# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_f_a
_database_code_depnum_ccdc_archive 'CCDC 2247204'
loop_
_audit_author_name
_audit_author_address
'Wu Shuquan'
;Guizhou Minzu University
China
;
_audit_update_record             
;
2023-03-08 deposited with the CCDC.	2025-03-22 downloaded from the CCDC.
;
_audit_creation_date             2022-11-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.30
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.1888(16)
_cell_length_b                   9.7914(11)
_cell_length_c                   10.6811(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.956(5)
_cell_angle_gamma                90
_cell_volume                     1411.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      62.425
_cell_measurement_theta_min      2.900
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5937
_diffrn_reflns_point_group_measured_fraction_full 0.860
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.304
_diffrn_reflns_theta_min         7.686
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.752
_reflns_Friedel_fraction_max     0.733
_reflns_number_gt                2139
_reflns_number_total             2369
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 781 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.116
_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)+(0.1420P)²+0.2015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2A), C14(H14), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.4397(3) 1.0949(4) 0.6866(4) 0.0749(11) Uani 1 1 d . . . . .
O2 O 0.6600(3) 0.3084(3) 0.4846(4) 0.0660(9) Uani 1 1 d . . . . .
O3 O 0.6835(3) 0.4816(4) 0.3617(5) 0.0773(11) Uani 1 1 d . . . . .
C1 C 0.3602(4) 1.0736(7) 0.7381(7) 0.0796(15) Uani 1 1 d . . . . .
H1A H 0.314167 1.009893 0.683300 0.119 Uiso 1 1 calc R U . . .
H1B H 0.327212 1.158747 0.740120 0.119 Uiso 1 1 calc R U . . .
H1C H 0.385225 1.037540 0.825697 0.119 Uiso 1 1 calc R U . . .
N2 N 0.6035(3) 0.6583(4) 0.4900(5) 0.0667(11) Uani 1 1 d . . . . .
H2 H 0.639(6) 0.682(7) 0.437(8) 0.080 Uiso 1 1 d . U . . .
C3 C 0.4748(3) 0.4730(4) 0.4356(4) 0.0518(9) Uani 1 1 d . . . . .
C4 C 0.4344(4) 0.3642(4) 0.4858(5) 0.0595(10) Uani 1 1 d . . . . .
H4 H 0.471186 0.321610 0.563295 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4779(3) 0.9807(4) 0.6429(5) 0.0559(10) Uani 1 1 d . . . . .
C2 C 0.5370(4) 1.0053(5) 0.5647(5) 0.0619(11) Uani 1 1 d . . . . .
H2A H 0.550012 1.094745 0.545593 0.074 Uiso 1 1 calc R U . . .
C14 C 0.5774(3) 0.8976(4) 0.5141(5) 0.0578(10) Uani 1 1 d . . . . .
H14 H 0.616782 0.915587 0.460674 0.069 Uiso 1 1 calc R U . . .
C15 C 0.5597(3) 0.7623(4) 0.5422(4) 0.0520(9) Uani 1 1 d . . . . .
C5 C 0.5818(3) 0.5159(4) 0.5030(5) 0.0536(10) Uani 1 1 d . . . . .
H5 H 0.599646 0.492893 0.596694 0.064 Uiso 1 1 calc R U . . .
C6 C 0.3396(4) 0.3198(6) 0.4204(6) 0.0741(13) Uani 1 1 d . . . . .
H6 H 0.313191 0.246079 0.453244 0.089 Uiso 1 1 calc R U . . .
C7 C 0.2836(4) 0.3840(7) 0.3064(7) 0.0801(16) Uani 1 1 d . . . . .
H7 H 0.219787 0.353804 0.262677 0.096 Uiso 1 1 calc R U . . .
C8 C 0.4595(4) 0.8471(5) 0.6727(5) 0.0593(10) Uani 1 1 d . . . . .
H8 H 0.419750 0.829598 0.725742 0.071 Uiso 1 1 calc R U . . .
C9 C 0.5011(4) 0.7395(5) 0.6224(5) 0.0597(10) Uani 1 1 d . . . . .
H9 H 0.489233 0.650203 0.643205 0.072 Uiso 1 1 calc R U . . .
C10 C 0.6482(3) 0.4360(4) 0.4411(4) 0.0537(9) Uani 1 1 d . . . . .
C11 C 0.7156(4) 0.2184(6) 0.4263(7) 0.0725(13) Uani 1 1 d . . . . .
H11A H 0.681667 0.209109 0.333831 0.109 Uiso 1 1 calc R U . . .
H11B H 0.721716 0.130307 0.467544 0.109 Uiso 1 1 calc R U . . .
H11C H 0.780351 0.255895 0.438669 0.109 Uiso 1 1 calc R U . . .
C12 C 0.3228(4) 0.4923(7) 0.2585(6) 0.0777(15) Uani 1 1 d . . . . .
H12 H 0.284802 0.536291 0.182542 0.093 Uiso 1 1 calc R U . . .
C13 C 0.4175(4) 0.5369(5) 0.3210(5) 0.0639(11) Uani 1 1 d . . . . .
H13 H 0.443392 0.610043 0.286593 0.077 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.414(7) . ?
O1 C16 1.384(5) . ?
O2 C10 1.326(5) . ?
O2 C11 1.446(6) . ?
O3 C10 1.197(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 H2 0.90(9) . ?
N2 C15 1.396(6) . ?
N2 C5 1.443(6) . ?
C3 C4 1.393(6) . ?
C3 C5 1.525(6) . ?
C3 C13 1.392(6) . ?
C4 H4 0.9300 . ?
C4 C6 1.381(7) . ?
C16 C2 1.376(7) . ?
C16 C8 1.390(6) . ?
C2 H2A 0.9300 . ?
C2 C14 1.387(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.398(6) . ?
C15 C9 1.383(6) . ?
C5 H5 0.9800 . ?
C5 C10 1.524(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(10) . ?
C7 H7 0.9300 . ?
C7 C12 1.367(10) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(7) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.375(8) . ?
C13 H13 0.9300 . ?

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
C16 O1 C1 117.0(4) . . ?
C10 O2 C11 116.7(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C15 N2 H2 118(5) . . ?
C15 N2 C5 122.1(4) . . ?
C5 N2 H2 119(5) . . ?
C4 C3 C5 119.8(4) . . ?
C13 C3 C4 119.0(4) . . ?
C13 C3 C5 121.2(4) . . ?
C3 C4 H4 120.1 . . ?
C6 C4 C3 119.9(5) . . ?
C6 C4 H4 120.1 . . ?
O1 C16 C8 124.2(4) . . ?
C2 C16 O1 116.0(4) . . ?
C2 C16 C8 119.8(4) . . ?
C16 C2 H2A 119.8 . . ?
C16 C2 C14 120.4(4) . . ?
C14 C2 H2A 119.8 . . ?
C2 C14 H14 119.6 . . ?
C2 C14 C15 120.9(4) . . ?
C15 C14 H14 119.6 . . ?
N2 C15 C14 118.3(4) . . ?
C9 C15 N2 123.8(4) . . ?
C9 C15 C14 118.0(4) . . ?
N2 C5 C3 115.6(4) . . ?
N2 C5 H5 109.0 . . ?
N2 C5 C10 106.0(4) . . ?
C3 C5 H5 109.0 . . ?
C10 C5 C3 108.2(4) . . ?
C10 C5 H5 109.0 . . ?
C4 C6 H6 119.7 . . ?
C4 C6 C7 120.5(6) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.2 . . ?
C12 C7 C6 119.5(5) . . ?
C12 C7 H7 120.2 . . ?
C16 C8 H8 120.3 . . ?
C16 C8 C9 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C15 C9 C8 121.6(4) . . ?
C15 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
O2 C10 C5 111.1(4) . . ?
O3 C10 O2 124.4(4) . . ?
O3 C10 C5 124.5(4) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12 119.5 . . ?
C7 C12 C13 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C3 C13 H13 119.9 . . ?
C12 C13 C3 120.1(5) . . ?
C12 C13 H13 119.9 . . ?

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 C16 C2 C14 -178.9(5) . . . . ?
O1 C16 C8 C9 179.4(4) . . . . ?
C1 O1 C16 C2 164.5(5) . . . . ?
C1 O1 C16 C8 -15.2(7) . . . . ?
N2 C15 C9 C8 179.6(5) . . . . ?
N2 C5 C10 O2 159.0(4) . . . . ?
N2 C5 C10 O3 -22.3(7) . . . . ?
C3 C4 C6 C7 -1.2(8) . . . . ?
C3 C5 C10 O2 -76.5(5) . . . . ?
C3 C5 C10 O3 102.2(6) . . . . ?
C4 C3 C5 N2 -151.2(4) . . . . ?
C4 C3 C5 C10 90.2(5) . . . . ?
C4 C3 C13 C12 -0.4(7) . . . . ?
C4 C6 C7 C12 0.0(9) . . . . ?
C16 C2 C14 C15 -0.6(7) . . . . ?
C16 C8 C9 C15 -0.6(7) . . . . ?
C2 C16 C8 C9 -0.2(7) . . . . ?
C2 C14 C15 N2 -179.1(4) . . . . ?
C2 C14 C15 C9 -0.3(7) . . . . ?
C14 C15 C9 C8 0.9(7) . . . . ?
C15 N2 C5 C3 63.5(6) . . . . ?
C15 N2 C5 C10 -176.7(4) . . . . ?
C5 N2 C15 C14 -173.8(4) . . . . ?
C5 N2 C15 C9 7.4(7) . . . . ?
C5 C3 C4 C6 -176.0(4) . . . . ?
C5 C3 C13 C12 176.9(5) . . . . ?
C6 C7 C12 C13 0.9(9) . . . . ?
C7 C12 C13 C3 -0.7(8) . . . . ?
C8 C16 C2 C14 0.8(7) . . . . ?
C11 O2 C10 O3 -3.1(8) . . . . ?
C11 O2 C10 C5 175.6(4) . . . . ?
C13 C3 C4 C6 1.3(7) . . . . ?
C13 C3 C5 N2 31.5(6) . . . . ?
C13 C3 C5 C10 -87.1(5) . . . . ?

_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_exp_8585
_database_code_depnum_ccdc_archive 'CCDC 2271403'
loop_
_audit_author_name
_audit_author_address
'Wu Shuquan'
;Guizhou Minzu University
China
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2025-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-06-21
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.6574(2)
_cell_length_b                   9.8640(3)
_cell_length_c                   12.4816(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.154(3)
_cell_angle_gamma                90.00
_cell_volume                     692.52(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2215
_cell_measurement_temperature    114.55(10)
_cell_measurement_theta_max      66.0490
_cell_measurement_theta_min      4.4480
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4143
_diffrn_reflns_theta_full        66.27
_diffrn_reflns_theta_max         66.27
_diffrn_reflns_theta_min         5.73
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      114.55(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9759
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -27.00    0.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega   27.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   76.00  120.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477 -125.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   48.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00   83.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   56.00  105.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -94.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   64.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477 -125.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  115.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -61.0000 -120.0000 76

#__ type_ start__ end____ width___ exp.time_
 10 omega   78.00  166.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   30.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
 11 omega  126.00  152.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  131.00  160.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   30.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
 13 omega   83.00  128.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   30.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
 14 omega   81.00  107.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   80.00  157.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   77.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega  103.00  164.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  125.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 17 omega  109.00  167.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  125.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   79.00  130.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   30.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 19 omega   51.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 20 omega   30.00   90.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
 21 omega   11.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000    0.0000 92

#__ type_ start__ end____ width___ exp.time_
 22 omega   60.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   57.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
 24 omega   58.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 25 omega  -16.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  120.0000 66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1328790000
_diffrn_orient_matrix_UB_12      -0.0020362000
_diffrn_orient_matrix_UB_13      0.1142420000
_diffrn_orient_matrix_UB_21      -0.1339242000
_diffrn_orient_matrix_UB_22      -0.1299554000
_diffrn_orient_matrix_UB_23      0.0255171000
_diffrn_orient_matrix_UB_31      0.1983067000
_diffrn_orient_matrix_UB_32      -0.0864802000
_diffrn_orient_matrix_UB_33      -0.0410504000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2252
_reflns_number_total             2375
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.93
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0477P)²+0.0125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0859
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) 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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5185(2) 0.07255(14) 0.74669(11) 0.0296(3) Uani 1 1 d . . .
O2 O 1.1688(2) -0.71870(12) 0.90391(10) 0.0278(3) Uani 1 1 d . . .
O1 O 1.4337(2) -0.54981(15) 0.91783(11) 0.0334(3) Uani 1 1 d . . .
C12 C 0.5875(3) -0.17040(18) 0.72376(14) 0.0218(4) Uani 1 1 d . . .
H12 H 0.4396 -0.1826 0.6811 0.026 Uiso 1 1 calc R . .
N1 N 1.1186(3) -0.37132(15) 0.82671(14) 0.0278(4) Uani 1 1 d . . .
H1 H 1.2494 -0.3546 0.8661 0.033 Uiso 1 1 d R . .
C14 C 0.8661(3) -0.02815(19) 0.82971(15) 0.0255(4) Uani 1 1 d . . .
H14 H 0.9091 0.0581 0.8596 0.031 Uiso 1 1 calc R . .
C1 C 1.0465(3) -0.51187(17) 0.82060(15) 0.0223(4) Uani 1 1 d . . .
H1A H 0.8938 -0.5222 0.8534 0.027 Uiso 1 1 calc R . .
C11 C 0.7407(3) -0.28035(18) 0.74512(15) 0.0228(4) Uani 1 1 d . . .
H11 H 0.6959 -0.3669 0.7163 0.027 Uiso 1 1 calc R . .
C13 C 0.6516(3) -0.0434(2) 0.76481(14) 0.0211(4) Uani 1 1 d . . .
C10 C 0.9574(3) -0.26565(17) 0.80777(14) 0.0203(4) Uani 1 1 d . . .
C15 C 1.0163(3) -0.13692(18) 0.85099(15) 0.0238(4) Uani 1 1 d . . .
H15 H 1.1618 -0.1248 0.8955 0.029 Uiso 1 1 calc R . .
C2 C 1.2409(3) -0.59356(18) 0.88679(14) 0.0225(4) Uani 1 1 d . . .
C9 C 1.3421(4) -0.8035(2) 0.96619(15) 0.0303(5) Uani 1 1 d . . .
H9A H 1.4816 -0.8151 0.9268 0.045 Uiso 1 1 calc R . .
H9B H 1.2716 -0.8923 0.9780 0.045 Uiso 1 1 calc R . .
H9C H 1.3902 -0.7604 1.0359 0.045 Uiso 1 1 calc R . .
C16 C 0.3227(3) 0.0682(2) 0.66497(15) 0.0282(4) Uani 1 1 d . . .
H16A H 0.3776 0.0372 0.5973 0.042 Uiso 1 1 calc R . .
H16B H 0.2537 0.1590 0.6549 0.042 Uiso 1 1 calc R . .
H16C H 0.2022 0.0054 0.6865 0.042 Uiso 1 1 calc R . .
C8 C 0.8346(3) -0.66072(19) 0.67519(15) 0.0234(4) Uani 1 1 d . . .
H8 H 0.7242 -0.6846 0.7242 0.028 Uiso 1 1 calc R . .
C4 C 1.1749(3) -0.5347(2) 0.63322(15) 0.0276(4) Uani 1 1 d . . .
H4 H 1.2983 -0.4714 0.6533 0.033 Uiso 1 1 calc R . .
C6 C 0.9751(4) -0.6843(2) 0.50107(16) 0.0295(4) Uani 1 1 d . . .
H6 H 0.9623 -0.7243 0.4315 0.035 Uiso 1 1 calc R . .
C5 C 1.1548(4) -0.5923(2) 0.53131(16) 0.0307(5) Uani 1 1 d . . .
H5 H 1.2647 -0.5685 0.4820 0.037 Uiso 1 1 calc R . .
C7 C 0.8147(3) -0.7174(2) 0.57268(15) 0.0286(4) Uani 1 1 d . . .
H7 H 0.6898 -0.7795 0.5518 0.034 Uiso 1 1 calc R . .
C3 C 1.0156(3) -0.56920(16) 0.70605(14) 0.0200(4) 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
O3 C13 1.375(2) . ?
O3 C16 1.423(2) . ?
O2 C2 1.325(2) . ?
O2 C9 1.450(2) . ?
O1 C2 1.198(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.396(3) . ?
C12 C13 1.387(3) . ?
N1 H1 0.8596 . ?
N1 C1 1.445(2) . ?
N1 C10 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.393(3) . ?
C14 C15 1.377(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.532(2) . ?
C1 C3 1.530(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.389(3) . ?
C10 C15 1.406(3) . ?
C15 H15 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C7 1.390(3) . ?
C8 C3 1.388(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C4 C3 1.389(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.385(3) . ?
C6 C7 1.379(3) . ?
C5 H5 0.9500 . ?
C7 H7 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
C13 O3 C16 117.60(15) . . ?
C2 O2 C9 114.95(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 119.93(15) . . ?
C1 N1 H1 115.8 . . ?
C10 N1 H1 117.6 . . ?
C10 N1 C1 122.36(15) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C15 C14 C13 120.62(18) . . ?
N1 C1 H1A 109.1 . . ?
N1 C1 C2 107.12(15) . . ?
N1 C1 C3 114.04(15) . . ?
C2 C1 H1A 109.1 . . ?
C3 C1 H1A 109.1 . . ?
C3 C1 C2 108.25(14) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 C12 121.24(16) . . ?
C10 C11 H11 119.4 . . ?
O3 C13 C12 125.02(15) . . ?
O3 C13 C14 115.70(17) . . ?
C12 C13 C14 119.28(17) . . ?
N1 C10 C11 122.76(16) . . ?
N1 C10 C15 119.25(15) . . ?
C11 C10 C15 117.96(16) . . ?
C14 C15 C10 120.92(16) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O2 C2 C1 111.21(15) . . ?
O1 C2 O2 124.66(17) . . ?
O1 C2 C1 124.12(17) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
C3 C8 C7 120.11(17) . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.32(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C7 C6 C5 119.55(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.29(17) . . ?
C6 C5 H5 119.9 . . ?
C8 C7 H7 119.8 . . ?
C6 C7 C8 120.48(18) . . ?
C6 C7 H7 119.8 . . ?
C8 C3 C1 120.44(16) . . ?
C8 C3 C4 119.24(16) . . ?
C4 C3 C1 120.25(15) . . ?

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
C12 C11 C10 N1 -177.10(17) . . . . ?
C12 C11 C10 C15 1.2(3) . . . . ?
N1 C1 C2 O2 167.33(15) . . . . ?
N1 C1 C2 O1 -13.4(2) . . . . ?
N1 C1 C3 C8 -142.87(17) . . . . ?
N1 C1 C3 C4 40.0(2) . . . . ?
N1 C10 C15 C14 176.90(17) . . . . ?
C1 N1 C10 C11 -24.5(3) . . . . ?
C1 N1 C10 C15 157.22(18) . . . . ?
C11 C12 C13 O3 178.14(16) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
C11 C10 C15 C14 -1.5(3) . . . . ?
C13 C12 C11 C10 0.4(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C10 N1 C1 C2 -158.21(16) . . . . ?
C10 N1 C1 C3 82.0(2) . . . . ?
C15 C14 C13 O3 -178.39(15) . . . . ?
C15 C14 C13 C12 1.6(3) . . . . ?
C2 C1 C3 C8 98.02(19) . . . . ?
C2 C1 C3 C4 -79.14(19) . . . . ?
C9 O2 C2 O1 0.8(3) . . . . ?
C9 O2 C2 C1 -179.98(15) . . . . ?
C16 O3 C13 C12 -11.9(2) . . . . ?
C16 O3 C13 C14 168.05(16) . . . . ?
C5 C4 C3 C1 176.49(17) . . . . ?
C5 C4 C3 C8 -0.7(3) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C7 C8 C3 C1 -176.85(17) . . . . ?
C7 C8 C3 C4 0.3(3) . . . . ?
C7 C6 C5 C4 0.6(3) . . . . ?
C3 C1 C2 O2 -69.27(18) . . . . ?
C3 C1 C2 O1 109.96(19) . . . . ?
C3 C8 C7 C6 0.5(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?

