# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_SM-306
_database_code_depnum_ccdc_archive 'CCDC 1858926'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Methyl 5-(5-bromo-2-hydroxybenzoyl) nicotinate'
_chemical_name_common            ?
_chemical_melting_point          450
_chemical_formula_moiety         'C14 H10 Br N O4'
_chemical_formula_sum            'C14 H10 Br N O4'
_chemical_formula_weight         336.14

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.5983(3)
_cell_length_b                   16.4240(7)
_cell_length_c                   20.8458(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2601.44(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9765
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.25

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.173
_shelx_estimated_absorpt_T_min   0.529
_shelx_estimated_absorpt_T_max   0.742
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            80416
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.480
_diffrn_reflns_theta_max         28.322
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3232
_reflns_number_gt                2729
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0297P)²+1.6989P] 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         3232
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_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
C1 C 0.2742(2) -0.00924(9) 0.41592(7) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.33492(17) -0.07795(7) 0.42208(6) 0.0306(3) Uani 1 1 d . . . . .
C2 C 0.2118(2) 0.03765(9) 0.47153(7) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.2588(2) 0.01262(9) 0.53378(8) 0.0211(3) Uani 1 1 d . . . . .
C4 C 0.2093(2) 0.05940(10) 0.58651(7) 0.0251(3) Uani 1 1 d . . . . .
H4 H 0.2471 0.0445 0.6278 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1052(2) 0.12733(10) 0.57854(8) 0.0256(3) Uani 1 1 d . . . . .
H5 H 0.0718 0.1586 0.6143 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0498(2) 0.14942(9) 0.51738(8) 0.0219(3) Uani 1 1 d . . . . .
C7 C 0.1036(2) 0.10626(9) 0.46429(7) 0.0207(3) Uani 1 1 d . . . . .
H7 H 0.0677 0.1228 0.4231 0.025 Uiso 1 1 calc R U . . .
O2 O 0.35386(17) -0.05533(7) 0.54534(6) 0.0294(3) Uani 1 1 d . . . . .
H2 H 0.3672 -0.0810 0.5114 0.044 Uiso 1 1 calc R U . . .
Br1 Br -0.09973(3) 0.24048(2) 0.50772(2) 0.03448(7) Uani 1 1 d . . . . .
C8 C 0.2683(2) 0.02678(10) 0.34998(7) 0.0232(3) Uani 1 1 d . . . . .
C9 C 0.2113(2) -0.02223(10) 0.29955(8) 0.0275(4) Uani 1 1 d . . . . .
H9 H 0.1701 -0.0748 0.3093 0.033 Uiso 1 1 calc R U . . .
N1 N 0.2119(2) 0.00116(9) 0.23818(7) 0.0323(4) Uani 1 1 d . . . . .
C10 C 0.2754(2) 0.07526(11) 0.22543(8) 0.0294(4) Uani 1 1 d . . . . .
H10 H 0.2781 0.0925 0.1824 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3376(2) 0.12837(10) 0.27218(8) 0.0244(3) Uani 1 1 d . . . . .
C12 C 0.3315(2) 0.10386(10) 0.33590(7) 0.0242(3) Uani 1 1 d . . . . .
H12 H 0.3696 0.1388 0.3688 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4123(3) 0.20968(11) 0.25577(8) 0.0289(4) Uani 1 1 d . . . . .
O3 O 0.4564(3) 0.25903(9) 0.29474(7) 0.0529(4) Uani 1 1 d . . . . .
O4 O 0.4265(2) 0.22033(8) 0.19295(6) 0.0388(3) Uani 1 1 d . . . . .
C14 C 0.4982(3) 0.29779(13) 0.17233(11) 0.0479(5) Uani 1 1 d . . . . .
H14A H 0.4308 0.3417 0.1914 0.072 Uiso 1 1 calc R U . . .
H14B H 0.4918 0.3016 0.1260 0.072 Uiso 1 1 calc R U . . .
H14C H 0.6200 0.3019 0.1858 0.072 Uiso 1 1 calc R U . . .


_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
C1 O1 1.2260(19) 1 ?
C1 O1 1.2260(19) . ?
C1 C2 1.470(2) . ?
C1 C8 1.497(2) . ?
O1 O1 0.000(4) 1 ?
C2 C7 1.403(2) . ?
C2 C3 1.407(2) . ?
C3 O2 1.3509(19) . ?
C3 C4 1.393(2) . ?
C4 C5 1.377(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.376(2) . ?
C6 Br1 1.8890(16) . ?
C7 H7 0.9400 . ?
O2 H2 0.8300 . ?
C8 C12 1.386(2) . ?
C8 C9 1.393(2) . ?
C9 N1 1.336(2) . ?
C9 H9 0.9400 . ?
N1 C10 1.336(2) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.389(2) . ?
C11 C13 1.491(2) . ?
C12 H12 0.9400 . ?
C13 O3 1.195(2) . ?
C13 O4 1.326(2) . ?
O4 C14 1.449(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?

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 C1 C2 121.40(14) 1 . ?
O1 C1 C2 121.40(14) . . ?
O1 C1 C8 118.11(14) 1 . ?
O1 C1 C8 118.11(14) . . ?
C2 C1 C8 120.48(14) . . ?
C7 C2 C3 118.84(14) . . ?
C7 C2 C1 121.66(14) . . ?
C3 C2 C1 119.49(14) . . ?
O2 C3 C4 117.34(14) . . ?
O2 C3 C2 122.78(14) . . ?
C4 C3 C2 119.86(14) . . ?
C5 C4 C3 120.45(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.71(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.86(15) . . ?
C7 C6 Br1 120.04(12) . . ?
C5 C6 Br1 119.10(12) . . ?
C6 C7 C2 120.08(14) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C3 O2 H2 109.5 . . ?
C12 C8 C9 118.42(15) . . ?
C12 C8 C1 123.03(14) . . ?
C9 C8 C1 118.28(15) . . ?
N1 C9 C8 123.74(16) . . ?
N1 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C10 N1 C9 116.99(15) . . ?
N1 C10 C11 123.70(16) . . ?
N1 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C12 C11 C10 118.51(15) . . ?
C12 C11 C13 119.44(15) . . ?
C10 C11 C13 122.04(15) . . ?
C8 C12 C11 118.61(15) . . ?
C8 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
O3 C13 O4 124.00(17) . . ?
O3 C13 C11 123.93(17) . . ?
O4 C13 C11 112.06(15) . . ?
C13 O4 C14 116.06(15) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C2 C1 O1 O1 0.00(6) . . . 1 ?
C8 C1 O1 O1 0.00(4) . . . 1 ?
O1 C1 C2 C7 -163.79(16) 1 . . . ?
O1 C1 C2 C7 -163.79(16) . . . . ?
C8 C1 C2 C7 17.5(2) . . . . ?
O1 C1 C2 C3 15.1(2) 1 . . . ?
O1 C1 C2 C3 15.1(2) . . . . ?
C8 C1 C2 C3 -163.68(15) . . . . ?
C7 C2 C3 O2 176.04(15) . . . . ?
C1 C2 C3 O2 -2.8(2) . . . . ?
C7 C2 C3 C4 -5.0(2) . . . . ?
C1 C2 C3 C4 176.14(15) . . . . ?
O2 C3 C4 C5 -176.89(15) . . . . ?
C2 C3 C4 C5 4.1(2) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 -2.7(3) . . . . ?
C4 C5 C6 Br1 177.75(13) . . . . ?
C5 C6 C7 C2 1.7(2) . . . . ?
Br1 C6 C7 C2 -178.74(12) . . . . ?
C3 C2 C7 C6 2.1(2) . . . . ?
C1 C2 C7 C6 -179.04(15) . . . . ?
O1 C1 C8 C12 -130.04(18) 1 . . . ?
O1 C1 C8 C12 -130.04(18) . . . . ?
C2 C1 C8 C12 48.7(2) . . . . ?
O1 C1 C8 C9 44.0(2) 1 . . . ?
O1 C1 C8 C9 44.0(2) . . . . ?
C2 C1 C8 C9 -137.26(16) . . . . ?
C12 C8 C9 N1 -0.9(3) . . . . ?
C1 C8 C9 N1 -175.18(17) . . . . ?
C8 C9 N1 C10 1.7(3) . . . . ?
C9 N1 C10 C11 -0.8(3) . . . . ?
N1 C10 C11 C12 -0.9(3) . . . . ?
N1 C10 C11 C13 178.17(18) . . . . ?
C9 C8 C12 C11 -0.9(2) . . . . ?
C1 C8 C12 C11 173.12(15) . . . . ?
C10 C11 C12 C8 1.7(3) . . . . ?
C13 C11 C12 C8 -177.40(16) . . . . ?
C12 C11 C13 O3 -6.0(3) . . . . ?
C10 C11 C13 O3 174.9(2) . . . . ?
C12 C11 C13 O4 173.11(16) . . . . ?
C10 C11 C13 O4 -6.0(3) . . . . ?
O3 C13 O4 C14 -0.8(3) . . . . ?
C11 C13 O4 C14 -179.94(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.83 1.88 2.6002(17) 144.6 1

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.063



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/ethyl acetate'
