# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_AMZ
_database_code_depnum_ccdc_archive 'CCDC 1948701'
loop_
_audit_author_name
_audit_author_address
'Kunal Prakash'
;Department of Chemistry University of Delhi 
India
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;
_audit_creation_date             2019-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_chemical_formula_moiety         '0.19(C13 H10 Br N O)'
_chemical_formula_sum            'C2.419 H1.86 Br0.186 N0.186 O0.186'
_chemical_formula_weight         51.37
_chemical_oxdiff_formula         'C N H O'
_chemical_oxdiff_usercomment     21-08-2019
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'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   8.1837(8)
_cell_length_b                   9.2427(10)
_cell_length_c                   30.229(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2286.5(4)
_cell_formula_units_Z            43
_cell_measurement_reflns_used    2494
_cell_measurement_temperature    237(80)
_cell_measurement_theta_max      22.7990
_cell_measurement_theta_min      3.3900
_exptl_absorpt_coefficient_mu    3.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.6042
_exptl_crystal_F_000             1102.2432
_diffrn_reflns_av_R_equivalents  0.1663
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            31290
_diffrn_reflns_theta_full        24.9993
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      237(80)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9926
_diffrn_measured_fraction_theta_max 0.9926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  88.00   1.00    2.50    --   19.00  77.00 150.00   94
  2  ω      4.00  87.00   1.00    2.50    --   19.00  57.00  90.00   83
  3  ω      0.00  85.00   1.00    2.50    --   19.00  57.00   0.00   85
  4  ω     10.00  87.00   1.00    2.50    --   19.00  57.00 -90.00   77
  5  ω    -25.00  59.00   1.00    2.50    --   19.00 -99.00 -60.00   84
  6  ω    -35.00  29.00   1.00    2.50    --  -15.17  38.00-120.00   64
  7  ω    -25.00  59.00   1.00    2.50    --   19.00 -99.00 150.00   84
  8  ω    -45.00  48.00   1.00    2.50    --   19.00 -77.00  30.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0126106000
_diffrn_orient_matrix_UB_12      0.0343319000
_diffrn_orient_matrix_UB_13      -0.0207042000
_diffrn_orient_matrix_UB_21      -0.0786049000
_diffrn_orient_matrix_UB_22      0.0320349000
_diffrn_orient_matrix_UB_23      0.0014659000
_diffrn_orient_matrix_UB_31      0.0343853000
_diffrn_orient_matrix_UB_32      0.0606363000
_diffrn_orient_matrix_UB_33      0.0109495000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              35
_reflns_limit_l_min              0
_reflns_number_gt                1393
_reflns_number_total             2003
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.6245
_refine_diff_density_min         -0.6588
_refine_diff_density_rms         0.1692
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.0050
_refine_ls_goodness_of_fit_ref   0.8854
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      0.8854
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1584
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00E(H00E), C00B(H00B), C009(H009), C00G(H00G),
 C00C(H00C), C00A(H00A), C006(H006), N003(H003)
;
_atom_sites_solution_primary     dual
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
Br01 Br 0.64116(8) 0.40490(7) 0.54350(2) 0.0460(3) Uani 1.000000 .
O002 O 0.6693(4) 0.3791(3) 0.65082(13) 0.0333(9) Uani 1.000000 .
N003 N 0.7541(5) 0.5952(4) 0.62355(13) 0.0249(9) Uani 1.000000 .
C004 C 0.8843(6) 0.5345(5) 0.59823(16) 0.0256(12) Uani 1.000000 .
C005 C 0.8571(6) 0.4406(5) 0.56367(18) 0.0271(12) Uani 1.000000 .
C006 C 0.4838(6) 0.5242(5) 0.71550(16) 0.0294(12) Uani 1.000000 .
C007 C 0.6562(6) 0.5106(5) 0.64897(16) 0.0241(11) Uani 1.000000 .
C008 C 0.5314(6) 0.5879(5) 0.67629(15) 0.0255(12) Uani 1.000000 .
C009 C 0.4615(6) 0.7183(5) 0.66406(17) 0.0325(13) Uani 1.000000 .
C00A C 0.3719(6) 0.5882(6) 0.74258(19) 0.0328(14) Uani 1.000000 .
C00B C 1.0431(7) 0.5694(5) 0.60901(18) 0.0356(14) Uani 1.000000 .
C00C C 0.3008(6) 0.7174(5) 0.72973(19) 0.0372(14) Uani 1.000000 .
C00D C 0.9859(8) 0.3766(6) 0.54166(17) 0.0391(15) Uani 1.000000 .
C00E C 1.1724(7) 0.5067(6) 0.5864(2) 0.0437(15) Uani 1.000000 .
C00F C 1.1416(7) 0.4094(6) 0.5530(2) 0.0435(17) Uani 1.000000 .
C00G C 0.3461(7) 0.7817(6) 0.6907(2) 0.0400(14) Uani 1.000000 .
H00D H 0.9658(8) 0.3109(6) 0.51899(17) 0.0470(18) Uiso 1.000000 R
H00F H 1.2281(7) 0.3659(6) 0.5382(2) 0.052(2) Uiso 1.000000 R
H00E H 1.2795(7) 0.5304(6) 0.5938(2) 0.0524(18) Uiso 1.000000 R
H00B H 1.0637(7) 0.6353(5) 0.63158(18) 0.0427(16) Uiso 1.000000 R
H009 H 0.4928(6) 0.7629(5) 0.63782(17) 0.0390(15) Uiso 1.000000 R
H00G H 0.2983(7) 0.8687(6) 0.6822(2) 0.0479(17) Uiso 1.000000 R
H00C H 0.2222(6) 0.7607(5) 0.74758(19) 0.0446(17) Uiso 1.000000 R
H00A H 0.3437(6) 0.5456(6) 0.76938(19) 0.0394(16) Uiso 1.000000 R
H006 H 0.5290(6) 0.4358(5) 0.72363(16) 0.0353(15) Uiso 1.000000 R
H003 H 0.7373(5) 0.6870(4) 0.62270(13) 0.0299(11) Uiso 1.000000 R


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
Br01 C005 1.898(5) . ?
O002 C007 1.222(5) . ?
N003 C004 1.427(6) . ?
N003 C007 1.358(6) . ?
N003 H003 0.8600 . ?
C004 C005 1.376(7) . ?
C004 C00B 1.378(7) . ?
C005 C00D 1.380(8) . ?
C006 C008 1.380(6) . ?
C006 C00A 1.363(7) . ?
C006 H006 0.9300 . ?
C007 C008 1.495(7) . ?
C008 C009 1.384(6) . ?
C009 C00G 1.372(7) . ?
C009 H009 0.9300 . ?
C00A C00C 1.384(7) . ?
C00A H00A 0.9300 . ?
C00B C00E 1.387(8) . ?
C00B H00B 0.9300 . ?
C00C C00G 1.373(8) . ?
C00C H00C 0.9300 . ?
C00D C00F 1.354(9) . ?
C00D H00D 0.9300 . ?
C00E C00F 1.374(8) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G H00G 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
C007 N003 C004 121.2(4) . . ?
H003 N003 C004 119.4(2) . . ?
H003 N003 C007 119.4(3) . . ?
C005 C004 N003 122.3(4) . . ?
C00B C004 N003 119.0(4) . . ?
C00B C004 C005 118.6(5) . . ?
C004 C005 Br01 120.3(4) . . ?
C00D C005 Br01 118.8(4) . . ?
C00D C005 C004 120.9(5) . . ?
C00A C006 C008 121.3(5) . . ?
H006 C006 C008 119.3(3) . . ?
H006 C006 C00A 119.3(3) . . ?
N003 C007 O002 123.2(4) . . ?
C008 C007 O002 120.7(4) . . ?
C008 C007 N003 116.1(4) . . ?
C007 C008 C006 117.6(4) . . ?
C009 C008 C006 119.0(5) . . ?
C009 C008 C007 123.4(4) . . ?
C00G C009 C008 120.0(5) . . ?
H009 C009 C008 120.0(3) . . ?
H009 C009 C00G 120.0(3) . . ?
C00C C00A C006 119.3(5) . . ?
H00A C00A C006 120.4(3) . . ?
H00A C00A C00C 120.4(3) . . ?
C00E C00B C004 120.4(5) . . ?
H00B C00B C004 119.8(3) . . ?
H00B C00B C00E 119.8(4) . . ?
C00G C00C C00A 120.1(5) . . ?
H00C C00C C00A 120.0(3) . . ?
H00C C00C C00G 120.0(3) . . ?
C00F C00D C005 120.0(5) . . ?
H00D C00D C005 120.0(3) . . ?
H00D C00D C00F 120.0(3) . . ?
C00F C00E C00B 119.7(6) . . ?
H00E C00E C00B 120.2(4) . . ?
H00E C00E C00F 120.2(3) . . ?
C00E C00F C00D 120.4(5) . . ?
H00F C00F C00D 119.8(3) . . ?
H00F C00F C00E 119.8(3) . . ?
C00C C00G C009 120.4(5) . . ?
H00G C00G C009 119.8(3) . . ?
H00G C00G C00C 119.8(3) . . ?

_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 1.641
_oxdiff_exptl_absorpt_empirical_full_min 0.675
