# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_hmk64-6
#TrackingRef '19126_web_deposit_cif_file_0_HardeshKMaurya_1364912196.X-ray of 10a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 Br N2 O3'
_chemical_formula_weight         405.29

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.9215(7)
_cell_length_b                   13.8042(18)
_cell_length_c                   26.079(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1771.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    2.341
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15064
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         28.35
_reflns_number_total             4349
_reflns_number_gt                4105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.2255P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_number_reflns         4349
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0583
_refine_ls_wR_factor_gt          0.0573
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_restrained_S_all      0.806
_refine_ls_shift/su_max          0.185
_refine_ls_shift/su_mean         0.013

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.098(5) 0.8190(14) 1.0100(8) 0.021(5) Uiso 1 1 d . . .
H9 H 0.324(6) 0.8358(19) 1.2109(10) 0.045(7) Uiso 1 1 d . . .
H5 H 0.560(5) 1.0685(15) 1.0769(8) 0.019(5) Uiso 1 1 d . . .
H14 H 0.444(5) 1.1057(14) 1.2418(8) 0.019(5) Uiso 1 1 d . . .
H8 H 0.671(4) 0.8860(14) 1.1539(8) 0.020(5) Uiso 1 1 d . . .
H13 H 0.709(5) 1.0451(15) 1.2499(8) 0.021(5) Uiso 1 1 d . . .
H12 H 0.173(6) 0.9799(17) 1.2681(9) 0.037(6) Uiso 1 1 d . . .
H3 H 0.796(6) 0.9576(19) 0.9197(11) 0.043(7) Uiso 1 1 d . . .
H6 H 0.721(5) 0.9809(15) 1.0982(7) 0.019(5) Uiso 1 1 d . . .
H2 H 0.177(7) 0.7735(19) 0.9270(11) 0.049(8) Uiso 1 1 d . . .
H7 H 0.849(6) 0.9205(16) 1.2004(9) 0.033(6) Uiso 1 1 d . . .
H4 H 0.748(6) 1.0031(19) 1.0028(10) 0.042(7) Uiso 1 1 d . . .
H11 H 0.376(5) 1.0082(17) 1.3134(9) 0.033(6) Uiso 1 1 d . . .
H20 H -0.480(5) 1.3334(17) 1.0982(10) 0.033(6) Uiso 1 1 d . . .
H16 H 0.385(5) 0.8354(16) 1.3007(10) 0.036(6) Uiso 1 1 d . . .
H15 H 0.662(6) 0.8790(17) 1.2918(9) 0.031(6) Uiso 1 1 d . . .
H17 H 0.606(5) 0.7756(15) 1.2216(8) 0.025(5) Uiso 1 1 d . . .
H18 H 0.003(5) 1.3132(17) 1.0400(9) 0.031(6) Uiso 1 1 d . . .
H21 H -0.247(5) 1.4131(16) 1.0973(8) 0.026(6) Uiso 1 1 d . . .
H22 H -0.416(6) 1.3947(17) 1.0500(10) 0.040(7) Uiso 1 1 d . . .
H19 H -0.237(5) 1.2309(18) 1.0414(10) 0.037(7) Uiso 1 1 d . . .
Br1 Br 0.56067(4) 0.831343(11) 0.844687(6) 0.02495(6) Uani 1 1 d . . .
O4 O -0.0324(3) 1.24103(8) 1.10587(4) 0.0189(2) Uani 1 1 d . . .
O3 O 0.1764(3) 1.13575(9) 1.05372(4) 0.0270(3) Uani 1 1 d . . .
N4 N 0.5258(3) 1.00693(9) 1.18917(5) 0.0171(3) Uani 1 1 d . . .
C9 C 0.4288(3) 1.04958(10) 1.14702(5) 0.0148(3) Uani 1 1 d . . .
N2 N -0.0046(3) 1.19663(12) 1.22430(5) 0.0258(3) Uani 1 1 d . . .
C4 C 0.4161(3) 0.91743(10) 1.01534(5) 0.0149(3) Uani 1 1 d . . .
O17 O 0.1669(3) 0.90588(8) 1.09256(5) 0.0207(2) Uani 1 1 d . . .
C14 C 0.4898(4) 0.88001(13) 1.27869(7) 0.0250(4) Uani 1 1 d . . .
C1 C 0.5026(3) 0.86613(11) 0.91390(6) 0.0179(3) Uani 1 1 d . . .
C10 C 0.5430(4) 1.01414(11) 1.09654(5) 0.0159(3) Uani 1 1 d . . .
C2 C 0.2932(4) 0.82234(12) 0.94093(6) 0.0212(3) Uani 1 1 d . . .
C3 C 0.2523(4) 0.84811(11) 0.99168(6) 0.0197(3) Uani 1 1 d . . .
C15 C 0.3653(4) 0.98115(14) 1.27843(7) 0.0240(4) Uani 1 1 d . . .
C11 C 0.1082(3) 1.16405(11) 1.18964(6) 0.0172(3) Uani 1 1 d . . .
C7 C 0.1341(3) 1.16495(11) 1.09692(6) 0.0171(3) Uani 1 1 d . . .
C16 C 0.5181(4) 1.04633(12) 1.24182(6) 0.0199(3) Uani 1 1 d . . .
C5 C 0.6266(4) 0.95991(12) 0.98754(6) 0.0208(3) Uani 1 1 d . . .
C8 C 0.2377(3) 1.12532(11) 1.14542(6) 0.0153(3) Uani 1 1 d . . .
C20 C 0.3570(3) 0.94296(11) 1.06995(6) 0.0146(3) Uani 1 1 d . . .
C13 C 0.5068(4) 0.84231(12) 1.22382(7) 0.0257(4) Uani 1 1 d . . .
C18 C -0.1512(4) 1.28468(13) 1.06053(6) 0.0229(4) Uani 1 1 d . . .
C6 C 0.6687(4) 0.93475(13) 0.93655(7) 0.0224(3) Uani 1 1 d . . .
C12 C 0.6602(4) 0.91122(12) 1.18875(6) 0.0204(3) Uani 1 1 d . . .
C30 C -0.3433(4) 1.36263(14) 1.07834(7) 0.0256(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.04092(10) 0.02237(8) 0.01157(7) -0.00102(6) 0.00530(7) 0.00444(7)
O4 0.0259(6) 0.0194(5) 0.0115(5) 0.0015(4) -0.0016(5) 0.0065(5)
O3 0.0410(7) 0.0284(6) 0.0115(5) -0.0012(5) -0.0012(5) 0.0131(6)
N4 0.0211(7) 0.0177(5) 0.0126(5) -0.0013(5) -0.0017(5) 0.0020(5)
C9 0.0161(6) 0.0158(6) 0.0124(6) -0.0008(5) 0.0001(6) -0.0024(6)
N2 0.0269(8) 0.0376(8) 0.0129(6) 0.0008(6) 0.0011(6) 0.0052(6)
C4 0.0166(7) 0.0166(6) 0.0114(6) -0.0002(5) 0.0016(6) 0.0043(6)
O17 0.0217(6) 0.0232(5) 0.0173(5) -0.0022(4) 0.0067(5) -0.0043(5)
C14 0.0337(11) 0.0251(8) 0.0162(7) 0.0026(6) -0.0006(7) -0.0049(7)
C1 0.0246(9) 0.0188(6) 0.0103(6) 0.0008(5) 0.0018(6) 0.0080(6)
C10 0.0164(7) 0.0192(6) 0.0121(6) 0.0009(5) 0.0002(6) 0.0003(6)
C2 0.0256(8) 0.0204(7) 0.0175(7) -0.0034(6) 0.0006(6) -0.0003(7)
C3 0.0212(8) 0.0200(8) 0.0179(7) -0.0007(6) 0.0035(6) -0.0021(6)
C15 0.0207(8) 0.0358(9) 0.0156(7) -0.0032(7) 0.0000(6) 0.0021(7)
C11 0.0181(7) 0.0203(6) 0.0132(6) 0.0039(6) -0.0020(5) -0.0010(6)
C7 0.0213(7) 0.0164(6) 0.0136(6) 0.0016(6) -0.0003(5) 0.0018(6)
C16 0.0270(10) 0.0196(7) 0.0131(7) -0.0032(5) -0.0071(6) 0.0036(6)
C5 0.0215(9) 0.0248(7) 0.0161(7) -0.0022(6) 0.0032(6) -0.0042(6)
C8 0.0191(7) 0.0154(6) 0.0113(7) 0.0015(5) -0.0001(5) -0.0018(6)
C20 0.0158(7) 0.0144(6) 0.0136(7) 0.0011(5) 0.0016(5) 0.0028(5)
C13 0.0398(11) 0.0185(7) 0.0189(7) -0.0015(6) -0.0040(7) 0.0007(7)
C18 0.0314(9) 0.0250(8) 0.0124(7) 0.0034(6) -0.0020(7) 0.0082(7)
C6 0.0235(8) 0.0280(8) 0.0159(7) 0.0002(6) 0.0071(7) -0.0024(7)
C12 0.0242(8) 0.0218(7) 0.0150(7) -0.0011(6) -0.0021(6) 0.0075(6)
C30 0.0300(9) 0.0278(8) 0.0191(8) 0.0047(7) -0.0013(7) 0.0097(8)

_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 1.8896(15) . ?
O4 C7 1.3523(19) . ?
O4 C18 1.4505(19) . ?
O3 C7 1.215(2) . ?
N4 C9 1.3350(19) . ?
N4 C12 1.478(2) . ?
N4 C16 1.4772(19) . ?
C9 C8 1.407(2) . ?
C9 C10 1.513(2) . ?
N2 C11 1.152(2) . ?
C4 C5 1.394(2) . ?
C4 C3 1.395(2) . ?
C4 C20 1.496(2) . ?
O17 C20 1.219(2) . ?
C14 C13 1.525(2) . ?
C14 C15 1.525(3) . ?
C1 C2 1.387(2) . ?
C1 C6 1.384(3) . ?
C10 C20 1.511(2) . ?
C2 C3 1.385(2) . ?
C15 C16 1.512(3) . ?
C11 C8 1.422(2) . ?
C7 C8 1.470(2) . ?
C5 C6 1.390(2) . ?
C13 C12 1.520(3) . ?
C18 C30 1.506(3) . ?

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
C7 O4 C18 115.22(12) . . ?
C9 N4 C12 123.24(13) . . ?
C9 N4 C16 126.42(13) . . ?
C12 N4 C16 110.34(12) . . ?
N4 C9 C8 126.23(13) . . ?
N4 C9 C10 116.18(13) . . ?
C8 C9 C10 117.57(13) . . ?
C5 C4 C3 119.21(14) . . ?
C5 C4 C20 122.73(14) . . ?
C3 C4 C20 118.06(15) . . ?
C13 C14 C15 109.29(14) . . ?
C2 C1 C6 121.36(15) . . ?
C2 C1 Br1 119.15(12) . . ?
C6 C1 Br1 119.49(12) . . ?
C9 C10 C20 112.62(14) . . ?
C3 C2 C1 118.78(16) . . ?
C2 C3 C4 120.99(16) . . ?
C16 C15 C14 110.35(15) . . ?
N2 C11 C8 177.43(17) . . ?
O3 C7 O4 121.46(14) . . ?
O3 C7 C8 127.98(15) . . ?
O4 C7 C8 110.53(13) . . ?
N4 C16 C15 112.37(14) . . ?
C6 C5 C4 120.21(16) . . ?
C9 C8 C11 123.72(13) . . ?
C9 C8 C7 122.29(13) . . ?
C11 C8 C7 113.73(14) . . ?
O17 C20 C4 120.74(15) . . ?
O17 C20 C10 121.07(14) . . ?
C4 C20 C10 118.18(13) . . ?
C12 C13 C14 112.22(14) . . ?
O4 C18 C30 107.37(14) . . ?
C1 C6 C5 119.43(16) . . ?
N4 C12 C13 109.42(15) . . ?

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
C12 N4 C9 C8 161.44(16) . . . . ?
C16 N4 C9 C8 -18.9(3) . . . . ?
C12 N4 C9 C10 -20.3(2) . . . . ?
C16 N4 C9 C10 159.30(16) . . . . ?
N4 C9 C10 C20 99.58(17) . . . . ?
C8 C9 C10 C20 -82.04(17) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
Br1 C1 C2 C3 179.87(12) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C5 C4 C3 C2 -1.1(2) . . . . ?
C20 C4 C3 C2 178.90(15) . . . . ?
C13 C14 C15 C16 -53.08(19) . . . . ?
C18 O4 C7 O3 -0.7(2) . . . . ?
C18 O4 C7 C8 -178.77(14) . . . . ?
C9 N4 C16 C15 120.59(18) . . . . ?
C12 N4 C16 C15 -59.74(19) . . . . ?
C14 C15 C16 N4 56.73(19) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C20 C4 C5 C6 -178.71(16) . . . . ?
N4 C9 C8 C11 -3.6(3) . . . . ?
C10 C9 C8 C11 178.23(14) . . . . ?
N4 C9 C8 C7 -177.31(15) . . . . ?
C10 C9 C8 C7 4.5(2) . . . . ?
N2 C11 C8 C9 -157(4) . . . . ?
N2 C11 C8 C7 17(4) . . . . ?
O3 C7 C8 C9 6.2(3) . . . . ?
O4 C7 C8 C9 -175.90(14) . . . . ?
O3 C7 C8 C11 -168.16(18) . . . . ?
O4 C7 C8 C11 9.78(19) . . . . ?
C5 C4 C20 O17 178.21(15) . . . . ?
C3 C4 C20 O17 -1.8(2) . . . . ?
C5 C4 C20 C10 -3.1(2) . . . . ?
C3 C4 C20 C10 176.87(14) . . . . ?
C9 C10 C20 O17 -13.5(2) . . . . ?
C9 C10 C20 C4 167.88(13) . . . . ?
C15 C14 C13 C12 55.0(2) . . . . ?
C7 O4 C18 C30 176.10(15) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
Br1 C1 C6 C5 -179.67(13) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C9 N4 C12 C13 -121.44(17) . . . . ?
C16 N4 C12 C13 58.88(18) . . . . ?
C14 C13 C12 N4 -58.02(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.065


_database_code_depnum_ccdc_archive 'CCDC 932166'