# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_4d
_database_code_depnum_ccdc_archive 'CCDC 1976461'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Institut of Organic Chemistry
Germany
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-03-26 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         'C17 H16 Br N O3, C H4 O'
_chemical_formula_sum            'C18 H20 Br N O4'
_chemical_formula_weight         394.26

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           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                   29.7250(14)
_cell_length_b                   7.9068(3)
_cell_length_c                   15.6809(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.574(4)
_cell_angle_gamma                90
_cell_volume                     3493.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    24068
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.374
_shelx_estimated_absorpt_T_min   0.435
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.4395
_exptl_absorpt_correction_T_max  0.7095
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.2150
0 1 0 0.2150
-1 0 2 0.1525
1 0 -2 0.1525
-1 0 0 0.0615
1 0 0 0.0615

_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 213 frames, detector distance = 80 mm
;
_diffrn_reflns_number            11566
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.660
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4172
_reflns_number_gt                3380
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SHELXT-2014
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0260P)²+16.4471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4172
_refine_ls_number_parameters     240
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.064
_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 0.45368(2) 0.30453(4) 0.04236(2) 0.03018(10) Uani 0.95 1 d . . P A 1
O22 O 0.4488(15) 0.335(3) 0.0647(18) 0.0296(5) Uani 0.05 1 d D . P A 2
C23 C 0.493(2) 0.218(9) 0.079(4) 0.0358(7) Uani 0.05 1 d . . P A 2
H23D H 0.517831 0.280474 0.065615 0.054 Uiso 0.05 1 calc R U P A 2
H23E H 0.483538 0.119448 0.039824 0.054 Uiso 0.05 1 calc R U P A 2
H23F H 0.503823 0.180586 0.142275 0.054 Uiso 0.05 1 calc R U P A 2
C1 C 0.44250(10) 0.4120(4) 0.14200(19) 0.0262(6) Uani 1 1 d D . . . .
C2 C 0.44503(10) 0.5872(4) 0.14885(19) 0.0242(6) Uani 1 1 d D . . . .
C3 C 0.43719(10) 0.6641(4) 0.2228(2) 0.0264(6) Uani 1 1 d . . . . .
H3 H 0.438492 0.783804 0.228424 0.032 Uiso 1 1 calc R U . . .
C4 C 0.42749(10) 0.5662(4) 0.2883(2) 0.0269(6) Uani 1 1 d . . . . .
H4 H 0.422894 0.620009 0.339102 0.032 Uiso 1 1 calc R U . . .
C5 C 0.42435(10) 0.3914(4) 0.28115(19) 0.0246(6) Uani 1 1 d . . . . .
C6 C 0.43190(10) 0.3143(4) 0.20680(19) 0.0269(6) Uani 1 1 d D . . . .
H6 H 0.429784 0.194787 0.200465 0.032 Uiso 1 1 calc R U . . .
O7 O 0.45526(7) 0.6738(3) 0.08222(13) 0.0273(4) Uani 1 1 d . . . . .
C8 C 0.45502(12) 0.8555(4) 0.0882(2) 0.0325(7) Uani 1 1 d . . . . .
H8A H 0.423325 0.894094 0.085870 0.049 Uiso 1 1 calc R U . . .
H8B H 0.463330 0.904357 0.037765 0.049 Uiso 1 1 calc R U . . .
H8C H 0.478243 0.891578 0.145034 0.049 Uiso 1 1 calc R U . . .
C9 C 0.41084(10) 0.2955(4) 0.35296(19) 0.0253(6) Uani 1 1 d . . . . .
H9 H 0.429171 0.344974 0.412604 0.030 Uiso 1 1 calc R U . . .
C10 C 0.42310(10) 0.1140(4) 0.35466(19) 0.0268(6) Uani 1 1 d . . . . .
N11 N 0.43139(10) -0.0275(4) 0.35750(18) 0.0325(6) Uani 1 1 d . . . . .
C12 C 0.35789(10) 0.3102(4) 0.34253(18) 0.0238(6) Uani 1 1 d . . . . .
C13 C 0.34404(10) 0.3782(4) 0.41254(19) 0.0250(6) Uani 1 1 d . . . . .
H13 H 0.367394 0.416034 0.465953 0.030 Uiso 1 1 calc R U . . .
C14 C 0.29633(10) 0.3906(4) 0.40428(19) 0.0254(6) Uani 1 1 d . . . . .
C15 C 0.26221(10) 0.3344(4) 0.3246(2) 0.0253(6) Uani 1 1 d D . . . .
C16 C 0.27600(11) 0.2685(4) 0.2558(2) 0.0289(6) Uani 1 1 d . . . . .
H16 H 0.252775 0.231128 0.202095 0.035 Uiso 1 1 calc R U . . .
C17 C 0.32396(11) 0.2563(4) 0.2647(2) 0.0292(6) Uani 1 1 d . . . . .
H17 H 0.333400 0.210755 0.216955 0.035 Uiso 1 1 calc R U . . .
O18 O 0.27809(15) 0.4542(6) 0.4664(2) 0.0350(8) Uani 0.95 1 d . . P B 1
C19 C 0.31155(15) 0.4808(5) 0.5551(3) 0.0364(8) Uani 0.95 1 d . . P B 1
H19A H 0.294384 0.511729 0.596810 0.055 Uiso 0.95 1 calc R U P B 1
H19B H 0.333439 0.572060 0.552825 0.055 Uiso 0.95 1 calc R U P B 1
H19C H 0.329546 0.376531 0.575894 0.055 Uiso 0.95 1 calc R U P B 1
Br2 Br 0.2829(5) 0.4735(18) 0.5052(9) 0.051(3) Uani 0.05 1 d . . P B 2
O20 O 0.21600(7) 0.3510(3) 0.32324(14) 0.0296(5) Uani 1 1 d D . . . .
C21 C 0.17986(11) 0.2924(5) 0.2449(2) 0.0358(7) Uani 1 1 d . . . . .
H21A H 0.148705 0.307769 0.252728 0.054 Uiso 1 1 calc R U . . .
H21B H 0.184883 0.172155 0.235669 0.054 Uiso 1 1 calc R U . . .
H21C H 0.181177 0.356974 0.192365 0.054 Uiso 1 1 calc R U . . .
O24 O 0.16394(10) 0.5151(4) 0.42166(17) 0.0511(7) Uani 1 1 d . . . . .
H24 H 0.1909(18) 0.480(6) 0.413(3) 0.077 Uiso 1 1 d . U . . .
C25 C 0.17701(14) 0.5649(5) 0.5127(2) 0.0429(8) Uani 1 1 d . . . . .
H25A H 0.149266 0.611229 0.525521 0.064 Uiso 1 1 calc R U . . .
H25B H 0.201844 0.651479 0.524439 0.064 Uiso 1 1 calc R U . . .
H25C H 0.189013 0.466698 0.551373 0.064 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 C1 1.898(3) . ?
O22 C1 1.42(2) . ?
O22 C23 1.55(7) . ?
C23 H23D 0.9800 . ?
C23 H23E 0.9800 . ?
C23 H23F 0.9800 . ?
C1 C2 1.390(4) . ?
C1 C6 1.390(4) . ?
C2 O7 1.362(3) . ?
C2 C3 1.394(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(4) . ?
C5 C9 1.514(4) . ?
C6 H6 0.9500 . ?
O7 C8 1.440(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.478(4) . ?
C9 C12 1.534(4) . ?
C9 H9 1.0000 . ?
C10 N11 1.144(4) . ?
C12 C17 1.380(4) . ?
C12 C13 1.397(4) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 O18 1.354(4) . ?
C14 C15 1.407(4) . ?
C14 Br2 1.870(14) . ?
C15 O20 1.373(3) . ?
C15 C16 1.374(4) . ?
C16 C17 1.391(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O18 C19 1.445(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O20 C21 1.428(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O24 C25 1.411(4) . ?
O24 H24 0.90(5) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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 O22 C23 117(3) . . ?
O22 C23 H23D 109.5 . . ?
O22 C23 H23E 109.5 . . ?
H23D C23 H23E 109.5 . . ?
O22 C23 H23F 109.5 . . ?
H23D C23 H23F 109.5 . . ?
H23E C23 H23F 109.5 . . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 O22 118.3(8) . . ?
C6 C1 O22 120.5(8) . . ?
C2 C1 Br1 119.4(2) . . ?
C6 C1 Br1 119.5(2) . . ?
O7 C2 C1 117.5(3) . . ?
O7 C2 C3 123.8(3) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 C9 117.7(3) . . ?
C6 C5 C9 123.6(3) . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C2 O7 C8 116.4(2) . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C5 112.2(2) . . ?
C10 C9 C12 108.3(2) . . ?
C5 C9 C12 112.9(2) . . ?
C10 C9 H9 107.8 . . ?
C5 C9 H9 107.8 . . ?
C12 C9 H9 107.8 . . ?
N11 C10 C9 177.5(3) . . ?
C17 C12 C13 119.9(3) . . ?
C17 C12 C9 120.5(3) . . ?
C13 C12 C9 119.6(3) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O18 C14 C13 126.3(3) . . ?
O18 C14 C15 114.6(3) . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 Br2 115.7(5) . . ?
C15 C14 Br2 125.0(5) . . ?
O20 C15 C16 124.8(3) . . ?
O20 C15 C14 114.7(3) . . ?
C16 C15 C14 120.4(3) . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.3(3) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C14 O18 C19 115.9(3) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 O20 C21 117.2(2) . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C25 O24 H24 106(3) . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C23 O22 C1 C2 116(3) . . . . ?
C23 O22 C1 C6 -67(4) . . . . ?
C6 C1 C2 O7 -179.5(3) . . . . ?
O22 C1 C2 O7 -2.5(19) . . . . ?
Br1 C1 C2 O7 0.4(4) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
O22 C1 C2 C3 177.7(19) . . . . ?
Br1 C1 C2 C3 -179.4(2) . . . . ?
O7 C2 C3 C4 -179.3(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C3 C4 C5 C9 -176.5(3) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
O22 C1 C6 C5 -178(2) . . . . ?
Br1 C1 C6 C5 179.0(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C9 C5 C6 C1 177.6(3) . . . . ?
C1 C2 O7 C8 176.6(3) . . . . ?
C3 C2 O7 C8 -3.6(4) . . . . ?
C4 C5 C9 C10 -162.1(3) . . . . ?
C6 C5 C9 C10 20.6(4) . . . . ?
C4 C5 C9 C12 75.2(3) . . . . ?
C6 C5 C9 C12 -102.1(3) . . . . ?
C10 C9 C12 C17 -65.7(4) . . . . ?
C5 C9 C12 C17 59.1(4) . . . . ?
C10 C9 C12 C13 114.1(3) . . . . ?
C5 C9 C12 C13 -121.1(3) . . . . ?
C17 C12 C13 C14 0.5(5) . . . . ?
C9 C12 C13 C14 -179.4(3) . . . . ?
C12 C13 C14 O18 -179.7(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C12 C13 C14 Br2 176.9(5) . . . . ?
O18 C14 C15 O20 -0.8(4) . . . . ?
C13 C14 C15 O20 179.6(3) . . . . ?
Br2 C14 C15 O20 2.8(6) . . . . ?
O18 C14 C15 C16 179.4(3) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
Br2 C14 C15 C16 -177.0(6) . . . . ?
O20 C15 C16 C17 -179.5(3) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C13 C12 C17 C16 -0.4(5) . . . . ?
C9 C12 C17 C16 179.4(3) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
C13 C14 O18 C19 -12.6(6) . . . . ?
C15 C14 O18 C19 167.8(3) . . . . ?
C16 C15 O20 C21 1.1(4) . . . . ?
C14 C15 O20 C21 -178.6(3) . . . . ?

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
O24 H24 O20 0.90(5) 2.05(5) 2.825(3) 143(4) . yes
O24 H24 O18 0.90(5) 2.47(5) 3.274(5) 149(4) . yes
O24 H24 Br2 0.90(5) 2.66(5) 3.372(14) 137(4) . yes

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.085

