# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_NIL
_database_code_depnum_ccdc_archive 'CCDC 2491318'
loop_
_audit_author_name
_audit_author_address
B.Hemalatha
;Periyar University
India
;

_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;
_publcif_datablock.id            {0c412580-6189-4c6a-8492-fc72974a91a2}

_audit_creation_date             '24-Sep-25 T15:21:07-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

_cell_length_a                   12.31200(10)
_cell_length_b                   9.83230(10)
_cell_length_c                   12.19680(10)
_cell_angle_alpha                90
_cell_angle_beta                 117.4110(10)
_cell_angle_gamma                90
_cell_volume                     1310.72(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w2 = 1/[s²(Fo²)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6351
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.018
_refine_ls_wR_factor_ref         0.042
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_shift/su_max          0

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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
F(1) F 0.268772 0.18073 0.597357 0.02 Uani 1 4
F(2) F 0.230733 0.229939 0.410629 0.025 Uani 1 4
F(3) F 0.345389 0.059005 0.503354 0.022 Uani 1 4
O(1) O 0.238783 0.46353 0.559509 0.021 Uani 1 4
O(2) O 0.357909 0.472931 0.757536 0.026 Uani 1 4
O(3) O 0.897129 0.287243 0.772776 0.015 Uani 1 4
O(4) O 0.621131 0.255034 0.363217 0.014 Uani 1 4
N(1) N 0.337522 0.447969 0.651709 0.015 Uani 1 4
N(2) N 0.733685 0.27364 0.576461 0.011 Uani 1 4
N(3) N 0.828121 0.203844 0.468505 0.013 Uani 1 4
C(1) C 0.543591 0.478778 0.677205 0.012 Uani 1 4
C(2) C 0.642052 0.438283 0.658415 0.012 Uani 1 4
C(3) C 0.634944 0.316501 0.597292 0.01 Uani 1 4
C(4) C 0.530162 0.235638 0.552814 0.012 Uani 1 4
C(5) C 0.430352 0.276857 0.568842 0.011 Uani 1 4
C(6) C 0.439623 0.398382 0.631934 0.011 Uani 1 4
C(7) C 0.31841 0.187155 0.519585 0.015 Uani 1 4
C(8) C 0.854494 0.264867 0.662617 0.011 Uani 1 4
C(9) C 0.926334 0.22149 0.594471 0.011 Uani 1 4
C(10) C 0.718175 0.243601 0.45571 0.011 Uani 1 4
C(11) C 1.014223 0.334828 0.600703 0.016 Uani 1 4
C(12) C 0.99422 0.088615 0.648864 0.017 Uani 1 4
H(1) H 0.544105 0.574007 0.722089 0.02923 Uiso 1 4
H(2) H 0.722124 0.502911 0.690683 0.02433 Uiso 1 4
H(3) H 0.844195 0.205359 0.398051 0.02313 Uiso 1 4
H(4) H 0.530692 0.140716 0.508017 0.02618 Uiso 1 4
H(11A) H 0.966572 0.427485 0.56676 0.02474 Uiso 1 4
H(11B) H 1.085809 0.345777 0.691852 0.02281 Uiso 1 4
H(11C) H 1.055628 0.305539 0.545094 0.03144 Uiso 1 4
H(12A) H 1.05536 0.098908 0.744135 0.02689 Uiso 1 4
H(12B) H 1.046354 0.062481 0.602897 0.02507 Uiso 1 4
H(12C) H 0.93053 0.010692 0.637316 0.02542 Uiso 1 4



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
F(1) 7.1555 0 -0.011(5) -0.017(5) -0.023(5) -0.091(6) 0.008(5) 0.017(5)
0.010(6) -0.003(6) 0.018(7) -0.008(7) 0.002(6) 0.024(7) 0.043(7) -0.011(7)
-0.039(7) 0.015(9) -0.013(9) 0.012(8) 0.026(9) 0.010(9) 0.000(9) 0.003(9)
0.004(9) 0.012(9) 0.991475 1.05(3) 1.05(3) 1.05(3) 1.05(3) 1.05(3)
F(2) 7.2424 0 -0.069(6) 0.048(6) -0.065(6) -0.037(7) -0.024(6) 0.080(7)
0.023(7) 0.036(7) 0.008(9) 0.032(8) 0.020(9) 0.022(8) -0.043(8) -0.008(9)
0.026(8) 0.045(11) -0.004(10) -0.027(11) 0.008(11) -0.003(11) -0.001(11)
-0.011(11) 0.013(10) -0.013(10) 0.991475 1.05(3) 1.05(3) 1.05(3) 1.05(3)
1.05(3)
F(3) 7.19 0 0.010(4) 0.018(5) 0.027(5) -0.075(5) 0.000(5) 0.025(6) -0.002(6)
-0.017(6) 0.010(7) 0.009(6) 0.032(7) -0.029(7) 0.038(7) -0.006(7) 0.019(7)
0.013(9) 0.006(8) -0.008(9) -0.013(9) 0.011(8) -0.001(9) 0.002(9) 0.008(9)
-0.006(9) 0.991475 1.05(3) 1.05(3) 1.05(3) 1.05(3) 1.05(3)
O(1) 6.2116 0 -0.0038 0.0047 -0.0644 -0.0711 -0.0085 -0.0009 -0.0679 0.0191
0.0583 -0.0409 0.0205 -0.0284 -0.0272 0.0104 0.0247 0 0 0 0 0 0 0 0 0 0.975018
1.09(2) 1.09(2) 1.09(2) 1.09(2) 1.09(2)
O(2) 6.24 0 -0.0302 0.0313 -0.0495 -0.086 0.0443 -0.0154 -0.0335 0.0065 0.0553
-0.0244 0.038 -0.0222 0.006 0.014 -0.0068 0 0 0 0 0 0 0 0 0 0.975018 1.09(2)
1.09(2) 1.09(2) 1.09(2) 1.09(2)
O(3) 6.29 0 0.024(5) 0.002(5) -0.045(5) 0.002(5) 0.006(5) -0.004(5) -0.080(5)
-0.005(5) 0.017(7) -0.015(6) 0.009(6) 0.021(6) 0.004(6) 0.028(6) 0.012(6) 0 0 0
0 0 0 0 0 0 0.99178 1.10(4) 1.10(4) 1.10(4) 1.10(4) 1.10(4)
O(4) 6.31 0 -0.008(5) -0.008(5) -0.086(7) -0.014(5) -0.015(5) 0.018(5)
-0.061(5) 0.006(5) 0.026(7) 0.010(6) 0.008(6) -0.009(6) 0.006(6) 0.007(6)
0.004(6) 0 0 0 0 0 0 0 0 0 0.99178 1.10(4) 1.10(4) 1.10(4) 1.10(4) 1.10(4)
N(1) 4.76 0 0.0066 -0.0263 -0.0177 0.0795 -0.0011 -0.0324 -0.1388 -0.0051
0.3009 -0.014 0.0524 0.226 -0.0061 -0.0479 0.0511 0 0 0 0 0 0 0 0 0 1.005288
0.820(10) 0.820(10) 0.820(10) 0.820(10) 0.820(10)
N(2) 5.29 0 0.0683 -0.1266 0.0219 -0.0101 0.0157 -0.0303 -0.1255 0.0414 0.326
-0.0145 0.2107 0.2256 -0.0249 0.0462 0.0429 0 0 0 0 0 0 0 0 0 0.991102
0.694(12) 0.694(12) 0.694(12) 0.694(12) 0.694(12)
N(3) 5.11 0 0.010(10) -0.010(10) -0.012(10) 0.012(8) -0.022(8) -0.008(8)
0.034(8) -0.010(8) 0.193(15) 0.036(10) -0.005(10) 0.117(12) -0.072(11)
0.052(11) -0.014(11) 0 0 0 0 0 0 0 0 0 0.980355 0.87(3) 0.87(3) 0.87(3) 0.87(3)
0.87(3)
C(1) 4.22 0 -0.018(15) 0.049(15) 0.030(17) 0.039(15) -0.020(13) -0.009(16)
-0.174(13) -0.029(12) 0.24(2) 0.007(15) -0.052(19) 0.209(17) -0.030(17)
0.027(14) -0.041(14) 0 0 0 0 0 0 0 0 0 0.99162 0.915(12) 0.915(12) 0.915(12)
0.915(12) 0.915(12)
C(2) 4.22 0 -0.027(12) 0.019(13) -0.013(13) 0.114(10) 0.021(10) 0.022(10)
-0.173(10) 0.015(10) 0.266(14) 0.004(12) 0.026(13) 0.159(13) -0.013(13)
-0.013(12) 0.024(12) 0 0 0 0 0 0 0 0 0 0.99162 0.915(12) 0.915(12) 0.915(12)
0.915(12) 0.915(12)
C(3) 3.8505 0 -0.011(10) 0.096(11) 0.085(12) 0.097(10) -0.027(8) -0.065(9)
-0.097(9) -0.005(8) 0.206(15) 0.020(11) -0.019(11) 0.162(13) -0.005(11)
0.011(10) 0.019(10) 0 0 0 0 0 0 0 0 0 1.005554 0.99(2) 0.99(2) 0.99(2) 0.99(2)
0.99(2)
C(4) 4.22 0 -0.010(12) -0.020(16) 0.007(14) 0.112(11) -0.008(10) 0.016(11)
-0.217(11) -0.018(12) 0.274(16) -0.012(13) 0.041(14) 0.167(15) -0.014(15)
0.007(14) 0.065(15) 0 0 0 0 0 0 0 0 0 0.99162 0.915(12) 0.915(12) 0.915(12)
0.915(12) 0.915(12)
C(5) 4.05 0 -0.015(15) 0.041(18) -0.004(16) 0.157(16) -0.014(12) -0.048(13)
-0.126(14) -0.013(11) 0.25(2) 0.064(16) -0.006(17) 0.22(2) -0.047(16)
-0.015(15) 0.016(15) 0 0 0 0 0 0 0 0 0 1.018725 0.85(2) 0.85(2) 0.85(2) 0.85(2)
0.85(2)
C(6) 4.08 0 0.017(11) 0.089(12) 0.004(11) 0.113(10) -0.007(9) -0.067(9)
-0.057(9) 0.012(8) 0.203(14) -0.002(11) 0.017(12) 0.164(13) -0.021(11)
-0.024(10) 0.031(10) 0 0 0 0 0 0 0 0 0 1.005554 0.99(2) 0.99(2) 0.99(2) 0.99(2)
0.99(2)
C(7) 3.77 0 0.067(12) -0.055(11) -0.076(11) -0.076(10) -0.104(10) 0.050(10)
0.025(9) -0.057(10) 0.246(17) 0.039(12) -0.006(13) 0.072(13) 0.072(13)
-0.015(12) -0.282(17) 0 0 0 0 0 0 0 0 0 0.979659 0.99(2) 0.99(2) 0.99(2)
0.99(2) 0.99(2)
C(8) 3.72 0 -0.009(10) -0.112(10) 0.085(11) 0.245(11) -0.029(9) 0.041(9)
-0.161(9) 0.023(9) 0.224(14) 0.003(12) 0.010(12) 0.164(12) -0.008(11)
-0.019(10) -0.002(11) 0 0 0 0 0 0 0 0 0 1.001593 0.993(9) 0.993(9) 0.993(9)
0.993(9) 0.993(9)
C(9) 4.07 0 -0.0392 0.0165 -0.0516 -0.0557 -0.0219 0.0407 0.0144 -0.0003 0.275
-0.0101 -0.0672 -0.0516 -0.0022 -0.0384 -0.22 0 0 0 0 0 0 0 0 0 1.003142
0.922(13) 0.922(13) 0.922(13) 0.922(13) 0.922(13)
C(10) 3.76 0 0.0417 0.048 0.1899 0.1733 -0.0443 -0.0437 -0.1625 -0.0059 0.265
0.0769 0.058 0.2254 -0.0484 0.0257 0.0529 0 0 0 0 0 0 0 0 0 1.001593 0.993(9)
0.993(9) 0.993(9) 0.993(9) 0.993(9)
C(11) 4.1 0 0.031(14) 0.058(14) 0.032(13) -0.011(12) -0.012(11) -0.014(12)
-0.055(11) -0.043(12) 0.303(18) -0.032(14) 0.017(15) -0.009(14) -0.023(14)
0.062(14) -0.254(16) 0 0 0 0 0 0 0 0 0 0.993924 0.856(14) 0.856(14) 0.856(14)
0.856(14) 0.856(14)
C(12) 4.15 0 -0.0754 0.0466 -0.0553 -0.011 -0.0102 -0.0005 -0.0345 0.0149
0.2546 -0.0506 0.0007 -0.0162 0.0383 -0.0282 -0.1993 0 0 0 0 0 0 0 0 0 0.993924
0.856(14) 0.856(14) 0.856(14) 0.856(14) 0.856(14)
H(1) 0.83 0 0 0 0.149(15) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2
1.2 1.2 1.2
H(2) 0.8 0 0 0 0.100(12) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2
1.2 1.2 1.2
H(3) 0.74 0 0 0 0.128(13) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2
1.2 1.2 1.2
H(4) 0.82 0 0 0 0.162(13) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2
1.2 1.2 1.2
H(11A) 0.8 0 0 0 0.0738 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2
1.2 1.2 1.2
H(11B) 0.78 0 0 0 0.1248 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2
1.2 1.2 1.2
H(11C) 0.81 0 0 0 0.1093 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2
1.2 1.2 1.2
H(12A) 0.8 0 0 0 0.096(12) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(12B) 0.81 0 0 0 0.122(11) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(12C) 0.8 0 0 0 0.110(11) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
F(1) C(7) Z F(1) F(3) Y
F(2) C(7) Z F(2) F(3) Y
F(3) C(7) Z F(3) F(2) Y
O(1) N(1) Z O(1) O(2) Y
O(2) N(1) Z O(2) O(1) Y
O(3) C(8) Z O(3) N(2) Y
O(4) C(10) Z O(4) N(3) Y
N(1) O(2) Z N(1) O(1) Y
N(2) C(8) Z N(2) C(3) Y
N(3) H(3) Z N(3) C(10) Y
C(1) H(1) Z C(1) C(6) Y
C(2) H(2) Z C(2) C(3) Y
C(3) C(2) Z C(3) C(4) Y
C(4) H(4) Z C(4) C(5) Y
C(5) C(4) Z C(5) C(6) Y
C(6) C(1) Z C(6) C(5) Y
C(7) F(2) Z C(7) F(3) Y
C(8) O(3) Z C(8) N(2) Y
C(9) N(3) Z C(9) C(8) Y
C(10) O(4) Z C(10) N(3) Y
C(11) H(11B) Z C(11) H(11A) Y
C(12) H(12B) Z C(12) H(12A) Y
H(1) C(1) Z H(1) C(6) Y
H(2) C(2) Z H(2) C(1) Y
H(3) N(3) Z H(3) C(10) Y
H(4) C(4) Z H(4) C(3) Y
H(11A) C(11) Z H(11A) H(11C) Y
H(11B) C(11) Z H(11B) H(11C) Y
H(11C) C(11) Z H(11C) H(11B) Y
H(12A) C(12) Z H(12A) H(12B) Y
H(12B) C(12) Z H(12B) H(12A) Y
H(12C) C(12) Z H(12C) H(12B) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F(1) C(7) 1.3457472502076 1_555 1_555 yes
F(2) C(7) 1.336941493496 1_555 1_555 yes
F(3) C(7) 1.3407810348367 1_555 1_555 yes
O(1) N(1) 1.2276591677107 1_555 1_555 yes
O(2) N(1) 1.2210536398232 1_555 1_555 yes
O(3) C(8) 1.2164674787528 1_555 1_555 yes
O(4) C(10) 1.2131765044776 1_555 1_555 yes
N(1) C(6) 1.4680823137426 1_555 1_555 yes
N(2) C(3) 1.4157923098738 1_555 1_555 yes
N(2) C(8) 1.3729233094959 1_555 1_555 yes
N(2) C(10) 1.4261195308438 1_555 1_555 yes
N(3) C(9) 1.4636211060084 1_555 1_555 yes
N(3) C(10) 1.3472329033779 1_555 1_555 yes
N(3) H(3) 0.96663801250755 1_555 1_555 yes
C(1) C(2) 1.3915494330188 1_555 1_555 yes
C(1) C(6) 1.3847369014089 1_555 1_555 yes
C(1) H(1) 1.0831605134707 1_555 1_555 yes
C(2) C(3) 1.3918060386205 1_555 1_555 yes
C(2) H(2) 1.0832030094374 1_555 1_555 yes
C(3) C(4) 1.3951130509583 1_555 1_555 yes
C(4) C(5) 1.3905954742703 1_555 1_555 yes
C(4) H(4) 1.0830086156644 1_555 1_555 yes
C(5) C(6) 1.3971504962784 1_555 1_555 yes
C(5) C(7) 1.5086249444127 1_555 1_555 yes
C(8) C(9) 1.5270730673938 1_555 1_555 yes
C(9) C(11) 1.530617467383 1_555 1_555 yes
C(9) C(12) 1.5280773973935 1_555 1_555 yes
C(11) H(11A) 1.0592129720197 1_555 1_555 yes
C(11) H(11B) 1.0593172666257 1_555 1_555 yes
C(11) H(11C) 1.0588602175998 1_555 1_555 yes
C(12) H(12A) 1.0591290364365 1_555 1_555 yes
C(12) H(12B) 1.0600482372436 1_555 1_555 yes
C(12) H(12C) 1.0583205867883 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) N(1) O(2) 125.3250540658 1_555 1_555 1_555 yes
O(1) N(1) C(6) 116.91132384219 1_555 1_555 1_555 yes
O(2) N(1) C(6) 117.74622487911 1_555 1_555 1_555 yes
C(3) N(2) C(8) 126.76647850179 1_555 1_555 1_555 yes
C(3) N(2) C(10) 121.94953887353 1_555 1_555 1_555 yes
C(8) N(2) C(10) 111.11441850389 1_555 1_555 1_555 yes
C(9) N(3) C(10) 112.8107336881 1_555 1_555 1_555 yes
C(9) N(3) H(3) 121.53486394263 1_555 1_555 1_555 yes
C(10) N(3) H(3) 119.90428991708 1_555 1_555 1_555 yes
C(2) C(1) C(6) 119.10802791551 1_555 1_555 1_555 yes
C(2) C(1) H(1) 121.85281429655 1_555 1_555 1_555 yes
C(6) C(1) H(1) 118.96232767299 1_555 1_555 1_555 yes
C(1) C(2) C(3) 119.31771506298 1_555 1_555 1_555 yes
C(1) C(2) H(2) 119.23896398806 1_555 1_555 1_555 yes
C(3) C(2) H(2) 121.43872314545 1_555 1_555 1_555 yes
N(2) C(3) C(2) 120.31543272799 1_555 1_555 1_555 yes
N(2) C(3) C(4) 118.50838964523 1_555 1_555 1_555 yes
C(2) C(3) C(4) 121.16036866947 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.87153365878 1_555 1_555 1_555 yes
C(3) C(4) H(4) 117.90635125368 1_555 1_555 1_555 yes
C(5) C(4) H(4) 122.21093974406 1_555 1_555 1_555 yes
C(4) C(5) C(6) 118.24635302948 1_555 1_555 1_555 yes
C(4) C(5) C(7) 118.55889369327 1_555 1_555 1_555 yes
C(6) C(5) C(7) 123.18391747943 1_555 1_555 1_555 yes
N(1) C(6) C(1) 116.69058894622 1_555 1_555 1_555 yes
N(1) C(6) C(5) 121.03026944922 1_555 1_555 1_555 yes
C(1) C(6) C(5) 122.27300233691 1_555 1_555 1_555 yes
F(1) C(7) F(2) 107.12947995092 1_555 1_555 1_555 yes
F(1) C(7) F(3) 106.48265618612 1_555 1_555 1_555 yes
F(1) C(7) C(5) 112.0131025998 1_555 1_555 1_555 yes
F(2) C(7) F(3) 106.88654473916 1_555 1_555 1_555 yes
F(2) C(7) C(5) 112.54701649296 1_555 1_555 1_555 yes
F(3) C(7) C(5) 111.41956899106 1_555 1_555 1_555 yes
O(3) C(8) N(2) 126.76828042842 1_555 1_555 1_555 yes
O(3) C(8) C(9) 126.02424215598 1_555 1_555 1_555 yes
N(2) C(8) C(9) 107.20747616783 1_555 1_555 1_555 yes
N(3) C(9) C(8) 101.46780456072 1_555 1_555 1_555 yes
N(3) C(9) C(11) 111.22127662583 1_555 1_555 1_555 yes
N(3) C(9) C(12) 112.13695756232 1_555 1_555 1_555 yes
C(8) C(9) C(11) 110.06071158177 1_555 1_555 1_555 yes
C(8) C(9) C(12) 109.91224299859 1_555 1_555 1_555 yes
C(11) C(9) C(12) 111.59401312293 1_555 1_555 1_555 yes
O(4) C(10) N(2) 123.19144218965 1_555 1_555 1_555 yes
O(4) C(10) N(3) 129.90362775717 1_555 1_555 1_555 yes
N(2) C(10) N(3) 106.90377570283 1_555 1_555 1_555 yes
C(9) C(11) H(11A) 110.79892803508 1_555 1_555 1_555 yes
C(9) C(11) H(11B) 110.71496148913 1_555 1_555 1_555 yes
C(9) C(11) H(11C) 107.93944664552 1_555 1_555 1_555 yes
H(11A) C(11) H(11B) 111.48778155763 1_555 1_555 1_555 yes
H(11A) C(11) H(11C) 109.08246324311 1_555 1_555 1_555 yes
H(11B) C(11) H(11C) 106.65254548588 1_555 1_555 1_555 yes
C(9) C(12) H(12A) 111.4108984674 1_555 1_555 1_555 yes
C(9) C(12) H(12B) 108.72217107314 1_555 1_555 1_555 yes
C(9) C(12) H(12C) 109.72494259712 1_555 1_555 1_555 yes
H(12A) C(12) H(12B) 107.80933915756 1_555 1_555 1_555 yes
H(12A) C(12) H(12C) 108.90573135063 1_555 1_555 1_555 yes
H(12B) C(12) H(12C) 110.24804219878 1_555 1_555 1_555 yes

loop_
_publcif_info_exptl_table_extra_item
?

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_chemical_name_systematic        Nilutamide
_exptl_crystal_colour            Colourless
_exptl_crystal_recrystallization_method 'slow evaporation'
####################################################################### 
# 
# 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_FLU
_database_code_depnum_ccdc_archive 'CCDC 2491319'
loop_
_audit_author_name
_audit_author_address
'Hemalatha Balasubramanian'
;Periyar University
India
;

_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;
_publcif_datablock.id            {558091bd-c0d4-4ab8-a7de-a9963196b46a}

_audit_creation_date             '24-Sep-25 T21:21:24-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2+X,1/2-Y,+Z
4 1/2-X,1/2+Y,1/2+Z

_cell_length_a                   11.903(2)
_cell_length_b                   20.311(4)
_cell_length_c                   4.8681(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1176.9(3)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w2 = 1/[s²(Fo²)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6892
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.019
_refine_ls_R_factor_gt           0.016
_refine_ls_wR_factor_ref         0.04
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_shift/su_max          0.00009

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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
F(1) F 0.570244 0.830379 1.028918 0.02 Uani 1 4
F(2) F 0.514032 0.860064 0.624512 0.021 Uani 1 4
F(3) F 0.686314 0.83189 0.689621 0.022 Uani 1 4
O(1) O 0.347061 0.707935 1.19532 0.022 Uani 1 4
O(2) O 0.351549 0.796286 0.943478 0.022 Uani 1 4
O(3) O 0.607897 0.516046 0.215345 0.02 Uani 1 4
N(1) N 0.383825 0.74026 1.001949 0.014 Uani 1 4
N(2) N 0.679256 0.620047 0.247954 0.013 Uani 1 4
C(1) C 0.55296 0.746252 0.693587 0.012 Uani 1 4
C(2) C 0.622598 0.71409 0.507716 0.012 Uani 1 4
C(3) C 0.606948 0.647133 0.443882 0.011 Uani 1 4
C(4) C 0.523211 0.611349 0.581035 0.013 Uani 1 4
C(5) C 0.454554 0.643078 0.770852 0.013 Uani 1 4
C(6) C 0.467092 0.7099 0.821584 0.012 Uani 1 4
C(7) C 0.5794 0.817438 0.75922 0.015 Uani 1 4
C(8) C 0.677525 0.556659 0.14545 0.012 Uani 1 4
C(9) C 0.772561 0.540899 -0.054308 0.015 Uani 1 4
C(10) C 0.884311 0.537715 0.103147 0.023 Uani 1 4
C(11) C 0.748376 0.475953 -0.20105 0.023 Uani 1 4
H(2) H 0.689622 0.740138 0.409907 0.01984 Uiso 1 4
H(2A) H 0.736513 0.650883 0.171839 0.02661 Uiso 1 4
H(4) H 0.51215 0.559375 0.545876 0.02105 Uiso 1 4
H(5) H 0.388191 0.617746 0.886582 0.0195 Uiso 1 4
H(9) H 0.775943 0.579829 -0.204525 0.02913 Uiso 1 4
H(10A) H 0.904145 0.582313 0.211306 0.03809 Uiso 1 4
H(10B) H 0.954597 0.528046 -0.017637 0.04062 Uiso 1 4
H(10C) H 0.88178 0.498142 0.251077 0.05321 Uiso 1 4
H(11A) H 0.80971 0.464269 -0.344614 0.03127 Uiso 1 4
H(11B) H 0.673043 0.478984 -0.310272 0.0358 Uiso 1 4
H(11C) H 0.744564 0.435008 -0.060404 0.03029 Uiso 1 4



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
F(1) 7.27(3) 0 -0.002(5) -0.009(5) -0.033(5) -0.059(5) 0.009(5) -0.004(5)
0.012(5) -0.001(5) 0.008(7) 0.013(6) 0.002(6) 0.033(7) 0.004(7) 0.011(7)
0.002(7) 0.032(8) -0.013(8) 0.007(8) -0.004(8) -0.007(8) 0.005(9) 0.014(9)
-0.011(9) 0.001(9) 0.9829(12) 1.32(3) 1.32(3) 1.32(3) 1.32(3) 1.32(3)
F(2) 7.21(3) 0 0.030(5) -0.090(6) -0.069(5) -0.043(6) -0.031(5) 0.002(5)
0.003(6) -0.016(6) 0.050(7) -0.003(6) -0.018(7) 0.042(7) 0.062(7) -0.058(7)
-0.013(7) 0.005(9) 0.008(8) -0.025(9) 0.000(9) -0.009(9) 0.012(9) -0.018(9)
-0.009(9) 0.018(9) 0.9829(12) 1.32(3) 1.32(3) 1.32(3) 1.32(3) 1.32(3)
F(3) 7.15(3) 0 -0.010(5) 0.094(6) 0.024(5) -0.090(6) 0.002(5) 0.001(6)
-0.009(6) -0.003(6) -0.059(7) 0.013(7) 0.007(7) -0.060(7) -0.082(7) 0.072(8)
-0.001(8) 0.007(9) 0.000(8) 0.009(9) -0.015(9) -0.008(9) -0.015(9) -0.010(10)
-0.023(10) -0.006(9) 0.9829(12) 1.32(3) 1.32(3) 1.32(3) 1.32(3) 1.32(3)
O(1) 6.2938 0 0.055(7) 0.015(5) -0.035(5) -0.074(6) 0.001(6) 0.015(5) -0.087(6)
0.011(6) -0.034(7) -0.038(8) 0.027(7) 0.068(8) 0.010(7) 0.029(8) 0.052(8) 0 0 0
0 0 0 0 0 0 0.9747(15) 1.370677 1.370677 1.370677 1.370677 1.370677
O(2) 6.3189 0 0.094(7) 0.030(6) -0.036(5) -0.073(5) 0.016(6) 0.014(5) -0.067(6)
0.013(6) -0.020(8) -0.043(8) -0.008(7) 0.086(8) 0.010(7) 0.075(8) 0.075(8) 0 0
0 0 0 0 0 0 0 0.9747(15) 1.370677 1.370677 1.370677 1.370677 1.370677
O(3) 6.2922 0 0.025(10) 0.014(9) -0.093(9) -0.021(7) 0.015(8) -0.010(7)
-0.081(8) 0.019(7) 0.004(10) -0.009(10) -0.016(8) 0.029(10) 0.003(9) 0.034(10)
0.054(10) 0 0 0 0 0 0 0 0 0 0.972(2) 1.041124 1.041124 1.041124 1.041124
1.041124
N(1) 4.6545 0 0.025(16) 0.006(15) 0.006(17) 0.130(15) 0.013(11) -0.038(11)
-0.112(14) 0.005(11) 0.23(2) 0.002(16) 0.053(17) 0.24(2) 0.013(15) 0.017(14)
0.026(15) 0 0 0 0 0 0 0 0 0 1.001(3) 0.88(3) 0.88(3) 0.88(3) 0.88(3) 0.88(3)
N(2) 5.255 0 0.012(17) 0.026(17) 0.008(16) -0.021(12) -0.017(11) -0.064(13)
0.022(12) 0.036(12) 0.20(3) 0.009(14) 0.019(14) 0.11(2) 0.029(15) -0.001(15)
0.018(14) 0 0 0 0 0 0 0 0 0 0.974(3) 0.88(4) 0.88(4) 0.88(4) 0.88(4) 0.88(4)
C(1) 3.95(10) 0 0.04(5) 0.16(5) -0.05(6) 0.14(4) 0.00(3) -0.12(4) -0.26(4)
-0.10(3) 0.54(8) 0.06(5) -0.06(5) 0.44(7) -0.06(4) 0.03(4) -0.10(5) 0 0 0 0 0 0
0 0 0 0.982(7) 0.69(3) 0.69(3) 0.69(3) 0.69(3) 0.69(3)
C(2) 4.297 0 0.09(4) 0.00(4) 0.04(4) 0.20(3) 0.02(2) 0.03(2) -0.23(3) -0.04(2)
0.48(4) -0.07(3) 0.05(3) 0.26(3) 0.06(3) 0.01(3) 0.07(3) 0 0 0 0 0 0 0 0 0
0.962(3) 0.782(15) 0.782(15) 0.782(15) 0.782(15) 0.782(15)
C(3) 4.095 0 -0.05(3) 0.04(2) -0.03(3) 0.083(18) -0.005(16) 0.009(16) -0.23(2)
-0.012(16) 0.38(4) 0.01(2) 0.09(3) 0.19(3) 0.02(2) 0.00(2) 0.02(2) 0 0 0 0 0 0
0 0 0 0.973(5) 0.89(2) 0.89(2) 0.89(2) 0.89(2) 0.89(2)
C(4) 4.3033 0 0.06(4) 0.07(4) 0.17(4) 0.28(3) 0.03(2) -0.01(2) -0.27(3) 0.04(2)
0.39(4) -0.12(3) 0.03(3) 0.30(4) 0.03(3) -0.11(3) -0.04(3) 0 0 0 0 0 0 0 0 0
0.962(3) 0.782(15) 0.782(15) 0.782(15) 0.782(15) 0.782(15)
C(5) 4.3387 0 -0.02(4) -0.05(4) 0.08(4) 0.12(3) 0.00(2) 0.02(2) -0.24(3)
0.05(2) 0.39(4) 0.02(3) -0.13(3) 0.20(3) 0.00(3) -0.02(3) 0.00(3) 0 0 0 0 0 0 0
0 0 0.962(3) 0.782(15) 0.782(15) 0.782(15) 0.782(15) 0.782(15)
C(6) 3.65(9) 0 -0.04(3) 0.04(3) 0.17(3) 0.15(2) 0.002(17) -0.084(18) 0.023(17)
-0.020(16) 0.31(3) 0.04(2) 0.08(2) 0.24(3) -0.01(2) 0.04(2) 0.01(2) 0 0 0 0 0 0
0 0 0 0.973(5) 0.89(2) 0.89(2) 0.89(2) 0.89(2) 0.89(2)
C(7) 3.85 0 0.10(3) -0.11(3) -0.07(3) 0.006(19) -0.066(18) 0.038(17) 0.031(17)
-0.009(17) 0.49(4) 0.11(2) -0.02(2) 0.04(2) 0.03(2) -0.06(2) -0.39(4) 0 0 0 0 0
0 0 0 0 0.943(7) 0.88(2) 0.88(2) 0.88(2) 0.88(2) 0.88(2)
C(8) 4.28(9) 0 0.05(3) -0.10(3) 0.08(3) 0.28(3) -0.020(17) 0.017(18) -0.20(2)
0.049(17) 0.35(4) -0.01(2) 0.07(3) 0.27(3) 0.04(2) -0.03(2) 0.02(2) 0 0 0 0 0 0
0 0 0 0.960(7) 0.86(3) 0.86(3) 0.86(3) 0.86(3) 0.86(3)
C(9) 3.89(10) 0 -0.04(4) -0.02(4) 0.06(4) 0.05(3) 0.00(2) 0.04(2) 0.05(3)
-0.01(2) 0.43(7) -0.08(3) -0.01(3) 0.01(3) 0.08(4) -0.05(3) -0.30(5) 0 0 0 0 0
0 0 0 0 0.980(8) 0.78(4) 0.78(4) 0.78(4) 0.78(4) 0.78(4)
C(10) 4.2882 0 -0.04(2) -0.02(2) 0.10(3) -0.014(18) -0.022(17) 0.013(15)
0.068(16) 0.038(16) 0.31(3) 0.03(2) 0.00(2) -0.08(2) 0.00(2) -0.07(2) -0.18(2)
0 0 0 0 0 0 0 0 0 0.971(4) 1.00(4) 1.00(4) 1.00(4) 1.00(4) 1.00(4)
C(11) 4.2786 0 -0.05(2) 0.01(2) 0.07(2) -0.012(17) -0.067(17) 0.027(15)
0.030(17) 0.023(15) 0.17(3) -0.05(2) -0.04(2) -0.04(2) -0.03(2) 0.04(2)
-0.15(2) 0 0 0 0 0 0 0 0 0 0.971(4) 1.00(4) 1.00(4) 1.00(4) 1.00(4) 1.00(4)
H(2) 0.71(3) 0 0 0 0.07(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(2A) 0.74(3) 0 0 0 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(4) 0.61(3) 0 0 0 0.09(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(5) 0.63(3) 0 0 0 0.15(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(9) 0.77(4) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(10A) 0.7944 0 0 0 0.12(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(10B) 0.91(4) 0 0 0 0.17(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(10C) 0.89(4) 0 0 0 0.03(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(11A) 0.72(3) 0 0 0 0.10(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(11B) 0.79(3) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(11C) 0.7588 0 0 0 0.23(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
F(1) C(7) Z F(1) F(3) Y
F(2) C(7) Z F(2) F(3) Y
F(3) C(7) Z F(3) F(2) Y
O(1) N(1) Z O(1) O(2) Y
O(2) N(1) Z O(2) O(1) Y
O(3) C(8) Z O(3) H(4) Y
N(1) O(1) Z N(1) O(2) Y
N(2) H(2A) Z N(2) C(8) Y
C(1) C(2) Z C(1) C(6) Y
C(2) H(2) Z C(2) C(1) Y
C(3) N(2) Z C(3) C(4) Y
C(4) H(4) Z C(4) C(5) Y
C(5) H(5) Z C(5) C(6) Y
C(6) C(5) Z C(6) C(1) Y
C(7) F(2) Z C(7) F(1) Y
C(8) O(3) Z C(8) N(2) Y
C(9) H(9) Z C(9) C(8) Y
C(10) H(10C) Z C(10) H(10B) Y
C(11) H(11C) Z C(11) H(11A) Y
H(2) C(2) Z H(2) C(3) Y
H(2A) N(2) Z H(2A) C(8) Y
H(4) C(4) Z H(4) C(5) Y
H(5) C(5) Z H(5) C(6) Y
H(9) C(9) Z H(9) C(8) Y
H(10A) C(10) Z H(10A) H(10B) Y
H(10B) C(10) Z H(10B) H(10C) Y
H(10C) C(10) Z H(10C) H(10B) Y
H(11A) C(11) Z H(11A) H(11C) Y
H(11B) C(11) Z H(11B) H(11A) Y
H(11C) C(11) Z H(11C) H(11A) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F(1) C(7) 1.3433978189157 1_555 1_555 yes
F(2) C(7) 1.3360492875131 1_555 1_555 yes
F(3) C(7) 1.3492362505534 1_555 1_555 yes
O(1) N(1) 1.2282958610726 1_555 1_555 yes
O(2) N(1) 1.2343349600501 1_555 1_555 yes
O(3) C(8) 1.2178314577669 1_555 1_555 yes
N(1) C(6) 1.4606591511036 1_555 1_555 yes
N(2) C(3) 1.3975554548823 1_555 1_555 yes
N(2) C(8) 1.3809699796771 1_555 1_555 yes
N(2) H(2A) 0.99702140239518 1_555 1_555 yes
C(1) C(2) 1.3901589014764 1_555 1_555 yes
C(1) C(6) 1.4064409648311 1_555 1_555 yes
C(1) C(7) 1.5138422105887 1_555 1_555 yes
C(2) C(3) 1.4074228491724 1_555 1_555 yes
C(2) H(2) 1.0691504797785 1_555 1_555 yes
C(3) C(4) 1.4026755777847 1_555 1_555 yes
C(4) C(5) 1.391775618712 1_555 1_555 yes
C(4) H(4) 1.0775231960655 1_555 1_555 yes
C(5) C(6) 1.387583491601 1_555 1_555 yes
C(5) H(5) 1.0982276624154 1_555 1_555 yes
C(8) C(9) 1.5256920458962 1_555 1_555 yes
C(9) C(10) 1.5365579387878 1_555 1_555 yes
C(9) C(11) 1.5275182903122 1_555 1_555 yes
C(9) H(9) 1.0777855304526 1_555 1_555 yes
C(10) H(10A) 1.0740235416147 1_555 1_555 yes
C(10) H(10B) 1.0412551785263 1_555 1_555 yes
C(10) H(10C) 1.0796176631704 1_555 1_555 yes
C(11) H(11A) 1.0381406589442 1_555 1_555 yes
C(11) H(11B) 1.0442870518072 1_555 1_555 yes
C(11) H(11C) 1.0781867896246 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) N(1) O(2) 123.96239887866 1_555 1_555 1_555 yes
O(1) N(1) C(6) 118.4743862857 1_555 1_555 1_555 yes
O(2) N(1) C(6) 117.5023541868 1_555 1_555 1_555 yes
C(3) N(2) C(8) 127.18767376787 1_555 1_555 1_555 yes
C(3) N(2) H(2A) 115.29708484231 1_555 1_555 1_555 yes
C(8) N(2) H(2A) 117.4893077737 1_555 1_555 1_555 yes
C(2) C(1) C(6) 118.35789900067 1_555 1_555 1_555 yes
C(2) C(1) C(7) 117.53166704703 1_555 1_555 1_555 yes
C(6) C(1) C(7) 123.98588966479 1_555 1_555 1_555 yes
C(1) C(2) C(3) 121.25655908401 1_555 1_555 1_555 yes
C(1) C(2) H(2) 120.14907065578 1_555 1_555 1_555 yes
C(3) C(2) H(2) 118.59437307705 1_555 1_555 1_555 yes
N(2) C(3) C(2) 116.71571716988 1_555 1_555 1_555 yes
N(2) C(3) C(4) 123.95110887209 1_555 1_555 1_555 yes
C(2) C(3) C(4) 119.318033701 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.55980972491 1_555 1_555 1_555 yes
C(3) C(4) H(4) 121.25651508989 1_555 1_555 1_555 yes
C(5) C(4) H(4) 119.1680463666 1_555 1_555 1_555 yes
C(4) C(5) C(6) 120.52694710907 1_555 1_555 1_555 yes
C(4) C(5) H(5) 123.09209466447 1_555 1_555 1_555 yes
C(6) C(5) H(5) 116.37975301981 1_555 1_555 1_555 yes
N(1) C(6) C(1) 122.5331944216 1_555 1_555 1_555 yes
N(1) C(6) C(5) 116.54862086565 1_555 1_555 1_555 yes
C(1) C(6) C(5) 120.85144658576 1_555 1_555 1_555 yes
F(1) C(7) F(2) 107.79758935337 1_555 1_555 1_555 yes
F(1) C(7) F(3) 106.22245565489 1_555 1_555 1_555 yes
F(1) C(7) C(1) 112.10348166632 1_555 1_555 1_555 yes
F(2) C(7) F(3) 106.56133465566 1_555 1_555 1_555 yes
F(2) C(7) C(1) 113.22079911823 1_555 1_555 1_555 yes
F(3) C(7) C(1) 110.54075939915 1_555 1_555 1_555 yes
O(3) C(8) N(2) 122.73175657502 1_555 1_555 1_555 yes
O(3) C(8) C(9) 122.72011171798 1_555 1_555 1_555 yes
N(2) C(8) C(9) 114.51040247748 1_555 1_555 1_555 yes
C(8) C(9) C(10) 109.43366981926 1_555 1_555 1_555 yes
C(8) C(9) C(11) 109.84858459417 1_555 1_555 1_555 yes
C(8) C(9) H(9) 107.83163482107 1_555 1_555 1_555 yes
C(10) C(9) C(11) 111.10524629803 1_555 1_555 1_555 yes
C(10) C(9) H(9) 109.69483762683 1_555 1_555 1_555 yes
C(11) C(9) H(9) 108.86327882055 1_555 1_555 1_555 yes
C(9) C(10) H(10A) 113.53682740069 1_555 1_555 1_555 yes
C(9) C(10) H(10B) 114.9466224282 1_555 1_555 1_555 yes
C(9) C(10) H(10C) 109.87233130654 1_555 1_555 1_555 yes
H(10A) C(10) H(10B) 105.02862952152 1_555 1_555 1_555 yes
H(10A) C(10) H(10C) 107.8820022826 1_555 1_555 1_555 yes
H(10B) C(10) H(10C) 104.99092064586 1_555 1_555 1_555 yes
C(9) C(11) H(11A) 112.31614395512 1_555 1_555 1_555 yes
C(9) C(11) H(11B) 110.42720916437 1_555 1_555 1_555 yes
C(9) C(11) H(11C) 112.15267111759 1_555 1_555 1_555 yes
H(11A) C(11) H(11B) 105.93473470056 1_555 1_555 1_555 yes
H(11A) C(11) H(11C) 106.30627758339 1_555 1_555 1_555 yes
H(11B) C(11) H(11C) 109.43064700729 1_555 1_555 1_555 yes

loop_
_publcif_info_exptl_table_extra_item
?

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_chemical_name_systematic        flutamide
