# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_exp_5932
_audit_block_doi                 10.5517/ccdc.csd.cc2198zm
_database_code_depnum_ccdc_archive 'CCDC 1885760'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment, South China Normal University
China
;
_audit_update_record             
;
2018-12-18 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 Br N2 O5 S'
_chemical_formula_sum            'C12 H13 Br N2 O5 S'
_chemical_formula_weight         377.21
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4406(6)
_cell_length_b                   12.7982(11)
_cell_length_c                   14.3406(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.550(7)
_cell_angle_gamma                90
_cell_volume                     1492.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1758
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23.8830
_cell_measurement_theta_min      3.6650
_shelx_estimated_absorpt_T_max   0.759
_shelx_estimated_absorpt_T_min   0.686
_exptl_absorpt_coefficient_mu    2.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7339
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.285
_diffrn_reflns_theta_min         3.351
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  12.00   1.00    7.50    --   15.49 -38.00 120.00   26
  2  ω    -20.00  23.00   1.00    7.50    --  -16.12 -99.00 120.00   43
  3  ω     -3.00  82.00   1.00    7.50    --   15.49  38.00 150.00   85
  4  ω    -37.00  38.00   1.00    7.50    --  -16.12  77.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0680936000
_diffrn_orient_matrix_UB_12      -0.0127796000
_diffrn_orient_matrix_UB_13      0.0394872000
_diffrn_orient_matrix_UB_21      -0.0142564000
_diffrn_orient_matrix_UB_22      -0.0538224000
_diffrn_orient_matrix_UB_23      -0.0105552000
_diffrn_orient_matrix_UB_31      0.0527605000
_diffrn_orient_matrix_UB_32      0.0019854000
_diffrn_orient_matrix_UB_33      -0.0310756000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2197
_reflns_number_total             3418
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+1.3078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2A,H2B)
2.b Ternary CH refined with riding coordinates:
 C3(H3)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.40426(5) 0.62200(4) 0.66727(3) 0.06134(18) Uani 1 1 d . . . . .
S1 S 0.96546(11) 0.71659(8) 0.63595(7) 0.0427(3) Uani 1 1 d . . . . .
O1 O 0.6909(4) 0.4000(2) 0.59640(19) 0.0502(7) Uani 1 1 d . . . . .
O2 O 0.9448(3) 0.4526(2) 0.69444(18) 0.0537(8) Uani 1 1 d . . . . .
O3 O 0.9920(3) 0.6449(2) 0.5648(2) 0.0539(8) Uani 1 1 d . . . . .
O4 O 1.0971(3) 0.7427(2) 0.7186(2) 0.0585(8) Uani 1 1 d . . . . .
O5 O 0.4281(4) 0.3866(3) 0.5984(2) 0.0766(10) Uani 1 1 d . . . . .
N1 N 0.8163(4) 0.6648(3) 0.6788(2) 0.0470(8) Uani 1 1 d . . . . .
N2 N 0.7672(4) 0.7235(3) 0.7498(3) 0.0628(11) Uani 1 1 d . . . . .
H2A H 0.6866 0.7024 0.7710 0.075 Uiso 1 1 d R . . . .
H2B H 0.8180 0.7803 0.7718 0.075 Uiso 1 1 d R . . . .
C1 C 0.5781(4) 0.5475(3) 0.6426(2) 0.0382(9) Uani 1 1 d . . . . .
C2 C 0.5510(5) 0.4379(4) 0.6114(3) 0.0491(11) Uani 1 1 d . . . . .
C3 C 0.8172(5) 0.4798(3) 0.6171(3) 0.0385(9) Uani 1 1 d . . . . .
H3 H 0.8561 0.4947 0.5600 0.046 Uiso 1 1 calc R . . . .
C4 C 1.0649(6) 0.3856(4) 0.6700(4) 0.0747(15) Uani 1 1 d . . . . .
H4A H 1.1103 0.4200 0.6236 0.112 Uiso 1 1 calc GR . . . .
H4B H 1.0132 0.3215 0.6430 0.112 Uiso 1 1 calc GR . . . .
H4C H 1.1512 0.3705 0.7273 0.112 Uiso 1 1 calc GR . . . .
C5 C 0.7314(4) 0.5740(3) 0.6453(2) 0.0342(8) Uani 1 1 d . . . . .
C6 C 0.8793(4) 0.8328(3) 0.5806(3) 0.0392(9) Uani 1 1 d . . . . .
C7 C 0.9168(5) 0.9262(3) 0.6290(3) 0.0521(11) Uani 1 1 d . . . . .
H7 H 0.9903 0.9280 0.6903 0.062 Uiso 1 1 calc R . . . .
C8 C 0.8450(6) 1.0166(4) 0.5863(3) 0.0589(12) Uani 1 1 d . . . . .
H8 H 0.8688 1.0792 0.6200 0.071 Uiso 1 1 calc R . . . .
C9 C 0.7383(5) 1.0170(4) 0.4945(3) 0.0533(11) Uani 1 1 d . . . . .
C10 C 0.7048(6) 0.9226(4) 0.4465(3) 0.0626(13) Uani 1 1 d . . . . .
H10 H 0.6341 0.9213 0.3844 0.075 Uiso 1 1 calc R . . . .
C11 C 0.7730(5) 0.8303(4) 0.4881(3) 0.0536(11) Uani 1 1 d . . . . .
H11 H 0.7484 0.7675 0.4548 0.064 Uiso 1 1 calc R . . . .
C12 C 0.6607(7) 1.1172(4) 0.4497(4) 0.0829(17) Uani 1 1 d . . . . .
H12A H 0.6466 1.1633 0.4997 0.124 Uiso 1 1 calc GR . . . .
H12B H 0.5555 1.1024 0.4057 0.124 Uiso 1 1 calc GR . . . .
H12C H 0.7305 1.1497 0.4152 0.124 Uiso 1 1 calc GR . . . .


_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 1.862(4) . ?
S1 O3 1.434(3) . ?
S1 O4 1.430(3) . ?
S1 N1 1.679(3) . ?
S1 C6 1.750(4) . ?
O1 C2 1.346(5) . ?
O1 C3 1.448(4) . ?
O2 C3 1.368(4) . ?
O2 C4 1.441(5) . ?
O5 C2 1.199(5) . ?
N1 N2 1.413(4) . ?
N1 C5 1.382(5) . ?
N2 H2A 0.8597 . ?
N2 H2B 0.8598 . ?
C1 C2 1.472(6) . ?
C1 C5 1.328(5) . ?
C3 H3 0.9800 . ?
C3 C5 1.517(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C7 1.376(5) . ?
C6 C11 1.388(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(6) . ?
C9 C10 1.381(6) . ?
C9 C12 1.503(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(6) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
O3 S1 N1 106.47(16) . . ?
O3 S1 C6 110.26(18) . . ?
O4 S1 O3 120.31(18) . . ?
O4 S1 N1 106.33(18) . . ?
O4 S1 C6 108.28(19) . . ?
N1 S1 C6 103.89(17) . . ?
C2 O1 C3 110.0(3) . . ?
C3 O2 C4 114.0(3) . . ?
N2 N1 S1 116.6(3) . . ?
C5 N1 S1 125.1(3) . . ?
C5 N1 N2 118.2(3) . . ?
N1 N2 H2A 120.0 . . ?
N1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C2 C1 Br1 118.7(3) . . ?
C5 C1 Br1 132.5(3) . . ?
C5 C1 C2 108.8(4) . . ?
O1 C2 C1 108.7(3) . . ?
O5 C2 O1 122.5(4) . . ?
O5 C2 C1 128.8(4) . . ?
O1 C3 H3 111.1 . . ?
O1 C3 C5 103.8(3) . . ?
O2 C3 O1 111.3(3) . . ?
O2 C3 H3 111.1 . . ?
O2 C3 C5 108.3(3) . . ?
C5 C3 H3 111.1 . . ?
O2 C4 H4A 109.5 . . ?
O2 C4 H4B 109.5 . . ?
O2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C3 121.4(3) . . ?
C1 C5 N1 129.4(4) . . ?
C1 C5 C3 108.7(3) . . ?
C7 C6 S1 119.8(3) . . ?
C7 C6 C11 120.3(4) . . ?
C11 C6 S1 119.8(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.5(4) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.7(4) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 117.7(4) . . ?
C8 C9 C12 120.6(5) . . ?
C10 C9 C12 121.7(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.9(4) . . ?
C11 C10 H10 119.1 . . ?
C6 C11 H11 120.6 . . ?
C10 C11 C6 118.8(4) . . ?
C10 C11 H11 120.6 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
Br1 C1 C2 O1 179.1(2) . . . . ?
Br1 C1 C2 O5 0.3(6) . . . . ?
Br1 C1 C5 N1 8.3(6) . . . . ?
Br1 C1 C5 C3 -179.6(3) . . . . ?
S1 N1 C5 C1 -149.7(3) . . . . ?
S1 N1 C5 C3 39.1(5) . . . . ?
S1 C6 C7 C8 -178.1(3) . . . . ?
S1 C6 C11 C10 179.1(3) . . . . ?
O1 C3 C5 N1 174.3(3) . . . . ?
O1 C3 C5 C1 1.4(4) . . . . ?
O2 C3 C5 N1 55.9(4) . . . . ?
O2 C3 C5 C1 -116.9(3) . . . . ?
O3 S1 N1 N2 -179.1(3) . . . . ?
O3 S1 N1 C5 -3.8(4) . . . . ?
O3 S1 C6 C7 -147.2(3) . . . . ?
O3 S1 C6 C11 32.9(4) . . . . ?
O4 S1 N1 N2 51.5(3) . . . . ?
O4 S1 N1 C5 -133.2(3) . . . . ?
O4 S1 C6 C7 -13.7(4) . . . . ?
O4 S1 C6 C11 166.4(3) . . . . ?
N1 S1 C6 C7 99.0(3) . . . . ?
N1 S1 C6 C11 -80.8(3) . . . . ?
N2 N1 C5 C1 25.5(6) . . . . ?
N2 N1 C5 C3 -145.7(3) . . . . ?
C2 O1 C3 O2 115.1(3) . . . . ?
C2 O1 C3 C5 -1.2(4) . . . . ?
C2 C1 C5 N1 -173.2(4) . . . . ?
C2 C1 C5 C3 -1.1(4) . . . . ?
C3 O1 C2 O5 179.4(4) . . . . ?
C3 O1 C2 C1 0.6(4) . . . . ?
C4 O2 C3 O1 83.9(4) . . . . ?
C4 O2 C3 C5 -162.6(4) . . . . ?
C5 C1 C2 O1 0.4(4) . . . . ?
C5 C1 C2 O5 -178.4(4) . . . . ?
C6 S1 N1 N2 -62.7(3) . . . . ?
C6 S1 N1 C5 112.6(3) . . . . ?
C6 C7 C8 C9 -1.5(7) . . . . ?
C7 C6 C11 C10 -0.8(6) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
C7 C8 C9 C12 179.7(4) . . . . ?
C8 C9 C10 C11 0.7(7) . . . . ?
C9 C10 C11 C6 -0.4(7) . . . . ?
C11 C6 C7 C8 1.8(6) . . . . ?
C12 C9 C10 C11 -178.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.467
_oxdiff_exptl_absorpt_empirical_full_min 0.714
####################################################################### 
# 
# 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_exp_6083
_audit_block_doi                 10.5517/ccdc.csd.cc21990p
_database_code_depnum_ccdc_archive 'CCDC 1885761'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment, South China Normal University
China
;
_audit_update_record             
;
2018-12-18 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;
_audit_creation_date             2018-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 Br N2 O3, Br'
_chemical_formula_sum            'C12 H14 Br2 N2 O3'
_chemical_formula_weight         394.07
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8741(11)
_cell_length_b                   7.9880(12)
_cell_length_c                   21.034(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.975(12)
_cell_angle_gamma                90
_cell_volume                     1480.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3730
_cell_measurement_theta_min      4.3250
_shelx_estimated_absorpt_T_max   0.584
_shelx_estimated_absorpt_T_min   0.273
_exptl_absorpt_coefficient_mu    5.482
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.1140
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9145
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_min         3.501
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  23.00   1.00    7.50    --  -16.28 -99.00-120.00   44
  2  ω     -5.00  20.00   1.00    7.50    --   15.49-106.00  48.00   25
  3  ω    -19.00   6.00   1.00    7.50    --  -16.28-106.00  48.00   25
  4  ω    -25.00  23.00   1.00    7.50    --  -16.28 -99.00 150.00   48
  5  ω     23.00  77.00   1.00    7.50    --   15.49  57.00 150.00   54
  6  ω     36.00  87.00   1.00    7.50    --   15.49 178.00   0.00   51
  7  ω     45.00  86.00   1.00    7.50    --   15.49 178.00  60.00   41
  8  ω    -28.00  -3.00   1.00    7.50    --  -16.28 106.00 147.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0713598000
_diffrn_orient_matrix_UB_12      0.0408703000
_diffrn_orient_matrix_UB_13      0.0046201000
_diffrn_orient_matrix_UB_21      -0.0090756000
_diffrn_orient_matrix_UB_22      0.0247798000
_diffrn_orient_matrix_UB_23      -0.0326403000
_diffrn_orient_matrix_UB_31      -0.0359662000
_diffrn_orient_matrix_UB_32      0.0749377000
_diffrn_orient_matrix_UB_33      0.0082345000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1663
_reflns_number_total             3180
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      2.249
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1367
_refine_special_details          ?
_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. Restrained distances
 Br1-Br2
 4 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C6(H6), C9(H9)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.51929(8) 0.24233(9) 0.84705(3) 0.0588(3) Uani 1 1 d D . . . .
Br2 Br 1.20065(8) 0.03972(10) 0.84015(4) 0.0662(3) Uani 1 1 d D . . . .
O3 O 1.0144(5) 0.5441(6) 0.8387(2) 0.0566(12) Uani 1 1 d . . . . .
N1 N 0.8145(5) 0.3291(6) 0.7564(2) 0.0381(12) Uani 1 1 d . . . . .
O2 O 0.9287(6) 0.4122(7) 0.9255(2) 0.0703(15) Uani 1 1 d . . . . .
C10 C 0.6872(7) 0.3697(8) 0.7178(3) 0.0448(16) Uani 1 1 d . . . . .
H10 H 0.601413 0.400369 0.736351 0.054 Uiso 1 1 calc R . . . .
C5 C 0.8227(7) 0.3436(7) 0.8229(3) 0.0395(15) Uani 1 1 d . . . . .
O1 O 0.7226(7) 0.3665(9) 0.9747(2) 0.106(2) Uani 1 1 d . . . . .
C1 C 0.7173(7) 0.3226(8) 0.8615(3) 0.0475(17) Uani 1 1 d . . . . .
N2 N 0.8048(7) 0.3197(9) 0.5611(3) 0.0693(18) Uani 1 1 d . . . . .
C7 C 0.9380(7) 0.2808(8) 0.6653(3) 0.0517(18) Uani 1 1 d . . . . .
H7 H 1.025085 0.247978 0.648123 0.062 Uiso 1 1 calc R . . . .
C6 C 0.9404(7) 0.2868(8) 0.7290(3) 0.0449(16) Uani 1 1 d . . . . .
H6 H 1.029785 0.261452 0.755012 0.054 Uiso 1 1 calc R . . . .
C3 C 0.9672(8) 0.3958(10) 0.8607(3) 0.0508(18) Uani 1 1 d . . . . .
C8 C 0.8082(8) 0.3225(8) 0.6240(3) 0.0484(17) Uani 1 1 d . . . . .
C9 C 0.6791(7) 0.3677(7) 0.6543(3) 0.0470(17) Uani 1 1 d . . . . .
H9 H 0.588707 0.396066 0.629488 0.056 Uiso 1 1 calc R . . . .
C2 C 0.7820(9) 0.3659(10) 0.9264(4) 0.065(2) Uani 1 1 d . . . . .
C4 C 1.1721(8) 0.5768(10) 0.8540(4) 0.085(3) Uani 1 1 d . . . . .
H4A H 1.229264 0.495786 0.833251 0.127 Uiso 1 1 calc GR . . . .
H4B H 1.198902 0.569598 0.899572 0.127 Uiso 1 1 calc GR . . . .
H4C H 1.194531 0.687052 0.839668 0.127 Uiso 1 1 calc GR . . . .
C11 C 0.9389(9) 0.2757(12) 0.5308(4) 0.100(3) Uani 1 1 d . . . . .
H11A H 1.025037 0.336754 0.550869 0.149 Uiso 1 1 calc GR . . . .
H11B H 0.922138 0.303642 0.486102 0.149 Uiso 1 1 calc GR . . . .
H11C H 0.957897 0.157746 0.535480 0.149 Uiso 1 1 calc GR . . . .
C12 C 0.6702(10) 0.3597(14) 0.5192(4) 0.117(4) Uani 1 1 d . . . . .
H12A H 0.609985 0.260565 0.510793 0.176 Uiso 1 1 calc GR . . . .
H12B H 0.697612 0.403388 0.479697 0.176 Uiso 1 1 calc GR . . . .
H12C H 0.612671 0.442170 0.539162 0.176 Uiso 1 1 calc GR . . . .
H3 H 1.035(5) 0.311(6) 0.860(2) 0.015(13) 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 1.861(7) . ?
O3 C3 1.356(8) . ?
O3 C4 1.422(7) . ?
N1 C10 1.348(7) . ?
N1 C5 1.398(7) . ?
N1 C6 1.361(7) . ?
O2 C3 1.452(7) . ?
O2 C2 1.355(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.329(8) . ?
C5 C1 1.321(8) . ?
C5 C3 1.483(9) . ?
O1 C2 1.201(8) . ?
C1 C2 1.456(9) . ?
N2 C8 1.320(8) . ?
N2 C11 1.459(9) . ?
N2 C12 1.431(9) . ?
C7 H7 0.9300 . ?
C7 C6 1.337(8) . ?
C7 C8 1.397(8) . ?
C6 H6 0.9300 . ?
C3 H3 0.90(5) . ?
C8 C9 1.423(8) . ?
C9 H9 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C3 O3 C4 114.8(6) . . ?
C10 N1 C5 121.5(5) . . ?
C10 N1 C6 118.4(5) . . ?
C6 N1 C5 119.9(5) . . ?
C2 O2 C3 108.9(5) . . ?
N1 C10 H10 118.6 . . ?
C9 C10 N1 122.8(5) . . ?
C9 C10 H10 118.6 . . ?
N1 C5 C3 119.7(5) . . ?
C1 C5 N1 130.5(6) . . ?
C1 C5 C3 109.7(6) . . ?
C5 C1 Br1 132.0(5) . . ?
C5 C1 C2 108.5(6) . . ?
C2 C1 Br1 119.5(5) . . ?
C8 N2 C11 121.4(7) . . ?
C8 N2 C12 121.9(6) . . ?
C12 N2 C11 116.7(6) . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.8(6) . . ?
C8 C7 H7 119.1 . . ?
N1 C6 H6 119.4 . . ?
C7 C6 N1 121.3(6) . . ?
C7 C6 H6 119.4 . . ?
O3 C3 O2 111.0(6) . . ?
O3 C3 C5 110.2(6) . . ?
O3 C3 H3 115(3) . . ?
O2 C3 C5 103.9(5) . . ?
O2 C3 H3 108(3) . . ?
C5 C3 H3 109(3) . . ?
N2 C8 C7 122.4(6) . . ?
N2 C8 C9 122.1(7) . . ?
C7 C8 C9 115.5(6) . . ?
C10 C9 C8 120.3(6) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O2 C2 C1 108.8(6) . . ?
O1 C2 O2 122.1(7) . . ?
O1 C2 C1 129.1(7) . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.984
_oxdiff_exptl_absorpt_empirical_full_min 0.522
