# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_AM-X3
_database_code_depnum_ccdc_archive 'CCDC 2064789'
loop_
_audit_author_name
_audit_author_address
'Eric Sperlich'
;University Potsdam
Germany
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
methyl 8-bromo-2-oxo-2,3-dihydro-1H-benzo[b]azepine-4-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Br N O3'
_chemical_formula_sum            'C12 H10 Br N O3'
_chemical_formula_weight         296.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2713 2.4705 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   23.452(5)
_cell_length_b                   4.5449(9)
_cell_length_c                   22.939(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.31(3)
_cell_angle_gamma                90
_cell_volume                     2277.8(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    17107
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      31.09

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_crystal_size_rad          0.08
_exptl_absorpt_coefficient_mu    3.609
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_T_max  0.9469

_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_radiation_source         'Genix Microfocus'
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'graded multilayer mirror'
_diffrn_radiation_collimation    '0.3 mm diameter'
_diffrn_ambient_temperature      210
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 
1408 frames, exposure time = 40 s per frame, 
detector distance = 60 mm, Δω = 0.5 ° 
;

_diffrn_reflns_number            12003
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.518
_diffrn_reflns_theta_max         26.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2363
_reflns_number_gt                1793
_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       
;
X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond (Blankenburg, 2020)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.86, Darmstadt 2018
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+3.6373P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2363
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.80143(2) 1.17450(8) 0.32830(2) 0.04254(15) Uani 1 1 d . . . . .
O1 O 0.45954(12) 0.3279(7) 0.32456(13) 0.0564(8) Uani 1 1 d . . . . .
O2 O 0.49428(11) 0.2125(6) 0.42592(12) 0.0401(6) Uani 1 1 d . . . . .
O3 O 0.67751(10) 0.1956(5) 0.50830(10) 0.0342(5) Uani 1 1 d . . . . .
N1 N 0.69490(11) 0.4828(5) 0.43687(11) 0.0247(6) Uani 1 1 d . . . . .
H1 H 0.729826 0.392181 0.446775 0.030 Uiso 1 1 calc R U . . .
C1 C 0.68406(14) 0.6961(6) 0.38986(14) 0.0233(6) Uani 1 1 d . . . . .
C2 C 0.62588(15) 0.7631(7) 0.34538(15) 0.0275(7) Uani 1 1 d . . . . .
C3 C 0.56985(14) 0.6156(7) 0.34216(15) 0.0314(7) Uani 1 1 d . . . . .
H3 H 0.539425 0.594768 0.302173 0.038 Uiso 1 1 calc R U . . .
C4 C 0.55707(13) 0.5065(7) 0.39009(15) 0.0269(7) Uani 1 1 d . . . . .
C5 C 0.60037(13) 0.5517(7) 0.45656(14) 0.0266(7) Uani 1 1 d . . . . .
H5A H 0.608143 0.762586 0.464372 0.032 Uiso 1 1 calc R U . . .
H5B H 0.581276 0.478711 0.485318 0.032 Uiso 1 1 calc R U . . .
C6 C 0.65998(14) 0.3952(6) 0.46930(14) 0.0255(7) Uani 1 1 d . . . . .
C7 C 0.62299(16) 0.9633(8) 0.29801(15) 0.0323(7) Uani 1 1 d . . . . .
H7 H 0.584455 1.009853 0.267969 0.039 Uiso 1 1 calc R U . . .
C8 C 0.67346(16) 1.0937(7) 0.29348(16) 0.0337(8) Uani 1 1 d . . . . .
H8 H 0.669860 1.232440 0.261952 0.040 Uiso 1 1 calc R U . . .
C9 C 0.73003(15) 1.0168(7) 0.33639(15) 0.0295(7) Uani 1 1 d . . . . .
C10 C 0.73608(14) 0.8240(7) 0.38428(14) 0.0252(6) Uani 1 1 d . . . . .
H10 H 0.775153 0.777810 0.413317 0.030 Uiso 1 1 calc R U . . .
C11 C 0.49901(14) 0.3428(7) 0.37577(16) 0.0323(7) Uani 1 1 d . . . . .
C12 C 0.43894(16) 0.0428(10) 0.41415(19) 0.0496(10) Uani 1 1 d . . . . .
H12A H 0.403792 0.173138 0.400354 0.074 Uiso 1 1 calc R U . . .
H12B H 0.440899 -0.056134 0.452298 0.074 Uiso 1 1 calc R U . . .
H12C H 0.435068 -0.102248 0.381910 0.074 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
Br1 C9 1.892(3) . ?
O1 C11 1.204(4) . ?
O2 C11 1.334(4) . ?
O2 C12 1.448(4) . ?
O3 C6 1.235(4) . ?
N1 C6 1.351(4) . ?
N1 C1 1.403(4) . ?
N1 H1 0.8700 . ?
C1 C10 1.399(4) . ?
C1 C2 1.408(4) . ?
C2 C7 1.400(5) . ?
C2 C3 1.453(5) . ?
C3 C4 1.336(5) . ?
C3 H3 0.9400 . ?
C4 C11 1.480(4) . ?
C4 C5 1.508(4) . ?
C5 C6 1.499(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C7 C8 1.361(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.379(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.372(4) . ?
C10 H10 0.9400 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 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
C11 O2 C12 115.2(3) . . ?
C6 N1 C1 130.6(3) . . ?
C6 N1 H1 114.7 . . ?
C1 N1 H1 114.7 . . ?
C10 C1 N1 115.9(3) . . ?
C10 C1 C2 119.4(3) . . ?
N1 C1 C2 124.3(3) . . ?
C7 C2 C1 117.6(3) . . ?
C7 C2 C3 118.2(3) . . ?
C1 C2 C3 123.9(3) . . ?
C4 C3 C2 126.8(3) . . ?
C4 C3 H3 116.6 . . ?
C2 C3 H3 116.6 . . ?
C3 C4 C11 117.9(3) . . ?
C3 C4 C5 120.8(3) . . ?
C11 C4 C5 121.3(3) . . ?
C6 C5 C4 111.7(3) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
O3 C6 N1 120.4(3) . . ?
O3 C6 C5 122.1(3) . . ?
N1 C6 C5 117.5(3) . . ?
C8 C7 C2 123.0(3) . . ?
C8 C7 H7 118.5 . . ?
C2 C7 H7 118.5 . . ?
C7 C8 C9 118.2(3) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 Br1 118.9(2) . . ?
C8 C9 Br1 119.3(3) . . ?
C9 C10 C1 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C1 C10 H10 120.0 . . ?
O1 C11 O2 122.7(3) . . ?
O1 C11 C4 124.3(3) . . ?
O2 C11 C4 113.0(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 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
C6 N1 C1 C10 153.6(3) . . . . ?
C6 N1 C1 C2 -33.2(5) . . . . ?
C10 C1 C2 C7 -1.6(4) . . . . ?
N1 C1 C2 C7 -174.6(3) . . . . ?
C10 C1 C2 C3 172.0(3) . . . . ?
N1 C1 C2 C3 -1.0(5) . . . . ?
C7 C2 C3 C4 -154.1(3) . . . . ?
C1 C2 C3 C4 32.3(5) . . . . ?
C2 C3 C4 C11 -175.1(3) . . . . ?
C2 C3 C4 C5 5.4(5) . . . . ?
C3 C4 C5 C6 -66.0(4) . . . . ?
C11 C4 C5 C6 114.5(3) . . . . ?
C1 N1 C6 O3 178.2(3) . . . . ?
C1 N1 C6 C5 -2.6(4) . . . . ?
C4 C5 C6 O3 -117.3(3) . . . . ?
C4 C5 C6 N1 63.5(3) . . . . ?
C1 C2 C7 C8 -0.1(5) . . . . ?
C3 C2 C7 C8 -174.1(3) . . . . ?
C2 C7 C8 C9 2.2(5) . . . . ?
C7 C8 C9 C10 -2.7(5) . . . . ?
C7 C8 C9 Br1 176.0(2) . . . . ?
C8 C9 C10 C1 1.1(5) . . . . ?
Br1 C9 C10 C1 -177.6(2) . . . . ?
N1 C1 C10 C9 174.7(3) . . . . ?
C2 C1 C10 C9 1.1(4) . . . . ?
C12 O2 C11 O1 1.9(5) . . . . ?
C12 O2 C11 C4 -178.5(3) . . . . ?
C3 C4 C11 O1 -8.3(5) . . . . ?
C5 C4 C11 O1 171.2(3) . . . . ?
C3 C4 C11 O2 172.1(3) . . . . ?
C5 C4 C11 O2 -8.4(4) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 O3 0.87 2.08 2.908(3) 159.4 7_656 yes
C5 H5A O3 0.98 2.52 3.418(4) 152.6 1_565 yes
C8 H8 Br1 0.94 3.13 4.039(3) 163.6 4_655 yes

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.085



