# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 
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data_mo_cy_zj1_0m
_database_code_depnum_ccdc_archive 'CCDC 1524709'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Br N O5'
_chemical_formula_sum            'C16 H14 Br N O5'
_chemical_formula_weight         380.19

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.4013(8)
_cell_length_b                   8.2636(13)
_cell_length_c                   17.057(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.759(2)
_cell_angle_gamma                90
_cell_volume                     752.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6374
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.93

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   0.2939
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          1.250
_exptl_crystal_size_mid          1.000
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    2.758
_shelx_estimated_absorpt_T_min   0.130
_shelx_estimated_absorpt_T_max   0.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7512
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.208
_diffrn_reflns_theta_max         30.929
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             4093
_reflns_number_gt                3798
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.770
_reflns_Friedel_fraction_full    0.884

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.1010P)²] 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_abs_structure_details 
;
 Flack x determined using 1509 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.135(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4093
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_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 0.38206(8) 0.24617(10) 1.06471(3) 0.01539(17) Uani 1 1 d . . . . .
C2 C 0.5067(10) 0.2841(7) 0.9095(4) 0.0156(11) Uani 1 1 d . . . . .
H2 H 0.6482 0.2192 0.9287 0.019 Uiso 1 1 calc R U . . .
C5 C 0.0856(10) 0.4743(7) 0.8548(3) 0.0105(10) Uani 1 1 d . . . . .
H5 H -0.0572 0.5380 0.8356 0.013 Uiso 1 1 calc R U . . .
O1 O 0.5800(7) 0.6695(5) 0.7510(3) 0.0134(7) Uani 1 1 d . . . . .
O3 O 0.6381(8) 0.9151(5) 0.5343(3) 0.0168(8) Uani 1 1 d . . . . .
C16 C 0.0686(14) 0.9883(9) 0.8325(4) 0.0220(14) Uani 1 1 d . . . . .
H16A H 0.0692 0.8749 0.8494 0.033 Uiso 1 1 calc R U . . .
H16B H -0.0031 1.0557 0.8707 0.033 Uiso 1 1 calc R U . . .
H16C H 0.2406 1.0232 0.8301 0.033 Uiso 1 1 calc R U . . .
C15 C -0.0858(11) 1.0051(7) 0.7523(4) 0.0162(11) Uani 1 1 d . . . . .
H15A H -0.2624 0.9771 0.7550 0.019 Uiso 1 1 calc R U . . .
H15B H -0.0798 1.1183 0.7336 0.019 Uiso 1 1 calc R U . . .
O5 O 0.0152(8) 0.8958(5) 0.6971(3) 0.0156(8) Uani 1 1 d . . . . .
C11 C 0.3157(11) 0.8473(7) 0.6133(4) 0.0100(10) Uani 1 1 d . . . . .
C9 C 0.3169(11) 0.6666(7) 0.6196(4) 0.0102(10) Uani 1 1 d . . . . .
H9 H 0.4373 0.6217 0.5862 0.012 Uiso 1 1 calc R U . . .
C10 C 0.4014(9) 0.6182(6) 0.7053(3) 0.0103(9) Uani 1 1 d . . . . .
N1 N 0.2331(8) 0.5020(6) 0.7270(3) 0.0097(8) Uani 1 1 d . . . . .
C4 C 0.2616(9) 0.4364(6) 0.8055(3) 0.0089(9) Uani 1 1 d . . . . .
C3 C 0.4724(10) 0.3414(7) 0.8318(3) 0.0127(10) Uani 1 1 d . . . . .
H3 H 0.5897 0.3166 0.7974 0.015 Uiso 1 1 calc R U . . .
C1 C 0.3324(10) 0.3224(7) 0.9586(3) 0.0121(10) Uani 1 1 d . . . . .
C7 C 0.0243(9) 0.4799(6) 0.6687(3) 0.0094(9) Uani 1 1 d . . . . .
O2 O -0.1514(7) 0.3937(5) 0.6764(3) 0.0138(8) Uani 1 1 d . . . . .
C14 C 0.1777(10) 0.9476(7) 0.6529(3) 0.0110(9) Uani 1 1 d . . . . .
O4 O 0.2171(8) 1.1064(5) 0.6467(2) 0.0141(8) Uani 1 1 d . . . . .
C13 C 0.4079(10) 1.1229(7) 0.5946(3) 0.0136(10) Uani 1 1 d . . . . .
H13A H 0.5567 1.1810 0.6220 0.016 Uiso 1 1 calc R U . . .
H13B H 0.3404 1.1828 0.5458 0.016 Uiso 1 1 calc R U . . .
C12 C 0.4753(10) 0.9505(6) 0.5750(3) 0.0105(9) Uani 1 1 d . . . . .
C6 C 0.1233(8) 0.4170(8) 0.9323(3) 0.0124(11) Uani 1 1 d . . . . .
H6 H 0.0071 0.4424 0.9670 0.015 Uiso 1 1 calc R U . . .
C8 C 0.0605(9) 0.5823(6) 0.5969(3) 0.0103(9) Uani 1 1 d . . . . .
H8A H -0.0751 0.6633 0.5855 0.012 Uiso 1 1 calc R U . . .
H8B H 0.0607 0.5132 0.5495 0.012 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 1.897(6) . ?
C2 C1 1.388(8) . ?
C2 C3 1.392(8) . ?
C2 H2 0.9500 . ?
C5 C6 1.390(7) . ?
C5 C4 1.396(7) . ?
C5 H5 0.9500 . ?
O1 C10 1.221(6) . ?
O3 C12 1.235(7) . ?
C16 C15 1.497(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 O5 1.469(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O5 C14 1.312(6) . ?
C11 C14 1.361(8) . ?
C11 C12 1.438(8) . ?
C11 C9 1.497(7) . ?
C9 C10 1.517(8) . ?
C9 C8 1.546(8) . ?
C9 H9 1.0000 . ?
C10 N1 1.410(7) . ?
N1 C7 1.398(7) . ?
N1 C4 1.431(7) . ?
C4 C3 1.399(7) . ?
C3 H3 0.9500 . ?
C1 C6 1.391(7) . ?
C7 O2 1.210(6) . ?
C7 C8 1.525(7) . ?
C14 O4 1.336(7) . ?
O4 C13 1.466(7) . ?
C13 C12 1.520(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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 C2 C3 119.5(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C6 C5 C4 118.8(5) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C15 C16 108.6(5) . . ?
O5 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
O5 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
C14 O5 C15 120.9(4) . . ?
C14 C11 C12 106.0(5) . . ?
C14 C11 C9 124.6(6) . . ?
C12 C11 C9 128.9(6) . . ?
C11 C9 C10 109.3(5) . . ?
C11 C9 C8 116.0(6) . . ?
C10 C9 C8 104.4(4) . . ?
C11 C9 H9 109.0 . . ?
C10 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
O1 C10 N1 123.2(5) . . ?
O1 C10 C9 128.1(5) . . ?
N1 C10 C9 108.8(4) . . ?
C7 N1 C10 112.6(4) . . ?
C7 N1 C4 125.2(4) . . ?
C10 N1 C4 121.5(4) . . ?
C5 C4 C3 121.9(5) . . ?
C5 C4 N1 119.4(5) . . ?
C3 C4 N1 118.6(5) . . ?
C2 C3 C4 118.7(5) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C2 C1 C6 121.7(5) . . ?
C2 C1 Br1 119.3(4) . . ?
C6 C1 Br1 119.0(4) . . ?
O2 C7 N1 124.1(5) . . ?
O2 C7 C8 127.8(5) . . ?
N1 C7 C8 108.1(4) . . ?
O5 C14 O4 119.7(5) . . ?
O5 C14 C11 123.4(5) . . ?
O4 C14 C11 116.9(5) . . ?
C14 O4 C13 105.9(4) . . ?
O4 C13 C12 105.1(4) . . ?
O4 C13 H13A 110.7 . . ?
C12 C13 H13A 110.7 . . ?
O4 C13 H13B 110.7 . . ?
C12 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
O3 C12 C11 129.9(5) . . ?
O3 C12 C13 124.1(5) . . ?
C11 C12 C13 106.0(5) . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C7 C8 C9 105.6(4) . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?

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
C16 C15 O5 C14 -94.5(6) . . . . ?
C14 C11 C9 C10 -59.2(8) . . . . ?
C12 C11 C9 C10 111.9(7) . . . . ?
C14 C11 C9 C8 58.4(9) . . . . ?
C12 C11 C9 C8 -130.5(6) . . . . ?
C11 C9 C10 O1 -46.7(8) . . . . ?
C8 C9 C10 O1 -171.4(5) . . . . ?
C11 C9 C10 N1 131.8(6) . . . . ?
C8 C9 C10 N1 7.1(6) . . . . ?
O1 C10 N1 C7 171.2(5) . . . . ?
C9 C10 N1 C7 -7.4(6) . . . . ?
O1 C10 N1 C4 0.2(8) . . . . ?
C9 C10 N1 C4 -178.4(5) . . . . ?
C6 C5 C4 C3 0.6(8) . . . . ?
C6 C5 C4 N1 -176.4(5) . . . . ?
C7 N1 C4 C5 -58.2(7) . . . . ?
C10 N1 C4 C5 111.6(6) . . . . ?
C7 N1 C4 C3 124.6(5) . . . . ?
C10 N1 C4 C3 -65.5(7) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
C5 C4 C3 C2 -0.2(8) . . . . ?
N1 C4 C3 C2 176.9(5) . . . . ?
C3 C2 C1 C6 0.0(9) . . . . ?
C3 C2 C1 Br1 -179.2(4) . . . . ?
C10 N1 C7 O2 -175.3(5) . . . . ?
C4 N1 C7 O2 -4.7(8) . . . . ?
C10 N1 C7 C8 4.3(6) . . . . ?
C4 N1 C7 C8 174.9(4) . . . . ?
C15 O5 C14 O4 -12.6(8) . . . . ?
C15 O5 C14 C11 166.1(6) . . . . ?
C12 C11 C14 O5 -177.9(5) . . . . ?
C9 C11 C14 O5 -5.1(10) . . . . ?
C12 C11 C14 O4 0.8(7) . . . . ?
C9 C11 C14 O4 173.5(6) . . . . ?
O5 C14 O4 C13 179.5(5) . . . . ?
C11 C14 O4 C13 0.8(7) . . . . ?
C14 O4 C13 C12 -1.9(5) . . . . ?
C14 C11 C12 O3 177.7(6) . . . . ?
C9 C11 C12 O3 5.3(11) . . . . ?
C14 C11 C12 C13 -1.9(6) . . . . ?
C9 C11 C12 C13 -174.2(6) . . . . ?
O4 C13 C12 O3 -177.3(5) . . . . ?
O4 C13 C12 C11 2.3(6) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C2 C1 C6 C5 0.4(9) . . . . ?
Br1 C1 C6 C5 179.7(4) . . . . ?
O2 C7 C8 C9 -179.9(5) . . . . ?
N1 C7 C8 C9 0.4(6) . . . . ?
C11 C9 C8 C7 -124.8(6) . . . . ?
C10 C9 C8 C7 -4.5(6) . . . . ?

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
C8 H8B O3 0.99 2.46 3.268(7) 138.4 2_646
C13 H13B O3 0.99 2.37 3.250(7) 147.9 2_656
C13 H13A O2 0.99 2.45 3.407(7) 163.1 1_665
C9 H9 O3 1.00 2.65 3.387(8) 130.1 2_646
C15 H15B O2 0.99 2.48 3.460(8) 169.0 1_565
C5 H5 O1 0.95 2.50 3.423(7) 164.6 1_455
C5 H5 Br1 0.95 3.14 3.791(6) 127.6 2_557
C8 H8B O3 0.99 2.46 3.268(7) 138.4 2_646
C8 H8A O3 0.99 2.66 3.629(7) 166.0 1_455
C13 H13B O3 0.99 2.37 3.250(7) 147.9 2_656
C13 H13A O2 0.99 2.45 3.407(7) 163.1 1_665
C9 H9 O3 1.00 2.65 3.387(8) 130.1 2_646
C15 H15B O2 0.99 2.48 3.460(8) 169.0 1_565
C5 H5 O1 0.95 2.50 3.423(7) 164.6 1_455
C5 H5 Br1 0.95 3.14 3.791(6) 127.6 2_557
C5 H5 Br1 0.95 3.14 3.791(6) 127.6 2_557
C5 H5 O1 0.95 2.50 3.423(7) 164.6 1_455
C15 H15B O2 0.99 2.48 3.460(8) 169.0 1_565
C9 H9 O3 1.00 2.65 3.387(8) 130.1 2_646
C13 H13A O2 0.99 2.45 3.407(7) 163.1 1_665
C13 H13B O3 0.99 2.37 3.250(7) 147.9 2_656
C8 H8B O3 0.99 2.46 3.268(7) 138.4 2_646

_refine_diff_density_max         1.404
_refine_diff_density_min         -1.570
_refine_diff_density_rms         0.174

