# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_gwg-1
_database_code_depnum_ccdc_archive 'CCDC 1536616'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Br N O5'
_chemical_formula_weight         370.20

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5887(8)
_cell_length_b                   10.3821(10)
_cell_length_c                   10.6032(8)
_cell_angle_alpha                96.304(7)
_cell_angle_beta                 112.149(8)
_cell_angle_gamma                105.649(8)
_cell_volume                     819.19(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1680
_cell_measurement_theta_min      4.1750
_cell_measurement_theta_max      25.6760

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    2.530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4070
_diffrn_standards_number         6916
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6669
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3617
_reflns_number_gt                2247
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0484P)²+0.3348P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3617
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.005
_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
Br1 Br 0.12591(7) 0.37743(5) -0.38005(5) 0.0828(2) Uani 1 1 d . . .
C1 C 0.2439(5) 0.5044(4) -0.2032(4) 0.0519(10) Uani 1 1 d . . .
C2 C 0.3748(7) 0.6245(5) -0.1806(5) 0.0727(13) Uani 1 1 d . . .
H2 H 0.4064 0.6450 -0.2528 0.087 Uiso 1 1 calc R . .
C3 C 0.4603(6) 0.7156(5) -0.0518(4) 0.0673(13) Uani 1 1 d . . .
H3 H 0.5500 0.7971 -0.0376 0.081 Uiso 1 1 calc R . .
C4 C 0.4157(4) 0.6886(4) 0.0561(3) 0.0383(8) Uani 1 1 d . . .
C5 C 0.2838(6) 0.5677(4) 0.0306(4) 0.0648(12) Uani 1 1 d . . .
H5 H 0.2508 0.5471 0.1021 0.078 Uiso 1 1 calc R . .
C6 C 0.1974(6) 0.4747(5) -0.0988(5) 0.0724(13) Uani 1 1 d . . .
H6 H 0.1083 0.3926 -0.1135 0.087 Uiso 1 1 calc R . .
C7 C 0.5048(4) 0.7840(4) 0.2025(3) 0.0396(8) Uani 1 1 d . . .
H7 H 0.5468 0.7294 0.2695 0.048 Uiso 1 1 calc R . .
C8 C 0.6682(4) 0.9032(4) 0.2220(4) 0.0464(9) Uani 1 1 d . . .
H8A H 0.7558 0.8673 0.2091 0.056 Uiso 1 1 calc R . .
H8B H 0.6334 0.9555 0.1522 0.056 Uiso 1 1 calc R . .
C9 C 0.3721(4) 0.8352(3) 0.2374(3) 0.0365(8) Uani 1 1 d . . .
C10 C 0.3277(5) 0.8063(4) 0.3416(4) 0.0467(9) Uani 1 1 d . . .
H10 H 0.2453 0.8433 0.3531 0.056 Uiso 1 1 calc R . .
C11 C 0.3932(6) 0.7226(5) 0.4416(4) 0.0691(13) Uani 1 1 d . . .
H11A H 0.4681 0.6820 0.4157 0.104 Uiso 1 1 calc R . .
H11B H 0.2933 0.6512 0.4390 0.104 Uiso 1 1 calc R . .
H11C H 0.4605 0.7805 0.5347 0.104 Uiso 1 1 calc R . .
C12 C 0.2930(4) 0.9213(4) 0.1511(3) 0.0393(8) Uani 1 1 d . . .
C13 C 0.1521(5) 0.9707(4) 0.1744(4) 0.0421(8) Uani 1 1 d . . .
C14 C 0.0863(6) 1.1674(5) 0.2419(5) 0.0616(11) Uani 1 1 d . . .
H14A H -0.0323 1.1200 0.1674 0.074 Uiso 1 1 calc R . .
H14B H 0.0810 1.1607 0.3309 0.074 Uiso 1 1 calc R . .
C15 C 0.1468(9) 1.3111(6) 0.2375(7) 0.106(2) Uani 1 1 d . . .
H15A H 0.2658 1.3564 0.3094 0.159 Uiso 1 1 calc R . .
H15B H 0.0683 1.3552 0.2527 0.159 Uiso 1 1 calc R . .
H15C H 0.1462 1.3167 0.1476 0.159 Uiso 1 1 calc R . .
N1 N 0.7483(4) 0.9948(4) 0.3650(4) 0.0548(9) Uani 1 1 d . . .
O1 O 0.7825(5) 0.9450(4) 0.4654(3) 0.0865(10) Uani 1 1 d . . .
O2 O 0.7724(6) 1.1159(4) 0.3740(4) 0.0964(11) Uani 1 1 d . . .
O3 O 0.3286(3) 0.9538(3) 0.0563(3) 0.0555(7) Uani 1 1 d . . .
O4 O 0.0036(4) 0.8951(3) 0.1422(3) 0.0680(8) Uani 1 1 d . . .
O5 O 0.2124(3) 1.1044(3) 0.2246(3) 0.0530(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0894(4) 0.0753(4) 0.0590(3) -0.0160(2) 0.0102(3) 0.0340(3)
C1 0.056(2) 0.047(2) 0.048(2) -0.0004(18) 0.0153(19) 0.024(2)
C2 0.094(4) 0.071(3) 0.053(2) 0.006(2) 0.043(3) 0.015(3)
C3 0.080(3) 0.058(3) 0.058(2) 0.000(2) 0.044(2) -0.003(2)
C4 0.0397(18) 0.040(2) 0.0424(18) 0.0095(15) 0.0209(16) 0.0190(16)
C5 0.083(3) 0.048(3) 0.059(2) 0.007(2) 0.042(2) 0.000(2)
C6 0.083(3) 0.048(3) 0.066(3) 0.000(2) 0.034(3) -0.005(2)
C7 0.0376(19) 0.045(2) 0.0399(18) 0.0096(16) 0.0189(16) 0.0152(17)
C8 0.0349(19) 0.059(2) 0.0438(19) -0.0005(17) 0.0205(16) 0.0121(18)
C9 0.0315(17) 0.042(2) 0.0356(17) 0.0050(15) 0.0166(15) 0.0101(15)
C10 0.042(2) 0.056(2) 0.046(2) 0.0106(18) 0.0231(18) 0.0165(18)
C11 0.083(3) 0.087(4) 0.061(3) 0.037(3) 0.043(3) 0.040(3)
C12 0.0322(18) 0.045(2) 0.0398(18) 0.0063(16) 0.0185(16) 0.0094(16)
C13 0.034(2) 0.048(2) 0.0438(19) 0.0100(17) 0.0165(16) 0.0135(18)
C14 0.063(3) 0.067(3) 0.069(3) 0.014(2) 0.031(2) 0.039(2)
C15 0.135(5) 0.067(4) 0.162(6) 0.045(4) 0.090(5) 0.058(4)
N1 0.0396(18) 0.065(3) 0.053(2) -0.0002(18) 0.0193(16) 0.0120(17)
O1 0.088(2) 0.103(3) 0.0489(18) 0.0074(18) 0.0138(17) 0.029(2)
O2 0.128(3) 0.060(2) 0.087(2) -0.0064(19) 0.048(2) 0.018(2)
O3 0.0601(17) 0.071(2) 0.0597(16) 0.0319(15) 0.0388(15) 0.0336(15)
O4 0.0411(16) 0.0622(19) 0.100(2) 0.0064(17) 0.0346(16) 0.0148(15)
O5 0.0470(15) 0.0500(17) 0.0659(17) 0.0086(13) 0.0261(13) 0.0212(13)

_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 1.893(4) . ?
C1 C6 1.350(5) . ?
C1 C2 1.361(6) . ?
C2 C3 1.373(6) . ?
C3 C4 1.371(5) . ?
C4 C5 1.363(5) . ?
C4 C7 1.528(5) . ?
C5 C6 1.386(6) . ?
C7 C9 1.523(4) . ?
C7 C8 1.527(5) . ?
C8 N1 1.490(5) . ?
C9 C10 1.337(4) . ?
C9 C12 1.461(5) . ?
C10 C11 1.488(5) . ?
C12 O3 1.212(4) . ?
C12 C13 1.524(4) . ?
C13 O4 1.196(4) . ?
C13 O5 1.311(4) . ?
C14 C15 1.454(7) . ?
C14 O5 1.463(4) . ?
N1 O2 1.204(5) . ?
N1 O1 1.206(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
C6 C1 C2 120.0(4) . . ?
C6 C1 Br1 119.4(3) . . ?
C2 C1 Br1 120.6(3) . . ?
C1 C2 C3 120.2(4) . . ?
C4 C3 C2 121.2(4) . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 C7 118.2(3) . . ?
C3 C4 C7 124.4(3) . . ?
C4 C5 C6 121.9(4) . . ?
C1 C6 C5 119.3(4) . . ?
C9 C7 C8 111.6(3) . . ?
C9 C7 C4 111.5(3) . . ?
C8 C7 C4 112.0(3) . . ?
N1 C8 C7 110.2(3) . . ?
C10 C9 C12 119.7(3) . . ?
C10 C9 C7 123.5(3) . . ?
C12 C9 C7 116.8(3) . . ?
C9 C10 C11 128.3(3) . . ?
O3 C12 C9 123.7(3) . . ?
O3 C12 C13 116.2(3) . . ?
C9 C12 C13 120.1(3) . . ?
O4 C13 O5 126.1(3) . . ?
O4 C13 C12 122.5(3) . . ?
O5 C13 C12 111.3(3) . . ?
C15 C14 O5 108.3(4) . . ?
O2 N1 O1 123.1(4) . . ?
O2 N1 C8 117.7(4) . . ?
O1 N1 C8 119.2(4) . . ?
C13 O5 C14 117.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.077
