# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_BE32m
_database_code_depnum_ccdc_archive 'CCDC 1566994'
_audit_update_record             
;
2017-08-05 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 O2'
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.32

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9384(9)
_cell_length_b                   9.9744(12)
_cell_length_c                   17.126(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1356.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6494
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15919
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.363
_diffrn_reflns_theta_max         28.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3293
_reflns_number_gt                3206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+0.5425P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1188 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3293
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_restrained_S_all      1.246
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5966(4) 0.8927(3) 0.81081(18) 0.0296(6) Uani 1 1 d . . . . .
C2 C 0.6893(5) 0.8436(3) 0.8718(2) 0.0395(8) Uani 1 1 d . . . . .
H2 H 0.7985 0.8135 0.8627 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6232(6) 0.8376(4) 0.9474(2) 0.0450(9) Uani 1 1 d . . . . .
H3 H 0.6894 0.8052 0.9881 0.054 Uiso 1 1 calc R U . . .
C4 C 0.4632(5) 0.8788(4) 0.96214(19) 0.0421(8) Uani 1 1 d . . . . .
H4 H 0.4214 0.8758 1.0128 0.050 Uiso 1 1 calc R U . . .
C5 C 0.3599(4) 0.9263(3) 0.90085(19) 0.0361(7) Uani 1 1 d . . . . .
C6 C 0.4254(4) 0.9322(3) 0.82401(18) 0.0298(6) Uani 1 1 d . . . . .
C7 C 0.3214(4) 0.9779(3) 0.76189(18) 0.0316(6) Uani 1 1 d . . . . .
C8 C 0.1596(4) 1.0170(4) 0.7779(2) 0.0433(8) Uani 1 1 d . . . . .
H8 H 0.0909 1.0471 0.7376 0.052 Uiso 1 1 calc R U . . .
C9 C 0.0962(5) 1.0121(4) 0.8542(3) 0.0525(10) Uani 1 1 d . . . . .
H9 H -0.0137 1.0399 0.8638 0.063 Uiso 1 1 calc R U . . .
C10 C 0.1922(5) 0.9677(4) 0.9144(2) 0.0467(9) Uani 1 1 d . . . . .
H10 H 0.1477 0.9646 0.9646 0.056 Uiso 1 1 calc R U . . .
C11 C 0.6703(4) 0.9062(3) 0.73106(19) 0.0339(7) Uani 1 1 d . . . . .
H11 H 0.7546 0.8356 0.7234 0.041 Uiso 1 1 calc R U . . .
C12 C 0.7702(5) 1.0629(5) 0.6433(2) 0.0522(10) Uani 1 1 d . . . . .
H12A H 0.8862 1.0493 0.6275 0.063 Uiso 1 1 calc R U . . .
H12B H 0.7398 1.1553 0.6327 0.063 Uiso 1 1 calc R U . . .
C13 C 0.6547(5) 0.9683(4) 0.5985(2) 0.0465(9) Uani 1 1 d . . . . .
H13A H 0.7192 0.9012 0.5704 0.056 Uiso 1 1 calc R U . . .
H13B H 0.5850 1.0172 0.5616 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5465(4) 0.9035(3) 0.66312(18) 0.0331(7) Uani 1 1 d . . . . .
C15 C 0.4871(6) 0.7608(4) 0.6452(2) 0.0461(9) Uani 1 1 d . . . . .
H15A H 0.5818 0.7080 0.6269 0.055 Uiso 1 1 calc R U . . .
H15B H 0.4451 0.7196 0.6927 0.055 Uiso 1 1 calc R U . . .
C16 C 0.3491(7) 0.7600(4) 0.5836(2) 0.0566(11) Uani 1 1 d . . . . .
H16A H 0.3946 0.7891 0.5339 0.068 Uiso 1 1 calc R U . . .
H16B H 0.3055 0.6697 0.5774 0.068 Uiso 1 1 calc R U . . .
C17 C 0.2093(6) 0.8528(5) 0.6086(3) 0.0569(11) Uani 1 1 d . . . . .
H17A H 0.1225 0.8539 0.5687 0.068 Uiso 1 1 calc R U . . .
H17B H 0.1593 0.8196 0.6565 0.068 Uiso 1 1 calc R U . . .
C18 C 0.3952(4) 0.9952(3) 0.68075(18) 0.0310(6) Uani 1 1 d . . . . .
H18 H 0.4386 1.0872 0.6787 0.037 Uiso 1 1 calc R U . . .
O1 O 0.7514(3) 1.0348(3) 0.72490(14) 0.0428(6) Uani 1 1 d . . . . .
O2 O 0.2700(3) 0.9864(3) 0.62084(14) 0.0435(6) 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 C2 1.368(4) . ?
C1 C6 1.433(4) . ?
C1 C11 1.492(4) . ?
C2 C3 1.399(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(5) . ?
C4 H4 0.9300 . ?
C5 C10 1.413(5) . ?
C5 C6 1.416(4) . ?
C6 C7 1.421(4) . ?
C7 C8 1.370(5) . ?
C7 C18 1.518(4) . ?
C8 C9 1.401(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.357(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.440(4) . ?
C11 C14 1.523(5) . ?
C11 H11 0.9800 . ?
C12 O1 1.433(4) . ?
C12 C13 1.524(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.543(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.531(5) . ?
C14 C18 1.540(4) . ?
C15 C16 1.521(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.507(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O2 1.433(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O2 1.431(4) . ?
C18 H18 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
C2 C1 C6 119.2(3) . . ?
C2 C1 C11 121.3(3) . . ?
C6 C1 C11 119.4(3) . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C10 C5 C4 121.5(3) . . ?
C10 C5 C6 119.1(3) . . ?
C4 C5 C6 119.4(3) . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 C1 118.9(3) . . ?
C7 C6 C1 121.4(3) . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 C18 120.9(3) . . ?
C6 C7 C18 119.8(3) . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C5 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
O1 C11 C1 108.8(3) . . ?
O1 C11 C14 104.4(3) . . ?
C1 C11 C14 116.4(3) . . ?
O1 C11 H11 109.0 . . ?
C1 C11 H11 109.0 . . ?
C14 C11 H11 109.0 . . ?
O1 C12 C13 107.9(3) . . ?
O1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 C14 103.4(3) . . ?
C12 C13 H13A 111.1 . . ?
C14 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.0 . . ?
C11 C14 C15 111.6(3) . . ?
C11 C14 C18 110.1(2) . . ?
C15 C14 C18 110.6(3) . . ?
C11 C14 C13 100.5(3) . . ?
C15 C14 C13 114.7(3) . . ?
C18 C14 C13 109.0(3) . . ?
C16 C15 C14 111.4(3) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 109.3(3) . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
O2 C17 C16 111.5(4) . . ?
O2 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
O2 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
O2 C18 C7 112.4(3) . . ?
O2 C18 C14 111.4(3) . . ?
C7 C18 C14 114.4(2) . . ?
O2 C18 H18 106.0 . . ?
C7 C18 H18 106.0 . . ?
C14 C18 H18 106.0 . . ?
C12 O1 C11 107.0(3) . . ?
C18 O2 C17 113.3(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
C6 C1 C2 C3 -3.4(5) . . . . ?
C11 C1 C2 C3 176.5(3) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C3 C4 C5 C10 179.0(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C10 C5 C6 C7 -0.8(4) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C10 C5 C6 C1 178.7(3) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C2 C1 C6 C5 3.5(4) . . . . ?
C11 C1 C6 C5 -176.4(3) . . . . ?
C2 C1 C6 C7 -177.0(3) . . . . ?
C11 C1 C6 C7 3.1(4) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C1 C6 C7 C8 -178.7(3) . . . . ?
C5 C6 C7 C18 175.0(3) . . . . ?
C1 C6 C7 C18 -4.4(4) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C18 C7 C8 C9 -174.3(3) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C8 C9 C10 C5 0.5(6) . . . . ?
C4 C5 C10 C9 -179.7(4) . . . . ?
C6 C5 C10 C9 0.2(5) . . . . ?
C2 C1 C11 O1 -87.7(3) . . . . ?
C6 C1 C11 O1 92.2(3) . . . . ?
C2 C1 C11 C14 154.8(3) . . . . ?
C6 C1 C11 C14 -25.3(4) . . . . ?
O1 C12 C13 C14 10.0(4) . . . . ?
O1 C11 C14 C15 162.9(3) . . . . ?
C1 C11 C14 C15 -77.2(4) . . . . ?
O1 C11 C14 C18 -73.9(3) . . . . ?
C1 C11 C14 C18 46.0(4) . . . . ?
O1 C11 C14 C13 40.9(3) . . . . ?
C1 C11 C14 C13 160.9(3) . . . . ?
C12 C13 C14 C11 -30.2(3) . . . . ?
C12 C13 C14 C15 -150.0(3) . . . . ?
C12 C13 C14 C18 85.4(3) . . . . ?
C11 C14 C15 C16 173.6(3) . . . . ?
C18 C14 C15 C16 50.7(4) . . . . ?
C13 C14 C15 C16 -73.0(4) . . . . ?
C14 C15 C16 C17 -53.5(5) . . . . ?
C15 C16 C17 O2 57.6(5) . . . . ?
C8 C7 C18 O2 -30.2(4) . . . . ?
C6 C7 C18 O2 155.6(3) . . . . ?
C8 C7 C18 C14 -158.6(3) . . . . ?
C6 C7 C18 C14 27.3(4) . . . . ?
C11 C14 C18 O2 -175.2(3) . . . . ?
C15 C14 C18 O2 -51.5(3) . . . . ?
C13 C14 C18 O2 75.5(3) . . . . ?
C11 C14 C18 C7 -46.4(3) . . . . ?
C15 C14 C18 C7 77.4(3) . . . . ?
C13 C14 C18 C7 -155.7(3) . . . . ?
C13 C12 O1 C11 16.1(4) . . . . ?
C1 C11 O1 C12 -161.2(3) . . . . ?
C14 C11 O1 C12 -36.3(3) . . . . ?
C7 C18 O2 C17 -72.7(4) . . . . ?
C14 C18 O2 C17 57.1(4) . . . . ?
C16 C17 O2 C18 -60.9(4) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_BE33
_database_code_depnum_ccdc_archive 'CCDC 1566995'
_audit_update_record             
;
2017-08-05 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 O3'
_chemical_formula_sum            'C18 H18 O3'
_chemical_formula_weight         282.32

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6396(10)
_cell_length_b                   9.6186(8)
_cell_length_c                   11.8318(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.3940(10)
_cell_angle_gamma                90
_cell_volume                     1399.33(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6351
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      28.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16004
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.689
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3379
_reflns_number_gt                2845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0715P)²+0.2905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3379
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.18375(10) -0.19382(12) 0.35295(11) 0.0370(3) Uani 1 1 d . . . . .
C2 C 0.20487(12) -0.29514(15) 0.44220(13) 0.0494(3) Uani 1 1 d . . . . .
H2 H 0.1522 -0.3615 0.4456 0.059 Uiso 1 1 calc R U . . .
C3 C 0.30096(13) -0.29714(15) 0.52305(13) 0.0524(4) Uani 1 1 d . . . . .
H3 H 0.3133 -0.3642 0.5813 0.063 Uiso 1 1 calc R U . . .
C4 C 0.38100(11) -0.19845(15) 0.51851(12) 0.0450(3) Uani 1 1 d . . . . .
H4 H 0.4466 -0.2004 0.5738 0.054 Uiso 1 1 calc R U . . .
C5 C 0.36377(10) -0.09894(13) 0.43361(10) 0.0364(3) Uani 1 1 d . . . . .
H5 H 0.4183 -0.0347 0.4314 0.044 Uiso 1 1 calc R U . . .
C6 C 0.26456(9) -0.09218(11) 0.34921(10) 0.0309(2) Uani 1 1 d . . . . .
C7 C 0.24370(9) 0.01258(12) 0.26169(9) 0.0304(2) Uani 1 1 d . . . . .
C8 C 0.14663(9) 0.01096(12) 0.18059(10) 0.0339(3) Uani 1 1 d . . . . .
C9 C 0.06579(10) -0.09015(14) 0.18361(12) 0.0416(3) Uani 1 1 d . . . . .
H9 H 0.0002 -0.0887 0.1282 0.050 Uiso 1 1 calc R U . . .
C10 C 0.08439(10) -0.18887(14) 0.26753(12) 0.0429(3) Uani 1 1 d . . . . .
H10 H 0.0309 -0.2548 0.2692 0.052 Uiso 1 1 calc R U . . .
C11 C 0.21120(10) 0.17687(13) 0.06300(10) 0.0368(3) Uani 1 1 d . . . . .
H11 H 0.2537 0.1095 0.0298 0.044 Uiso 1 1 calc R U . . .
C12 C 0.28528(9) 0.24018(12) 0.17114(10) 0.0346(3) Uani 1 1 d . . . . .
C13 C 0.32561(9) 0.12466(12) 0.25915(10) 0.0332(3) Uani 1 1 d . . . . .
H13 H 0.3480 0.1659 0.3368 0.040 Uiso 1 1 calc R U . . .
C14 C 0.10782(12) 0.38293(16) 0.01769(14) 0.0520(4) Uani 1 1 d . . . . .
H14A H 0.0440 0.3439 0.0382 0.062 Uiso 1 1 calc R U . . .
H14B H 0.0833 0.4490 -0.0448 0.062 Uiso 1 1 calc R U . . .
C15 C 0.17544(13) 0.45765(15) 0.12126(14) 0.0540(4) Uani 1 1 d . . . . .
H15A H 0.1305 0.5245 0.1500 0.065 Uiso 1 1 calc R U . . .
H15B H 0.2335 0.5080 0.0982 0.065 Uiso 1 1 calc R U . . .
C16 C 0.22415(12) 0.35497(14) 0.21787(12) 0.0444(3) Uani 1 1 d . . . . .
H16A H 0.2735 0.4036 0.2804 0.053 Uiso 1 1 calc R U . . .
H16B H 0.1665 0.3145 0.2490 0.053 Uiso 1 1 calc R U . . .
C17 C 0.39200(11) 0.28823(15) 0.14191(13) 0.0475(3) Uani 1 1 d . . . . .
H17A H 0.3792 0.3200 0.0621 0.057 Uiso 1 1 calc R U . . .
H17B H 0.4250 0.3631 0.1930 0.057 Uiso 1 1 calc R U . . .
C18 C 0.46379(12) 0.16043(19) 0.16036(15) 0.0571(4) Uani 1 1 d . . . . .
H18A H 0.4659 0.1190 0.0862 0.069 Uiso 1 1 calc R U . . .
H18B H 0.5374 0.1854 0.2001 0.069 Uiso 1 1 calc R U . . .
O1 O 0.12072(7) 0.10493(9) 0.09140(8) 0.0426(2) Uani 1 1 d . . . . .
O2 O 0.16765(8) 0.27342(10) -0.02219(8) 0.0460(3) Uani 1 1 d . . . . .
O3 O 0.41955(7) 0.06480(11) 0.22848(9) 0.0489(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 C2 1.4161(18) . ?
C1 C10 1.4187(18) . ?
C1 C6 1.4219(16) . ?
C2 C3 1.361(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3679(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.4120(16) . ?
C5 H5 0.9300 . ?
C6 C7 1.4251(16) . ?
C7 C8 1.3715(16) . ?
C7 C13 1.4998(15) . ?
C8 O1 1.3704(14) . ?
C8 C9 1.4169(17) . ?
C9 C10 1.3545(19) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O2 1.3872(14) . ?
C11 O1 1.4414(15) . ?
C11 C12 1.5263(17) . ?
C11 H11 0.9800 . ?
C12 C16 1.5230(18) . ?
C12 C13 1.5273(16) . ?
C12 C17 1.5392(17) . ?
C13 O3 1.4397(15) . ?
C13 H13 0.9800 . ?
C14 O2 1.4385(17) . ?
C14 C15 1.504(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.528(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.513(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O3 1.4203(16) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 122.49(12) . . ?
C2 C1 C6 118.92(12) . . ?
C10 C1 C6 118.59(11) . . ?
C3 C2 C1 121.15(13) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.96(13) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.67(13) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.05(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.23(11) . . ?
C5 C6 C7 122.07(10) . . ?
C1 C6 C7 119.70(10) . . ?
C8 C7 C6 119.03(10) . . ?
C8 C7 C13 120.27(10) . . ?
C6 C7 C13 120.70(10) . . ?
O1 C8 C7 123.14(10) . . ?
O1 C8 C9 115.28(10) . . ?
C7 C8 C9 121.58(11) . . ?
C10 C9 C8 119.73(11) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C1 121.36(11) . . ?
C9 C10 H10 119.3 . . ?
C1 C10 H10 119.3 . . ?
O2 C11 O1 106.73(9) . . ?
O2 C11 C12 113.90(10) . . ?
O1 C11 C12 111.21(9) . . ?
O2 C11 H11 108.3 . . ?
O1 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C16 C12 C11 109.22(10) . . ?
C16 C12 C13 113.40(10) . . ?
C11 C12 C13 108.93(9) . . ?
C16 C12 C17 114.12(11) . . ?
C11 C12 C17 109.31(10) . . ?
C13 C12 C17 101.55(9) . . ?
O3 C13 C7 109.33(10) . . ?
O3 C13 C12 106.48(9) . . ?
C7 C13 C12 114.43(9) . . ?
O3 C13 H13 108.8 . . ?
C7 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
O2 C14 C15 111.99(12) . . ?
O2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
O2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 110.79(12) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C12 C16 C15 110.33(11) . . ?
C12 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C12 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C12 104.54(11) . . ?
C18 C17 H17A 110.8 . . ?
C12 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C12 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
O3 C18 C17 107.83(11) . . ?
O3 C18 H18A 110.1 . . ?
C17 C18 H18A 110.1 . . ?
O3 C18 H18B 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.5 . . ?
C8 O1 C11 115.80(9) . . ?
C11 O2 C14 113.72(10) . . ?
C18 O3 C13 109.88(10) . . ?

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
C10 C1 C2 C3 -179.91(14) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C1 -1.53(17) . . . . ?
C4 C5 C6 C7 178.42(12) . . . . ?
C2 C1 C6 C5 1.44(18) . . . . ?
C10 C1 C6 C5 -179.18(11) . . . . ?
C2 C1 C6 C7 -178.51(11) . . . . ?
C10 C1 C6 C7 0.87(17) . . . . ?
C5 C6 C7 C8 178.36(11) . . . . ?
C1 C6 C7 C8 -1.69(17) . . . . ?
C5 C6 C7 C13 -2.70(17) . . . . ?
C1 C6 C7 C13 177.24(10) . . . . ?
C6 C7 C8 O1 -178.09(10) . . . . ?
C13 C7 C8 O1 2.97(18) . . . . ?
C6 C7 C8 C9 1.60(18) . . . . ?
C13 C7 C8 C9 -177.34(11) . . . . ?
O1 C8 C9 C10 179.05(12) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C8 C9 C10 C1 -0.2(2) . . . . ?
C2 C1 C10 C9 179.43(13) . . . . ?
C6 C1 C10 C9 0.08(19) . . . . ?
O2 C11 C12 C16 54.25(13) . . . . ?
O1 C11 C12 C16 -66.40(12) . . . . ?
O2 C11 C12 C13 178.61(10) . . . . ?
O1 C11 C12 C13 57.95(12) . . . . ?
O2 C11 C12 C17 -71.25(13) . . . . ?
O1 C11 C12 C17 168.09(10) . . . . ?
C8 C7 C13 O3 -112.26(12) . . . . ?
C6 C7 C13 O3 68.82(13) . . . . ?
C8 C7 C13 C12 7.06(16) . . . . ?
C6 C7 C13 C12 -171.87(10) . . . . ?
C16 C12 C13 O3 -153.29(10) . . . . ?
C11 C12 C13 O3 84.86(11) . . . . ?
C17 C12 C13 O3 -30.41(12) . . . . ?
C16 C12 C13 C7 85.81(13) . . . . ?
C11 C12 C13 C7 -36.04(13) . . . . ?
C17 C12 C13 C7 -151.31(11) . . . . ?
O2 C14 C15 C16 -53.79(16) . . . . ?
C11 C12 C16 C15 -51.91(14) . . . . ?
C13 C12 C16 C15 -173.59(11) . . . . ?
C17 C12 C16 C15 70.77(15) . . . . ?
C14 C15 C16 C12 53.21(16) . . . . ?
C16 C12 C17 C18 150.84(12) . . . . ?
C11 C12 C17 C18 -86.53(13) . . . . ?
C13 C12 C17 C18 28.45(14) . . . . ?
C12 C17 C18 O3 -17.33(16) . . . . ?
C7 C8 O1 C11 19.67(16) . . . . ?
C9 C8 O1 C11 -160.03(11) . . . . ?
O2 C11 O1 C8 -175.57(10) . . . . ?
C12 C11 O1 C8 -50.78(14) . . . . ?
O1 C11 O2 C14 66.72(13) . . . . ?
C12 C11 O2 C14 -56.41(14) . . . . ?
C15 C14 O2 C11 55.77(15) . . . . ?
C17 C18 O3 C13 -2.13(16) . . . . ?
C7 C13 O3 C18 145.20(11) . . . . ?
C12 C13 O3 C18 21.09(14) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_KA287_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1578489'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O4'
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.13(4)
_cell_length_b                   12.87(4)
_cell_length_c                   7.80(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.51(2)
_cell_angle_gamma                90
_cell_volume                     1270(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6498
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      30.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6418

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19377
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         30.759
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3941
_reflns_number_gt                2274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²+0.2547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3941
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.2015
_refine_ls_wR_factor_gt          0.1725
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.53955(14) 0.21455(17) 0.6334(3) 0.0557(5) Uani 1 1 d . . . . .
C2 C 0.53564(14) 0.32034(17) 0.6377(3) 0.0591(5) Uani 1 1 d . . . . .
H2 H 0.5913 0.3584 0.7089 0.071 Uiso 1 1 calc R U . . .
C3 C 0.44787(14) 0.36945(15) 0.5347(3) 0.0537(5) Uani 1 1 d . . . . .
H3 H 0.4435 0.4416 0.5374 0.064 Uiso 1 1 calc R U . . .
C4 C 0.36621(12) 0.31349(13) 0.4277(2) 0.0438(4) Uani 1 1 d . . . . .
C5 C 0.37209(14) 0.20695(15) 0.4290(3) 0.0545(5) Uani 1 1 d . . . . .
H5 H 0.3164 0.1685 0.3589 0.065 Uiso 1 1 calc R U . . .
C6 C 0.45869(16) 0.15649(16) 0.5320(3) 0.0616(5) Uani 1 1 d . . . . .
H6 H 0.4624 0.0843 0.5329 0.074 Uiso 1 1 calc R U . . .
C7 C 0.27231(13) 0.36846(13) 0.3139(2) 0.0465(4) Uani 1 1 d . . . . .
H7 H 0.2390 0.3240 0.2124 0.056 Uiso 1 1 calc R U . . .
C8 C 0.19093(13) 0.39420(14) 0.4155(2) 0.0477(4) Uani 1 1 d . . . . .
H8 H 0.2258 0.4320 0.5245 0.057 Uiso 1 1 calc R U . . .
C9 C 0.10481(15) 0.46034(15) 0.3038(2) 0.0537(5) Uani 1 1 d . . . . .
C10 C 0.00468(16) 0.43529(18) 0.2836(3) 0.0662(6) Uani 1 1 d . . . . .
H10 H -0.0471 0.4757 0.2083 0.079 Uiso 1 1 calc R U . . .
C11 C -0.02879(16) 0.3466(2) 0.3743(3) 0.0734(6) Uani 1 1 d . . . . .
H11A H -0.0538 0.2909 0.2897 0.088 Uiso 1 1 calc R U . . .
H11B H -0.0865 0.3675 0.4226 0.088 Uiso 1 1 calc R U . . .
C12 C 0.06176(16) 0.3087(2) 0.5213(3) 0.0715(6) Uani 1 1 d . . . . .
H12A H 0.0750 0.3574 0.6198 0.086 Uiso 1 1 calc R U . . .
H12B H 0.0440 0.2420 0.5636 0.086 Uiso 1 1 calc R U . . .
C13 C 0.22452(17) 0.51251(18) 0.1264(3) 0.0683(6) Uani 1 1 d . . . . .
H13A H 0.1915 0.4655 0.0304 0.082 Uiso 1 1 calc R U . . .
H13B H 0.2524 0.5714 0.0757 0.082 Uiso 1 1 calc R U . . .
C14 C 0.14389(18) 0.54948(17) 0.2176(3) 0.0698(6) Uani 1 1 d . . . . .
H14A H 0.1754 0.6011 0.3066 0.084 Uiso 1 1 calc R U . . .
H14B H 0.0852 0.5817 0.1314 0.084 Uiso 1 1 calc R U . . .
N1 N 0.63329(15) 0.16142(19) 0.7412(3) 0.0793(6) Uani 1 1 d . . . . .
O1 O 0.64112(16) 0.06883(17) 0.7243(3) 0.1134(8) Uani 1 1 d . . . . .
O2 O 0.69922(15) 0.21349(19) 0.8450(3) 0.1150(8) Uani 1 1 d . . . . .
O3 O 0.15410(9) 0.29832(11) 0.46103(19) 0.0601(4) Uani 1 1 d . . . . .
O4 O 0.30778(10) 0.46084(11) 0.24975(16) 0.0579(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
C1 C2 1.363(5) . ?
C1 C6 1.365(4) . ?
C1 N1 1.462(4) . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C4 C7 1.491(4) . ?
C5 C6 1.368(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O4 1.416(4) . ?
C7 C8 1.527(4) . ?
C7 H7 0.9800 . ?
C8 O3 1.405(4) . ?
C8 C9 1.495(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.322(5) . ?
C9 C14 1.488(4) . ?
C10 C11 1.471(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.496(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O3 1.419(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O4 1.415(3) . ?
C13 C14 1.502(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 O1 1.206(5) . ?
N1 O2 1.216(4) . ?

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
C2 C1 C6 122.2(2) . . ?
C2 C1 N1 119.0(2) . . ?
C6 C1 N1 118.8(3) . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.04(19) . . ?
C5 C4 C7 120.94(17) . . ?
C3 C4 C7 120.0(2) . . ?
C6 C5 C4 120.97(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O4 C7 C4 108.1(2) . . ?
O4 C7 C8 110.1(2) . . ?
C4 C7 C8 112.1(2) . . ?
O4 C7 H7 108.8 . . ?
C4 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
O3 C8 C9 112.9(2) . . ?
O3 C8 C7 106.07(19) . . ?
C9 C8 C7 110.3(2) . . ?
O3 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C10 C9 C14 125.89(19) . . ?
C10 C9 C8 120.3(2) . . ?
C14 C9 C8 113.8(3) . . ?
C9 C10 C11 123.20(19) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C10 C11 C12 110.1(2) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
O3 C12 C11 110.6(3) . . ?
O3 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O4 C13 C14 109.9(3) . . ?
O4 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
O4 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C9 C14 C13 110.0(2) . . ?
C9 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C9 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O1 N1 O2 123.4(2) . . ?
O1 N1 C1 118.9(2) . . ?
O2 N1 C1 117.7(3) . . ?
C8 O3 C12 112.57(19) . . ?
C13 O4 C7 111.6(2) . . ?

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
C6 C1 C2 C3 -0.8(3) . . . . ?
N1 C1 C2 C3 179.33(17) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
C2 C3 C4 C7 -178.78(17) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C7 C4 C5 C6 179.32(17) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
N1 C1 C6 C5 -178.80(17) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C5 C4 C7 O4 -143.83(19) . . . . ?
C3 C4 C7 O4 37.0(2) . . . . ?
C5 C4 C7 C8 94.7(2) . . . . ?
C3 C4 C7 C8 -84.5(2) . . . . ?
O4 C7 C8 O3 175.29(13) . . . . ?
C4 C7 C8 O3 -64.36(19) . . . . ?
O4 C7 C8 C9 52.7(2) . . . . ?
C4 C7 C8 C9 173.09(15) . . . . ?
O3 C8 C9 C10 11.7(2) . . . . ?
C7 C8 C9 C10 130.1(2) . . . . ?
O3 C8 C9 C14 -165.88(16) . . . . ?
C7 C8 C9 C14 -47.4(2) . . . . ?
C14 C9 C10 C11 -179.34(19) . . . . ?
C8 C9 C10 C11 3.4(3) . . . . ?
C9 C10 C11 C12 14.3(3) . . . . ?
C10 C11 C12 O3 -47.1(3) . . . . ?
C10 C9 C14 C13 -128.2(3) . . . . ?
C8 C9 C14 C13 49.3(3) . . . . ?
O4 C13 C14 C9 -56.4(2) . . . . ?
C2 C1 N1 O1 -172.9(2) . . . . ?
C6 C1 N1 O1 7.2(3) . . . . ?
C2 C1 N1 O2 7.7(3) . . . . ?
C6 C1 N1 O2 -172.1(2) . . . . ?
C9 C8 O3 C12 -46.1(3) . . . . ?
C7 C8 O3 C12 -166.94(15) . . . . ?
C11 C12 O3 C8 65.5(2) . . . . ?
C14 C13 O4 C7 65.2(3) . . . . ?
C4 C7 O4 C13 174.21(15) . . . . ?
C8 C7 O4 C13 -63.1(3) . . . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.048

