# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1957077'
loop_
_audit_author_name
_audit_author_address
'Gulsum Gundogdu'
;Bilkent University
Turkey
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;
_audit_creation_date             2018-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        
1-((4S,5S)-2-methyl-5-nitro-4-phenyl-4,5-dihydrofuran-3-yl)ethan-1-one
_chemical_name_common            'C13 H13 N O4'
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.4498(3)
_cell_length_b                   8.4498(4)
_cell_length_c                   11.1317(8)
_cell_angle_alpha                107.098(8)
_cell_angle_beta                 91.985(7)
_cell_angle_gamma                109.401(8)
_cell_volume                     624.89(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11433
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      28.20
_cell_measurement_temperature    293
_exptl_absorpt_coefficient_mu    0.098
_exptl_crystal_colour            dull
_exptl_crystal_colour_lustre     dull
_exptl_crystal_density_diffrn    1.3139
_exptl_crystal_F_000             260.0
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.187
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16255
_diffrn_reflns_theta_full        28.2466
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         3.20
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_device_type  'Rigaku RAXIS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2335
_reflns_number_total             3088
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.2464
_refine_diff_density_min         -0.2846
_refine_diff_density_rms         0.0689
_refine_ls_d_res_high            0.7509
_refine_ls_d_res_low             6.3743
_refine_ls_goodness_of_fit_ref   1.0306
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.0306
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0663P)²+0.1534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1372
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C1(H1), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13c,H13b,H13a), C11(H11b,H11a,H11c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O 0.29078(14) 0.82213(14) 0.63903(10) 0.0505(3) Uani 1.000000 .
O2 O 0.77804(16) 0.67120(18) 0.65475(12) 0.0644(3) Uani 1.000000 .
O3 O 0.2631(3) 1.0154(2) 0.95708(15) 0.0933(5) Uani 1.000000 .
O4 O 0.4397(3) 1.11761(18) 0.83027(18) 0.1003(6) Uani 1.000000 .
N1 N 0.3214(2) 1.00007(18) 0.85524(15) 0.0629(4) Uani 1.000000 .
C1 C -0.0551(2) 0.1644(2) 0.73764(18) 0.0654(5) Uani 1.000000 .
H1 H -0.1370(2) 0.0486(2) 0.72486(18) 0.0784(6) Uiso 1.000000 R
C2 C -0.0148(2) 0.2237(2) 0.63543(16) 0.0600(4) Uani 1.000000 .
H2 H -0.0706(2) 0.1481(2) 0.55367(16) 0.0720(5) Uiso 1.000000 R
C3 C 0.1085(2) 0.39561(19) 0.65367(13) 0.0480(3) Uani 1.000000 .
H3 H 0.1343(2) 0.43514(19) 0.58426(13) 0.0576(4) Uiso 1.000000 R
C4 C 0.19364(17) 0.50895(17) 0.77545(12) 0.0389(3) Uani 1.000000 .
C5 C 0.1504(2) 0.4487(2) 0.87777(14) 0.0513(4) Uani 1.000000 .
H5 H 0.2051(2) 0.5240(2) 0.95980(14) 0.0615(4) Uiso 1.000000 R
C6 C 0.0261(3) 0.2766(2) 0.85869(17) 0.0638(4) Uani 1.000000 .
H6 H -0.0024(3) 0.2372(2) 0.92788(17) 0.0765(5) Uiso 1.000000 R
C7 C 0.33429(18) 0.69613(17) 0.79725(12) 0.0391(3) Uani 1.000000 .
H7 H 0.39351(18) 0.75179(17) 0.88653(12) 0.0469(3) Uiso 1.000000 R
C8 C 0.48848(17) 0.70534(16) 0.71110(12) 0.0387(3) Uani 1.000000 .
C9 C 0.44863(18) 0.77077(17) 0.62139(13) 0.0418(3) Uani 1.000000 .
C10 C 0.2391(2) 0.81273(18) 0.75694(14) 0.0450(3) Uani 1.000000 .
H10 H 0.0989(2) 0.76267(18) 0.75168(14) 0.0540(4) Uiso 1.000000 R
C11 C 0.5316(2) 0.7910(2) 0.50607(15) 0.0560(4) Uani 1.000000 .
H11b H 0.4299(3) 0.7492(17) 0.4363(3) 0.0840(6) Uiso 1.000000 GR
H11a H 0.6050(16) 0.9139(3) 0.5204(5) 0.0840(6) Uiso 1.000000 GR
H11c H 0.6139(15) 0.7232(15) 0.4864(7) 0.0840(6) Uiso 1.000000 GR
C12 C 0.65159(18) 0.64636(18) 0.72137(14) 0.0433(3) Uani 1.000000 .
C13 C 0.6598(2) 0.5574(2) 0.81861(16) 0.0566(4) Uani 1.000000 .
H13c H 0.5439(9) 0.4560(10) 0.8035(8) 0.0850(6) Uiso 1.000000 GR
H13b H 0.7685(11) 0.5200(16) 0.8126(8) 0.0850(6) Uiso 1.000000 GR
H13a H 0.6723(19) 0.6392(6) 0.90197(17) 0.0850(6) Uiso 1.000000 GR


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 C9 1.3838(16) . ?
O1 C10 1.3976(17) . ?
O2 C12 1.2206(18) . ?
O3 N1 1.215(2) . ?
O4 N1 1.199(2) . ?
N1 C10 1.539(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.375(3) . ?
C2 C3 1.386(2) . ?
C3 C4 1.3894(19) . ?
C4 C5 1.3848(19) . ?
C4 C7 1.5212(17) . ?
C5 C6 1.388(2) . ?
C7 C8 1.5186(18) . ?
C7 C10 1.5418(18) . ?
C8 C9 1.3432(18) . ?
C8 C12 1.4711(17) . ?
C9 C11 1.474(2) . ?
C12 C13 1.498(2) . ?

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
C10 O1 C9 107.88(10) . . ?
O4 N1 O3 124.41(17) . . ?
C10 N1 O3 115.46(14) . . ?
C10 N1 O4 120.09(16) . . ?
C6 C1 C2 119.86(15) . . ?
C3 C2 C1 120.38(15) . . ?
C4 C3 C2 120.14(14) . . ?
C5 C4 C3 119.05(13) . . ?
C7 C4 C3 121.00(12) . . ?
C7 C4 C5 119.95(12) . . ?
C6 C5 C4 120.43(14) . . ?
C5 C6 C1 120.13(15) . . ?
C8 C7 C4 113.71(10) . . ?
C10 C7 C4 112.47(10) . . ?
C10 C7 C8 99.41(10) . . ?
C9 C8 C7 109.03(11) . . ?
C12 C8 C7 125.55(11) . . ?
C12 C8 C9 125.39(13) . . ?
C8 C9 O1 112.41(12) . . ?
C11 C9 O1 113.99(12) . . ?
C11 C9 C8 133.53(13) . . ?
N1 C10 O1 108.82(12) . . ?
C7 C10 O1 107.59(11) . . ?
C7 C10 N1 108.01(11) . . ?
C8 C12 O2 121.50(13) . . ?
C13 C12 O2 120.79(13) . . ?
C13 C12 C8 117.70(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1957076'
loop_
_audit_author_name
_audit_author_address
'Gulsum Gundogdu'
;Bilkent University
Turkey
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        (Z)-1-(2-bromo-2-nitrovinyl)-4-methylbenzene
_chemical_name_common            'C9 H8 Br N O2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 Br N O2'
_chemical_formula_sum            'C9 H8 Br N O2'
_chemical_formula_weight         242.07

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'
Br Br -0.2901 2.4595 '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 1 21/a 1'
_space_group_name_Hall           '-P 2yab'

_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.
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   6.8836(13)
_cell_length_b                   14.397(3)
_cell_length_c                   9.6929(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.332(7)
_cell_angle_gamma                90
_cell_volume                     957.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    5891
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      28.30
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_F_000             480.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.750
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.065
_exptl_absorpt_correction_T_max  0.426
_diffrn_ambient_temperature      303(2)
_diffrn_measurement_device_type  'Rigaku RAXIS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_source                   'Rotating Anode'
_diffrn_reflns_number            24386
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.1012
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.288
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2379
_reflns_number_gt                1289
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.1000P)²] 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         2379
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1830
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
Br1 Br 0.49599(7) 0.31835(4) 0.76465(6) 0.1009(3) Uani 1 1 d . . . . .
O1 O 0.1543(6) 0.4012(3) 0.8561(4) 0.1054(11) Uani 1 1 d . . . . .
O2 O 0.0045(5) 0.4476(3) 0.6676(5) 0.1035(12) Uani 1 1 d . . . . .
N1 N 0.1424(6) 0.4130(3) 0.7326(5) 0.0777(10) Uani 1 1 d . . . . .
C3 C 0.7589(6) 0.3420(3) 0.3398(5) 0.0772(12) Uani 1 1 d . . . . .
H3 H 0.884163 0.318908 0.359527 0.093 Uiso 1 1 calc R U . . .
C1 C 0.8356(9) 0.3506(4) 0.0912(6) 0.1119(18) Uani 1 1 d . . . . .
H1A H 0.965806 0.340833 0.131261 0.168 Uiso 1 1 calc R U . . .
H1B H 0.832476 0.404944 0.033689 0.168 Uiso 1 1 calc R U . . .
H1C H 0.794822 0.297588 0.036231 0.168 Uiso 1 1 calc R U . . .
C6 C 0.3915(6) 0.4113(3) 0.2837(5) 0.0737(11) Uani 1 1 d . . . . .
H6 H 0.267925 0.435948 0.262642 0.088 Uiso 1 1 calc R U . . .
C8 C 0.3109(6) 0.4041(3) 0.5224(5) 0.0674(10) Uani 1 1 d . . . . .
H8 H 0.199463 0.435553 0.488238 0.081 Uiso 1 1 calc R U . . .
C9 C 0.3117(6) 0.3831(3) 0.6550(5) 0.0679(10) Uani 1 1 d . . . . .
C4 C 0.6393(6) 0.3531(3) 0.4464(5) 0.0738(11) Uani 1 1 d . . . . .
H4 H 0.684305 0.337498 0.536279 0.089 Uiso 1 1 calc R U . . .
C2 C 0.6990(7) 0.3638(3) 0.2055(5) 0.0784(12) Uani 1 1 d . . . . .
C7 C 0.5152(7) 0.3983(3) 0.1790(6) 0.0829(13) Uani 1 1 d . . . . .
H7 H 0.471992 0.413530 0.088599 0.099 Uiso 1 1 calc R U . . .
C5 C 0.4492(6) 0.3880(3) 0.4197(5) 0.0639(10) 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
Br1 C9 1.845(4) . ?
O1 N1 1.206(5) . ?
O2 N1 1.207(5) . ?
N1 C9 1.497(5) . ?
C3 C2 1.372(7) . ?
C3 C4 1.378(6) . ?
C1 C2 1.519(6) . ?
C6 C7 1.386(7) . ?
C6 C5 1.388(6) . ?
C8 C9 1.320(6) . ?
C8 C5 1.447(6) . ?
C4 C5 1.407(6) . ?
C2 C7 1.366(7) . ?

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
O1 N1 O2 124.6(4) . . ?
O1 N1 C9 117.5(4) . . ?
O2 N1 C9 117.9(4) . . ?
C2 C3 C4 122.0(4) . . ?
C7 C6 C5 121.0(4) . . ?
C9 C8 C5 132.7(4) . . ?
C8 C9 N1 118.5(4) . . ?
C8 C9 Br1 129.0(3) . . ?
N1 C9 Br1 112.5(3) . . ?
C3 C4 C5 120.2(4) . . ?
C7 C2 C3 118.0(4) . . ?
C7 C2 C1 121.6(5) . . ?
C3 C2 C1 120.3(5) . . ?
C2 C7 C6 121.5(5) . . ?
C6 C5 C4 117.2(4) . . ?
C6 C5 C8 117.3(4) . . ?
C4 C5 C8 125.5(4) . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.105

