# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 1956332'
loop_
_audit_author_name
_audit_author_address
'Liang Wu'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 Br N O4'
_chemical_formula_weight         410.30

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'
Br Br -0.6763 1.2805 '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 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.4837(7)
_cell_length_b                   21.349(2)
_cell_length_c                   9.5572(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.070(7)
_cell_angle_gamma                90
_cell_volume                     1927.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      4.64
_cell_measurement_theta_max      68.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   0.5408
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.095
_shelx_estimated_absorpt_T_min   0.576
_shelx_estimated_absorpt_T_max   0.576
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker V8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18309
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.645
_diffrn_reflns_theta_max         68.181
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             6958
_reflns_number_gt                6866
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.973

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+0.0969P] 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 3213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6958
_refine_ls_number_parameters     461
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0534
_refine_ls_wR_factor_gt          0.0530
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_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
Br1 Br 1.02744(3) 0.40346(2) 0.83032(3) 0.04057(9) Uani 1 1 d . . . . .
C1 C 0.7456(2) 0.41133(11) 0.9106(2) 0.0240(5) Uani 1 1 d . . . . .
O1 O 0.6097(2) 0.41294(11) 1.2462(2) 0.0411(5) Uani 1 1 d . . . . .
N1 N 0.5347(2) 0.41565(10) 1.0108(2) 0.0300(5) Uani 1 1 d . . . . .
Br2 Br 0.46693(3) 0.58285(2) 0.25381(3) 0.04279(9) Uani 1 1 d . . . . .
C2 C 0.8265(2) 0.41081(12) 0.7984(3) 0.0277(5) Uani 1 1 d . . . . .
N2 N 0.2930(2) 0.57438(11) 0.7464(2) 0.0306(4) Uani 1 1 d . . . . .
O2 O 0.80112(18) 0.51943(8) 1.0791(2) 0.0277(4) Uani 1 1 d . . . . .
O3 O 1.00615(18) 0.57347(9) 1.1059(2) 0.0349(4) Uani 1 1 d . . . . .
C3 C 0.7661(3) 0.41417(12) 0.6594(3) 0.0343(6) Uani 1 1 d . . . . .
O4 O 0.79283(19) 0.61781(8) 1.03692(19) 0.0296(4) Uani 1 1 d . . . . .
C4 C 0.6200(3) 0.41750(13) 0.6388(3) 0.0373(6) Uani 1 1 d . . . . .
H4 H 0.577061 0.419689 0.545312 0.045 Uiso 1 1 calc R U . . .
O5 O 0.0551(2) 0.56852(11) 0.6750(2) 0.0416(5) Uani 1 1 d . . . . .
C5 C 0.5331(3) 0.41780(13) 0.7486(3) 0.0330(6) Uani 1 1 d . . . . .
H5 H 0.433038 0.419840 0.731413 0.040 Uiso 1 1 calc R U . . .
O7 O 0.1608(2) 0.39895(11) 0.32253(19) 0.0383(4) Uani 1 1 d . . . . .
C7 C 0.7813(2) 0.40889(13) 1.0680(2) 0.0245(5) Uani 1 1 d . . . . .
O6 O 0.2378(2) 0.46330(8) 0.50029(19) 0.0282(4) Uani 1 1 d . . . . .
C6 C 0.5979(3) 0.41500(11) 0.8837(3) 0.0268(5) Uani 1 1 d . . . . .
C9 C 0.8557(4) 0.41511(18) 0.5368(3) 0.0498(8) Uani 1 1 d . . . . .
H9A H 0.794427 0.419036 0.449138 0.075 Uiso 1 1 calc R U . . .
H9B H 0.910046 0.376110 0.535329 0.075 Uiso 1 1 calc R U . . .
H9C H 0.920856 0.450785 0.546203 0.075 Uiso 1 1 calc R U . . .
O8 O 0.27492(19) 0.36518(9) 0.52767(18) 0.0289(4) Uani 1 1 d . . . . .
C8 C 0.6334(3) 0.41339(12) 1.1231(3) 0.0280(5) Uani 1 1 d . . . . .
C10 C 0.3837(3) 0.41128(16) 1.0238(4) 0.0437(7) Uani 1 1 d . . . . .
H10A H 0.333710 0.442193 0.961992 0.066 Uiso 1 1 calc R U . . .
H10B H 0.364957 0.419554 1.121344 0.066 Uiso 1 1 calc R U . . .
H10C H 0.350487 0.369128 0.997006 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8734(3) 0.46294(12) 1.1252(3) 0.0271(5) Uani 1 1 d . . . . .
H11A H 0.886080 0.461305 1.229100 0.033 Uiso 1 1 calc R U . . .
H11B H 0.967786 0.460963 1.088632 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8808(3) 0.57116(12) 1.0761(2) 0.0252(5) Uani 1 1 d . . . . .
C13 C 0.8460(3) 0.68217(12) 1.0167(3) 0.0324(6) Uani 1 1 d . . . . .
C14 C 0.9323(4) 0.70559(13) 1.1476(3) 0.0395(7) Uani 1 1 d . . . . .
H14A H 1.024372 0.684426 1.156807 0.059 Uiso 1 1 calc R U . . .
H14B H 0.881645 0.696565 1.230322 0.059 Uiso 1 1 calc R U . . .
H14C H 0.946640 0.750885 1.140167 0.059 Uiso 1 1 calc R U . . .
C15 C 0.9293(4) 0.68305(15) 0.8894(3) 0.0451(7) Uani 1 1 d . . . . .
H15A H 0.870724 0.666417 0.808234 0.068 Uiso 1 1 calc R U . . .
H15B H 1.014252 0.657113 0.907311 0.068 Uiso 1 1 calc R U . . .
H15C H 0.957082 0.726176 0.869965 0.068 Uiso 1 1 calc R U . . .
C16 C 0.7087(4) 0.71813(16) 0.9923(4) 0.0482(8) Uani 1 1 d . . . . .
H16A H 0.729257 0.762822 0.982455 0.072 Uiso 1 1 calc R U . . .
H16B H 0.652309 0.711921 1.072275 0.072 Uiso 1 1 calc R U . . .
H16C H 0.655581 0.702954 0.906347 0.072 Uiso 1 1 calc R U . . .
C17 C 0.8463(3) 0.34584(12) 1.1213(3) 0.0307(5) Uani 1 1 d . . . . .
H17A H 0.944918 0.343016 1.095364 0.037 Uiso 1 1 calc R U . . .
H17B H 0.849077 0.344556 1.225019 0.037 Uiso 1 1 calc R U . . .
C20 C 0.3902(2) 0.57807(12) 0.5358(2) 0.0242(4) Uani 1 1 d . . . . .
C21 C 0.5014(2) 0.58003(13) 0.4530(2) 0.0268(5) Uani 1 1 d . . . . .
C22 C 0.6426(2) 0.58008(14) 0.5113(3) 0.0321(5) Uani 1 1 d . . . . .
C23 C 0.6662(3) 0.57934(15) 0.6565(3) 0.0357(6) Uani 1 1 d . . . . .
H23 H 0.761104 0.579302 0.697696 0.043 Uiso 1 1 calc R U . . .
C24 C 0.5575(3) 0.57866(15) 0.7441(3) 0.0327(5) Uani 1 1 d . . . . .
H24 H 0.576371 0.579001 0.843356 0.039 Uiso 1 1 calc R U . . .
C25 C 0.4203(2) 0.57745(12) 0.6816(2) 0.0257(4) Uani 1 1 d . . . . .
C26 C 0.2316(2) 0.57502(13) 0.5019(2) 0.0249(5) Uani 1 1 d . . . . .
C27 C 0.1788(3) 0.57177(12) 0.6497(3) 0.0294(5) Uani 1 1 d . . . . .
C28 C 0.7651(3) 0.5798(2) 0.4212(4) 0.0483(7) Uani 1 1 d . . . . .
H28A H 0.756350 0.543870 0.357138 0.072 Uiso 1 1 calc R U . . .
H28B H 0.854078 0.576649 0.481235 0.072 Uiso 1 1 calc R U . . .
H28C H 0.764582 0.618641 0.366547 0.072 Uiso 1 1 calc R U . . .
C29 C 0.2843(3) 0.57429(16) 0.8971(3) 0.0418(6) Uani 1 1 d . . . . .
H29A H 0.192743 0.557034 0.918119 0.063 Uiso 1 1 calc R U . . .
H29B H 0.293395 0.617273 0.932787 0.063 Uiso 1 1 calc R U . . .
H29C H 0.360784 0.548517 0.942290 0.063 Uiso 1 1 calc R U . . .
C30 C 0.1813(3) 0.51611(12) 0.4204(3) 0.0275(5) Uani 1 1 d . . . . .
H30A H 0.076629 0.514334 0.409781 0.033 Uiso 1 1 calc R U . . .
H30B H 0.216184 0.516216 0.325811 0.033 Uiso 1 1 calc R U . . .
C31 C 0.2188(2) 0.40703(14) 0.4378(2) 0.0268(5) Uani 1 1 d . . . . .
C32 C 0.2834(3) 0.29826(13) 0.4881(3) 0.0317(5) Uani 1 1 d . . . . .
C33 C 0.3683(4) 0.29160(16) 0.3623(4) 0.0499(8) Uani 1 1 d . . . . .
H33A H 0.314694 0.309356 0.279255 0.075 Uiso 1 1 calc R U . . .
H33B H 0.386849 0.247161 0.345999 0.075 Uiso 1 1 calc R U . . .
H33C H 0.458300 0.313978 0.380075 0.075 Uiso 1 1 calc R U . . .
C34 C 0.1351(4) 0.27134(15) 0.4641(4) 0.0437(7) Uani 1 1 d . . . . .
H34A H 0.086361 0.290084 0.379506 0.066 Uiso 1 1 calc R U . . .
H34B H 0.082380 0.280709 0.545243 0.066 Uiso 1 1 calc R U . . .
H34C H 0.140740 0.225862 0.451870 0.066 Uiso 1 1 calc R U . . .
C35 C 0.3616(3) 0.27044(14) 0.6190(3) 0.0417(7) Uani 1 1 d . . . . .
H35A H 0.373473 0.225276 0.605931 0.063 Uiso 1 1 calc R U . . .
H35B H 0.306959 0.277801 0.699849 0.063 Uiso 1 1 calc R U . . .
H35C H 0.454717 0.290263 0.635776 0.063 Uiso 1 1 calc R U . . .
C36 C 0.1664(3) 0.63268(13) 0.4242(3) 0.0315(6) Uani 1 1 d . . . . .
H36A H 0.198256 0.633636 0.328330 0.038 Uiso 1 1 calc R U . . .
H36B H 0.062143 0.628140 0.414913 0.038 Uiso 1 1 calc R U . . .
C37 C 0.2038(3) 0.69367(15) 0.4948(4) 0.0434(7) Uani 1 1 d . . . . .
H37 H 0.186235 0.697739 0.590760 0.052 Uiso 1 1 calc R U . . .
C38 C 0.2583(4) 0.74151(18) 0.4354(6) 0.0660(12) Uani 1 1 d . . . . .
H38A H 0.277362 0.739301 0.339573 0.079 Uiso 1 1 calc R U . . .
H38B H 0.279023 0.778739 0.487632 0.079 Uiso 1 1 calc R U . . .
C19 C 0.6759(4) 0.25815(19) 1.1255(7) 0.0765(13) Uani 1 1 d . . . . .
H19A H 0.658459 0.268444 1.219149 0.092 Uiso 1 1 calc R U . . .
H19B H 0.628128 0.223786 1.079405 0.092 Uiso 1 1 calc R U . . .
C18 C 0.7640(4) 0.29068(15) 1.0613(4) 0.0468(8) Uani 1 1 d . . . . .
H18 H 0.778311 0.278766 0.967841 0.056 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
Br1 C2 1.910(2) . ?
C1 C2 1.373(4) . ?
C1 C6 1.403(3) . ?
C1 C7 1.513(3) . ?
O1 C8 1.217(3) . ?
N1 C8 1.361(3) . ?
N1 C6 1.401(3) . ?
N1 C10 1.452(3) . ?
Br2 C21 1.904(2) . ?
C2 C3 1.401(3) . ?
N2 C27 1.361(3) . ?
N2 C25 1.406(3) . ?
N2 C29 1.450(3) . ?
O2 C12 1.340(3) . ?
O2 C11 1.437(3) . ?
O3 C12 1.198(3) . ?
C3 C4 1.384(4) . ?
C3 C9 1.507(4) . ?
O4 C12 1.332(3) . ?
O4 C13 1.482(3) . ?
C4 C5 1.390(4) . ?
C4 H4 0.9500 . ?
O5 C27 1.220(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
O7 C31 1.199(3) . ?
C7 C11 1.520(3) . ?
C7 C8 1.545(3) . ?
C7 C17 1.548(4) . ?
O6 C31 1.347(3) . ?
O6 C30 1.438(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O8 C31 1.319(3) . ?
O8 C32 1.482(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C15 1.508(4) . ?
C13 C16 1.512(4) . ?
C13 C14 1.518(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.498(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C20 C21 1.374(3) . ?
C20 C25 1.398(3) . ?
C20 C26 1.511(3) . ?
C21 C22 1.404(3) . ?
C22 C23 1.386(4) . ?
C22 C28 1.506(4) . ?
C23 C24 1.385(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C26 C30 1.533(4) . ?
C26 C36 1.538(4) . ?
C26 C27 1.542(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C32 C33 1.512(4) . ?
C32 C35 1.518(4) . ?
C32 C34 1.518(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C37 1.495(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.298(5) . ?
C37 H37 0.9500 . ?
C38 H38A 0.9500 . ?
C38 H38B 0.9500 . ?
C19 C18 1.284(6) . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C18 H18 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
C2 C1 C6 118.3(2) . . ?
C2 C1 C7 133.2(2) . . ?
C6 C1 C7 108.5(2) . . ?
C8 N1 C6 111.5(2) . . ?
C8 N1 C10 123.0(2) . . ?
C6 N1 C10 125.1(2) . . ?
C1 C2 C3 122.0(2) . . ?
C1 C2 Br1 119.65(17) . . ?
C3 C2 Br1 118.3(2) . . ?
C27 N2 C25 111.4(2) . . ?
C27 N2 C29 124.2(2) . . ?
C25 N2 C29 124.3(2) . . ?
C12 O2 C11 116.32(18) . . ?
C4 C3 C2 117.2(2) . . ?
C4 C3 C9 121.0(3) . . ?
C2 C3 C9 121.8(3) . . ?
C12 O4 C13 121.2(2) . . ?
C3 C4 C5 123.1(2) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C6 C5 C4 117.4(2) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C1 C7 C11 113.8(2) . . ?
C1 C7 C8 101.93(18) . . ?
C11 C7 C8 109.9(2) . . ?
C1 C7 C17 113.9(2) . . ?
C11 C7 C17 110.01(18) . . ?
C8 C7 C17 106.8(2) . . ?
C31 O6 C30 115.78(19) . . ?
C5 C6 N1 128.4(2) . . ?
C5 C6 C1 121.9(2) . . ?
N1 C6 C1 109.7(2) . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C31 O8 C32 121.0(2) . . ?
O1 C8 N1 126.1(2) . . ?
O1 C8 C7 125.5(2) . . ?
N1 C8 C7 108.3(2) . . ?
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 . . ?
O2 C11 C7 106.45(19) . . ?
O2 C11 H11A 110.4 . . ?
C7 C11 H11A 110.4 . . ?
O2 C11 H11B 110.4 . . ?
C7 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
O3 C12 O4 128.3(2) . . ?
O3 C12 O2 125.3(2) . . ?
O4 C12 O2 106.36(19) . . ?
O4 C13 C15 109.0(2) . . ?
O4 C13 C16 101.1(2) . . ?
C15 C13 C16 112.0(3) . . ?
O4 C13 C14 111.2(2) . . ?
C15 C13 C14 112.2(3) . . ?
C16 C13 C14 110.7(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C7 112.3(2) . . ?
C18 C17 H17A 109.2 . . ?
C7 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C7 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C21 C20 C25 118.3(2) . . ?
C21 C20 C26 132.7(2) . . ?
C25 C20 C26 108.98(19) . . ?
C20 C21 C22 121.7(2) . . ?
C20 C21 Br2 120.24(16) . . ?
C22 C21 Br2 118.03(18) . . ?
C23 C22 C21 117.5(2) . . ?
C23 C22 C28 120.5(2) . . ?
C21 C22 C28 122.0(2) . . ?
C24 C23 C22 122.8(2) . . ?
C24 C23 H23 118.6 . . ?
C22 C23 H23 118.6 . . ?
C25 C24 C23 117.5(2) . . ?
C25 C24 H24 121.2 . . ?
C23 C24 H24 121.2 . . ?
C24 C25 C20 122.1(2) . . ?
C24 C25 N2 128.5(2) . . ?
C20 C25 N2 109.36(19) . . ?
C20 C26 C30 113.8(2) . . ?
C20 C26 C36 114.8(2) . . ?
C30 C26 C36 108.54(19) . . ?
C20 C26 C27 101.72(18) . . ?
C30 C26 C27 108.5(2) . . ?
C36 C26 C27 109.2(2) . . ?
O5 C27 N2 126.1(2) . . ?
O5 C27 C26 125.5(2) . . ?
N2 C27 C26 108.5(2) . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N2 C29 H29A 109.5 . . ?
N2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O6 C30 C26 106.82(19) . . ?
O6 C30 H30A 110.4 . . ?
C26 C30 H30A 110.4 . . ?
O6 C30 H30B 110.4 . . ?
C26 C30 H30B 110.4 . . ?
H30A C30 H30B 108.6 . . ?
O7 C31 O8 128.8(3) . . ?
O7 C31 O6 124.6(3) . . ?
O8 C31 O6 106.55(19) . . ?
O8 C32 C33 109.8(2) . . ?
O8 C32 C35 101.6(2) . . ?
C33 C32 C35 111.3(3) . . ?
O8 C32 C34 109.5(2) . . ?
C33 C32 C34 113.3(3) . . ?
C35 C32 C34 110.8(2) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C26 114.2(2) . . ?
C37 C36 H36A 108.7 . . ?
C26 C36 H36A 108.7 . . ?
C37 C36 H36B 108.7 . . ?
C26 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
C38 C37 C36 125.1(4) . . ?
C38 C37 H37 117.4 . . ?
C36 C37 H37 117.4 . . ?
C37 C38 H38A 120.0 . . ?
C37 C38 H38B 120.0 . . ?
H38A C38 H38B 120.0 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C19 C18 C17 125.6(4) . . ?
C19 C18 H18 117.2 . . ?
C17 C18 H18 117.2 . . ?

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 0.4(4) . . . . ?
C7 C1 C2 C3 -179.4(3) . . . . ?
C6 C1 C2 Br1 -178.24(18) . . . . ?
C7 C1 C2 Br1 2.0(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
Br1 C2 C3 C4 178.03(19) . . . . ?
C1 C2 C3 C9 178.5(3) . . . . ?
Br1 C2 C3 C9 -2.8(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C9 C3 C4 C5 -179.0(3) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C2 C1 C7 C11 60.2(4) . . . . ?
C6 C1 C7 C11 -119.6(2) . . . . ?
C2 C1 C7 C8 178.4(3) . . . . ?
C6 C1 C7 C8 -1.3(3) . . . . ?
C2 C1 C7 C17 -67.0(4) . . . . ?
C6 C1 C7 C17 113.3(2) . . . . ?
C4 C5 C6 N1 178.9(2) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C8 N1 C6 C5 -178.8(3) . . . . ?
C10 N1 C6 C5 8.5(4) . . . . ?
C8 N1 C6 C1 0.8(3) . . . . ?
C10 N1 C6 C1 -171.9(2) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C7 C1 C6 C5 -179.9(2) . . . . ?
C2 C1 C6 N1 -179.4(2) . . . . ?
C7 C1 C6 N1 0.5(3) . . . . ?
C6 N1 C8 O1 -179.5(3) . . . . ?
C10 N1 C8 O1 -6.7(4) . . . . ?
C6 N1 C8 C7 -1.7(3) . . . . ?
C10 N1 C8 C7 171.2(2) . . . . ?
C1 C7 C8 O1 179.7(3) . . . . ?
C11 C7 C8 O1 -59.4(3) . . . . ?
C17 C7 C8 O1 59.9(3) . . . . ?
C1 C7 C8 N1 1.8(3) . . . . ?
C11 C7 C8 N1 122.8(2) . . . . ?
C17 C7 C8 N1 -117.9(2) . . . . ?
C12 O2 C11 C7 -158.5(2) . . . . ?
C1 C7 C11 O2 54.7(3) . . . . ?
C8 C7 C11 O2 -58.8(3) . . . . ?
C17 C7 C11 O2 -176.1(2) . . . . ?
C13 O4 C12 O3 3.8(4) . . . . ?
C13 O4 C12 O2 -177.5(2) . . . . ?
C11 O2 C12 O3 1.5(3) . . . . ?
C11 O2 C12 O4 -177.33(19) . . . . ?
C12 O4 C13 C15 68.8(3) . . . . ?
C12 O4 C13 C16 -173.1(2) . . . . ?
C12 O4 C13 C14 -55.5(3) . . . . ?
C1 C7 C17 C18 -47.7(3) . . . . ?
C11 C7 C17 C18 -176.7(3) . . . . ?
C8 C7 C17 C18 64.0(3) . . . . ?
C25 C20 C21 C22 1.4(4) . . . . ?
C26 C20 C21 C22 -177.2(3) . . . . ?
C25 C20 C21 Br2 -178.6(2) . . . . ?
C26 C20 C21 Br2 2.8(4) . . . . ?
C20 C21 C22 C23 -1.3(4) . . . . ?
Br2 C21 C22 C23 178.7(2) . . . . ?
C20 C21 C22 C28 177.7(3) . . . . ?
Br2 C21 C22 C28 -2.4(4) . . . . ?
C21 C22 C23 C24 -0.1(5) . . . . ?
C28 C22 C23 C24 -179.0(3) . . . . ?
C22 C23 C24 C25 1.3(5) . . . . ?
C23 C24 C25 C20 -1.2(4) . . . . ?
C23 C24 C25 N2 177.6(3) . . . . ?
C21 C20 C25 C24 -0.1(4) . . . . ?
C26 C20 C25 C24 178.8(3) . . . . ?
C21 C20 C25 N2 -179.0(2) . . . . ?
C26 C20 C25 N2 -0.1(3) . . . . ?
C27 N2 C25 C24 -177.8(3) . . . . ?
C29 N2 C25 C24 2.5(5) . . . . ?
C27 N2 C25 C20 1.1(3) . . . . ?
C29 N2 C25 C20 -178.6(3) . . . . ?
C21 C20 C26 C30 61.6(4) . . . . ?
C25 C20 C26 C30 -117.1(2) . . . . ?
C21 C20 C26 C36 -64.3(4) . . . . ?
C25 C20 C26 C36 117.0(3) . . . . ?
C21 C20 C26 C27 178.0(3) . . . . ?
C25 C20 C26 C27 -0.7(3) . . . . ?
C25 N2 C27 O5 179.6(3) . . . . ?
C29 N2 C27 O5 -0.6(5) . . . . ?
C25 N2 C27 C26 -1.6(3) . . . . ?
C29 N2 C27 C26 178.2(3) . . . . ?
C20 C26 C27 O5 -179.8(3) . . . . ?
C30 C26 C27 O5 -59.6(3) . . . . ?
C36 C26 C27 O5 58.5(3) . . . . ?
C20 C26 C27 N2 1.4(3) . . . . ?
C30 C26 C27 N2 121.6(2) . . . . ?
C36 C26 C27 N2 -120.3(2) . . . . ?
C31 O6 C30 C26 -172.65(19) . . . . ?
C20 C26 C30 O6 54.1(3) . . . . ?
C36 C26 C30 O6 -176.8(2) . . . . ?
C27 C26 C30 O6 -58.3(3) . . . . ?
C32 O8 C31 O7 5.4(4) . . . . ?
C32 O8 C31 O6 -174.8(2) . . . . ?
C30 O6 C31 O7 0.9(4) . . . . ?
C30 O6 C31 O8 -178.9(2) . . . . ?
C31 O8 C32 C33 59.0(3) . . . . ?
C31 O8 C32 C35 176.8(2) . . . . ?
C31 O8 C32 C34 -66.0(3) . . . . ?
C20 C26 C36 C37 -53.1(3) . . . . ?
C30 C26 C36 C37 178.4(3) . . . . ?
C27 C26 C36 C37 60.3(3) . . . . ?
C26 C36 C37 C38 126.7(3) . . . . ?
C7 C17 C18 C19 -101.5(4) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1965672'
loop_
_audit_author_name
_audit_author_address
'Liang Wu'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-11-14 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18

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      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                   4.5388(9)
_cell_length_b                   13.550(3)
_cell_length_c                   14.103(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     867.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7096
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      68.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   0.6360
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.777
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker d8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8405
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.525
_diffrn_reflns_theta_max         68.206
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1578
_reflns_number_gt                1396
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.990

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+0.0127P] 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 498 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1578
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O1 O 0.0986(3) 0.27818(11) 0.37193(13) 0.0810(5) Uani 1 1 d . . . . .
C1 C 0.5644(4) 0.48738(12) 0.34658(14) 0.0542(4) Uani 1 1 d . . . . .
N1 N 0.2748(3) 0.41091(10) 0.45742(12) 0.0578(4) Uani 1 1 d . . . . .
O2 O 0.3419(3) 0.39262(13) 0.20761(10) 0.0759(5) Uani 1 1 d . . . . .
C2 C 0.7506(5) 0.55993(15) 0.31270(18) 0.0703(6) Uani 1 1 d . . . . .
H2 H 0.821880 0.557740 0.250905 0.084 Uiso 1 1 calc R U . . .
C4 C 0.7218(5) 0.64018(15) 0.4647(2) 0.0781(7) Uani 1 1 d . . . . .
H4 H 0.776592 0.692230 0.503871 0.094 Uiso 1 1 calc R U . . .
C3 C 0.8287(5) 0.63655(16) 0.3738(2) 0.0801(7) Uani 1 1 d . . . . .
H3 H 0.955053 0.685870 0.352567 0.096 Uiso 1 1 calc R U . . .
C6 C 0.4597(4) 0.49207(11) 0.43932(14) 0.0526(4) Uani 1 1 d . . . . .
C5 C 0.5349(5) 0.56842(13) 0.49932(17) 0.0672(5) Uani 1 1 d . . . . .
H5 H 0.462321 0.571412 0.560915 0.081 Uiso 1 1 calc R U . . .
C8 C 0.4464(4) 0.39618(13) 0.30389(14) 0.0552(4) Uani 1 1 d . . . . .
C7 C 0.2486(4) 0.35212(13) 0.37928(14) 0.0588(5) Uani 1 1 d . . . . .
C10 C 0.1294(5) 0.39160(17) 0.54709(17) 0.0753(6) Uani 1 1 d . . . . .
H10A H 0.031021 0.450322 0.568255 0.113 Uiso 1 1 calc R U . . .
H10B H 0.273130 0.372057 0.593360 0.113 Uiso 1 1 calc R U . . .
H10C H -0.012185 0.339650 0.539000 0.113 Uiso 1 1 calc R U . . .
C9 C 0.5902(4) 0.33275(17) 0.23436(17) 0.0740(6) Uani 1 1 d . . . . .
H9A H 0.783224 0.352277 0.211534 0.089 Uiso 1 1 calc R U . . .
H9B H 0.560188 0.262098 0.239699 0.089 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 C7 1.216(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.393(3) . ?
C1 C8 1.475(2) . ?
N1 C7 1.365(3) . ?
N1 C6 1.407(2) . ?
N1 C10 1.450(3) . ?
O2 C9 1.439(3) . ?
O2 C8 1.439(2) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.372(4) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C6 C5 1.380(3) . ?
C5 H5 0.9300 . ?
C8 C9 1.458(3) . ?
C8 C7 1.514(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 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 C6 120.07(19) . . ?
C2 C1 C8 132.6(2) . . ?
C6 C1 C8 107.30(14) . . ?
C7 N1 C6 111.21(15) . . ?
C7 N1 C10 123.98(17) . . ?
C6 N1 C10 124.80(18) . . ?
C9 O2 C8 60.87(13) . . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C3 C2 120.93(19) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C6 C1 121.71(17) . . ?
C5 C6 N1 128.51(19) . . ?
C1 C6 N1 109.78(16) . . ?
C6 C5 C4 117.6(2) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
O2 C8 C9 59.56(14) . . ?
O2 C8 C1 122.20(15) . . ?
C9 C8 C1 127.28(16) . . ?
O2 C8 C7 116.98(14) . . ?
C9 C8 C7 120.35(17) . . ?
C1 C8 C7 105.01(16) . . ?
O1 C7 N1 126.78(18) . . ?
O1 C7 C8 126.66(19) . . ?
N1 C7 C8 106.56(15) . . ?
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 . . ?
O2 C9 C8 59.57(12) . . ?
O2 C9 H9A 117.8 . . ?
C8 C9 H9A 117.8 . . ?
O2 C9 H9B 117.8 . . ?
C8 C9 H9B 117.8 . . ?
H9A C9 H9B 115.0 . . ?

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 0.1(3) . . . . ?
C8 C1 C2 C3 -177.79(17) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C8 C1 C6 C5 178.90(16) . . . . ?
C2 C1 C6 N1 179.85(16) . . . . ?
C8 C1 C6 N1 -1.77(18) . . . . ?
C7 N1 C6 C5 178.52(17) . . . . ?
C10 N1 C6 C5 -1.4(3) . . . . ?
C7 N1 C6 C1 -0.75(19) . . . . ?
C10 N1 C6 C1 179.37(16) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
N1 C6 C5 C4 -179.92(17) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C9 O2 C8 C1 117.4(2) . . . . ?
C9 O2 C8 C7 -111.00(19) . . . . ?
C2 C1 C8 O2 -42.2(3) . . . . ?
C6 C1 C8 O2 139.71(16) . . . . ?
C2 C1 C8 C9 32.0(3) . . . . ?
C6 C1 C8 C9 -146.1(2) . . . . ?
C2 C1 C8 C7 -178.57(19) . . . . ?
C6 C1 C8 C7 3.34(17) . . . . ?
C6 N1 C7 O1 -177.96(17) . . . . ?
C10 N1 C7 O1 1.9(3) . . . . ?
C6 N1 C7 C8 2.85(18) . . . . ?
C10 N1 C7 C8 -177.27(16) . . . . ?
O2 C8 C7 O1 38.0(3) . . . . ?
C9 C8 C7 O1 -30.9(3) . . . . ?
C1 C8 C7 O1 177.05(17) . . . . ?
O2 C8 C7 N1 -142.84(15) . . . . ?
C9 C8 C7 N1 148.31(17) . . . . ?
C1 C8 C7 N1 -3.77(17) . . . . ?
C1 C8 C9 O2 -109.2(2) . . . . ?
C7 C8 C9 O2 105.41(18) . . . . ?

_refine_diff_density_max         0.094
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.024



