# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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data_testo1
_database_code_depnum_ccdc_archive 'CCDC 2070018'
loop_
_audit_author_name
_audit_author_address
'Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 Cl N2 O3'
_chemical_formula_sum            'C16 H21 Cl N2 O3'
_chemical_formula_weight         324.80
_chemical_absolute_configuration ad
_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'
Cl Cl 0.1484 0.1585 '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                   10.8233(2)
_cell_length_b                   11.9161(3)
_cell_length_c                   12.3076(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1587.33(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4257
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0755 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.7499. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.396
_exptl_crystal_size_min          0.166
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14647
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.906
_diffrn_reflns_theta_min         2.379
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3478
_reflns_number_total             3800
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.023
_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)+(0.0351P)²+0.1478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0691
_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:
 C3(H3), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C9(H9)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C)
;
_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
Cl1 Cl 0.27835(4) 0.74765(4) 0.57178(4) 0.01836(12) Uani 1 1 d . . . . .
O2 O 0.53055(13) 0.59012(14) 0.04675(12) 0.0172(3) Uani 1 1 d . . . . .
O1 O 0.39986(13) 0.30424(12) 0.49724(12) 0.0152(3) Uani 1 1 d . . . . .
O3 O 0.51404(13) 0.76430(13) 0.54095(11) 0.0172(3) Uani 1 1 d . . . . .
N2 N 0.44310(14) 0.58653(14) 0.56796(14) 0.0116(3) Uani 1 1 d . . . . .
N1 N 0.55359(15) 0.42661(14) 0.54521(13) 0.0120(4) Uani 1 1 d . . . . .
C6 C 0.37559(18) 0.44632(18) 0.26884(17) 0.0138(4) Uani 1 1 d . . . . .
H6 H 0.354990 0.371501 0.288384 0.017 Uiso 1 1 calc R . . . .
C2 C 0.43649(19) 0.39717(18) 0.52735(16) 0.0124(4) Uani 1 1 d . . . . .
C8 C 0.47054(17) 0.57466(19) 0.14338(16) 0.0134(4) Uani 1 1 d . . . . .
C4 C 0.27111(18) 0.51264(17) 0.44176(15) 0.0129(4) Uani 1 1 d . . . . .
H4A H 0.220205 0.444351 0.432039 0.015 Uiso 1 1 calc R . . . .
H4B H 0.214036 0.576257 0.454308 0.015 Uiso 1 1 calc R . . . .
C5 C 0.34158(17) 0.53409(19) 0.33776(16) 0.0129(4) Uani 1 1 d . . . . .
C3 C 0.35203(17) 0.49737(17) 0.54389(16) 0.0115(4) Uani 1 1 d . . . . .
H3 H 0.298215 0.484556 0.608766 0.014 Uiso 1 1 calc R . . . .
C7 C 0.43888(18) 0.46566(19) 0.17226(16) 0.0144(4) Uani 1 1 d . . . . .
H7 H 0.460356 0.404663 0.126290 0.017 Uiso 1 1 calc R . . . .
C11 C 0.60227(18) 0.54326(18) 0.71182(17) 0.0131(4) Uani 1 1 d . . . . .
C1 C 0.56802(17) 0.54006(17) 0.58872(15) 0.0114(4) Uani 1 1 d . . . . .
H1 H 0.631010 0.582207 0.545496 0.014 Uiso 1 1 calc R . . . .
C10 C 0.3740(2) 0.64264(19) 0.30639(17) 0.0167(4) Uani 1 1 d . . . . .
H10 H 0.351227 0.704015 0.351396 0.020 Uiso 1 1 calc R . . . .
C16 C 0.43302(19) 0.69779(18) 0.55555(16) 0.0138(4) Uani 1 1 d . . . . .
C9 C 0.4388(2) 0.66332(18) 0.21103(17) 0.0160(4) Uani 1 1 d . . . . .
H9 H 0.461377 0.737872 0.192190 0.019 Uiso 1 1 calc R . . . .
C15 C 0.65686(19) 0.34986(19) 0.52846(19) 0.0186(5) Uani 1 1 d . . . . .
H15A H 0.665668 0.301102 0.592114 0.028 Uiso 1 1 calc GR . . . .
H15B H 0.733003 0.393066 0.518134 0.028 Uiso 1 1 calc GR . . . .
H15C H 0.641276 0.303865 0.463895 0.028 Uiso 1 1 calc GR . . . .
C13 C 0.5191(2) 0.4642(2) 0.77665(17) 0.0196(5) Uani 1 1 d . . . . .
H13A H 0.432460 0.484790 0.765061 0.029 Uiso 1 1 calc GR . . . .
H13B H 0.539006 0.470247 0.854112 0.029 Uiso 1 1 calc GR . . . .
H13C H 0.532573 0.386832 0.752364 0.029 Uiso 1 1 calc GR . . . .
C12 C 0.5879(2) 0.66226(19) 0.75636(18) 0.0191(5) Uani 1 1 d . . . . .
H12A H 0.637458 0.714207 0.712661 0.029 Uiso 1 1 calc GR . . . .
H12B H 0.616153 0.664445 0.831972 0.029 Uiso 1 1 calc GR . . . .
H12C H 0.500766 0.684452 0.753006 0.029 Uiso 1 1 calc GR . . . .
C14 C 0.7387(2) 0.5103(2) 0.72544(19) 0.0230(5) Uani 1 1 d . . . . .
H14A H 0.749273 0.430879 0.707061 0.034 Uiso 1 1 calc GR . . . .
H14B H 0.764075 0.522855 0.800912 0.034 Uiso 1 1 calc GR . . . .
H14C H 0.789829 0.556246 0.677020 0.034 Uiso 1 1 calc GR . . . .
H2 H 0.545(2) 0.662(2) 0.040(2) 0.028(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.788(2) . ?
O2 C8 1.368(2) . ?
O2 H2 0.87(3) . ?
O1 C2 1.233(3) . ?
O3 C16 1.196(3) . ?
N2 C3 1.479(3) . ?
N2 C1 1.483(2) . ?
N2 C16 1.339(3) . ?
N1 C2 1.333(3) . ?
N1 C1 1.462(3) . ?
N1 C15 1.459(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.396(3) . ?
C6 C7 1.391(3) . ?
C2 C3 1.517(3) . ?
C8 C7 1.389(3) . ?
C8 C9 1.388(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.512(3) . ?
C4 C3 1.543(3) . ?
C5 C10 1.395(3) . ?
C3 H3 1.0000 . ?
C7 H7 0.9500 . ?
C11 C1 1.560(3) . ?
C11 C13 1.528(3) . ?
C11 C12 1.528(3) . ?
C11 C14 1.537(3) . ?
C1 H1 1.0000 . ?
C10 H10 0.9500 . ?
C10 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 O2 H2 107.5(18) . . ?
C3 N2 C1 111.94(16) . . ?
C16 N2 C3 129.35(17) . . ?
C16 N2 C1 117.62(16) . . ?
C2 N1 C1 113.90(16) . . ?
C2 N1 C15 122.69(18) . . ?
C15 N1 C1 123.32(16) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C7 C6 C5 121.7(2) . . ?
O1 C2 N1 126.26(19) . . ?
O1 C2 C3 123.58(18) . . ?
N1 C2 C3 110.09(17) . . ?
O2 C8 C7 117.74(19) . . ?
O2 C8 C9 122.4(2) . . ?
C9 C8 C7 119.80(19) . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
C5 C4 C3 115.05(15) . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C6 C5 C4 121.39(19) . . ?
C10 C5 C6 117.40(19) . . ?
C10 C5 C4 121.21(19) . . ?
N2 C3 C2 100.99(15) . . ?
N2 C3 C4 117.17(16) . . ?
N2 C3 H3 109.7 . . ?
C2 C3 C4 108.99(16) . . ?
C2 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C13 C11 C1 110.62(17) . . ?
C13 C11 C12 108.95(18) . . ?
C13 C11 C14 110.58(18) . . ?
C12 C11 C1 110.29(17) . . ?
C12 C11 C14 107.20(18) . . ?
C14 C11 C1 109.14(16) . . ?
N2 C1 C11 112.01(15) . . ?
N2 C1 H1 110.0 . . ?
N1 C1 N2 100.64(15) . . ?
N1 C1 C11 113.80(17) . . ?
N1 C1 H1 110.0 . . ?
C11 C1 H1 110.0 . . ?
C5 C10 H10 119.2 . . ?
C9 C10 C5 121.7(2) . . ?
C9 C10 H10 119.2 . . ?
O3 C16 Cl1 118.90(16) . . ?
O3 C16 N2 127.87(19) . . ?
N2 C16 Cl1 113.12(15) . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O2 H2 O1 0.87(3) 1.86(3) 2.715(2) 167(3) 3_655 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
O2 C8 C7 C6 -178.73(17) . . . . ?
O2 C8 C9 C10 177.73(18) . . . . ?
O1 C2 C3 N2 -174.44(19) . . . . ?
O1 C2 C3 C4 -50.5(3) . . . . ?
N1 C2 C3 N2 2.8(2) . . . . ?
N1 C2 C3 C4 126.73(17) . . . . ?
C6 C5 C10 C9 -0.7(3) . . . . ?
C2 N1 C1 N2 -14.1(2) . . . . ?
C2 N1 C1 C11 105.88(19) . . . . ?
C4 C5 C10 C9 179.96(19) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C5 C4 C3 N2 53.3(2) . . . . ?
C5 C4 C3 C2 -60.5(2) . . . . ?
C5 C10 C9 C8 1.3(3) . . . . ?
C3 N2 C1 N1 15.72(19) . . . . ?
C3 N2 C1 C11 -105.53(19) . . . . ?
C3 N2 C16 Cl1 30.6(3) . . . . ?
C3 N2 C16 O3 -153.3(2) . . . . ?
C3 C4 C5 C6 92.7(2) . . . . ?
C3 C4 C5 C10 -88.0(2) . . . . ?
C7 C6 C5 C4 179.07(18) . . . . ?
C7 C6 C5 C10 -0.3(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C1 N2 C3 C2 -11.9(2) . . . . ?
C1 N2 C3 C4 -130.07(17) . . . . ?
C1 N2 C16 Cl1 -162.34(13) . . . . ?
C1 N2 C16 O3 13.7(3) . . . . ?
C1 N1 C2 O1 -175.40(19) . . . . ?
C1 N1 C2 C3 7.5(2) . . . . ?
C16 N2 C3 C2 155.7(2) . . . . ?
C16 N2 C3 C4 37.5(3) . . . . ?
C16 N2 C1 N1 -153.48(17) . . . . ?
C16 N2 C1 C11 85.3(2) . . . . ?
C9 C8 C7 C6 0.0(3) . . . . ?
C15 N1 C2 O1 1.3(3) . . . . ?
C15 N1 C2 C3 -175.78(18) . . . . ?
C15 N1 C1 N2 169.21(17) . . . . ?
C15 N1 C1 C11 -70.8(2) . . . . ?
C13 C11 C1 N2 66.3(2) . . . . ?
C13 C11 C1 N1 -47.0(2) . . . . ?
C12 C11 C1 N2 -54.3(2) . . . . ?
C12 C11 C1 N1 -167.62(16) . . . . ?
C14 C11 C1 N2 -171.81(17) . . . . ?
C14 C11 C1 N1 74.9(2) . . . . ?

_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_testm1
_database_code_depnum_ccdc_archive 'CCDC 2070019'
loop_
_audit_author_name
_audit_author_address
'Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2016-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H22 N2 O3'
_chemical_formula_sum            'C16 H22 N2 O3'
_chemical_formula_weight         290.35
_chemical_absolute_configuration unk
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.7583(3)
_cell_length_b                   13.5711(6)
_cell_length_c                   9.6541(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.964(3)
_cell_angle_gamma                90
_cell_volume                     750.35(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2145
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0890 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.8522.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.136
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10338
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.992
_diffrn_reflns_theta_min         2.121
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                2950
_reflns_number_total             3447
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3447
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.025
_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)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0867
_refine_special_details          
;
Absolute structure not determined.
;
_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:
 C2(H2), C3(H3A), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0401(3) 0.88863(12) 0.2481(2) 0.0222(4) Uani 1 1 d . . . . .
O2 O 0.4346(3) 0.58380(13) 0.30837(17) 0.0175(4) Uani 1 1 d . . . . .
O3 O 0.5574(3) 0.34569(14) -0.12432(19) 0.0236(4) Uani 1 1 d . . . . .
N1 N 0.8082(3) 0.83087(15) 0.4091(2) 0.0148(4) Uani 1 1 d . . . . .
N2 N 0.7786(3) 0.66974(15) 0.3495(2) 0.0124(4) Uani 1 1 d . . . . .
C1 C 0.9429(4) 0.82077(18) 0.3039(2) 0.0151(5) Uani 1 1 d . . . . .
C2 C 0.7165(4) 0.73755(17) 0.4583(2) 0.0132(5) Uani 1 1 d . . . . .
H2 H 0.5426 0.7419 0.4548 0.016 Uiso 1 1 calc R . . . .
C3 C 0.9554(4) 0.71273(17) 0.2682(2) 0.0132(5) Uani 1 1 d . . . . .
H3A H 1.1138 0.6853 0.2984 0.016 Uiso 1 1 calc R . . . .
C4 C 0.8752(4) 0.68426(17) 0.1166(3) 0.0157(5) Uani 1 1 d . . . . .
H4A H 1.0103 0.6664 0.0661 0.019 Uiso 1 1 calc R . . . .
H4B H 0.7896 0.7393 0.0670 0.019 Uiso 1 1 calc R . . . .
C5 C 0.7127(4) 0.59439(19) 0.1288(2) 0.0140(5) Uani 1 1 d . . . . .
C6 C 0.6182(4) 0.61393(16) 0.2709(3) 0.0138(5) Uani 1 1 d . . . . .
C7 C 0.7349(5) 0.9269(2) 0.4549(3) 0.0274(7) Uani 1 1 d . . . . .
H7A H 0.8379 0.9476 0.5369 0.041 Uiso 1 1 calc GR . . . .
H7B H 0.5739 0.9228 0.4789 0.041 Uiso 1 1 calc GR . . . .
H7C H 0.7433 0.9749 0.3799 0.041 Uiso 1 1 calc GR . . . .
C8 C 0.8183(4) 0.70578(18) 0.6059(2) 0.0144(5) Uani 1 1 d . . . . .
C9 C 1.0862(4) 0.7057(2) 0.6178(3) 0.0205(6) Uani 1 1 d . . . . .
H9A H 1.1396 0.6609 0.5480 0.031 Uiso 1 1 calc GR . . . .
H9B H 1.1477 0.6837 0.7111 0.031 Uiso 1 1 calc GR . . . .
H9C H 1.1424 0.7725 0.6018 0.031 Uiso 1 1 calc GR . . . .
C10 C 0.7328(4) 0.77524(19) 0.7151(3) 0.0190(6) Uani 1 1 d . . . . .
H10A H 0.8047 0.8402 0.7075 0.029 Uiso 1 1 calc GR . . . .
H10B H 0.7764 0.7484 0.8084 0.029 Uiso 1 1 calc GR . . . .
H10C H 0.5626 0.7816 0.6992 0.029 Uiso 1 1 calc GR . . . .
C11 C 0.7282(5) 0.6019(2) 0.6317(3) 0.0203(6) Uani 1 1 d . . . . .
H11A H 0.5572 0.6025 0.6230 0.030 Uiso 1 1 calc GR . . . .
H11B H 0.7877 0.5804 0.7257 0.030 Uiso 1 1 calc GR . . . .
H11C H 0.7822 0.5564 0.5630 0.030 Uiso 1 1 calc GR . . . .
C12 C 0.8473(4) 0.49826(19) 0.1415(3) 0.0173(5) Uani 1 1 d . . . . .
H12 H 0.9966 0.4976 0.1936 0.021 Uiso 1 1 calc R . . . .
C13 C 0.7661(5) 0.41555(19) 0.0834(3) 0.0187(5) Uani 1 1 d . . . . .
H13 H 0.8588 0.3578 0.0982 0.022 Uiso 1 1 calc R . . . .
C14 C 0.5368(5) 0.40689(19) -0.0047(3) 0.0188(6) Uani 1 1 d . . . . .
H14 H 0.4257 0.3735 0.0531 0.023 Uiso 1 1 calc R . . . .
C15 C 0.4365(4) 0.50600(19) -0.0439(2) 0.0180(5) Uani 1 1 d . . . . .
H15 H 0.3102 0.5092 -0.1154 0.022 Uiso 1 1 calc R . . . .
C16 C 0.5137(4) 0.5894(2) 0.0151(2) 0.0168(5) Uani 1 1 d . . . . .
H16 H 0.4397 0.6491 -0.0159 0.020 Uiso 1 1 calc R . . . .
H3 H 0.682(5) 0.367(2) -0.161(3) 0.020(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.231(3) . ?
O2 C6 1.223(3) . ?
O3 C14 1.438(3) . ?
O3 H3 0.88(3) . ?
N1 C1 1.347(3) . ?
N1 C2 1.470(3) . ?
N1 C7 1.453(3) . ?
N2 C2 1.468(3) . ?
N2 C3 1.469(3) . ?
N2 C6 1.363(3) . ?
C1 C3 1.510(3) . ?
C2 H2 1.0000 . ?
C2 C8 1.545(3) . ?
C3 H3A 1.0000 . ?
C3 C4 1.538(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.549(3) . ?
C5 C6 1.550(3) . ?
C5 C12 1.516(3) . ?
C5 C16 1.504(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.535(3) . ?
C8 C10 1.533(3) . ?
C8 C11 1.531(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.319(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.499(4) . ?
C14 H14 1.0000 . ?
C14 C15 1.497(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.323(4) . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O3 H3 105.6(19) . . ?
C1 N1 C2 114.20(19) . . ?
C1 N1 C7 122.0(2) . . ?
C7 N1 C2 123.3(2) . . ?
C2 N2 C3 111.52(19) . . ?
C6 N2 C2 123.0(2) . . ?
C6 N2 C3 113.00(19) . . ?
O1 C1 N1 125.3(2) . . ?
O1 C1 C3 126.3(2) . . ?
N1 C1 C3 108.4(2) . . ?
N1 C2 H2 109.3 . . ?
N1 C2 C8 115.07(19) . . ?
N2 C2 N1 100.77(18) . . ?
N2 C2 H2 109.3 . . ?
N2 C2 C8 112.80(19) . . ?
C8 C2 H2 109.3 . . ?
N2 C3 C1 102.21(19) . . ?
N2 C3 H3A 111.0 . . ?
N2 C3 C4 104.61(18) . . ?
C1 C3 H3A 111.0 . . ?
C1 C3 C4 116.4(2) . . ?
C4 C3 H3A 111.0 . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C3 C4 C5 104.41(19) . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C4 C5 C6 101.74(19) . . ?
C12 C5 C4 112.08(19) . . ?
C12 C5 C6 107.42(19) . . ?
C16 C5 C4 113.6(2) . . ?
C16 C5 C6 110.0(2) . . ?
C16 C5 C12 111.4(2) . . ?
O2 C6 N2 125.3(2) . . ?
O2 C6 C5 126.8(2) . . ?
N2 C6 C5 107.9(2) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C2 110.57(19) . . ?
C10 C8 C2 110.2(2) . . ?
C10 C8 C9 109.9(2) . . ?
C11 C8 C2 107.74(19) . . ?
C11 C8 C9 110.0(2) . . ?
C11 C8 C10 108.4(2) . . ?
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 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12 118.6 . . ?
C13 C12 C5 122.8(2) . . ?
C13 C12 H12 118.6 . . ?
C12 C13 H13 118.0 . . ?
C12 C13 C14 124.1(2) . . ?
C14 C13 H13 118.0 . . ?
O3 C14 C13 111.1(2) . . ?
O3 C14 H14 107.2 . . ?
O3 C14 C15 112.2(2) . . ?
C13 C14 H14 107.2 . . ?
C15 C14 C13 111.5(2) . . ?
C15 C14 H14 107.2 . . ?
C14 C15 H15 118.1 . . ?
C16 C15 C14 123.7(2) . . ?
C16 C15 H15 118.1 . . ?
C5 C16 H16 118.3 . . ?
C15 C16 C5 123.4(2) . . ?
C15 C16 H16 118.3 . . ?

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 C3 N2 -170.9(2) . . . . ?
O1 C1 C3 C4 -57.6(3) . . . . ?
O3 C14 C15 C16 -138.7(3) . . . . ?
N1 C1 C3 N2 9.7(2) . . . . ?
N1 C1 C3 C4 123.0(2) . . . . ?
N1 C2 C8 C9 -52.5(3) . . . . ?
N1 C2 C8 C10 69.2(2) . . . . ?
N1 C2 C8 C11 -172.8(2) . . . . ?
N2 C2 C8 C9 62.4(3) . . . . ?
N2 C2 C8 C10 -175.9(2) . . . . ?
N2 C2 C8 C11 -57.9(2) . . . . ?
N2 C3 C4 C5 -21.2(2) . . . . ?
C1 N1 C2 N2 -10.3(2) . . . . ?
C1 N1 C2 C8 111.3(2) . . . . ?
C1 C3 C4 C5 -133.1(2) . . . . ?
C2 N1 C1 O1 -179.0(2) . . . . ?
C2 N1 C1 C3 0.4(3) . . . . ?
C2 N2 C3 C1 -16.7(2) . . . . ?
C2 N2 C3 C4 -138.52(19) . . . . ?
C2 N2 C6 O2 -28.8(4) . . . . ?
C2 N2 C6 C5 152.3(2) . . . . ?
C3 N2 C2 N1 16.7(2) . . . . ?
C3 N2 C2 C8 -106.5(2) . . . . ?
C3 N2 C6 O2 -167.5(2) . . . . ?
C3 N2 C6 C5 13.6(3) . . . . ?
C3 C4 C5 C6 28.0(2) . . . . ?
C3 C4 C5 C12 -86.5(2) . . . . ?
C3 C4 C5 C16 146.2(2) . . . . ?
C4 C5 C6 O2 155.2(2) . . . . ?
C4 C5 C6 N2 -26.0(2) . . . . ?
C4 C5 C12 C13 -143.2(2) . . . . ?
C4 C5 C16 C15 141.5(3) . . . . ?
C5 C12 C13 C14 1.8(4) . . . . ?
C6 N2 C2 N1 -122.5(2) . . . . ?
C6 N2 C2 C8 114.3(2) . . . . ?
C6 N2 C3 C1 126.8(2) . . . . ?
C6 N2 C3 C4 5.0(3) . . . . ?
C6 C5 C12 C13 105.8(3) . . . . ?
C6 C5 C16 C15 -105.2(3) . . . . ?
C7 N1 C1 O1 9.3(4) . . . . ?
C7 N1 C1 C3 -171.3(2) . . . . ?
C7 N1 C2 N2 161.2(2) . . . . ?
C7 N1 C2 C8 -77.1(3) . . . . ?
C12 C5 C6 O2 -87.0(3) . . . . ?
C12 C5 C6 N2 91.9(2) . . . . ?
C12 C5 C16 C15 13.8(4) . . . . ?
C12 C13 C14 O3 138.3(3) . . . . ?
C12 C13 C14 C15 12.4(4) . . . . ?
C13 C14 C15 C16 -13.4(4) . . . . ?
C14 C15 C16 C5 0.2(4) . . . . ?
C16 C5 C6 O2 34.4(3) . . . . ?
C16 C5 C6 N2 -146.7(2) . . . . ?
C16 C5 C12 C13 -14.7(3) . . . . ?

_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_le166_4
_database_code_depnum_ccdc_archive 'CCDC 2070024'
loop_
_audit_author_name
_audit_author_address
'Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H24 N2 O3'
_chemical_formula_sum            'C17 H24 N2 O3'
_chemical_formula_weight         304.38
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.7444(2)
_cell_length_b                   12.0901(5)
_cell_length_c                   12.1546(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.471(3)
_cell_angle_gamma                90
_cell_volume                     840.30(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0549 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.8376. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6822
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.082
_diffrn_reflns_theta_min         2.381
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.579
_reflns_Friedel_fraction_full    0.684
_reflns_Friedel_fraction_max     0.638
_reflns_number_gt                2596
_reflns_number_total             3061
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042

_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.020
_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)+(0.0369P)²+0.2057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0903
_refine_special_details          
;
Absolute structure based on synthesis.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.0010(4) 0.24117(17) 0.07517(18) 0.0271(5) Uani 1 1 d . . . . .
O2 O 0.2960(4) 0.88248(16) 0.05586(19) 0.0284(5) Uani 1 1 d . . . . .
H2 H 0.208777 0.843457 0.012086 0.043 Uiso 1 1 calc GR . . . .
O3 O 0.6629(3) 0.50155(16) 0.30498(16) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.2800(4) 0.23045(19) 0.2218(2) 0.0201(5) Uani 1 1 d . . . . .
N2 N 0.3124(4) 0.41010(18) 0.27270(18) 0.0156(5) Uani 1 1 d . . . . .
C1 C 0.3868(5) 0.2998(2) 0.3126(2) 0.0166(6) Uani 1 1 d . . . . .
H1 H 0.560956 0.294291 0.315307 0.020 Uiso 1 1 calc R . . . .
C2 C 0.1214(5) 0.2837(2) 0.1526(2) 0.0199(6) Uani 1 1 d . . . . .
C3 C 0.1216(5) 0.4041(2) 0.1837(2) 0.0164(6) Uani 1 1 d . . . . .
H3 H -0.030967 0.426736 0.210128 0.020 Uiso 1 1 calc R . . . .
C4 C 0.1982(5) 0.4850(2) 0.0964(2) 0.0185(6) Uani 1 1 d . . . . .
H4A H 0.061451 0.521351 0.055769 0.022 Uiso 1 1 calc R . . . .
H4B H 0.290162 0.446790 0.043014 0.022 Uiso 1 1 calc R . . . .
C5 C 0.3512(5) 0.5702(2) 0.1668(2) 0.0168(6) Uani 1 1 d . . . . .
C6 C 0.5345(5) 0.6235(2) 0.1051(2) 0.0202(6) Uani 1 1 d . . . . .
H6 H 0.637796 0.577222 0.069401 0.024 Uiso 1 1 calc R . . . .
C7 C 0.5596(5) 0.7315(2) 0.0978(2) 0.0213(6) Uani 1 1 d . . . . .
H7 H 0.686663 0.758434 0.060869 0.026 Uiso 1 1 calc R . . . .
C8 C 0.4024(5) 0.8144(2) 0.1434(3) 0.0202(6) Uani 1 1 d . . . . .
H8 H 0.501431 0.863311 0.195045 0.024 Uiso 1 1 calc R . . . .
C9 C 0.2189(5) 0.7624(2) 0.2080(2) 0.0180(6) Uani 1 1 d . . . . .
C10 C 0.1988(5) 0.6533(2) 0.2183(2) 0.0178(6) Uani 1 1 d . . . . .
H10 H 0.080807 0.626088 0.260860 0.021 Uiso 1 1 calc R . . . .
C11 C 0.0546(5) 0.8402(3) 0.2572(3) 0.0260(7) Uani 1 1 d . . . . .
H11A H -0.017582 0.889217 0.199412 0.039 Uiso 1 1 calc GR . . . .
H11B H 0.141268 0.884614 0.314874 0.039 Uiso 1 1 calc GR . . . .
H11C H -0.067353 0.797851 0.289516 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.4669(4) 0.4928(2) 0.2567(2) 0.0155(5) Uani 1 1 d . . . . .
C13 C 0.3095(5) 0.2742(2) 0.4276(3) 0.0205(6) Uani 1 1 d . . . . .
C14 C 0.0427(5) 0.2731(3) 0.4249(3) 0.0264(7) Uani 1 1 d . . . . .
H14A H -0.021142 0.215526 0.373818 0.040 Uiso 1 1 calc GR . . . .
H14B H -0.019401 0.345273 0.399948 0.040 Uiso 1 1 calc GR . . . .
H14C H -0.002282 0.257728 0.499146 0.040 Uiso 1 1 calc GR . . . .
C15 C 0.4079(5) 0.1619(3) 0.4692(3) 0.0309(8) Uani 1 1 d . . . . .
H15A H 0.575827 0.158886 0.460997 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.328012 0.102320 0.425803 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.382431 0.152772 0.547258 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.4103(5) 0.3647(3) 0.5061(3) 0.0284(7) Uani 1 1 d . . . . .
H16A H 0.338918 0.435887 0.483912 0.043 Uiso 1 1 calc GR . . . .
H16B H 0.579871 0.369075 0.503067 0.043 Uiso 1 1 calc GR . . . .
H16C H 0.376518 0.347163 0.581700 0.043 Uiso 1 1 calc GR . . . .
C17 C 0.3510(7) 0.1168(3) 0.2026(3) 0.0387(9) Uani 1 1 d . . . . .
H17A H 0.278730 0.067224 0.253402 0.058 Uiso 1 1 calc GR . . . .
H17B H 0.521595 0.110908 0.215430 0.058 Uiso 1 1 calc GR . . . .
H17C H 0.300402 0.095771 0.126217 0.058 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 C2 1.232(3) . ?
O2 H2 0.8400 . ?
O2 C8 1.435(3) . ?
O3 C12 1.224(3) . ?
N1 C1 1.472(4) . ?
N1 C2 1.344(4) . ?
N1 C17 1.459(4) . ?
N2 C1 1.468(3) . ?
N2 C3 1.467(3) . ?
N2 C12 1.363(3) . ?
C1 H1 1.0000 . ?
C1 C13 1.538(4) . ?
C2 C3 1.504(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.537(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.556(4) . ?
C5 C6 1.496(4) . ?
C5 C10 1.507(4) . ?
C5 C12 1.540(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.318(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.490(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.510(4) . ?
C9 C10 1.331(4) . ?
C9 C11 1.497(4) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.530(4) . ?
C13 C15 1.537(4) . ?
C13 C16 1.529(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O2 H2 109.5 . . ?
C2 N1 C1 113.9(2) . . ?
C2 N1 C17 122.3(3) . . ?
C17 N1 C1 123.6(3) . . ?
C3 N2 C1 111.9(2) . . ?
C12 N2 C1 122.7(2) . . ?
C12 N2 C3 112.5(2) . . ?
N1 C1 H1 109.3 . . ?
N1 C1 C13 115.5(2) . . ?
N2 C1 N1 100.5(2) . . ?
N2 C1 H1 109.3 . . ?
N2 C1 C13 112.5(2) . . ?
C13 C1 H1 109.3 . . ?
O1 C2 N1 125.6(3) . . ?
O1 C2 C3 125.6(3) . . ?
N1 C2 C3 108.8(2) . . ?
N2 C3 C2 102.4(2) . . ?
N2 C3 H3 111.4 . . ?
N2 C3 C4 103.6(2) . . ?
C2 C3 H3 111.4 . . ?
C2 C3 C4 115.9(2) . . ?
C4 C3 H3 111.4 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
C3 C4 C5 103.0(2) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C6 C5 C4 113.4(2) . . ?
C6 C5 C10 112.6(2) . . ?
C6 C5 C12 109.9(2) . . ?
C10 C5 C4 110.5(2) . . ?
C10 C5 C12 109.8(2) . . ?
C12 C5 C4 99.9(2) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 C5 123.2(3) . . ?
C7 C6 H6 118.4 . . ?
C6 C7 H7 117.7 . . ?
C6 C7 C8 124.5(3) . . ?
C8 C7 H7 117.7 . . ?
O2 C8 C7 109.9(2) . . ?
O2 C8 H8 107.6 . . ?
O2 C8 C9 110.8(2) . . ?
C7 C8 H8 107.6 . . ?
C7 C8 C9 113.0(2) . . ?
C9 C8 H8 107.6 . . ?
C10 C9 C8 122.2(2) . . ?
C10 C9 C11 121.5(3) . . ?
C11 C9 C8 116.4(2) . . ?
C5 C10 H10 117.9 . . ?
C9 C10 C5 124.3(3) . . ?
C9 C10 H10 117.9 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N2 125.3(3) . . ?
O3 C12 C5 127.1(3) . . ?
N2 C12 C5 107.7(2) . . ?
C14 C13 C1 110.9(2) . . ?
C14 C13 C15 109.6(2) . . ?
C15 C13 C1 110.4(2) . . ?
C16 C13 C1 107.3(2) . . ?
C16 C13 C14 109.8(3) . . ?
C16 C13 C15 108.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C2 C3 N2 -174.7(3) . . . . ?
O1 C2 C3 C4 -62.7(4) . . . . ?
O2 C8 C9 C10 121.6(3) . . . . ?
O2 C8 C9 C11 -56.5(3) . . . . ?
N1 C1 C13 C14 -51.9(3) . . . . ?
N1 C1 C13 C15 69.8(3) . . . . ?
N1 C1 C13 C16 -171.9(2) . . . . ?
N1 C2 C3 N2 4.1(3) . . . . ?
N1 C2 C3 C4 116.1(2) . . . . ?
N2 C1 C13 C14 62.7(3) . . . . ?
N2 C1 C13 C15 -175.6(2) . . . . ?
N2 C1 C13 C16 -57.2(3) . . . . ?
N2 C3 C4 C5 -28.2(3) . . . . ?
C1 N1 C2 O1 -175.1(3) . . . . ?
C1 N1 C2 C3 6.1(3) . . . . ?
C1 N2 C3 C2 -12.9(3) . . . . ?
C1 N2 C3 C4 -133.8(2) . . . . ?
C1 N2 C12 O3 -26.1(4) . . . . ?
C1 N2 C12 C5 153.0(2) . . . . ?
C2 N1 C1 N2 -13.4(3) . . . . ?
C2 N1 C1 C13 107.9(3) . . . . ?
C2 C3 C4 C5 -139.5(2) . . . . ?
C3 N2 C1 N1 15.9(3) . . . . ?
C3 N2 C1 C13 -107.5(2) . . . . ?
C3 N2 C12 O3 -164.2(2) . . . . ?
C3 N2 C12 C5 14.9(3) . . . . ?
C3 C4 C5 C6 152.3(2) . . . . ?
C3 C4 C5 C10 -80.1(3) . . . . ?
C3 C4 C5 C12 35.5(2) . . . . ?
C4 C5 C6 C7 126.9(3) . . . . ?
C4 C5 C10 C9 -126.1(3) . . . . ?
C4 C5 C12 O3 147.6(3) . . . . ?
C4 C5 C12 N2 -31.5(3) . . . . ?
C5 C6 C7 C8 -3.9(5) . . . . ?
C6 C5 C10 C9 1.8(4) . . . . ?
C6 C5 C12 O3 28.1(4) . . . . ?
C6 C5 C12 N2 -151.0(2) . . . . ?
C6 C7 C8 O2 -119.7(3) . . . . ?
C6 C7 C8 C9 4.6(4) . . . . ?
C7 C8 C9 C10 -2.3(4) . . . . ?
C7 C8 C9 C11 179.6(3) . . . . ?
C8 C9 C10 C5 -0.8(5) . . . . ?
C10 C5 C6 C7 0.5(4) . . . . ?
C10 C5 C12 O3 -96.3(3) . . . . ?
C10 C5 C12 N2 84.6(3) . . . . ?
C11 C9 C10 C5 177.2(3) . . . . ?
C12 N2 C1 N1 -122.4(3) . . . . ?
C12 N2 C1 C13 114.2(3) . . . . ?
C12 N2 C3 C2 129.7(2) . . . . ?
C12 N2 C3 C4 8.9(3) . . . . ?
C12 C5 C6 C7 -122.3(3) . . . . ?
C12 C5 C10 C9 124.7(3) . . . . ?
C17 N1 C1 N2 162.0(3) . . . . ?
C17 N1 C1 C13 -76.7(3) . . . . ?
C17 N1 C2 O1 9.4(4) . . . . ?
C17 N1 C2 C3 -169.4(3) . . . . ?

_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_le172_f23_27
_database_code_depnum_ccdc_archive 'CCDC 2070023'
loop_
_audit_author_name
_audit_author_address
'Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H26 N2 O3'
_chemical_formula_sum            'C16 H26 N2 O3'
_chemical_formula_weight         294.39
_chemical_absolute_configuration .
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.94680(10)
_cell_length_b                   13.2423(3)
_cell_length_c                   10.0750(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.9895(15)
_cell_angle_gamma                90
_cell_volume                     785.70(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8311
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0630 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.8471. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.074
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18866
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.966
_diffrn_reflns_theta_min         2.041
_diffrn_ambient_temperature      99.97
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3588
_reflns_number_total             3773
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.051
_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)+(0.0510P)²+0.0717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0812
_refine_special_details          
;
 The absolute structure parameter is meaningless because the compound is a weak
 anomalous scatterer, therefore the Flack parameter has been removed from the
 CIF.

 The hydrogen atom on the oxygen was found by difference map after all other
 atoms had been refined. All other hydrogens were placed geometrically and
 refined using a riding model.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7151(3) 0.69017(12) 0.96666(17) 0.0128(3) Uani 1 1 d . . . . .
H1 H 0.5496 0.7009 0.9700 0.015 Uiso 1 1 calc R . . . .
C2 C 0.9071(3) 0.75998(13) 0.79791(18) 0.0141(3) Uani 1 1 d . . . . .
C3 C 0.8947(3) 0.64742(13) 0.77224(17) 0.0130(3) Uani 1 1 d . . . . .
H3 H 1.0478 0.6156 0.7944 0.016 Uiso 1 1 calc R . . . .
C4 C 0.7783(3) 0.61239(13) 0.63363(17) 0.0152(3) Uani 1 1 d . . . . .
H4A H 0.8913 0.5873 0.5781 0.018 Uiso 1 1 calc R . . . .
H4B H 0.6909 0.6682 0.5855 0.018 Uiso 1 1 calc R . . . .
C5 C 0.6191(3) 0.52655(13) 0.66638(17) 0.0132(3) Uani 1 1 d . . . . .
C6 C 0.4003(3) 0.51650(14) 0.56740(18) 0.0168(4) Uani 1 1 d . . . . .
H6A H 0.2893 0.4759 0.6092 0.020 Uiso 1 1 calc R . . . .
H6B H 0.3341 0.5844 0.5483 0.020 Uiso 1 1 calc R . . . .
C7 C 0.4390(3) 0.46688(15) 0.43568(19) 0.0202(4) Uani 1 1 d . . . . .
H7A H 0.2921 0.4597 0.3768 0.024 Uiso 1 1 calc R . . . .
H7B H 0.5391 0.5102 0.3892 0.024 Uiso 1 1 calc R . . . .
C8 C 0.5474(3) 0.36345(15) 0.46155(19) 0.0197(4) Uani 1 1 d . . . . .
H8 H 0.4450 0.3226 0.5113 0.024 Uiso 1 1 calc R . . . .
C9 C 0.7739(3) 0.37388(15) 0.55181(19) 0.0198(4) Uani 1 1 d . . . . .
H9A H 0.8787 0.4150 0.5058 0.024 Uiso 1 1 calc R . . . .
H9B H 0.8426 0.3062 0.5692 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7431(3) 0.42377(13) 0.68495(18) 0.0166(4) Uani 1 1 d . . . . .
H10A H 0.8941 0.4340 0.7384 0.020 Uiso 1 1 calc R . . . .
H10B H 0.6554 0.3779 0.7359 0.020 Uiso 1 1 calc R . . . .
C11 C 0.5634(3) 0.55882(12) 0.80375(16) 0.0121(3) Uani 1 1 d . . . . .
C12 C 0.8331(3) 0.66163(13) 1.10869(17) 0.0144(3) Uani 1 1 d . . . . .
C13 C 0.7567(3) 0.73352(15) 1.21294(19) 0.0199(4) Uani 1 1 d . . . . .
H13A H 0.8102 0.8020 1.1977 0.030 Uiso 1 1 calc GR . . . .
H13B H 0.8204 0.7111 1.3030 0.030 Uiso 1 1 calc GR . . . .
H13C H 0.5905 0.7335 1.2048 0.030 Uiso 1 1 calc GR . . . .
C14 C 1.0917(3) 0.66459(15) 1.11445(19) 0.0194(4) Uani 1 1 d . . . . .
H14A H 1.1375 0.6194 1.0459 0.029 Uiso 1 1 calc GR . . . .
H14B H 1.1633 0.6426 1.2032 0.029 Uiso 1 1 calc GR . . . .
H14C H 1.1399 0.7337 1.0979 0.029 Uiso 1 1 calc GR . . . .
C15 C 0.7568(3) 0.55462(14) 1.13992(19) 0.0195(4) Uani 1 1 d . . . . .
H15A H 0.5914 0.5534 1.1370 0.029 Uiso 1 1 calc GR . . . .
H15B H 0.8290 0.5347 1.2295 0.029 Uiso 1 1 calc GR . . . .
H15C H 0.8012 0.5074 1.0733 0.029 Uiso 1 1 calc GR . . . .
C16 C 0.7628(3) 0.88179(14) 0.9484(2) 0.0212(4) Uani 1 1 d . . . . .
H16A H 0.8787 0.9019 1.0225 0.032 Uiso 1 1 calc GR . . . .
H16B H 0.6126 0.8847 0.9778 0.032 Uiso 1 1 calc GR . . . .
H16C H 0.7669 0.9278 0.8726 0.032 Uiso 1 1 calc GR . . . .
N1 N 0.8074(3) 0.77959(11) 0.90742(15) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.7416(2) 0.61386(11) 0.86567(14) 0.0122(3) Uani 1 1 d . . . . .
O1 O 0.9955(2) 0.82335(10) 0.73243(14) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.5694(3) 0.31086(12) 0.34024(15) 0.0278(3) Uani 1 1 d . . . . .
H2 H 0.702(5) 0.318(2) 0.321(3) 0.038(7) Uiso 1 1 d . . . . .
O3 O 0.3928(2) 0.53798(10) 0.85286(13) 0.0164(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 1.0000 . ?
C1 C12 1.550(2) . ?
C1 N1 1.467(2) . ?
C1 N2 1.458(2) . ?
C2 C3 1.513(2) . ?
C2 N1 1.348(2) . ?
C2 O1 1.230(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.541(2) . ?
C3 N2 1.467(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.544(2) . ?
C5 C6 1.531(2) . ?
C5 C10 1.547(2) . ?
C5 C11 1.528(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.527(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.521(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.523(3) . ?
C8 O2 1.428(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.529(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.363(2) . ?
C11 O3 1.221(2) . ?
C12 C13 1.533(2) . ?
C12 C14 1.532(2) . ?
C12 C15 1.534(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 N1 1.450(2) . ?
O2 H2 0.84(3) . ?

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
C12 C1 H1 108.9 . . ?
N1 C1 H1 108.9 . . ?
N1 C1 C12 115.19(14) . . ?
N2 C1 H1 108.9 . . ?
N2 C1 C12 113.34(14) . . ?
N2 C1 N1 101.12(13) . . ?
N1 C2 C3 108.25(14) . . ?
O1 C2 C3 126.51(16) . . ?
O1 C2 N1 125.23(16) . . ?
C2 C3 H3 110.9 . . ?
C2 C3 C4 117.16(14) . . ?
C4 C3 H3 110.9 . . ?
N2 C3 C2 102.05(14) . . ?
N2 C3 H3 110.9 . . ?
N2 C3 C4 104.44(13) . . ?
C3 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C3 C4 C5 103.86(13) . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C4 C5 C10 112.18(14) . . ?
C6 C5 C4 114.55(14) . . ?
C6 C5 C10 110.49(14) . . ?
C11 C5 C4 101.77(13) . . ?
C11 C5 C6 110.04(14) . . ?
C11 C5 C10 107.23(14) . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.72(14) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.50(15) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8 107.4 . . ?
C7 C8 C9 109.84(15) . . ?
C9 C8 H8 107.4 . . ?
O2 C8 C7 112.30(16) . . ?
O2 C8 H8 107.4 . . ?
O2 C8 C9 112.14(15) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C10 111.05(15) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C5 C10 H10A 109.0 . . ?
C5 C10 H10B 109.0 . . ?
C9 C10 C5 112.79(15) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C5 108.15(14) . . ?
O3 C11 C5 126.92(15) . . ?
O3 C11 N2 124.90(15) . . ?
C13 C12 C1 110.00(14) . . ?
C13 C12 C15 108.00(14) . . ?
C14 C12 C1 110.60(14) . . ?
C14 C12 C13 110.48(15) . . ?
C14 C12 C15 109.88(15) . . ?
C15 C12 C1 107.81(14) . . ?
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 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
C2 N1 C1 114.18(14) . . ?
C2 N1 C16 122.11(15) . . ?
C16 N1 C1 122.94(15) . . ?
C1 N2 C3 112.01(13) . . ?
C11 N2 C1 122.51(14) . . ?
C11 N2 C3 112.37(14) . . ?
C8 O2 H2 110(2) . . ?

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
O2 H2 O1 0.84(3) 1.95(3) 2.790(2) 174(3) 2_746

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
C2 C3 C4 C5 -133.66(15) . . . . ?
C2 C3 N2 C1 -15.68(17) . . . . ?
C2 C3 N2 C11 126.81(15) . . . . ?
C3 C2 N1 C1 -1.07(19) . . . . ?
C3 C2 N1 C16 -171.29(16) . . . . ?
C3 C4 C5 C6 148.22(14) . . . . ?
C3 C4 C5 C10 -84.78(17) . . . . ?
C3 C4 C5 C11 29.53(16) . . . . ?
C4 C3 N2 C1 -138.15(14) . . . . ?
C4 C3 N2 C11 4.33(18) . . . . ?
C4 C5 C6 C7 76.18(19) . . . . ?
C4 C5 C10 C9 -78.70(18) . . . . ?
C4 C5 C11 N2 -28.20(17) . . . . ?
C4 C5 C11 O3 153.32(17) . . . . ?
C5 C6 C7 C8 57.0(2) . . . . ?
C5 C11 N2 C1 153.39(15) . . . . ?
C5 C11 N2 C3 15.42(18) . . . . ?
C6 C5 C10 C9 50.45(19) . . . . ?
C6 C5 C11 N2 -150.06(14) . . . . ?
C6 C5 C11 O3 31.5(2) . . . . ?
C6 C7 C8 C9 -59.35(19) . . . . ?
C6 C7 C8 O2 175.13(15) . . . . ?
C7 C8 C9 C10 58.4(2) . . . . ?
C8 C9 C10 C5 -54.6(2) . . . . ?
C10 C5 C6 C7 -51.7(2) . . . . ?
C10 C5 C11 N2 89.73(16) . . . . ?
C10 C5 C11 O3 -88.8(2) . . . . ?
C11 C5 C6 C7 -169.90(15) . . . . ?
C11 C5 C10 C9 170.38(14) . . . . ?
C12 C1 N1 C2 114.32(16) . . . . ?
C12 C1 N1 C16 -75.6(2) . . . . ?
C12 C1 N2 C3 -108.93(16) . . . . ?
C12 C1 N2 C11 112.96(17) . . . . ?
N1 C1 C12 C13 76.07(18) . . . . ?
N1 C1 C12 C14 -46.2(2) . . . . ?
N1 C1 C12 C15 -166.40(14) . . . . ?
N1 C1 N2 C3 14.93(17) . . . . ?
N1 C1 N2 C11 -123.18(16) . . . . ?
N1 C2 C3 C4 123.23(16) . . . . ?
N1 C2 C3 N2 9.89(17) . . . . ?
N2 C1 C12 C13 -168.15(14) . . . . ?
N2 C1 C12 C14 69.54(18) . . . . ?
N2 C1 C12 C15 -50.61(18) . . . . ?
N2 C1 N1 C2 -8.27(18) . . . . ?
N2 C1 N1 C16 161.86(16) . . . . ?
N2 C3 C4 C5 -21.67(17) . . . . ?
O1 C2 C3 C4 -57.8(2) . . . . ?
O1 C2 C3 N2 -171.19(17) . . . . ?
O1 C2 N1 C1 179.99(16) . . . . ?
O1 C2 N1 C16 9.8(3) . . . . ?
O2 C8 C9 C10 -176.02(16) . . . . ?
O3 C11 N2 C1 -28.1(3) . . . . ?
O3 C11 N2 C3 -166.06(16) . . . . ?

_olex2_exptl_crystal_mounting_method 'Oil on glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
