# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2038333'
loop_
_audit_author_name
_audit_author_address
'Jian-Qiang Zhao'
;Chengdu University
China
;
_audit_update_record             
;
2020-10-14 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2 O3'
_chemical_formula_weight         370.39

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_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'
'-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                   22.8325(5)
_cell_length_b                   9.9872(3)
_cell_length_c                   16.8182(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.658(2)
_cell_angle_gamma                90.00
_cell_volume                     3768.94(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    3403
_cell_measurement_theta_min      3.9368
_cell_measurement_theta_max      69.4008

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7896
_exptl_absorpt_correction_T_max  0.8484
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7695
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.94
_diffrn_reflns_theta_max         65.08
_reflns_number_total             3190
_reflns_number_gt                2589
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0826P)²+1.2897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00056(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     254
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.32788(6) 0.28401(16) 0.73382(9) 0.0662(4) Uani 1 1 d . . .
N2 N 0.23908(6) 0.30431(16) 0.76439(10) 0.0502(4) Uani 1 1 d . . .
H2 H 0.2479 0.3881 0.7671 0.060 Uiso 1 1 calc R . .
O2 O 0.27628(7) 0.09694(16) 0.75020(11) 0.0760(5) Uani 1 1 d . . .
O1 O 0.04341(6) 0.12365(16) 0.67519(10) 0.0685(4) Uani 1 1 d . . .
N1 N 0.07188(7) 0.18876(17) 0.80495(10) 0.0574(4) Uani 1 1 d . . .
H1 H 0.0383 0.1608 0.8149 0.069 Uiso 1 1 calc R . .
C21 C 0.51124(13) 0.1096(5) 0.91476(19) 0.1097(11) Uani 1 1 d U . .
H21 H 0.5413 0.0847 0.9574 0.132 Uiso 1 1 calc R . .
C8 C 0.14217(7) 0.20676(18) 0.71526(12) 0.0485(4) Uani 1 1 d . . .
C7 C 0.18137(7) 0.26450(17) 0.77602(11) 0.0472(4) Uani 1 1 d . . .
C9 C 0.08295(8) 0.16901(19) 0.72936(13) 0.0537(5) Uani 1 1 d . . .
C6 C 0.16643(8) 0.29080(18) 0.85416(12) 0.0490(4) Uani 1 1 d . . .
C1 C 0.11020(8) 0.25001(19) 0.86704(12) 0.0524(5) Uani 1 1 d . . .
C15 C 0.14986(9) 0.0573(2) 0.59843(13) 0.0605(5) Uani 1 1 d . . .
H15 H 0.1404 -0.0152 0.6284 0.073 Uiso 1 1 calc R . .
C5 C 0.20490(9) 0.3527(2) 0.91799(13) 0.0583(5) Uani 1 1 d . . .
H5 H 0.2424 0.3804 0.9107 0.070 Uiso 1 1 calc R . .
C10 C 0.15373(7) 0.18503(18) 0.63229(12) 0.0496(4) Uani 1 1 d . . .
C18 C 0.42366(8) 0.1776(2) 0.78781(12) 0.0524(5) Uani 1 1 d . . .
C2 C 0.09333(9) 0.2712(2) 0.94212(13) 0.0630(6) Uani 1 1 d . . .
H2A H 0.0560 0.2439 0.9503 0.076 Uiso 1 1 calc R . .
C14 C 0.15984(10) 0.0373(2) 0.52108(14) 0.0669(6) Uani 1 1 d . . .
H14 H 0.1574 -0.0486 0.4994 0.080 Uiso 1 1 calc R . .
C11 C 0.16685(10) 0.2910(2) 0.58567(13) 0.0614(5) Uani 1 1 d . . .
H11 H 0.1692 0.3773 0.6068 0.074 Uiso 1 1 calc R . .
C16 C 0.28040(8) 0.2165(2) 0.74936(11) 0.0496(4) Uani 1 1 d . . .
C4 C 0.18794(11) 0.3731(2) 0.99160(14) 0.0669(6) Uani 1 1 d . . .
H4 H 0.2140 0.4143 1.0335 0.080 Uiso 1 1 calc R . .
C3 C 0.13182(11) 0.3320(2) 1.00305(14) 0.0693(6) Uani 1 1 d . . .
H3 H 0.1205 0.3461 1.0527 0.083 Uiso 1 1 calc R . .
C17 C 0.37702(10) 0.2057(3) 0.71496(14) 0.0790(8) Uani 1 1 d . . .
H17B H 0.3950 0.2537 0.6755 0.095 Uiso 1 1 calc R . .
H17A H 0.3618 0.1215 0.6908 0.095 Uiso 1 1 calc R . .
C13 C 0.17337(10) 0.1434(2) 0.47555(14) 0.0696(6) Uani 1 1 d . . .
H13 H 0.1803 0.1296 0.4234 0.083 Uiso 1 1 calc R . .
C19 C 0.45554(11) 0.2794(3) 0.83047(15) 0.0743(6) Uani 1 1 d U . .
H19 H 0.4476 0.3685 0.8163 0.089 Uiso 1 1 calc R . .
C23 C 0.43653(12) 0.0475(3) 0.81029(18) 0.0803(7) Uani 1 1 d . . .
H23 H 0.4147 -0.0208 0.7812 0.096 Uiso 1 1 calc R . .
C20 C 0.50159(12) 0.2442(4) 0.89781(18) 0.0981(8) Uani 1 1 d U . .
H20 H 0.5241 0.3097 0.9289 0.118 Uiso 1 1 calc R . .
C22 C 0.47925(17) 0.0159(4) 0.8724(2) 0.1114(11) Uani 1 1 d . . .
H22 H 0.4866 -0.0735 0.8860 0.134 Uiso 1 1 calc R . .
C12 C 0.17650(11) 0.2697(2) 0.50780(14) 0.0720(6) Uani 1 1 d . . .
H12 H 0.1852 0.3419 0.4771 0.086 Uiso 1 1 calc R . .


_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 C16 1.343(2) . ?
O3 C17 1.450(3) . ?
N2 C16 1.346(2) . ?
N2 C7 1.424(2) . ?
N2 H2 0.8600 . ?
O2 C16 1.198(2) . ?
O1 C9 1.243(2) . ?
N1 C9 1.356(3) . ?
N1 C1 1.375(3) . ?
N1 H1 0.8600 . ?
C21 C22 1.313(5) . ?
C21 C20 1.383(5) . ?
C21 H21 0.9300 . ?
C8 C7 1.356(3) . ?
C8 C9 1.465(2) . ?
C8 C10 1.483(3) . ?
C7 C6 1.442(3) . ?
C6 C5 1.399(3) . ?
C6 C1 1.401(3) . ?
C1 C2 1.403(3) . ?
C15 C14 1.376(3) . ?
C15 C10 1.393(3) . ?
C15 H15 0.9300 . ?
C5 C4 1.379(3) . ?
C5 H5 0.9300 . ?
C10 C11 1.382(3) . ?
C18 C23 1.369(3) . ?
C18 C19 1.373(3) . ?
C18 C17 1.494(3) . ?
C2 C3 1.363(3) . ?
C2 H2A 0.9300 . ?
C14 C13 1.376(3) . ?
C14 H14 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C4 C3 1.392(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C17 H17B 0.9700 . ?
C17 H17A 0.9700 . ?
C13 C12 1.369(3) . ?
C13 H13 0.9300 . ?
C19 C20 1.439(4) . ?
C19 H19 0.9300 . ?
C23 C22 1.329(5) . ?
C23 H23 0.9300 . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?
C12 H12 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 O3 C17 117.19(19) . . ?
C16 N2 C7 122.86(16) . . ?
C16 N2 H2 118.6 . . ?
C7 N2 H2 118.6 . . ?
C9 N1 C1 125.02(16) . . ?
C9 N1 H1 117.5 . . ?
C1 N1 H1 117.5 . . ?
C22 C21 C20 122.0(3) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C7 C8 C9 119.19(17) . . ?
C7 C8 C10 124.31(16) . . ?
C9 C8 C10 116.42(16) . . ?
C8 C7 N2 120.91(16) . . ?
C8 C7 C6 122.00(16) . . ?
N2 C7 C6 117.08(16) . . ?
O1 C9 N1 120.28(17) . . ?
O1 C9 C8 122.82(18) . . ?
N1 C9 C8 116.88(17) . . ?
C5 C6 C1 118.24(18) . . ?
C5 C6 C7 123.99(17) . . ?
C1 C6 C7 117.76(17) . . ?
N1 C1 C6 118.97(17) . . ?
N1 C1 C2 120.57(18) . . ?
C6 C1 C2 120.5(2) . . ?
C14 C15 C10 120.7(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C11 C10 C15 118.23(19) . . ?
C11 C10 C8 121.10(17) . . ?
C15 C10 C8 120.64(17) . . ?
C23 C18 C19 119.5(2) . . ?
C23 C18 C17 119.3(2) . . ?
C19 C18 C17 121.2(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
O2 C16 O3 124.80(17) . . ?
O2 C16 N2 126.00(17) . . ?
O3 C16 N2 109.19(17) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
O3 C17 C18 112.64(17) . . ?
O3 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
O3 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
H17B C17 H17A 107.8 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C18 C19 C20 118.0(3) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C22 C23 C18 122.1(3) . . ?
C22 C23 H23 119.0 . . ?
C18 C23 H23 119.0 . . ?
C21 C20 C19 117.7(3) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?

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
C9 C8 C7 N2 -179.14(16) . . . . ?
C10 C8 C7 N2 -2.7(3) . . . . ?
C9 C8 C7 C6 -0.4(3) . . . . ?
C10 C8 C7 C6 176.05(16) . . . . ?
C16 N2 C7 C8 -64.6(2) . . . . ?
C16 N2 C7 C6 116.63(19) . . . . ?
C1 N1 C9 O1 -173.43(18) . . . . ?
C1 N1 C9 C8 5.0(3) . . . . ?
C7 C8 C9 O1 175.26(18) . . . . ?
C10 C8 C9 O1 -1.5(3) . . . . ?
C7 C8 C9 N1 -3.1(3) . . . . ?
C10 C8 C9 N1 -179.85(16) . . . . ?
C8 C7 C6 C5 -178.58(18) . . . . ?
N2 C7 C6 C5 0.2(3) . . . . ?
C8 C7 C6 C1 2.4(3) . . . . ?
N2 C7 C6 C1 -178.85(15) . . . . ?
C9 N1 C1 C6 -3.1(3) . . . . ?
C9 N1 C1 C2 176.97(18) . . . . ?
C5 C6 C1 N1 -179.86(17) . . . . ?
C7 C6 C1 N1 -0.7(3) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?
C7 C6 C1 C2 179.19(16) . . . . ?
C1 C6 C5 C4 -0.1(3) . . . . ?
C7 C6 C5 C4 -179.12(18) . . . . ?
C14 C15 C10 C11 1.0(3) . . . . ?
C14 C15 C10 C8 179.18(18) . . . . ?
C7 C8 C10 C11 -58.3(3) . . . . ?
C9 C8 C10 C11 118.2(2) . . . . ?
C7 C8 C10 C15 123.6(2) . . . . ?
C9 C8 C10 C15 -59.9(2) . . . . ?
N1 C1 C2 C3 179.94(19) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C10 C15 C14 C13 -0.5(3) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
C8 C10 C11 C12 -178.84(19) . . . . ?
C17 O3 C16 O2 1.4(3) . . . . ?
C17 O3 C16 N2 -179.14(16) . . . . ?
C7 N2 C16 O2 -6.3(3) . . . . ?
C7 N2 C16 O3 174.33(16) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C16 O3 C17 C18 -93.4(2) . . . . ?
C23 C18 C17 O3 119.6(2) . . . . ?
C19 C18 C17 O3 -63.2(3) . . . . ?
C15 C14 C13 C12 -0.4(3) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?
C17 C18 C19 C20 -177.25(19) . . . . ?
C19 C18 C23 C22 -0.1(4) . . . . ?
C17 C18 C23 C22 177.1(2) . . . . ?
C22 C21 C20 C19 -1.2(4) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C20 C21 C22 C23 1.0(5) . . . . ?
C18 C23 C22 C21 -0.3(5) . . . . ?
C14 C13 C12 C11 0.7(4) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.86 2.16 2.948(2) 151.6 4_556
N1 H1 O1 0.86 1.94 2.791(2) 169.8 2_556

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        65.08
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.260
_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. 
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#######################################################################

data_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2038339'
loop_
_audit_author_name
_audit_author_address
'Jian-Qiang Zhao'
;Chengdu University
China
;
_audit_update_record             
;
2020-10-14 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Br N2 O4'
_chemical_formula_weight         467.31

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.1989(2)
_cell_length_b                   14.7652(12)
_cell_length_c                   16.2473(10)
_cell_angle_alpha                111.325(7)
_cell_angle_beta                 91.273(4)
_cell_angle_gamma                91.541(4)
_cell_volume                     1160.69(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    2209
_cell_measurement_theta_min      3.5093
_cell_measurement_theta_max      29.0966

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    1.800
_shelx_estimated_absorpt_T_min   0.572
_shelx_estimated_absorpt_T_max   0.633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      289(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            10518
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.516
_diffrn_reflns_theta_max         29.161
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5265
_reflns_number_gt                3146
_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       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013


_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)+(0.0813P)²+1.6077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5265
_refine_ls_number_parameters     279
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2120
_refine_ls_wR_factor_gt          0.1940
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.127
_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 0.05565(11) 0.16983(5) 0.65910(4) 0.0743(3) Uani 1 1 d . . . . .
O2 O 0.2381(6) -0.0654(3) 0.0173(2) 0.0550(9) Uani 1 1 d . . . . .
N1 N 0.0227(7) 0.0040(4) 0.1455(3) 0.0475(10) Uani 1 1 d . . . . .
N2 N 0.3617(8) 0.0852(3) 0.1054(3) 0.0512(10) Uani 1 1 d . . . . .
O3 O 0.2282(9) 0.1886(3) 0.2389(3) 0.0873(14) Uani 1 1 d . . . . .
O4 O 0.5320(10) 0.2322(3) 0.1629(3) 0.0935(16) Uani 1 1 d . U . . .
O1 O -0.1795(9) 0.1014(3) 0.2990(3) 0.0871(14) Uani 1 1 d . . . . .
C15 C 0.2034(8) 0.0028(4) 0.0853(3) 0.0454(11) Uani 1 1 d . . . . .
C5 C -0.4471(9) 0.1234(4) 0.4456(3) 0.0540(12) Uani 1 1 d . . . . .
C6 C -0.2649(9) 0.1119(4) 0.5036(3) 0.0536(12) Uani 1 1 d . . . . .
H6 H -0.1892 0.0522 0.4911 0.064 Uiso 1 1 calc R U . . .
C14 C -0.1555(8) -0.0708(4) 0.1392(3) 0.0440(10) Uani 1 1 d . . . . .
C10 C -0.5154(9) -0.1310(4) 0.1989(4) 0.0580(13) Uani 1 1 d . . . . .
H10 H -0.6336 -0.1220 0.2431 0.070 Uiso 1 1 calc R U . . .
C9 C -0.3338(8) -0.0563(4) 0.2079(3) 0.0485(11) Uani 1 1 d . . . . .
C7 C -0.5182(10) 0.0409(5) 0.3607(3) 0.0604(14) Uani 1 1 d . . . . .
H7A H -0.6896 0.0500 0.3409 0.072 Uiso 1 1 calc R U . . .
H7B H -0.5224 -0.0196 0.3715 0.072 Uiso 1 1 calc R U . . .
C13 C -0.1683(10) -0.1588(4) 0.0685(4) 0.0622(14) Uani 1 1 d . . . . .
H13 H -0.0509 -0.1700 0.0238 0.075 Uiso 1 1 calc R U . . .
C8 C -0.3305(9) 0.0332(4) 0.2880(3) 0.0546(12) Uani 1 1 d . . . . .
C1 C -0.1951(9) 0.1887(4) 0.5801(3) 0.0534(12) Uani 1 1 d . . . . .
C16 C 0.3603(11) 0.1711(5) 0.1751(4) 0.0657(15) Uani 1 1 d . . . . .
C12 C -0.3509(11) -0.2297(5) 0.0631(4) 0.0688(15) Uani 1 1 d . . . . .
H12 H -0.3559 -0.2879 0.0146 0.083 Uiso 1 1 calc R U . . .
C11 C -0.5267(11) -0.2166(5) 0.1281(4) 0.0701(16) Uani 1 1 d . . . . .
H11 H -0.6504 -0.2649 0.1238 0.084 Uiso 1 1 calc R U . . .
C2 C -0.3012(13) 0.2767(5) 0.6012(4) 0.0783(17) Uani 1 1 d . . . . .
H2A H -0.2506 0.3279 0.6529 0.094 Uiso 1 1 calc R U . . .
C18 C 0.6857(13) 0.3939(5) 0.2029(4) 0.0891(19) Uani 1 1 d D U . . .
C4 C -0.5579(14) 0.2120(6) 0.4661(4) 0.0841(19) Uani 1 1 d . . . . .
H4 H -0.6814 0.2211 0.4279 0.101 Uiso 1 1 calc R U . . .
C3 C -0.4850(16) 0.2884(6) 0.5445(5) 0.098(2) Uani 1 1 d . . . . .
H3 H -0.5622 0.3480 0.5585 0.118 Uiso 1 1 calc R U . . .
C17 C 0.5914(18) 0.3195(6) 0.2365(5) 0.113(2) Uani 1 1 d . U . . .
H17A H 0.7223 0.3080 0.2747 0.136 Uiso 1 1 calc R U . . .
H17B H 0.4389 0.3413 0.2704 0.136 Uiso 1 1 calc R U . . .
C20 C 0.713(2) 0.5605(10) 0.2125(7) 0.165(4) Uani 1 1 d D U . . .
H20 H 0.6648 0.6242 0.2413 0.198 Uiso 1 1 calc R U . . .
C21 C 0.879(2) 0.5397(7) 0.1426(7) 0.142(4) Uani 1 1 d D U . . .
H21 H 0.9385 0.5866 0.1212 0.171 Uiso 1 1 calc R U . . .
C23 C 0.8629(19) 0.3707(7) 0.1362(6) 0.146(4) Uani 1 1 d D U . . .
H23 H 0.9219 0.3079 0.1116 0.175 Uiso 1 1 calc R U . . .
C22 C 0.950(3) 0.4433(7) 0.1071(8) 0.178(5) Uani 1 1 d D U . . .
H22 H 1.0630 0.4264 0.0608 0.213 Uiso 1 1 calc R U . . .
C19 C 0.625(2) 0.4913(5) 0.2381(7) 0.140(3) Uani 1 1 d D U . . .
H19 H 0.5109 0.5091 0.2841 0.167 Uiso 1 1 calc R U . . .
H1 H 0.024(10) 0.050(4) 0.185(4) 0.056(18) Uiso 1 1 d . . . . .
H2 H 0.474(10) 0.087(4) 0.068(4) 0.061(15) Uiso 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
Br1 C1 1.905(5) . ?
O2 C15 1.215(5) . ?
N1 C15 1.368(6) . ?
N1 C14 1.396(6) . ?
N1 H1 0.75(5) . ?
N2 C16 1.360(7) . ?
N2 C15 1.381(6) . ?
N2 H2 0.86(6) . ?
O3 C16 1.208(6) . ?
O4 C16 1.321(7) . ?
O4 C17 1.424(8) . ?
O1 C8 1.218(6) . ?
C5 C4 1.374(8) . ?
C5 C6 1.379(7) . ?
C5 C7 1.501(8) . ?
C6 C1 1.377(7) . ?
C6 H6 0.9300 . ?
C14 C13 1.385(7) . ?
C14 C9 1.426(6) . ?
C10 C11 1.363(8) . ?
C10 C9 1.397(7) . ?
C10 H10 0.9300 . ?
C9 C8 1.478(7) . ?
C7 C8 1.523(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 C12 1.372(8) . ?
C13 H13 0.9300 . ?
C1 C2 1.354(8) . ?
C12 C11 1.375(8) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C2 C3 1.370(9) . ?
C2 H2A 0.9300 . ?
C18 C23 1.3893(10) . ?
C18 C19 1.3896(10) . ?
C18 C17 1.471(10) . ?
C4 C3 1.396(10) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C20 C19 1.313(14) . ?
C20 C21 1.3893(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.3895(10) . ?
C21 H21 0.9300 . ?
C23 C22 1.3899(10) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C19 H19 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
C15 N1 C14 126.6(5) . . ?
C15 N1 H1 115(4) . . ?
C14 N1 H1 119(4) . . ?
C16 N2 C15 130.0(4) . . ?
C16 N2 H2 111(4) . . ?
C15 N2 H2 118(4) . . ?
C16 O4 C17 116.5(5) . . ?
O2 C15 N1 125.0(5) . . ?
O2 C15 N2 118.2(4) . . ?
N1 C15 N2 116.7(4) . . ?
C4 C5 C6 118.8(5) . . ?
C4 C5 C7 120.9(5) . . ?
C6 C5 C7 120.3(5) . . ?
C1 C6 C5 120.0(5) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C13 C14 N1 122.7(4) . . ?
C13 C14 C9 118.3(4) . . ?
N1 C14 C9 118.9(4) . . ?
C11 C10 C9 122.8(5) . . ?
C11 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C10 C9 C14 117.9(5) . . ?
C10 C9 C8 119.3(4) . . ?
C14 C9 C8 122.8(4) . . ?
C5 C7 C8 112.6(4) . . ?
C5 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C5 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C12 C13 C14 121.3(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
O1 C8 C9 122.3(4) . . ?
O1 C8 C7 118.1(5) . . ?
C9 C8 C7 119.6(5) . . ?
C2 C1 C6 122.0(5) . . ?
C2 C1 Br1 119.1(4) . . ?
C6 C1 Br1 118.8(4) . . ?
O3 C16 O4 125.2(6) . . ?
O3 C16 N2 125.9(5) . . ?
O4 C16 N2 108.8(4) . . ?
C13 C12 C11 121.3(6) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C10 C11 C12 118.4(5) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C1 C2 C3 118.3(6) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C23 C18 C19 115.2(8) . . ?
C23 C18 C17 120.3(7) . . ?
C19 C18 C17 124.3(7) . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 C4 120.9(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O4 C17 C18 108.3(6) . . ?
O4 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
O4 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C19 C20 C21 120.7(12) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 114.9(11) . . ?
C22 C21 H21 122.5 . . ?
C20 C21 H21 122.5 . . ?
C18 C23 C22 118.6(9) . . ?
C18 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C21 C22 C23 124.4(11) . . ?
C21 C22 H22 117.8 . . ?
C23 C22 H22 117.8 . . ?
C18 C19 C20 126.1(10) . . ?
C18 C19 H19 117.0 . . ?
C20 C19 H19 117.0 . . ?

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
C14 N1 C15 O2 -1.4(8) . . . . ?
C14 N1 C15 N2 -179.6(4) . . . . ?
C16 N2 C15 O2 178.3(5) . . . . ?
C16 N2 C15 N1 -3.4(8) . . . . ?
C4 C5 C6 C1 -0.7(7) . . . . ?
C7 C5 C6 C1 178.1(4) . . . . ?
C15 N1 C14 C13 0.6(7) . . . . ?
C15 N1 C14 C9 -178.9(4) . . . . ?
C11 C10 C9 C14 0.6(8) . . . . ?
C11 C10 C9 C8 -178.4(5) . . . . ?
C13 C14 C9 C10 -1.4(7) . . . . ?
N1 C14 C9 C10 178.1(4) . . . . ?
C13 C14 C9 C8 177.5(5) . . . . ?
N1 C14 C9 C8 -3.0(7) . . . . ?
C4 C5 C7 C8 96.1(6) . . . . ?
C6 C5 C7 C8 -82.7(6) . . . . ?
N1 C14 C13 C12 -178.0(5) . . . . ?
C9 C14 C13 C12 1.4(8) . . . . ?
C10 C9 C8 O1 -178.9(5) . . . . ?
C14 C9 C8 O1 2.3(8) . . . . ?
C10 C9 C8 C7 2.2(7) . . . . ?
C14 C9 C8 C7 -176.7(4) . . . . ?
C5 C7 C8 O1 -13.5(8) . . . . ?
C5 C7 C8 C9 165.5(5) . . . . ?
C5 C6 C1 C2 0.4(8) . . . . ?
C5 C6 C1 Br1 179.6(3) . . . . ?
C17 O4 C16 O3 9.9(11) . . . . ?
C17 O4 C16 N2 -168.7(7) . . . . ?
C15 N2 C16 O3 7.2(10) . . . . ?
C15 N2 C16 O4 -174.2(5) . . . . ?
C14 C13 C12 C11 -0.6(9) . . . . ?
C9 C10 C11 C12 0.3(9) . . . . ?
C13 C12 C11 C10 -0.3(10) . . . . ?
C6 C1 C2 C3 0.5(9) . . . . ?
Br1 C1 C2 C3 -178.7(5) . . . . ?
C6 C5 C4 C3 0.2(9) . . . . ?
C7 C5 C4 C3 -178.7(6) . . . . ?
C1 C2 C3 C4 -1.1(11) . . . . ?
C5 C4 C3 C2 0.8(12) . . . . ?
C16 O4 C17 C18 -155.1(7) . . . . ?
C23 C18 C17 O4 -44.6(11) . . . . ?
C19 C18 C17 O4 140.7(9) . . . . ?
C19 C20 C21 C22 -3.1(19) . . . . ?
C19 C18 C23 C22 -3.9(16) . . . . ?
C17 C18 C23 C22 -179.1(11) . . . . ?
C20 C21 C22 C23 1(2) . . . . ?
C18 C23 C22 C21 3(2) . . . . ?
C23 C18 C19 C20 2.0(17) . . . . ?
C17 C18 C19 C20 177.0(11) . . . . ?
C21 C20 C19 C18 2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.75(5) 2.15(6) 2.764(6) 140(5) .
N1 H1 O1 0.75(5) 2.05(6) 2.643(6) 136(6) .
N2 H2 O2 0.86(6) 2.01(6) 2.860(5) 168(5) 2_655

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.013 0.500 0.500 132 19 ' '
2 0.500 0.500 0.000 26 1 ' '
_platon_squeeze_details          
;
;

_refine_diff_density_max         0.723
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.093

_shelxl_version_number           2013-4



