 C38 -167.5(7) . . . . ?
C35 N2 C27 C26 177.9(4) . . . . ?
C35 N2 C27 C28 3.5(7) . . . . ?
C35 C30 C31 C32 -44.1(7) . . . . ?
C35 C30 C31 C36 49.0(7) . . . . ?
C36 C31 C32 C33 -27.3(4) . . . . ?
C36 C33 C34 C35 -48.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT020_ate226              
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.184 Report
RESPONSE: The overall quality of the data is poor due to the crystal quality.
;
_vrf_PLAT907_ate226              
;
PROBLEM: Flack x > 0.5, Structure Needs to be Inverted? .       2.20 Check 
RESPONSE: The chirality of the compound is determined by the synthesis.
;
_vrf_RINTA01_ate226              
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The overall quality of the data is poor due to the crystal quality.
;
_vrf_STRVA01_ate226              
;
PROBLEM: Chirality of atom sites is inverted?
RESPONSE: The chirality of the compound is determined by the synthesis.
;
####################################################################### 
# 
# 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_lb-04-02
_database_code_depnum_ccdc_archive 'CCDC 2036679'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2020-10-12 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2020-09-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
''
aurelien.crochet@unifr.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O2'
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23
_chemical_absolute_configuration syn
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.0488(6)
_cell_length_b                   7.7427(5)
_cell_length_c                   10.6551(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1076.52(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      26.61
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9609
_exptl_absorpt_correction_T_min  00.8162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, , Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12251
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         3.059
_diffrn_ambient_temperature      250(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'STOE IPDS2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Stoe IPDS2'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                1753
_reflns_number_total             2163
_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       'X-Area (Stoe & Cie, 2009)'
_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.0083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0732
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44379(12) 0.9175(2) 0.47075(16) 0.0545(4) Uani 1 1 d . . . . .
O2 O 0.54783(10) 0.7000(2) 0.51771(16) 0.0511(4) Uani 1 1 d . . . . .
H1 H 0.122(3) 0.718(4) 0.447(3) 0.093(10) Uiso 1 1 d . . . . .
N1 N 0.18677(13) 0.6622(2) 0.38008(16) 0.0404(4) Uani 1 1 d . . . . .
C1 C 0.46290(14) 0.7829(3) 0.5253(2) 0.0382(5) Uani 1 1 d . . . . .
C2 C 0.38451(15) 0.7027(3) 0.6112(2) 0.0396(5) Uani 1 1 d . . . . .
C3 C 0.40089(19) 0.7122(3) 0.7398(2) 0.0521(6) Uani 1 1 d . . . . .
H3 H 0.461252 0.760472 0.770202 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3282(2) 0.6507(4) 0.8231(2) 0.0633(7) Uani 1 1 d . . . . .
H4 H 0.339711 0.657951 0.909073 0.076 Uiso 1 1 calc R U . . .
C5 C 0.2386(2) 0.5785(4) 0.7785(3) 0.0632(8) Uani 1 1 d . . . . .
H5 H 0.189514 0.537374 0.834265 0.076 Uiso 1 1 calc R U . . .
C6 C 0.22221(18) 0.5675(3) 0.6513(2) 0.0534(6) Uani 1 1 d . . . . .
H6 H 0.161877 0.517905 0.621938 0.064 Uiso 1 1 calc R U . . .
C7 C 0.29392(16) 0.6289(3) 0.5654(2) 0.0406(5) Uani 1 1 d . . . . .
C8 C 0.27746(16) 0.6102(3) 0.4287(2) 0.0419(5) Uani 1 1 d . . . . .
C9 C 0.35064(17) 0.5402(3) 0.3506(2) 0.0537(6) Uani 1 1 d . . . . .
H9 H 0.412968 0.503098 0.383204 0.064 Uiso 1 1 calc R U . . .
C10 C 0.33121(19) 0.5254(3) 0.2240(3) 0.0606(7) Uani 1 1 d . . . . .
H10 H 0.380349 0.478582 0.170767 0.073 Uiso 1 1 calc R U . . .
C11 C 0.23952(19) 0.5799(3) 0.1773(2) 0.0556(6) Uani 1 1 d . . . . .
H11 H 0.225952 0.570436 0.091884 0.067 Uiso 1 1 calc R U . . .
C12 C 0.16701(17) 0.6489(3) 0.2566(2) 0.0466(6) Uani 1 1 d . . . . .
C13 C 0.0658(2) 0.7139(4) 0.2110(2) 0.0595(7) Uani 1 1 d . . . . .
H13A H 0.057736 0.685248 0.123898 0.089 Uiso 1 1 calc R U . . .
H13B H 0.062876 0.837051 0.221053 0.089 Uiso 1 1 calc R U . . .
H13C H 0.011800 0.661274 0.258726 0.089 Uiso 1 1 calc R U . . .


_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 C1 1.219(3) . ?
O2 C1 1.283(2) . ?
N1 H1 1.19(4) . ?
N1 C8 1.353(3) . ?
N1 C12 1.345(3) . ?
C1 C2 1.506(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.400(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.393(3) . ?
C7 C8 1.480(3) . ?
C8 C9 1.378(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(3) . ?
C12 C13 1.495(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C8 N1 H1 120.0(17) . . ?
C12 N1 H1 118.7(17) . . ?
C12 N1 C8 121.30(18) . . ?
O1 C1 O2 125.05(19) . . ?
O1 C1 C2 120.22(18) . . ?
O2 C1 C2 114.72(17) . . ?
C3 C2 C1 118.21(19) . . ?
C3 C2 C7 119.7(2) . . ?
C7 C2 C1 122.02(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C8 120.34(18) . . ?
C6 C7 C2 118.6(2) . . ?
C6 C7 C8 121.1(2) . . ?
N1 C8 C7 118.33(18) . . ?
N1 C8 C9 119.5(2) . . ?
C9 C8 C7 122.2(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
N1 C12 C11 119.9(2) . . ?
N1 C12 C13 117.51(19) . . ?
C11 C12 C13 122.6(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 1.19(4) 1.38(4) 2.564(2) 174(3) 3_465 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -106.7(2) . . . . ?
O1 C1 C2 C7 69.5(3) . . . . ?
O2 C1 C2 C3 72.4(3) . . . . ?
O2 C1 C2 C7 -111.4(2) . . . . ?
N1 C8 C9 C10 0.6(3) . . . . ?
C1 C2 C3 C4 175.8(2) . . . . ?
C1 C2 C7 C6 -175.8(2) . . . . ?
C1 C2 C7 C8 6.8(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C7 C8 N1 -132.2(2) . . . . ?
C2 C7 C8 C9 48.5(3) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
C3 C2 C7 C8 -177.1(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C5 C6 C7 C8 177.5(2) . . . . ?
C6 C7 C8 N1 50.5(3) . . . . ?
C6 C7 C8 C9 -128.7(2) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
C7 C8 C9 C10 179.9(2) . . . . ?
C8 N1 C12 C11 0.6(3) . . . . ?
C8 N1 C12 C13 -178.4(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 N1 -0.1(4) . . . . ?
C10 C11 C12 C13 178.9(2) . . . . ?
C12 N1 C8 C7 179.90(19) . . . . ?
C12 N1 C8 C9 -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT353_lb-04-02            
;
PROBLEM: Long N-H (N0.87,N1.01A) N1 - H1 . 1.19 Ang.
RESPONSE: H-bonds between the pyridine and the carboxylate
 of the neighbouring molecule.
;
####################################################################### 
# 
# 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_ate253
_database_code_depnum_ccdc_archive 'CCDC 2036678'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg, Chemistry Department
Switzerland
;
_audit_update_record             
;
2020-10-12 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2018-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N O'
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.33
_chemical_absolute_configuration syn
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.0872(8)
_cell_length_b                   12.3506(16)
_cell_length_c                   16.599(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1452.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5105
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      23.97
_cell_measurement_theta_min      2.06
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9255
_exptl_absorpt_correction_T_min  0.7551
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
'Stoe & Cie (2002). X-SHAPE. Stoe & Cie, Darmstadt, Germany'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method 
'The material was recrystallised from diethylether by slow evaporation'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1351
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20659
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.945
_diffrn_reflns_theta_min         2.055
_diffrn_ambient_temperature      250(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'STOE IPDS2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Stoe IPDS2'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                1507
_reflns_number_total             3105
_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       'X-Area (Stoe & Cie, 2009)'
_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      0.964
_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)+(0.0417P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7725(5) 0.5365(2) 0.58675(15) 0.0715(10) Uani 1 1 d . . . . .
N1 N 0.7911(5) 0.5567(2) 0.44785(16) 0.0496(9) Uani 1 1 d . . . . .
C1 C 0.7828(6) 0.5944(3) 0.5271(2) 0.0543(11) Uani 1 1 d . . . . .
C2 C 0.7852(6) 0.7128(3) 0.5214(3) 0.0542(10) Uani 1 1 d . . . . .
C3 C 0.7829(7) 0.7896(3) 0.5819(3) 0.0666(13) Uani 1 1 d . . . . .
H3 H 0.778301 0.769234 0.636481 0.080 Uiso 1 1 calc R . . . .
C4 C 0.7878(8) 0.8974(4) 0.5596(3) 0.0775(15) Uani 1 1 d . . . . .
H4 H 0.787839 0.951429 0.599475 0.093 Uiso 1 1 calc R . . . .
C5 C 0.7925(8) 0.9266(3) 0.4796(3) 0.0805(14) Uani 1 1 d . . . . .
H5 H 0.792675 1.000546 0.466140 0.097 Uiso 1 1 calc R . . . .
C6 C 0.7969(7) 0.8510(3) 0.4188(3) 0.0713(12) Uani 1 1 d . . . . .
H6 H 0.801217 0.872156 0.364435 0.086 Uiso 1 1 calc R . . . .
C7 C 0.7947(6) 0.7419(3) 0.4405(2) 0.0532(10) Uani 1 1 d . . . . .
C8 C 0.8013(6) 0.6437(3) 0.3930(2) 0.0508(9) Uani 1 1 d . . . . .
C9 C 0.8187(7) 0.6250(3) 0.3138(2) 0.0626(12) Uani 1 1 d . . . . .
H9 H 0.821525 0.683138 0.277220 0.075 Uiso 1 1 calc R . . . .
C10 C 0.8331(7) 0.5154(3) 0.2851(2) 0.0623(12) Uani 1 1 d . . . . .
H10 H 0.847934 0.502584 0.229590 0.075 Uiso 1 1 calc R . . . .
C11 C 0.8256(6) 0.4313(3) 0.3358(2) 0.0491(10) Uani 1 1 d . . . . .
C12 C 0.8383(6) 0.3145(3) 0.3125(2) 0.0561(11) Uani 1 1 d . . . . .
H12 H 0.869605 0.300205 0.255342 0.067 Uiso 1 1 calc R . . . .
C13 C 0.9605(7) 0.2547(4) 0.3750(3) 0.0715(14) Uani 1 1 d . . . . .
H13A H 1.063842 0.298037 0.397368 0.086 Uiso 1 1 calc R . . . .
H13B H 1.004383 0.183134 0.357681 0.086 Uiso 1 1 calc R . . . .
C14 C 0.7804(7) 0.2527(3) 0.4274(2) 0.0667(13) Uani 1 1 d . . . . .
H14 H 0.764541 0.188608 0.462616 0.080 Uiso 1 1 calc R . . . .
C15 C 0.7661(7) 0.3613(3) 0.4683(2) 0.0656(14) Uani 1 1 d . . . . .
H15 H 0.738440 0.367671 0.523490 0.079 Uiso 1 1 calc R . . . .
C16 C 0.7946(6) 0.4479(3) 0.4221(2) 0.0506(10) Uani 1 1 d . . . . .
C17 C 0.6670(6) 0.2512(4) 0.3465(2) 0.0589(11) Uani 1 1 d . . . . .
C18 C 0.4748(7) 0.3051(4) 0.3431(3) 0.0831(16) Uani 1 1 d . . . . .
H18A H 0.479080 0.373087 0.372234 0.125 Uiso 1 1 calc GR . . . .
H18B H 0.381451 0.257893 0.367483 0.125 Uiso 1 1 calc GR . . . .
H18C H 0.440907 0.318665 0.287374 0.125 Uiso 1 1 calc GR . . . .
C19 C 0.6498(8) 0.1362(3) 0.3114(3) 0.0775(15) Uani 1 1 d . . . . .
H19A H 0.592832 0.139810 0.258317 0.116 Uiso 1 1 calc GR . . . .
H19B H 0.571605 0.092276 0.346485 0.116 Uiso 1 1 calc GR . . . .
H19C H 0.774296 0.103960 0.307225 0.116 Uiso 1 1 calc GR . . . .


_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 C1 1.223(4) . ?
N1 C1 1.397(4) . ?
N1 C8 1.410(4) . ?
N1 C16 1.411(4) . ?
C1 C2 1.465(5) . ?
C2 C3 1.381(5) . ?
C2 C7 1.393(5) . ?
C3 H3 0.9400 . ?
C3 C4 1.383(6) . ?
C4 H4 0.9400 . ?
C4 C5 1.375(6) . ?
C5 H5 0.9400 . ?
C5 C6 1.376(6) . ?
C6 H6 0.9400 . ?
C6 C7 1.395(5) . ?
C7 C8 1.446(5) . ?
C8 C9 1.342(5) . ?
C9 H9 0.9400 . ?
C9 C10 1.439(6) . ?
C10 H10 0.9400 . ?
C10 C11 1.338(5) . ?
C11 C12 1.496(5) . ?
C11 C16 1.463(5) . ?
C12 H12 0.9900 . ?
C12 C13 1.541(6) . ?
C12 C17 1.551(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C14 1.545(6) . ?
C14 H14 0.9900 . ?
C14 C15 1.507(5) . ?
C14 C17 1.566(6) . ?
C15 H15 0.9400 . ?
C15 C16 1.332(5) . ?
C17 C18 1.517(7) . ?
C17 C19 1.540(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 110.9(3) . . ?
C1 N1 C16 127.1(3) . . ?
C8 N1 C16 122.0(3) . . ?
O1 C1 N1 124.8(3) . . ?
O1 C1 C2 129.5(4) . . ?
N1 C1 C2 105.7(3) . . ?
C3 C2 C1 129.7(4) . . ?
C3 C2 C7 121.7(4) . . ?
C7 C2 C1 108.7(3) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(4) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(4) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C7 117.8(4) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C6 119.9(4) . . ?
C2 C7 C8 108.1(3) . . ?
C6 C7 C8 132.0(4) . . ?
N1 C8 C7 106.6(3) . . ?
C9 C8 N1 120.4(3) . . ?
C9 C8 C7 132.9(3) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 125.7(3) . . ?
C10 C11 C16 120.8(3) . . ?
C16 C11 C12 113.4(3) . . ?
C11 C12 H12 115.7 . . ?
C11 C12 C13 108.8(4) . . ?
C11 C12 C17 110.2(4) . . ?
C13 C12 H12 115.7 . . ?
C13 C12 C17 87.3(3) . . ?
C17 C12 H12 115.7 . . ?
C12 C13 H13A 114.4 . . ?
C12 C13 H13B 114.4 . . ?
C12 C13 C14 85.5(3) . . ?
H13A C13 H13B 111.5 . . ?
C14 C13 H13A 114.4 . . ?
C14 C13 H13B 114.4 . . ?
C13 C14 H14 116.0 . . ?
C13 C14 C17 86.6(3) . . ?
C15 C14 C13 107.1(4) . . ?
C15 C14 H14 116.0 . . ?
C15 C14 C17 111.2(4) . . ?
C17 C14 H14 116.0 . . ?
C14 C15 H15 121.8 . . ?
C16 C15 C14 116.4(3) . . ?
C16 C15 H15 121.8 . . ?
N1 C16 C11 115.7(3) . . ?
C15 C16 N1 126.0(3) . . ?
C15 C16 C11 118.3(3) . . ?
C12 C17 C14 84.5(3) . . ?
C18 C17 C12 117.9(4) . . ?
C18 C17 C14 119.2(4) . . ?
C18 C17 C19 108.7(4) . . ?
C19 C17 C12 112.9(4) . . ?
C19 C17 C14 112.1(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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 C1 C2 C3 2.5(9) . . . . ?
O1 C1 C2 C7 -178.8(5) . . . . ?
N1 C1 C2 C3 -178.7(5) . . . . ?
N1 C1 C2 C7 0.0(6) . . . . ?
N1 C8 C9 C10 -2.0(7) . . . . ?
C1 N1 C8 C7 -1.3(4) . . . . ?
C1 N1 C8 C9 177.1(4) . . . . ?
C1 N1 C16 C11 -173.2(4) . . . . ?
C1 N1 C16 C15 9.3(7) . . . . ?
C1 C2 C3 C4 179.5(5) . . . . ?
C1 C2 C7 C6 179.4(4) . . . . ?
C1 C2 C7 C8 -0.8(6) . . . . ?
C2 C3 C4 C5 0.7(9) . . . . ?
C2 C7 C8 N1 1.3(5) . . . . ?
C2 C7 C8 C9 -176.8(5) . . . . ?
C3 C2 C7 C6 -1.8(7) . . . . ?
C3 C2 C7 C8 178.0(5) . . . . ?
C3 C4 C5 C6 -1.5(9) . . . . ?
C4 C5 C6 C7 0.6(8) . . . . ?
C5 C6 C7 C2 1.0(7) . . . . ?
C5 C6 C7 C8 -178.8(5) . . . . ?
C6 C7 C8 N1 -178.9(5) . . . . ?
C6 C7 C8 C9 3.0(9) . . . . ?
C7 C2 C3 C4 0.9(8) . . . . ?
C7 C8 C9 C10 175.9(5) . . . . ?
C8 N1 C1 O1 179.7(4) . . . . ?
C8 N1 C1 C2 0.8(5) . . . . ?
C8 N1 C16 C11 5.0(6) . . . . ?
C8 N1 C16 C15 -172.5(5) . . . . ?
C8 C9 C10 C11 1.3(8) . . . . ?
C9 C10 C11 C12 179.8(5) . . . . ?
C9 C10 C11 C16 2.6(8) . . . . ?
C10 C11 C12 C13 139.7(5) . . . . ?
C10 C11 C12 C17 -126.2(5) . . . . ?
C10 C11 C16 N1 -5.6(7) . . . . ?
C10 C11 C16 C15 172.1(5) . . . . ?
C11 C12 C13 C14 80.5(4) . . . . ?
C11 C12 C17 C14 -79.5(4) . . . . ?
C11 C12 C17 C18 40.7(5) . . . . ?
C11 C12 C17 C19 168.8(4) . . . . ?
C12 C11 C16 N1 176.9(4) . . . . ?
C12 C11 C16 C15 -5.4(6) . . . . ?
C12 C13 C14 C15 -81.6(4) . . . . ?
C12 C13 C14 C17 29.6(3) . . . . ?
C13 C12 C17 C14 29.5(3) . . . . ?
C13 C12 C17 C18 149.7(4) . . . . ?
C13 C12 C17 C19 -82.2(4) . . . . ?
C13 C14 C15 C16 46.0(5) . . . . ?
C13 C14 C17 C12 -29.4(3) . . . . ?
C13 C14 C17 C18 -148.4(4) . . . . ?
C13 C14 C17 C19 83.1(4) . . . . ?
C14 C15 C16 N1 -178.9(4) . . . . ?
C14 C15 C16 C11 3.6(6) . . . . ?
C15 C14 C17 C12 77.7(4) . . . . ?
C15 C14 C17 C18 -41.3(6) . . . . ?
C15 C14 C17 C19 -169.8(4) . . . . ?
C16 N1 C1 O1 -1.9(7) . . . . ?
C16 N1 C1 C2 179.2(4) . . . . ?
C16 N1 C8 C7 -179.8(4) . . . . ?
C16 N1 C8 C9 -1.4(6) . . . . ?
C16 C11 C12 C13 -43.0(5) . . . . ?
C16 C11 C12 C17 51.2(5) . . . . ?
C17 C12 C13 C14 -29.9(3) . . . . ?
C17 C14 C15 C16 -47.1(6) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop in oil'
_olex2_submission_special_instructions 'No special instructions were received'
