# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_mo_023VB5A_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1841265'
loop_
_audit_author_name
_audit_author_address
'Merce Font-Bardia'
;University of Barcelona
Spain
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Br2 N5 O, C3 H6 O'
_chemical_formula_sum            'C16 H15 Br2 N5 O2'
_chemical_formula_weight         469.15

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.4913(6)
_cell_length_b                   4.76720(10)
_cell_length_c                   19.3160(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.258(2)
_cell_angle_gamma                90
_cell_volume                     1698.04(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      30.53

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    4.795
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41290
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         30.623
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5209
_reflns_number_gt                4434
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0685P)²+14.7200P] 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         5209
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1626
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.31284(3) 1.40708(11) 0.71829(3) 0.02848(15) Uani 1 1 d . . . . .
Br2 Br 0.85300(2) -0.46256(9) 0.64295(3) 0.02137(13) Uani 1 1 d . . . . .
O1 O 0.35918(16) 1.4377(7) 0.56849(16) 0.0160(6) Uani 1 1 d . . . . .
N1 N 0.44428(17) 1.0928(7) 0.57419(17) 0.0108(6) Uani 1 1 d . . . . .
H1 H 0.451987 1.122386 0.530379 0.013 Uiso 1 1 calc R U . . .
N2 N 0.53138(17) 0.7463(7) 0.57192(17) 0.0109(6) Uani 1 1 d . . . . .
N3 N 0.61656(18) 0.4005(7) 0.57035(17) 0.0122(6) Uani 1 1 d . . . . .
H3 H 0.613383 0.439588 0.525698 0.015 Uiso 1 1 calc R U . . .
N4 N 0.5214(2) 0.5786(8) 0.78026(18) 0.0190(7) Uani 1 1 d . . . . .
H4A H 0.550511 0.449078 0.799159 0.023 Uiso 1 1 calc R U . . .
H4B H 0.492003 0.670538 0.805930 0.023 Uiso 1 1 calc R U . . .
N5 N 0.56815(19) 0.4884(7) 0.67613(18) 0.0139(6) Uani 1 1 d . . . . .
C1 C 0.3925(2) 1.2538(8) 0.6024(2) 0.0135(7) Uani 1 1 d . . . . .
C2 C 0.3824(3) 1.1940(10) 0.6752(2) 0.0219(9) Uani 1 1 d . . . . .
C3 C 0.4236(2) 1.0041(9) 0.7126(2) 0.0162(7) Uani 1 1 d . . . . .
H3A H 0.417510 0.977622 0.760551 0.019 Uiso 1 1 calc R U . . .
C4 C 0.4763(2) 0.8441(8) 0.6790(2) 0.0126(7) Uani 1 1 d . . . . .
C5 C 0.4852(2) 0.8884(8) 0.6089(2) 0.0109(7) Uani 1 1 d . . . . .
C6 C 0.5220(2) 0.6365(9) 0.7117(2) 0.0130(7) Uani 1 1 d . . . . .
C7 C 0.5709(2) 0.5493(8) 0.6085(2) 0.0110(6) Uani 1 1 d . . . . .
C8 C 0.6680(2) 0.1944(8) 0.5910(2) 0.0123(7) Uani 1 1 d . . . . .
C9 C 0.6794(2) 0.0824(9) 0.6579(2) 0.0152(7) Uani 1 1 d . . . . .
H9 H 0.650203 0.143364 0.693386 0.018 Uiso 1 1 calc R U . . .
C10 C 0.7332(2) -0.1177(9) 0.6729(2) 0.0177(8) Uani 1 1 d . . . . .
H10 H 0.740355 -0.195158 0.718193 0.021 Uiso 1 1 calc R U . . .
C11 C 0.7763(2) -0.2026(9) 0.6208(2) 0.0166(8) Uani 1 1 d . . . . .
C12 C 0.7648(2) -0.1014(9) 0.5536(2) 0.0188(8) Uani 1 1 d . . . . .
H12 H 0.793554 -0.166662 0.518102 0.023 Uiso 1 1 calc R U . . .
C13 C 0.7108(2) 0.0964(9) 0.5389(2) 0.0163(7) Uani 1 1 d . . . . .
H13 H 0.702652 0.166672 0.492941 0.020 Uiso 1 1 calc R U . . .
O1W O 0.4330(5) 0.879(2) 0.8816(4) 0.104(2) Uani 1 1 d . . . . .
C3W C 0.4584(7) 1.264(3) 0.9545(5) 0.104(2) Uani 1 1 d . . . . .
H3WA H 0.508830 1.204781 0.951763 0.156 Uiso 1 1 calc R U . . .
H3WB H 0.446310 1.260918 1.003084 0.156 Uiso 1 1 calc R U . . .
H3WC H 0.452353 1.455350 0.936222 0.156 Uiso 1 1 calc R U . . .
C1W C 0.3349(7) 1.135(3) 0.9171(5) 0.104(2) Uani 1 1 d . . . . .
H1WA H 0.325216 1.322696 0.898006 0.156 Uiso 1 1 calc R U . . .
H1WB H 0.323646 1.130691 0.965838 0.156 Uiso 1 1 calc R U . . .
H1WC H 0.304471 0.997603 0.890650 0.156 Uiso 1 1 calc R U . . .
C2W C 0.4086(8) 1.067(3) 0.9122(6) 0.104(2) 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 C2 1.881(4) . ?
Br2 C11 1.908(4) . ?
O1 C1 1.232(5) . ?
N1 C1 1.372(5) . ?
N1 C5 1.377(5) . ?
N1 H1 0.8800 . ?
N2 C5 1.338(5) . ?
N2 C7 1.355(5) . ?
N3 C7 1.361(5) . ?
N3 C8 1.404(5) . ?
N3 H3 0.8800 . ?
N4 C6 1.355(5) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 C6 1.335(5) . ?
N5 C7 1.343(5) . ?
C1 C2 1.460(6) . ?
C2 C3 1.356(6) . ?
C3 C4 1.430(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(5) . ?
C4 C6 1.419(5) . ?
C8 C9 1.399(5) . ?
C8 C13 1.406(6) . ?
C9 C10 1.393(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(6) . ?
C12 C13 1.388(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O1W C2W 1.184(14) . ?
C3W C2W 1.51(2) . ?
C3W H3WA 0.9800 . ?
C3W H3WB 0.9800 . ?
C3W H3WC 0.9800 . ?
C1W C2W 1.411(16) . ?
C1W H1WA 0.9800 . ?
C1W H1WB 0.9800 . ?
C1W H1WC 0.9800 . ?

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
C1 N1 C5 125.2(3) . . ?
C1 N1 H1 117.4 . . ?
C5 N1 H1 117.4 . . ?
C5 N2 C7 114.4(3) . . ?
C7 N3 C8 130.2(3) . . ?
C7 N3 H3 114.9 . . ?
C8 N3 H3 114.9 . . ?
C6 N4 H4A 120.0 . . ?
C6 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C6 N5 C7 117.2(3) . . ?
O1 C1 N1 121.6(4) . . ?
O1 C1 C2 123.8(4) . . ?
N1 C1 C2 114.6(4) . . ?
C3 C2 C1 122.4(4) . . ?
C3 C2 Br1 120.0(3) . . ?
C1 C2 Br1 117.4(3) . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C5 C4 C6 115.4(4) . . ?
C5 C4 C3 119.6(4) . . ?
C6 C4 C3 125.0(4) . . ?
N2 C5 N1 116.6(3) . . ?
N2 C5 C4 124.7(4) . . ?
N1 C5 C4 118.7(4) . . ?
N5 C6 N4 116.5(4) . . ?
N5 C6 C4 121.5(4) . . ?
N4 C6 C4 122.0(4) . . ?
N5 C7 N2 126.8(4) . . ?
N5 C7 N3 118.9(3) . . ?
N2 C7 N3 114.3(3) . . ?
C9 C8 N3 125.6(4) . . ?
C9 C8 C13 118.6(4) . . ?
N3 C8 C13 115.8(3) . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 Br2 119.7(3) . . ?
C10 C11 Br2 119.0(3) . . ?
C11 C12 C13 119.1(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C2W C3W H3WA 109.5 . . ?
C2W C3W H3WB 109.5 . . ?
H3WA C3W H3WB 109.5 . . ?
C2W C3W H3WC 109.5 . . ?
H3WA C3W H3WC 109.5 . . ?
H3WB C3W H3WC 109.5 . . ?
C2W C1W H1WA 109.5 . . ?
C2W C1W H1WB 109.5 . . ?
H1WA C1W H1WB 109.5 . . ?
C2W C1W H1WC 109.5 . . ?
H1WA C1W H1WC 109.5 . . ?
H1WB C1W H1WC 109.5 . . ?
O1W C2W C1W 127.7(17) . . ?
O1W C2W C3W 120.2(13) . . ?
C1W C2W C3W 112.0(12) . . ?

_refine_diff_density_max         1.780
_refine_diff_density_min         -2.479
_refine_diff_density_rms         0.191

