# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_btp
_database_code_depnum_ccdc_archive 'CCDC 1935235'
loop_
_audit_author_name
_audit_author_address
'B. Satish Kumar'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2019-10-28 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         'C24 H27 N3 O6'
_chemical_formula_sum            'C24 H27 N3 O6'
_chemical_formula_weight         453.48

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.5562(3)
_cell_length_b                   7.5770(3)
_cell_length_c                   19.0345(8)
_cell_angle_alpha                80.335(2)
_cell_angle_beta                 85.586(2)
_cell_angle_gamma                86.0240(10)
_cell_volume                     1069.37(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9848
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.7158
_shelx_estimated_absorpt_T_max   0.7459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7158
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53415
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.708
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4943
_reflns_number_gt                4161
_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    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.1000P)²+0.8191P] 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         4943
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_restrained_S_all      0.810
_refine_ls_shift/su_max          0.000
_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
O3 O 0.81909(14) -0.17510(13) 0.51752(5) 0.0153(2) Uani 1 1 d . . . . .
O1 O 0.34917(13) 0.76875(13) 0.23918(5) 0.0153(2) Uani 1 1 d . . . . .
O5 O 0.82763(13) -0.15967(13) 0.04798(5) 0.0148(2) Uani 1 1 d . . . . .
O6 O 0.68553(14) 0.10975(14) 0.04955(5) 0.0177(2) Uani 1 1 d . . . . .
O2 O 0.45557(14) 0.61696(13) 0.34031(5) 0.0168(2) Uani 1 1 d . . . . .
O4 O 0.87282(14) -0.28682(14) 0.41531(5) 0.0194(2) Uani 1 1 d . . . . .
N3 N 0.83599(15) -0.19017(15) 0.26877(6) 0.0117(2) Uani 1 1 d . . . . .
N2 N 0.62030(15) 0.28674(16) 0.39299(6) 0.0122(2) Uani 1 1 d . . . . .
N1 N 0.57904(15) 0.35036(15) 0.14107(6) 0.0117(2) Uani 1 1 d . . . . .
C4 C 0.59301(17) 0.32457(17) 0.25947(7) 0.0115(3) Uani 1 1 d . . . . .
C5 C 0.63567(17) 0.23700(18) 0.20059(7) 0.0111(3) Uani 1 1 d . . . . .
C16 C 0.43731(17) 0.62857(18) 0.27657(7) 0.0119(3) Uani 1 1 d . . . . .
C12 C 0.85002(17) -0.21579(18) 0.19957(7) 0.0121(3) Uani 1 1 d . . . . .
C7 C 0.68243(18) 0.15568(18) 0.44448(7) 0.0125(3) Uani 1 1 d . . . . .
C8 C 0.74685(17) 0.01027(18) 0.41200(7) 0.0114(3) Uani 1 1 d . . . . .
C13 C 0.77805(17) -0.06162(18) 0.15837(7) 0.0118(3) Uani 1 1 d . . . . .
C14 C 0.71892(17) 0.06268(18) 0.20657(7) 0.0109(3) Uani 1 1 d . . . . .
C10 C 0.64065(17) 0.23241(18) 0.32694(7) 0.0113(3) Uani 1 1 d . . . . .
C22 C 0.75791(17) -0.02588(18) 0.08177(7) 0.0120(3) Uani 1 1 d . . . . .
C15 C 0.75853(17) -0.02313(18) 0.27502(7) 0.0114(3) Uani 1 1 d . . . . .
C19 C 0.81877(18) -0.16255(19) 0.44635(7) 0.0131(3) Uani 1 1 d . . . . .
C9 C 0.72164(17) 0.05860(18) 0.33667(7) 0.0107(3) Uani 1 1 d . . . . .
C3 C 0.50495(17) 0.49493(18) 0.23270(7) 0.0117(3) Uani 1 1 d . . . . .
C2 C 0.50034(18) 0.50541(18) 0.15910(7) 0.0126(3) Uani 1 1 d . . . . .
C11 C 0.93643(19) -0.38689(18) 0.18112(8) 0.0153(3) Uani 1 1 d . . . . .
H11A H 1.0653 -0.3863 0.1839 0.023 Uiso 1 1 calc R U . . .
H11B H 0.9103 -0.3983 0.1325 0.023 Uiso 1 1 calc R U . . .
H11C H 0.8903 -0.4883 0.2148 0.023 Uiso 1 1 calc R U . . .
C17 C 0.28426(19) 0.91343(19) 0.27742(8) 0.0144(3) Uani 1 1 d . . . . .
H17A H 0.3818 0.9554 0.3011 0.017 Uiso 1 1 calc R U . . .
H17B H 0.1890 0.8732 0.3141 0.017 Uiso 1 1 calc R U . . .
C18 C 0.21328(19) 1.06085(19) 0.22157(8) 0.0164(3) Uani 1 1 d . . . . .
H18A H 0.3089 1.0977 0.1854 0.025 Uiso 1 1 calc R U . . .
H18B H 0.1682 1.1636 0.2441 0.025 Uiso 1 1 calc R U . . .
H18C H 0.1166 1.0171 0.1989 0.025 Uiso 1 1 calc R U . . .
C6 C 0.67096(19) 0.18427(19) 0.52050(7) 0.0158(3) Uani 1 1 d . . . . .
H6A H 0.6116 0.3019 0.5241 0.024 Uiso 1 1 calc R U . . .
H6B H 0.7910 0.1794 0.5372 0.024 Uiso 1 1 calc R U . . .
H6C H 0.6028 0.0903 0.5501 0.024 Uiso 1 1 calc R U . . .
C20 C 0.8800(2) -0.34737(19) 0.55630(7) 0.0158(3) Uani 1 1 d . . . . .
H20A H 1.0013 -0.3821 0.5379 0.019 Uiso 1 1 calc R U . . .
H20B H 0.7995 -0.4412 0.5508 0.019 Uiso 1 1 calc R U . . .
C23 C 0.8025(2) -0.13727(19) -0.02810(7) 0.0159(3) Uani 1 1 d . . . . .
H23A H 0.8615 -0.0303 -0.0539 0.019 Uiso 1 1 calc R U . . .
H23B H 0.6743 -0.1229 -0.0367 0.019 Uiso 1 1 calc R U . . .
C1 C 0.43198(19) 0.64852(19) 0.10220(7) 0.0152(3) Uani 1 1 d . . . . .
H1A H 0.4875 0.6294 0.0556 0.023 Uiso 1 1 calc R U . . .
H1B H 0.4608 0.7661 0.1117 0.023 Uiso 1 1 calc R U . . .
H1C H 0.3027 0.6441 0.1019 0.023 Uiso 1 1 calc R U . . .
C21 C 0.8798(2) -0.3264(2) 0.63356(8) 0.0177(3) Uani 1 1 d . . . . .
H21A H 0.9648 -0.2381 0.6385 0.027 Uiso 1 1 calc R U . . .
H21B H 0.9139 -0.4420 0.6622 0.027 Uiso 1 1 calc R U . . .
H21C H 0.7605 -0.2856 0.6503 0.027 Uiso 1 1 calc R U . . .
C24 C 0.8851(2) -0.3048(2) -0.05260(8) 0.0235(3) Uani 1 1 d . . . . .
H24A H 1.0122 -0.3157 -0.0445 0.035 Uiso 1 1 calc R U . . .
H24B H 0.8697 -0.2984 -0.1036 0.035 Uiso 1 1 calc R U . . .
H24C H 0.8273 -0.4095 -0.0256 0.035 Uiso 1 1 calc R U . . .
H1 H 0.596(3) 0.321(3) 0.0974(11) 0.024(5) Uiso 1 1 d . . . . .
H3 H 0.866(2) -0.265(3) 0.3046(10) 0.018(4) Uiso 1 1 d . . . . .
H2 H 0.573(3) 0.398(3) 0.3972(11) 0.030(5) Uiso 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
O3 C19 1.3420(16) . ?
O3 C20 1.4513(16) . ?
O1 C16 1.3414(16) . ?
O1 C17 1.4527(16) . ?
O5 C22 1.3460(16) . ?
O5 C23 1.4553(16) . ?
O6 C22 1.2221(17) . ?
O2 C16 1.2195(17) . ?
O4 C19 1.2242(17) . ?
N3 C12 1.3586(18) . ?
N3 C15 1.3768(17) . ?
N3 H3 0.847(19) . ?
N2 C7 1.3588(18) . ?
N2 C10 1.3817(17) . ?
N2 H2 0.90(2) . ?
N1 C2 1.3634(18) . ?
N1 C5 1.3789(17) . ?
N1 H1 0.89(2) . ?
C4 C5 1.4017(18) . ?
C4 C10 1.4147(18) . ?
C4 C3 1.4426(18) . ?
C5 C14 1.4137(18) . ?
C16 C3 1.4594(18) . ?
C12 C13 1.3947(19) . ?
C12 C11 1.4934(18) . ?
C7 C8 1.3932(19) . ?
C7 C6 1.4940(18) . ?
C8 C9 1.4431(18) . ?
C8 C19 1.4512(19) . ?
C13 C14 1.4480(18) . ?
C13 C22 1.4554(18) . ?
C14 C15 1.3995(18) . ?
C10 C9 1.4024(18) . ?
C15 C9 1.4171(18) . ?
C3 C2 1.3928(19) . ?
C2 C1 1.4932(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C17 C18 1.5071(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C20 C21 1.5051(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C23 C24 1.504(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C19 O3 C20 116.25(11) . . ?
C16 O1 C17 116.67(11) . . ?
C22 O5 C23 115.97(10) . . ?
C12 N3 C15 111.01(11) . . ?
C12 N3 H3 126.6(13) . . ?
C15 N3 H3 122.4(13) . . ?
C7 N2 C10 110.81(11) . . ?
C7 N2 H2 128.8(13) . . ?
C10 N2 H2 120.4(13) . . ?
C2 N1 C5 110.91(11) . . ?
C2 N1 H1 127.2(13) . . ?
C5 N1 H1 121.9(13) . . ?
C5 C4 C10 117.09(12) . . ?
C5 C4 C3 106.72(12) . . ?
C10 C4 C3 136.19(13) . . ?
N1 C5 C4 107.29(12) . . ?
N1 C5 C14 129.76(12) . . ?
C4 C5 C14 122.94(12) . . ?
O2 C16 O1 122.44(12) . . ?
O2 C16 C3 125.02(12) . . ?
O1 C16 C3 112.54(11) . . ?
N3 C12 C13 107.83(12) . . ?
N3 C12 C11 119.34(12) . . ?
C13 C12 C11 132.80(12) . . ?
N2 C7 C8 107.96(12) . . ?
N2 C7 C6 120.02(12) . . ?
C8 C7 C6 132.02(13) . . ?
C7 C8 C9 107.35(12) . . ?
C7 C8 C19 127.51(12) . . ?
C9 C8 C19 125.08(12) . . ?
C12 C13 C14 107.18(11) . . ?
C12 C13 C22 128.67(12) . . ?
C14 C13 C22 124.12(12) . . ?
C15 C14 C5 117.18(12) . . ?
C15 C14 C13 106.37(12) . . ?
C5 C14 C13 136.45(12) . . ?
N2 C10 C9 107.42(11) . . ?
N2 C10 C4 129.77(12) . . ?
C9 C10 C4 122.82(12) . . ?
O6 C22 O5 121.67(12) . . ?
O6 C22 C13 125.15(12) . . ?
O5 C22 C13 113.18(11) . . ?
N3 C15 C14 107.60(12) . . ?
N3 C15 C9 129.58(12) . . ?
C14 C15 C9 122.82(13) . . ?
O4 C19 O3 122.18(12) . . ?
O4 C19 C8 124.97(12) . . ?
O3 C19 C8 112.85(12) . . ?
C10 C9 C15 117.12(12) . . ?
C10 C9 C8 106.46(11) . . ?
C15 C9 C8 136.42(13) . . ?
C2 C3 C4 107.24(12) . . ?
C2 C3 C16 127.98(12) . . ?
C4 C3 C16 124.78(12) . . ?
N1 C2 C3 107.84(12) . . ?
N1 C2 C1 119.65(12) . . ?
C3 C2 C1 132.50(13) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C17 C18 105.53(11) . . ?
O1 C17 H17A 110.6 . . ?
C18 C17 H17A 110.6 . . ?
O1 C17 H17B 110.6 . . ?
C18 C17 H17B 110.6 . . ?
H17A C17 H17B 108.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C20 C21 106.84(11) . . ?
O3 C20 H20A 110.4 . . ?
C21 C20 H20A 110.4 . . ?
O3 C20 H20B 110.4 . . ?
C21 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
O5 C23 C24 105.85(11) . . ?
O5 C23 H23A 110.6 . . ?
C24 C23 H23A 110.6 . . ?
O5 C23 H23B 110.6 . . ?
C24 C23 H23B 110.6 . . ?
H23A C23 H23B 108.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_bripe
_database_code_depnum_ccdc_archive 'CCDC 1935236'
loop_
_audit_author_name
_audit_author_address
'B. Satish Kumar'
;Research Scholar, School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2019-10-28 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         'C8 H9 Br I N O2'
_chemical_formula_sum            'C8 H9 Br I N O2'
_chemical_formula_weight         357.97

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -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'

_cell_length_a                   9.9046(5)
_cell_length_b                   8.2466(4)
_cell_length_c                   14.0533(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.4160(10)
_cell_angle_gamma                90
_cell_volume                     1106.56(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      25.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.149
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    6.475
_shelx_estimated_absorpt_T_min   0.7158
_shelx_estimated_absorpt_T_max   0.7459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7158
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18333
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.825
_diffrn_reflns_theta_max         25.108
_diffrn_reflns_theta_full        25.108
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3616
_reflns_number_gt                3530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.962

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2933P] 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_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3616
_refine_ls_number_parameters     239
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_refine_ls_shift/su_max          0.000
_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
I1 I 0.70732(8) 0.95041(9) 0.68257(6) 0.0618(3) Uani 1 1 d . . . . .
I2 I 0.19700(13) 0.80270(16) 0.04546(8) 0.0864(4) Uani 1 1 d . . . . .
Br2 Br 0.09416(12) 0.94872(14) 0.26792(9) 0.0539(3) Uani 1 1 d . . . . .
Br1 Br 0.80898(13) 0.85401(17) 0.95431(10) 0.0613(4) Uani 1 1 d . . . . .
O3 O 0.5019(11) 0.6331(14) 0.0780(7) 0.065(2) Uani 1 1 d . . . . .
O4 O 0.6618(9) 0.6043(11) 0.2256(6) 0.0510(18) Uani 1 1 d . . . . .
O2 O 0.2350(10) 0.7091(14) 0.6168(7) 0.063(2) Uani 1 1 d . . . . .
O1 O 0.4091(12) 0.8105(15) 0.5571(7) 0.073(3) Uani 1 1 d . . . . .
N2 N 0.3727(10) 0.8217(12) 0.3472(7) 0.0437(19) Uani 1 1 d . . . . .
H2 H 0.3698 0.8477 0.4058 0.052 Uiso 1 1 calc R U . . .
N1 N 0.5240(10) 0.7292(12) 0.8877(7) 0.0440(19) Uani 1 1 d . . . . .
H1 H 0.5262 0.7016 0.9472 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3118(12) 0.7904(12) 0.1865(7) 0.043(2) Uani 1 1 d . . . . .
C4 C 0.5906(11) 0.8347(12) 0.7624(9) 0.041(2) Uani 1 1 d . . . . .
C13 C 0.7642(16) 0.5372(16) 0.1783(10) 0.057(3) Uani 1 1 d . . . . .
H13A H 0.7258 0.4434 0.1387 0.069 Uiso 1 1 calc R U . . .
H13B H 0.7897 0.6176 0.1357 0.069 Uiso 1 1 calc R U . . .
C12 C 0.2686(14) 0.8504(14) 0.2663(9) 0.049(2) Uani 1 1 d . . . . .
C00F C 0.5393(13) 0.6502(14) 0.1693(8) 0.045(2) Uani 1 1 d . . . . .
C3 C 0.4505(10) 0.7683(12) 0.7266(7) 0.0378(19) Uani 1 1 d . . . . .
C10 C 0.4523(10) 0.7259(11) 0.2257(7) 0.0375(19) Uani 1 1 d . . . . .
C2 C 0.4175(12) 0.7015(12) 0.8090(8) 0.042(2) Uani 1 1 d . . . . .
C9 C 0.4840(10) 0.7468(14) 0.3263(8) 0.041(2) Uani 1 1 d . . . . .
C8 C 0.6153(13) 0.703(2) 0.4069(9) 0.060(3) Uani 1 1 d . . . . .
H8A H 0.6001 0.7245 0.4704 0.090 Uiso 1 1 calc R U . . .
H8B H 0.6927 0.7667 0.3990 0.090 Uiso 1 1 calc R U . . .
H8C H 0.6359 0.5899 0.4022 0.090 Uiso 1 1 calc R U . . .
C5 C 0.6319(12) 0.8096(15) 0.8599(8) 0.047(2) Uani 1 1 d . . . . .
C1 C 0.2905(13) 0.6191(17) 0.8216(9) 0.049(3) Uani 1 1 d . . . . .
H1A H 0.3165 0.5432 0.8752 0.074 Uiso 1 1 calc R U . . .
H1B H 0.2452 0.5626 0.7620 0.074 Uiso 1 1 calc R U . . .
H1C H 0.2275 0.6982 0.8358 0.074 Uiso 1 1 calc R U . . .
C7 C 0.1437(17) 0.705(3) 0.5182(11) 0.074(5) Uani 1 1 d . . . . .
H7A H 0.1723 0.6198 0.4800 0.089 Uiso 1 1 calc R U . . .
H7B H 0.1462 0.8077 0.4853 0.089 Uiso 1 1 calc R U . . .
C14 C 0.8866(19) 0.491(3) 0.2573(15) 0.086(5) Uani 1 1 d . . . . .
H14A H 0.8566 0.4396 0.3094 0.129 Uiso 1 1 calc R U . . .
H14B H 0.9403 0.5861 0.2824 0.129 Uiso 1 1 calc R U . . .
H14C H 0.9434 0.4171 0.2319 0.129 Uiso 1 1 calc R U . . .
C6 C 0.3685(12) 0.7677(16) 0.6269(9) 0.047(2) Uani 1 1 d . . . . .
C15 C 0.001(2) 0.672(4) 0.5284(16) 0.095(6) Uani 1 1 d . . . . .
H15A H -0.0153 0.7364 0.5814 0.143 Uiso 1 1 calc R U . . .
H15B H -0.0081 0.5595 0.5423 0.143 Uiso 1 1 calc R U . . .
H15C H -0.0673 0.7003 0.4680 0.143 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
I1 C4 2.049(10) . ?
I2 C11 2.008(9) . ?
Br2 C12 1.914(13) . ?
Br1 C5 1.932(12) . ?
O3 C00F 1.245(16) . ?
O4 C00F 1.316(15) . ?
O4 C13 1.462(15) . ?
O2 C6 1.380(16) . ?
O2 C7 1.440(16) . ?
O1 C6 1.208(17) . ?
N2 C12 1.337(16) . ?
N2 C9 1.362(16) . ?
N2 H2 0.8600 . ?
N1 C2 1.330(15) . ?
N1 C5 1.399(16) . ?
N1 H1 0.8600 . ?
C11 C12 1.394(17) . ?
C11 C10 1.454(14) . ?
C4 C5 1.338(17) . ?
C4 C3 1.452(15) . ?
C13 C14 1.46(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C00F C10 1.458(15) . ?
C3 C2 1.397(15) . ?
C3 C6 1.420(16) . ?
C10 C9 1.375(15) . ?
C2 C1 1.480(16) . ?
C9 C8 1.524(16) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C7 C15 1.49(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C00F O4 C13 118.4(9) . . ?
C6 O2 C7 116.6(12) . . ?
C12 N2 C9 112.5(10) . . ?
C12 N2 H2 123.7 . . ?
C9 N2 H2 123.7 . . ?
C2 N1 C5 110.2(9) . . ?
C2 N1 H1 124.9 . . ?
C5 N1 H1 124.9 . . ?
C12 C11 C10 107.0(9) . . ?
C12 C11 I2 124.2(9) . . ?
C10 C11 I2 128.8(8) . . ?
C5 C4 C3 107.5(9) . . ?
C5 C4 I1 124.7(9) . . ?
C3 C4 I1 127.8(8) . . ?
C14 C13 O4 106.8(11) . . ?
C14 C13 H13A 110.4 . . ?
O4 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
O4 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
N2 C12 C11 106.8(10) . . ?
N2 C12 Br2 124.0(9) . . ?
C11 C12 Br2 129.2(9) . . ?
O3 C00F O4 124.2(11) . . ?
O3 C00F C10 123.5(11) . . ?
O4 C00F C10 112.3(9) . . ?
C2 C3 C6 128.2(11) . . ?
C2 C3 C4 105.9(9) . . ?
C6 C3 C4 125.9(10) . . ?
C9 C10 C11 106.1(9) . . ?
C9 C10 C00F 127.3(10) . . ?
C11 C10 C00F 126.5(10) . . ?
N1 C2 C3 108.2(10) . . ?
N1 C2 C1 119.4(10) . . ?
C3 C2 C1 132.3(11) . . ?
N2 C9 C10 107.5(9) . . ?
N2 C9 C8 121.8(10) . . ?
C10 C9 C8 130.6(10) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C5 N1 108.1(10) . . ?
C4 C5 Br1 130.4(9) . . ?
N1 C5 Br1 121.3(8) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C7 C15 106.4(15) . . ?
O2 C7 H7A 110.4 . . ?
C15 C7 H7A 110.4 . . ?
O2 C7 H7B 110.4 . . ?
C15 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C6 O2 122.4(12) . . ?
O1 C6 C3 125.0(12) . . ?
O2 C6 C3 112.6(10) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         1.015
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.129

