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

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

data_xudaw1_0m
_database_code_depnum_ccdc_archive 'CCDC 1861781'
_audit_update_record             
;
2018-11-26 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H17 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         227.30
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2+x,1/2-y,-z
3 -x,1/2+y,1/2-z
4 1/2-x,-y,1/2+z

_cell_length_a                   7.1064(12)
_cell_length_b                   10.3163(18)
_cell_length_c                   15.973(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1171.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9800
_cell_measurement_theta_min      2.5504
_cell_measurement_theta_max      26.4637

_cell_special_details            
;
;

_exptl_crystal_description       fragment
_exptl_crystal_colour            'clear colourless'


_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.186
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_T_max  0.7454


#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             F. Kaiser
scanspeed                           60 s per frame
dx                                  35 mm
1199 frames measured in 7 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Triumph monochromator'


_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Apex II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            14663
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2068
# number of observed reflections (> n sig(I))
_reflns_number_gt                2002
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX III Control Software (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL2014 (Sheldrick, 2014), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2014)'



#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0387P)²+0.1643P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall            - refined all H-atom parameters
# refxyz            - refined H-atom coordinates only
# refU              - refined H-atom U only
# noref             - no refinement of H-atom parameters
# constr            - H-atom parameters constrained
# hetero            - H-atom parameters constrained for H on C,
#                     all H-atom parameters refined for H on
#                     heteroatoms
# heteroxyz         - H-atom parameters constrained for H on C,
#                     refined H-atom coordinates only for H
#                     on heteroatoms
# heteroU           - H-atom parameters constrained for H on C,
#                     refined H-atom U's only for H on
#                     heteroatoms
# heteronoref       - H-atom parameters constrained for H on C,
#                     no refinement of H-atom parameters for
#                     H on heteroatoms
# hetero-mixed      - H-atom parameters constrained for H on C
#                     and some heteroatoms, all H-atom
#                     parameters refined for H on remaining
#                     heteroatoms.
# heteroxyz-mixed   - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     coordinates only for H on remaining
#                     heteroatoms.
# heteroU-mixed     - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     U's only for H on remaining heteroatoms
# heteronoref-mixed - H-atom parameters constrained for H on C
#                     and some heteroatoms, no refinement of
#                     H-atom parameters for H on remaining
#                     heteroatoms
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none


# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration unk

_refine_ls_number_reflns         2068
_refine_ls_number_parameters     205
_refine_ls_number_restraints     116
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0736
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.0596(7) 0.4932(3) 0.6506(4) 0.0238(10) Uani 0.92(2) 1 d . U P A 3
O1A O 0.107(7) 0.506(3) 0.679(4) 0.029(6) Uani 0.08(2) 1 d . U P A 4
N1 N 0.1817(2) 0.29603(14) 0.68742(9) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.3171(3) 0.19929(16) 0.67903(10) 0.0172(4) Uani 1 1 d . . . . .
C2 C 0.2957(3) 0.07884(17) 0.71884(11) 0.0199(4) Uani 1 1 d . . . . .
H2 H 0.188407 0.062817 0.752768 0.024 Uiso 1 1 calc R U . . .
C3 C 0.4298(3) -0.01593(17) 0.70879(11) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.413989 -0.097324 0.735715 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5878(3) 0.00586(18) 0.65981(11) 0.0228(4) Uani 1 1 d . . . . .
H4 H 0.680197 -0.059984 0.653554 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6100(3) 0.12360(17) 0.62029(11) 0.0199(4) Uani 1 1 d . . . . .
H5 H 0.717912 0.137606 0.586378 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4773(2) 0.22319(17) 0.62887(10) 0.0166(4) Uani 1 1 d . . . . .
C7 C 0.4964(2) 0.34825(17) 0.58731(10) 0.0173(4) Uani 1 1 d . . . . .
C8 C 0.3579(3) 0.43761(18) 0.59374(11) 0.0213(4) Uani 1 1 d . . . . .
C9 C 0.1905(3) 0.41378(17) 0.64526(11) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.0203(3) 0.2728(2) 0.74225(13) 0.0273(4) Uani 1 1 d . . . . .
H10A H -0.055618 0.351879 0.746168 0.041 Uiso 1 1 calc R U . . .
H10B H 0.064912 0.248455 0.798134 0.041 Uiso 1 1 calc R U . . .
H10C H -0.056609 0.202487 0.719184 0.041 Uiso 1 1 calc R U . . .
C15 C 0.6722(3) 0.37303(17) 0.53656(12) 0.0221(4) Uani 1 1 d D . . . .
H15A H 0.668910 0.318045 0.485784 0.027 Uiso 1 1 calc R U . B 1
H15B H 0.783160 0.346831 0.569983 0.027 Uiso 1 1 calc R U . B 1
C11 C 0.3588(3) 0.5674(2) 0.54766(16) 0.0195(5) Uani 0.904(4) 1 d . U P C 1
H11 H 0.232814 0.578967 0.520813 0.023 Uiso 0.904(4) 1 calc R U P C 1
C12 C 0.3889(3) 0.68009(19) 0.60911(13) 0.0238(5) Uani 0.904(4) 1 d . U P C 1
H12A H 0.375350 0.762596 0.579309 0.036 Uiso 0.904(4) 1 calc R U P C 1
H12B H 0.515360 0.674371 0.633262 0.036 Uiso 0.904(4) 1 calc R U P C 1
H12C H 0.295026 0.675181 0.653962 0.036 Uiso 0.904(4) 1 calc R U P C 1
C13 C 0.5076(3) 0.5682(2) 0.47835(12) 0.0218(5) Uani 0.904(4) 1 d D U P C 1
H13A H 0.525958 0.658080 0.458125 0.026 Uiso 0.904(4) 1 calc R U P C 1
H13B H 0.463185 0.515110 0.430682 0.026 Uiso 0.904(4) 1 calc R U P C 1
C14 C 0.6956(5) 0.5145(3) 0.5101(2) 0.0210(9) Uani 0.904(4) 1 d D U P C 1
H14A H 0.791353 0.520682 0.465284 0.025 Uiso 0.904(4) 1 calc R U P C 1
H14B H 0.739471 0.566493 0.558392 0.025 Uiso 0.904(4) 1 calc R U P C 1
C11A C 0.413(3) 0.589(2) 0.5871(15) 0.020(3) Uani 0.096(4) 1 d . U P C 2
H11A H 0.383144 0.635451 0.640540 0.025 Uiso 0.096(4) 1 calc R U P C 2
C12A C 0.276(3) 0.629(2) 0.5182(14) 0.030(4) Uani 0.096(4) 1 d . U P C 2
H12D H 0.280343 0.723108 0.510631 0.044 Uiso 0.096(4) 1 calc R U P C 2
H12E H 0.147788 0.602993 0.533909 0.044 Uiso 0.096(4) 1 calc R U P C 2
H12F H 0.310920 0.586054 0.465714 0.044 Uiso 0.096(4) 1 calc R U P C 2
C13A C 0.622(3) 0.6120(18) 0.5609(11) 0.020(3) Uani 0.096(4) 1 d D U P C 2
H13C H 0.638662 0.699058 0.535906 0.024 Uiso 0.096(4) 1 calc R U P C 2
H13D H 0.707044 0.603730 0.609777 0.024 Uiso 0.096(4) 1 calc R U P C 2
C14A C 0.661(7) 0.508(2) 0.498(2) 0.023(5) Uani 0.096(4) 1 d D U P C 2
H14C H 0.781882 0.526724 0.469039 0.027 Uiso 0.096(4) 1 calc R U P C 2
H14D H 0.560682 0.508273 0.454682 0.027 Uiso 0.096(4) 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.242(3) . ?
O1A C9 1.24(3) . ?
N1 C9 1.390(2) . ?
N1 C1 1.392(2) . ?
N1 C10 1.463(2) . ?
C1 C2 1.404(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.457(2) . ?
C7 C8 1.352(3) . ?
C7 C15 1.511(2) . ?
C8 C9 1.467(3) . ?
C8 C11 1.528(3) . ?
C8 C11A 1.62(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C15 C14A 1.52(2) . ?
C15 C14 1.528(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11 C13 1.531(3) . ?
C11 C12 1.537(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.532(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11A C12A 1.52(3) . ?
C11A C13A 1.57(3) . ?
C11A H11A 1.0000 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A C14A 1.50(3) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?

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
C9 N1 C1 123.28(15) . . ?
C9 N1 C10 117.91(15) . . ?
C1 N1 C10 118.80(15) . . ?
N1 C1 C2 121.06(16) . . ?
N1 C1 C6 119.06(15) . . ?
C2 C1 C6 119.87(16) . . ?
C3 C2 C1 120.11(17) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.78(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.60(17) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.63(17) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.00(16) . . ?
C5 C6 C7 122.81(15) . . ?
C1 C6 C7 119.18(15) . . ?
C8 C7 C6 120.08(16) . . ?
C8 C7 C15 121.81(16) . . ?
C6 C7 C15 118.11(15) . . ?
C7 C8 C9 121.23(17) . . ?
C7 C8 C11 123.90(16) . . ?
C9 C8 C11 114.86(16) . . ?
C7 C8 C11A 118.7(8) . . ?
C9 C8 C11A 113.2(7) . . ?
O1 C9 N1 120.61(19) . . ?
O1A C9 N1 116.1(17) . . ?
O1 C9 C8 122.36(19) . . ?
O1A C9 C8 120.0(16) . . ?
N1 C9 C8 117.01(16) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C15 C14A 109.4(17) . . ?
C7 C15 C14 113.6(2) . . ?
C7 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C7 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C8 C11 C13 110.89(17) . . ?
C8 C11 C12 110.85(19) . . ?
C13 C11 C12 111.19(18) . . ?
C8 C11 H11 107.9 . . ?
C13 C11 H11 107.9 . . ?
C12 C11 H11 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 111.1(2) . . ?
C11 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C11 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 110.0(2) . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C12A C11A C13A 112.0(17) . . ?
C12A C11A C8 98.9(17) . . ?
C13A C11A C8 113.1(15) . . ?
C12A C11A H11A 110.8 . . ?
C13A C11A H11A 110.8 . . ?
C8 C11A H11A 110.8 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C14A C13A C11A 104(2) . . ?
C14A C13A H13C 110.9 . . ?
C11A C13A H13C 110.9 . . ?
C14A C13A H13D 110.9 . . ?
C11A C13A H13D 110.9 . . ?
H13C C13A H13D 108.9 . . ?
C13A C14A C15 113(2) . . ?
C13A C14A H14C 109.0 . . ?
C15 C14A H14C 109.0 . . ?
C13A C14A H14D 109.0 . . ?
C15 C14A H14D 109.0 . . ?
H14C C14A H14D 107.8 . . ?




#===END
