# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2151105'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2022-02-01
_audit_creation_method           'CRYSTALS_ver_14.61_build_7932 '

_oxford_structure_analysis_title 7144
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
;Upon refinement the structure was tested for twinning using the software 
ROTAX within CRYSTALS.  This suggested the presence of merohedral twinning 
with two components related by a rotation of 180/% about the  b axis 
and the following twin laws:

1(Identity)

2(Rotation about c)          (h') (-1 0  0) (h)
                             (k')=(-1.014  1  0.513).(k)
                             (l')= (0 0 -1) (l)

Subsequent refinement of the structure assumed a two-component twin with final
 partial contributions to the intensities of the diffracted peaks of 0.678(4)
and 0.322(4) respectively.

The raw intensity data were re-examined and although this twin-law did index 
for some of the additional features, it did not account for all of them.,Twin
;

_cell_length_a                   9.5572(6)
_cell_length_b                   12.2819(10)
_cell_length_c                   12.4294(6)
_cell_angle_alpha                101.237(6)
_cell_angle_beta                 99.446(5)
_cell_angle_gamma                110.609(7)
_cell_volume                     1295.68(17)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C16 H19 N1 O2 
# Dc =      1.32 Fooo =    552.00 Mu =      6.89 M =    257.33
# Found Formula = C16 H19.00 N1 O2 
# Dc =      1.32 FOOO =    552.00 Mu =      6.89 M =    257.33

_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_moiety         'C16 H19 N O2'
_chemical_compound_source        .
_chemical_formula_weight         257.33


_cell_measurement_reflns_used    5384
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      75.45
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.19

_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             551.996
_exptl_absorpt_coefficient_mu    0.689

# Sheldrick geometric approximatio 0.90 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            21905
_diffrn_reflns_av_unetI/netI     0.076
_reflns_number_total             5401
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.0756
# Number of reflections with Friedels Law is 5401 
# Theoretical number of reflections is about 10935 


_diffrn_reflns_theta_min         3.748
_diffrn_reflns_theta_max         76.811
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        75.275
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -12
_reflns_limit_h_max              11
_reflns_limit_k_min              -15
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   4.13
_oxford_diffrn_Wilson_scale      0.05

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.28


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5401
_refine_ls_R_factor_ref          0.0839
_refine_ls_wR_factor_ref         0.2172
_refine_ls_goodness_of_fit_ref   0.9940
_refine_ls_shift/su_max          0.0001002
_refine_ls_shift/su_mean         0.0000092


# Computed with I/sigma = -10 
_reflns_number_all               5401
_refine_ls_R_factor_all          0.0839
_refine_ls_wR_factor_all         0.2172

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4112
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_gt          0.1975


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.12P)² + 0.42P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.2780(4) 0.3719(3) 0.5017(3) 0.0575 1.0000 Uani . . . . . .
C2 C 0.2198(4) 0.2712(3) 0.3896(3) 0.0585 1.0000 Uani . . . . . .
N3 N 0.2471(3) 0.1690(2) 0.4196(2) 0.0443 1.0000 Uani . . . . . .
C4 C 0.1362(3) 0.0524(2) 0.3467(2) 0.0449 1.0000 Uani . . . . . .
C5 C 0.1460(3) -0.0510(2) 0.3925(2) 0.0408 1.0000 Uani . . . . . .
C6 C 0.0743(3) -0.1685(2) 0.3193(2) 0.0436 1.0000 Uani . . . . . .
C7 C 0.0774(3) -0.2617(2) 0.3634(2) 0.0435 1.0000 Uani . . . . . .
O8 O 0.0106(2) -0.38359(17) 0.30956(18) 0.0537 1.0000 Uani . . . . . .
C9 C 0.0674(4) -0.4389(3) 0.3877(3) 0.0554 1.0000 Uani . . . . . .
O10 O 0.1283(3) -0.35254(17) 0.49685(18) 0.0531 1.0000 Uani . . . . . .
C11 C 0.1465(3) -0.2429(2) 0.4758(2) 0.0427 1.0000 Uani . . . . . .
C12 C 0.2165(3) -0.1289(2) 0.5493(2) 0.0416 1.0000 Uani . . . . . .
C13 C 0.2158(3) -0.0307(2) 0.5063(2) 0.0393 1.0000 Uani . . . . . .
C14 C 0.2940(3) 0.0956(2) 0.5870(2) 0.0403 1.0000 Uani . . . . . .
C15 C 0.2377(3) 0.1818(2) 0.5369(2) 0.0408 1.0000 Uani . . . . . .
C16 C 0.3286(3) 0.3165(2) 0.5937(3) 0.0475 1.0000 Uani . . . . . .
C17 C 0.5040(3) 0.3522(2) 0.6239(3) 0.0503 1.0000 Uani . . . . . .
C18 C 0.5483(3) 0.2705(2) 0.6887(3) 0.0488 1.0000 Uani . . . . . .
C19 C 0.4707(3) 0.1394(2) 0.6144(2) 0.0457 1.0000 Uani . . . . . .
C51 C 0.6195(4) 0.3872(3) 0.1938(3) 0.0685 1.0000 Uani . . . . . .
C52 C 0.5771(4) 0.2859(3) 0.2517(3) 0.0627 1.0000 Uani . . . . . .
N53 N 0.4423(3) 0.1860(2) 0.1707(2) 0.0474 1.0000 Uani . . . . . .
C54 C 0.4291(3) 0.0691(3) 0.1856(2) 0.0465 1.0000 Uani . . . . . .
C55 C 0.3106(3) -0.0331(2) 0.0878(2) 0.0414 1.0000 Uani . . . . . .
C56 C 0.2541(3) -0.1493(3) 0.1036(2) 0.0462 1.0000 Uani . . . . . .
C57 C 0.1532(3) -0.2426(2) 0.0131(3) 0.0458 1.0000 Uani . . . . . .
O58 O 0.0858(3) -0.3635(2) 0.0086(2) 0.0619 1.0000 Uani . . . . . .
C59 C -0.0181(4) -0.4208(3) -0.1021(3) 0.0580 1.0000 Uani . . . . . .
O60 O 0.0081(3) -0.33520(18) -0.16664(19) 0.0586 1.0000 Uani . . . . . .
C61 C 0.1068(3) -0.2256(2) -0.0906(2) 0.0450 1.0000 Uani . . . . . .
C62 C 0.1589(3) -0.1133(2) -0.1086(2) 0.0436 1.0000 Uani . . . . . .
C63 C 0.2639(3) -0.0146(2) -0.0166(2) 0.0401 1.0000 Uani . . . . . .
C64 C 0.3212(3) 0.1109(2) -0.0343(2) 0.0419 1.0000 Uani . . . . . .
C65 C 0.4649(3) 0.1957(2) 0.0594(2) 0.0438 1.0000 Uani . . . . . .
C66 C 0.5153(3) 0.3317(2) 0.0712(3) 0.0532 1.0000 Uani . . . . . .
C67 C 0.3769(4) 0.3681(2) 0.0575(3) 0.0543 1.0000 Uani . . . . . .
C68 C 0.2519(4) 0.2880(3) -0.0503(3) 0.0540 1.0000 Uani . . . . . .
C69 C 0.1918(3) 0.1581(2) -0.0432(3) 0.0509 1.0000 Uani . . . . . .
H151 H 0.1278 0.1611 0.5391 0.0487 1.0000 Uiso R . . . . .
H161 H 0.2956 0.3416 0.6636 0.0567 1.0000 Uiso R . . . . .
H171 H 0.5564 0.4379 0.6675 0.0594 1.0000 Uiso R . . . . .
H172 H 0.5360 0.3444 0.5529 0.0595 1.0000 Uiso R . . . . .
H181 H 0.5148 0.2773 0.7592 0.0588 1.0000 Uiso R . . . . .
H182 H 0.6611 0.2985 0.7075 0.0594 1.0000 Uiso R . . . . .
H191 H 0.5027 0.0853 0.6520 0.0545 1.0000 Uiso R . . . . .
H192 H 0.5029 0.1344 0.5427 0.0544 1.0000 Uiso R . . . . .
H11 H 0.1946 0.3965 0.5164 0.0689 1.0000 Uiso R . . . . .
H12 H 0.3626 0.4423 0.4992 0.0693 1.0000 Uiso R . . . . .
H22 H 0.1085 0.2486 0.3600 0.0698 1.0000 Uiso R . . . . .
H21 H 0.2743 0.2966 0.3341 0.0707 1.0000 Uiso R . . . . .
H42 H 0.0317 0.0503 0.3401 0.0530 1.0000 Uiso R . . . . .
H41 H 0.1541 0.0416 0.2702 0.0540 1.0000 Uiso R . . . . .
H61 H 0.0237 -0.1839 0.2407 0.0527 1.0000 Uiso R . . . . .
H91 H -0.0174 -0.5106 0.3915 0.0662 1.0000 Uiso R . . . . .
H92 H 0.1501 -0.4619 0.3643 0.0662 1.0000 Uiso R . . . . .
H121 H 0.2619 -0.1153 0.6258 0.0499 1.0000 Uiso R . . . . .
H141 H 0.2632 0.0919 0.6592 0.0481 1.0000 Uiso R . . . . .
H511 H 0.7272 0.4133 0.1920 0.0820 1.0000 Uiso R . . . . .
H512 H 0.6041 0.4573 0.2315 0.0826 1.0000 Uiso R . . . . .
H521 H 0.5505 0.3122 0.3225 0.0752 1.0000 Uiso R . . . . .
H522 H 0.6637 0.2603 0.2674 0.0746 1.0000 Uiso R . . . . .
H541 H 0.5306 0.0634 0.1873 0.0558 1.0000 Uiso R . . . . .
H542 H 0.4012 0.0608 0.2570 0.0560 1.0000 Uiso R . . . . .
H561 H 0.2873 -0.1615 0.1732 0.0561 1.0000 Uiso R . . . . .
H592 H 0.0053 -0.4885 -0.1368 0.0701 1.0000 Uiso R . . . . .
H591 H -0.1242 -0.4474 -0.0944 0.0702 1.0000 Uiso R . . . . .
H621 H 0.1282 -0.1012 -0.1794 0.0520 1.0000 Uiso R . . . . .
H641 H 0.3517 0.1046 -0.1075 0.0492 1.0000 Uiso R . . . . .
H651 H 0.5515 0.1734 0.0468 0.0525 1.0000 Uiso R . . . . .
H661 H 0.5727 0.3563 0.0148 0.0637 1.0000 Uiso R . . . . .
H671 H 0.4104 0.4517 0.0548 0.0643 1.0000 Uiso R . . . . .
H672 H 0.3313 0.3607 0.1234 0.0647 1.0000 Uiso R . . . . .
H681 H 0.1664 0.3154 -0.0575 0.0649 1.0000 Uiso R . . . . .
H682 H 0.2945 0.2938 -0.1154 0.0651 1.0000 Uiso R . . . . .
H691 H 0.1513 0.1568 0.0254 0.0608 1.0000 Uiso R . . . . .
H692 H 0.1066 0.1032 -0.1108 0.0614 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.83(17)

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33

1 0.678(4) 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000
2 0.322(4) -1.0000 0.0000 0.0000 1.0140 1.0000 0.5130 0.0000 0.0000 -1.0000
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.540(5) yes
C1 . C16 . 1.534(4) yes
C1 . H11 . 0.977 no
C1 . H12 . 0.965 no
C2 . N3 . 1.470(3) yes
C2 . H22 . 0.984 no
C2 . H21 . 0.966 no
N3 . C4 . 1.451(3) yes
N3 . C15 . 1.457(3) yes
C4 . C5 . 1.514(3) yes
C4 . H42 . 0.978 no
C4 . H41 . 0.986 no
C5 . C6 . 1.403(4) yes
C5 . C13 . 1.394(4) yes
C6 . C7 . 1.369(4) yes
C6 . H61 . 0.966 no
C7 . O8 . 1.376(3) yes
C7 . C11 . 1.380(4) yes
O8 . C9 . 1.430(4) yes
C9 . O10 . 1.432(3) yes
C9 . H91 . 0.980 no
C9 . H92 . 0.994 no
O10 . C11 . 1.378(3) yes
C11 . C12 . 1.373(3) yes
C12 . C13 . 1.412(3) yes
C12 . H121 . 0.934 no
C13 . C14 . 1.517(3) yes
C14 . C15 . 1.532(3) yes
C14 . C19 . 1.536(3) yes
C14 . H141 . 0.993 no
C15 . C16 . 1.524(3) yes
C15 . H151 . 0.997 no
C16 . C17 . 1.535(4) yes
C16 . H161 . 1.001 no
C17 . C18 . 1.530(4) yes
C17 . H171 . 0.984 no
C17 . H172 . 0.979 no
C18 . C19 . 1.534(4) yes
C18 . H181 . 0.980 no
C18 . H182 . 0.980 no
C19 . H191 . 0.984 no
C19 . H192 . 0.987 no
C51 . C52 . 1.523(5) yes
C51 . C66 . 1.549(4) yes
C51 . H511 . 0.970 no
C51 . H512 . 0.967 no
C52 . N53 . 1.469(4) yes
C52 . H521 . 0.981 no
C52 . H522 . 0.988 no
N53 . C54 . 1.448(4) yes
N53 . C65 . 1.456(4) yes
C54 . C55 . 1.513(4) yes
C54 . H541 . 0.994 no
C54 . H542 . 0.980 no
C55 . C56 . 1.402(4) yes
C55 . C63 . 1.389(4) yes
C56 . C57 . 1.368(4) yes
C56 . H561 . 0.931 no
C57 . O58 . 1.380(3) yes
C57 . C61 . 1.373(4) yes
O58 . C59 . 1.434(4) yes
C59 . O60 . 1.421(4) yes
C59 . H592 . 0.974 no
C59 . H591 . 0.978 no
O60 . C61 . 1.383(3) yes
C61 . C62 . 1.369(4) yes
C62 . C63 . 1.418(3) yes
C62 . H621 . 0.938 no
C63 . C64 . 1.517(3) yes
C64 . C65 . 1.524(3) yes
C64 . C69 . 1.537(3) yes
C64 . H641 . 0.997 no
C65 . C66 . 1.536(4) yes
C65 . H651 . 0.985 no
C66 . C67 . 1.534(4) yes
C66 . H661 . 0.988 no
C67 . C68 . 1.524(4) yes
C67 . H671 . 0.971 no
C67 . H672 . 0.994 no
C68 . C69 . 1.521(4) yes
C68 . H681 . 0.985 no
C68 . H682 . 0.967 no
C69 . H691 . 0.994 no
C69 . H692 . 0.996 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C16 . 105.6(2) yes
C2 . C1 . H11 . 109.9 no
C16 . C1 . H11 . 110.8 no
C2 . C1 . H12 . 111.5 no
C16 . C1 . H12 . 111.2 no
H11 . C1 . H12 . 107.8 no
C1 . C2 . N3 . 105.3(2) yes
C1 . C2 . H22 . 108.8 no
N3 . C2 . H22 . 110.2 no
C1 . C2 . H21 . 111.7 no
N3 . C2 . H21 . 110.9 no
H22 . C2 . H21 . 109.8 no
C2 . N3 . C4 . 112.9(2) yes
C2 . N3 . C15 . 105.1(2) yes
C4 . N3 . C15 . 111.1(2) yes
N3 . C4 . C5 . 112.0(2) yes
N3 . C4 . H42 . 109.2 no
C5 . C4 . H42 . 108.7 no
N3 . C4 . H41 . 109.5 no
C5 . C4 . H41 . 109.5 no
H42 . C4 . H41 . 107.7 no
C4 . C5 . C6 . 118.2(2) yes
C4 . C5 . C13 . 120.8(2) yes
C6 . C5 . C13 . 120.9(2) yes
C5 . C6 . C7 . 117.6(2) yes
C5 . C6 . H61 . 121.7 no
C7 . C6 . H61 . 120.8 no
C6 . C7 . O8 . 127.9(3) yes
C6 . C7 . C11 . 122.2(2) yes
O8 . C7 . C11 . 109.9(2) yes
C7 . O8 . C9 . 105.0(2) yes
O8 . C9 . O10 . 107.5(2) yes
O8 . C9 . H91 . 109.8 no
O10 . C9 . H91 . 109.1 no
O8 . C9 . H92 . 110.5 no
O10 . C9 . H92 . 109.9 no
H91 . C9 . H92 . 110.1 no
C9 . O10 . C11 . 105.2(2) yes
C7 . C11 . O10 . 109.5(2) yes
C7 . C11 . C12 . 121.3(2) yes
O10 . C11 . C12 . 129.2(3) yes
C11 . C12 . C13 . 117.9(2) yes
C11 . C12 . H121 . 122.0 no
C13 . C12 . H121 . 120.1 no
C12 . C13 . C5 . 120.1(2) yes
C12 . C13 . C14 . 118.0(2) yes
C5 . C13 . C14 . 121.8(2) yes
C13 . C14 . C15 . 109.5(2) yes
C13 . C14 . C19 . 111.3(2) yes
C15 . C14 . C19 . 112.0(2) yes
C13 . C14 . H141 . 107.7 no
C15 . C14 . H141 . 108.7 no
C19 . C14 . H141 . 107.4 no
C14 . C15 . N3 . 110.8(2) yes
C14 . C15 . C16 . 116.5(2) yes
N3 . C15 . C16 . 103.7(2) yes
C14 . C15 . H151 . 108.4 no
N3 . C15 . H151 . 108.8 no
C16 . C15 . H151 . 108.4 no
C1 . C16 . C15 . 101.5(2) yes
C1 . C16 . C17 . 111.8(2) yes
C15 . C16 . C17 . 112.8(2) yes
C1 . C16 . H161 . 110.6 no
C15 . C16 . H161 . 110.3 no
C17 . C16 . H161 . 109.6 no
C16 . C17 . C18 . 111.4(2) yes
C16 . C17 . H171 . 109.5 no
C18 . C17 . H171 . 111.4 no
C16 . C17 . H172 . 107.7 no
C18 . C17 . H172 . 109.5 no
H171 . C17 . H172 . 107.3 no
C17 . C18 . C19 . 109.2(2) yes
C17 . C18 . H181 . 109.6 no
C19 . C18 . H181 . 110.1 no
C17 . C18 . H182 . 108.0 no
C19 . C18 . H182 . 111.1 no
H181 . C18 . H182 . 108.8 no
C14 . C19 . C18 . 110.7(2) yes
C14 . C19 . H191 . 109.4 no
C18 . C19 . H191 . 111.0 no
C14 . C19 . H192 . 108.8 no
C18 . C19 . H192 . 109.3 no
H191 . C19 . H192 . 107.5 no
C52 . C51 . C66 . 105.6(3) yes
C52 . C51 . H511 . 110.1 no
C66 . C51 . H511 . 109.6 no
C52 . C51 . H512 . 113.0 no
C66 . C51 . H512 . 110.7 no
H511 . C51 . H512 . 107.8 no
C51 . C52 . N53 . 105.5(3) yes
C51 . C52 . H521 . 110.6 no
N53 . C52 . H521 . 110.3 no
C51 . C52 . H522 . 110.2 no
N53 . C52 . H522 . 110.1 no
H521 . C52 . H522 . 110.1 no
C52 . N53 . C54 . 112.5(2) yes
C52 . N53 . C65 . 105.0(2) yes
C54 . N53 . C65 . 111.3(2) yes
N53 . C54 . C55 . 111.6(2) yes
N53 . C54 . H541 . 108.1 no
C55 . C54 . H541 . 107.4 no
N53 . C54 . H542 . 109.9 no
C55 . C54 . H542 . 109.8 no
H541 . C54 . H542 . 110.0 no
C54 . C55 . C56 . 118.0(2) yes
C54 . C55 . C63 . 121.5(2) yes
C56 . C55 . C63 . 120.5(2) yes
C55 . C56 . C57 . 117.8(3) yes
C55 . C56 . H561 . 120.2 no
C57 . C56 . H561 . 122.0 no
C56 . C57 . O58 . 127.8(3) yes
C56 . C57 . C61 . 122.2(3) yes
O58 . C57 . C61 . 110.0(3) yes
C57 . O58 . C59 . 105.3(2) yes
O58 . C59 . O60 . 108.4(2) yes
O58 . C59 . H592 . 107.5 no
O60 . C59 . H592 . 110.1 no
O58 . C59 . H591 . 108.8 no
O60 . C59 . H591 . 110.1 no
H592 . C59 . H591 . 111.9 no
C59 . O60 . C61 . 105.6(2) yes
O60 . C61 . C57 . 109.9(2) yes
O60 . C61 . C62 . 128.7(3) yes
C57 . C61 . C62 . 121.4(3) yes
C61 . C62 . C63 . 117.8(3) yes
C61 . C62 . H621 . 121.8 no
C63 . C62 . H621 . 120.4 no
C62 . C63 . C55 . 120.3(2) yes
C62 . C63 . C64 . 118.6(2) yes
C55 . C63 . C64 . 121.1(2) yes
C63 . C64 . C65 . 110.1(2) yes
C63 . C64 . C69 . 110.6(2) yes
C65 . C64 . C69 . 112.5(2) yes
C63 . C64 . H641 . 107.8 no
C65 . C64 . H641 . 107.5 no
C69 . C64 . H641 . 108.0 no
C64 . C65 . N53 . 111.2(2) yes
C64 . C65 . C66 . 116.8(2) yes
N53 . C65 . C66 . 103.0(2) yes
C64 . C65 . H651 . 108.2 no
N53 . C65 . H651 . 109.2 no
C66 . C65 . H651 . 108.2 no
C65 . C66 . C51 . 101.7(3) yes
C65 . C66 . C67 . 111.8(2) yes
C51 . C66 . C67 . 111.3(3) yes
C65 . C66 . H661 . 111.4 no
C51 . C66 . H661 . 112.0 no
C67 . C66 . H661 . 108.5 no
C66 . C67 . C68 . 111.6(2) yes
C66 . C67 . H671 . 110.0 no
C68 . C67 . H671 . 108.9 no
C66 . C67 . H672 . 109.6 no
C68 . C67 . H672 . 108.4 no
H671 . C67 . H672 . 108.3 no
C67 . C68 . C69 . 109.1(2) yes
C67 . C68 . H681 . 109.4 no
C69 . C68 . H681 . 109.4 no
C67 . C68 . H682 . 109.5 no
C69 . C68 . H682 . 110.3 no
H681 . C68 . H682 . 109.2 no
C64 . C69 . C68 . 111.1(2) yes
C64 . C69 . H691 . 109.8 no
C68 . C69 . H691 . 107.4 no
C64 . C69 . H692 . 108.2 no
C68 . C69 . H692 . 111.6 no
H691 . C69 . H692 . 108.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O10 2_546 148 0.98 2.45 3.326(4) yes
C59 . H592 . O8 2_545 145 0.97 2.35 3.193(4) yes


