data_2013798
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o1
_journal_page_last  o5
_publ_section_title
;
Four trifluoromethylnitrobenzene analogues
;
loop_
_publ_author_name
  'Daniel E. Lynch'
  'Ian McClenaghan'
_chemical_formula_moiety  'C17 H16 F3 N3 O2'
_chemical_formula_sum  'C17 H16 F3 N3 O2'
_chemical_formula_iupac  'C17 H16 F3 N3 O2'
_chemical_formula_weight  351.33
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y+1/2, z+1/2'
  '-x, -y, -z'
  '-x, y-1/2, -z-1/2'
_cell_length_a  30.6687(12)
_cell_length_b  9.9731(3)
_cell_length_c  10.4592(3)
_cell_angle_alpha  90
_cell_angle_beta  95.8496(10)
_cell_angle_gamma  90
_cell_volume  3182.41(18)
_cell_formula_units_Z  8
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.467
_diffrn_ambient_temperature  150(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  C1A 0.09429(9) 0.1451(3) 0.0310(3) 0.0213(7) Uani d . 1 . . C
  C2A 0.06807(9) 0.2612(2) 0.0111(2) 0.0202(7) Uani d . 1 . . C
  N21A 0.08262(9) 0.3937(2) 0.0587(2) 0.0284(6) Uani d . 1 . . N
  O21A 0.12176(7) 0.42108(19) 0.0617(2) 0.0394(6) Uani d . 1 . . O
  O22A 0.05467(7) 0.47313(18) 0.08779(19) 0.0402(6) Uani d . 1 . . O
  C3A 0.02849(9) 0.2609(3) -0.0655(3) 0.0242(7) Uani d . 1 . . C
  H3A 0.0109 0.3395 -0.0727 0.030 Uiso calc R 1 . . H
  C4A 0.01447(9) 0.1455(3) -0.1317(3) 0.0224(7) Uani d . 1 . . C
  C41A -0.02757(10) 0.1464(3) -0.2158(3) 0.0299(8) Uani d . 1 . . C
  F41A -0.04239(5) 0.02284(15) -0.24613(16) 0.0416(5) Uani d . 1 . . F
  F42A -0.05967(5) 0.20914(16) -0.16140(16) 0.0454(5) Uani d . 1 . . F
  F43A -0.02484(5) 0.20959(16) -0.32835(16) 0.0431(5) Uani d . 1 . . F
  C5A 0.04093(9) 0.0334(3) -0.1199(3) 0.0269(7) Uani d . 1 . . C
  H5A 0.0324 -0.0447 -0.1681 0.034 Uiso calc R 1 . . H
  C6A 0.07947(9) 0.0321(3) -0.0400(3) 0.0254(7) Uani d . 1 . . C
  H6A 0.0965 -0.0476 -0.0329 0.032 Uiso calc R 1 . . H
  N7A 0.13233(7) 0.1413(2) 0.1165(2) 0.0230(6) Uani d . 1 . . N
  C8A 0.12967(9) 0.1877(3) 0.2488(3) 0.0251(7) Uani d . 1 . . C
  H81A 0.1153 0.1182 0.2974 0.031 Uiso calc R 1 . . H
  H82A 0.1117 0.2702 0.2476 0.031 Uiso calc R 1 . . H
  C9A 0.17492(8) 0.2161(3) 0.3145(3) 0.0248(7) Uani d . 1 . . C
  H91A 0.1887 0.2889 0.2685 0.031 Uiso calc R 1 . . H
  H92A 0.1726 0.2462 0.4038 0.031 Uiso calc R 1 . . H
  N10A 0.20232(7) 0.0947(2) 0.3160(2) 0.0223(6) Uani d . 1 . . N
  C11A 0.20436(9) 0.0436(3) 0.1865(3) 0.0273(7) Uani d . 1 . . C
  H10A 0.2214 -0.0409 0.1906 0.034 Uiso calc R 1 . . H
  H11A 0.2198 0.1093 0.1363 0.034 Uiso calc R 1 . . H
  C12A 0.15895(9) 0.0179(3) 0.1186(3) 0.0257(7) Uani d . 1 . . C
  H12A 0.1615 -0.0123 0.0295 0.032 Uiso calc R 1 . . H
  H13A 0.1444 -0.0540 0.1638 0.032 Uiso calc R 1 . . H
  C13A 0.24301(9) 0.1055(2) 0.3942(3) 0.0240(7) Uani d . 1 . . C
  C14A 0.24276(10) 0.1389(3) 0.5232(3) 0.0286(8) Uani d . 1 . . C
  H14A 0.2156 0.1529 0.5576 0.036 Uiso calc R 1 . . H
  C15A 0.28161(11) 0.1520(3) 0.6022(3) 0.0380(9) Uani d . 1 . . C
  H15A 0.2809 0.1752 0.6900 0.047 Uiso calc R 1 . . H
  C16A 0.32162(11) 0.1312(3) 0.5536(3) 0.0391(9) Uani d . 1 . . C
  H16A 0.3483 0.1410 0.6074 0.049 Uiso calc R 1 . . H
  C17A 0.32200(10) 0.0965(3) 0.4273(3) 0.0360(8) Uani d . 1 . . C
  H17A 0.3493 0.0816 0.3939 0.045 Uiso calc R 1 . . H
  C18A 0.28327(9) 0.0824(3) 0.3465(3) 0.0301(8) Uani d . 1 . . C
  H18A 0.2842 0.0572 0.2593 0.038 Uiso calc R 1 . . H
  C1B 0.42414(10) 0.6388(3) 0.5830(3) 0.0283(7) Uani d . 1 . . C
  C2B 0.45093(9) 0.7455(3) 0.5503(3) 0.0263(7) Uani d . 1 . . C
  N21B 0.43331(8) 0.8595(2) 0.4719(3) 0.0329(7) Uani d . 1 . . N
  O21B 0.40595(7) 0.8366(2) 0.3810(2) 0.0464(6) Uani d . 1 . . O
  O22B 0.44769(7) 0.9713(2) 0.4996(2) 0.0491(7) Uani d . 1 . . O
  C3B 0.49575(9) 0.7473(3) 0.5831(3) 0.0296(8) Uani d . 1 . . C
  H3B 0.5125 0.8226 0.5618 0.037 Uiso calc R 1 . . H
  C4B 0.51600(9) 0.6397(3) 0.6465(3) 0.0289(8) Uani d . 1 . . C
  C41B 0.56374(11) 0.6436(3) 0.6882(3) 0.0414(9) Uani d . 1 . . C
  F41B 0.58253(5) 0.52277(17) 0.69733(17) 0.0507(5) Uani d . 1 . . F
  F42B 0.57224(6) 0.69977(17) 0.80571(19) 0.0583(6) Uani d . 1 . . F
  F43B 0.58638(6) 0.71653(19) 0.6102(2) 0.0647(6) Uani d . 1 . . F
  C5B 0.49123(10) 0.5304(3) 0.6744(3) 0.0357(8) Uani d . 1 . . C
  H5B 0.5052 0.4543 0.7150 0.045 Uiso calc R 1 . . H
  C6B 0.44634(10) 0.5300(3) 0.6441(3) 0.0338(8) Uani d . 1 . . C
  H6B 0.4300 0.4537 0.6654 0.042 Uiso calc R 1 . . H
  N7B 0.37900(7) 0.6412(2) 0.5570(2) 0.0290(6) Uani d . 1 . . N
  C8B 0.35391(9) 0.5169(3) 0.5639(3) 0.0326(8) Uani d . 1 . . C
  H81B 0.3475 0.5005 0.6534 0.041 Uiso calc R 1 . . H
  H82B 0.3711 0.4401 0.5360 0.041 Uiso calc R 1 . . H
  C9B 0.31135(9) 0.5306(3) 0.4763(3) 0.0299(8) Uani d . 1 . . C
  H91B 0.3181 0.5428 0.3865 0.037 Uiso calc R 1 . . H
  H92B 0.2940 0.4473 0.4803 0.037 Uiso calc R 1 . . H
  N10B 0.28563(7) 0.6441(2) 0.5139(2) 0.0252(6) Uani d . 1 . . N
  C11B 0.31132(9) 0.7689(3) 0.5122(3) 0.0296(8) Uani d . 1 . . C
  H10B 0.2941 0.8444 0.5423 0.037 Uiso calc R 1 . . H
  H11B 0.3177 0.7885 0.4233 0.037 Uiso calc R 1 . . H
  C12B 0.35379(9) 0.7553(3) 0.5982(3) 0.0297(8) Uani d . 1 . . C
  H12B 0.3712 0.8385 0.5944 0.037 Uiso calc R 1 . . H
  H13B 0.3474 0.7418 0.6882 0.037 Uiso calc R 1 . . H
  C13B 0.24282(9) 0.6581(3) 0.4467(3) 0.0245(7) Uani d . 1 . . C
  C14B 0.22729(10) 0.5759(3) 0.3458(3) 0.0333(8) Uani d . 1 . . C
  H14B 0.2454 0.5066 0.3182 0.042 Uiso calc R 1 . . H
  C15B 0.18538(11) 0.5938(3) 0.2845(3) 0.0393(9) Uani d . 1 . . C
  H15B 0.1751 0.5365 0.2153 0.049 Uiso calc R 1 . . H
  C16B 0.15846(10) 0.6934(3) 0.3226(3) 0.0385(9) Uani d . 1 . . C
  H16B 0.1298 0.7056 0.2801 0.048 Uiso calc R 1 . . H
  C17B 0.17397(10) 0.7755(3) 0.4242(3) 0.0395(9) Uani d . 1 . . C
  H17B 0.1558 0.8451 0.4511 0.049 Uiso calc R 1 . . H
  C18B 0.21527(10) 0.7575(3) 0.4865(3) 0.0313(8) Uani d . 1 . . C
  H18B 0.2251 0.8133 0.5572 0.039 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  C1A 0.0187(18) 0.0259(16) 0.0203(16) -0.0005(13) 0.0062(14) 0.0007(14)
  C2A 0.0226(18) 0.0161(15) 0.0217(16) -0.0027(13) 0.0020(14) -0.0038(13)
  N21A 0.0318(17) 0.0238(14) 0.0290(16) 0.0025(13) -0.0007(13) 0.0004(12)
  O21A 0.0252(14) 0.0364(12) 0.0556(15) -0.0088(11) 0.0003(12) -0.0049(11)
  O22A 0.0388(15) 0.0283(12) 0.0528(15) 0.0073(11) 0.0018(12) -0.0115(10)
  C3A 0.0209(18) 0.0244(16) 0.0282(18) 0.0048(13) 0.0061(14) 0.0029(14)
  C4A 0.0197(17) 0.0241(17) 0.0234(18) -0.0002(13) 0.0017(14) 0.0037(14)
  C41A 0.031(2) 0.0256(18) 0.033(2) -0.0013(15) 0.0011(17) 0.0038(15)
  F41A 0.0330(11) 0.0294(10) 0.0589(13) -0.0087(8) -0.0123(9) -0.0013(9)
  F42A 0.0219(11) 0.0570(11) 0.0560(13) 0.0094(9) -0.0023(9) -0.0108(10)
  F43A 0.0415(12) 0.0474(11) 0.0379(11) -0.0040(9) -0.0083(9) 0.0126(9)
  C5A 0.029(2) 0.0241(17) 0.0272(18) -0.0033(14) -0.0002(15) -0.0022(14)
  C6A 0.0241(19) 0.0218(16) 0.0301(18) 0.0036(14) 0.0009(15) 0.0017(14)
  N7A 0.0180(14) 0.0265(13) 0.0242(15) 0.0059(11) 0.0010(12) -0.0051(11)
  C8A 0.0189(18) 0.0286(16) 0.0282(18) 0.0034(14) 0.0043(14) -0.0036(14)
  C9A 0.0214(18) 0.0271(17) 0.0255(17) 0.0011(14) 0.0010(14) -0.0052(13)
  N10A 0.0181(14) 0.0245(13) 0.0238(15) 0.0027(11) 0.0003(11) -0.0019(11)
  C11A 0.0228(19) 0.0260(16) 0.0331(19) 0.0050(13) 0.0032(15) -0.0037(14)
  C12A 0.0193(18) 0.0267(16) 0.0302(18) 0.0055(14) -0.0016(14) -0.0058(14)
  C13A 0.0222(18) 0.0176(15) 0.031(2) -0.0019(13) -0.0038(15) 0.0035(13)
  C14A 0.0223(19) 0.0317(17) 0.031(2) 0.0030(14) 0.0008(16) -0.0015(15)
  C15A 0.042(2) 0.0324(18) 0.036(2) 0.0002(16) -0.0099(19) -0.0027(15)
  C16A 0.027(2) 0.0340(19) 0.051(2) -0.0030(16) -0.0168(19) 0.0033(17)
  C17A 0.0201(19) 0.0383(19) 0.049(2) -0.0008(15) -0.0010(17) 0.0080(17)
  C18A 0.0227(19) 0.0328(17) 0.035(2) 0.0030(15) 0.0021(16) 0.0033(15)
  C1B 0.0207(19) 0.0298(17) 0.0342(19) -0.0037(14) 0.0021(15) 0.0001(15)
  C2B 0.0205(18) 0.0258(16) 0.0321(19) 0.0026(14) 0.0006(15) 0.0032(14)
  N21B 0.0221(16) 0.0355(17) 0.0417(18) -0.0015(13) 0.0052(14) 0.0064(14)
  O21B 0.0406(16) 0.0540(14) 0.0421(15) -0.0092(12) -0.0081(13) 0.0150(12)
  O22B 0.0403(15) 0.0262(13) 0.0784(18) -0.0052(11) -0.0052(13) 0.0075(12)
  C3B 0.0240(19) 0.0288(17) 0.0368(19) -0.0058(14) 0.0065(15) -0.0048(15)
  C4B 0.0221(19) 0.0296(18) 0.035(2) 0.0010(15) 0.0017(15) -0.0020(15)
  C41B 0.026(2) 0.038(2) 0.059(3) -0.0001(17) -0.0034(19) -0.0050(19)
  F41B 0.0280(11) 0.0421(11) 0.0798(15) 0.0127(9) -0.0045(10) -0.0072(10)
  F42B 0.0377(13) 0.0573(12) 0.0746(15) 0.0084(10) -0.0202(11) -0.0250(11)
  F43B 0.0197(11) 0.0688(13) 0.1061(18) -0.0045(10) 0.0091(11) 0.0236(13)
  C5B 0.027(2) 0.0341(19) 0.045(2) 0.0073(16) 0.0005(17) 0.0071(16)
  C6B 0.025(2) 0.0311(18) 0.045(2) -0.0047(15) 0.0021(16) 0.0100(15)
  N7B 0.0170(15) 0.0241(13) 0.0461(17) -0.0041(11) 0.0042(13) -0.0007(12)
  C8B 0.0198(18) 0.0250(17) 0.054(2) -0.0014(14) 0.0069(16) 0.0047(15)
  C9B 0.0218(19) 0.0221(16) 0.046(2) -0.0064(14) 0.0039(16) 0.0010(15)
  N10B 0.0167(14) 0.0202(13) 0.0384(16) -0.0006(11) 0.0024(12) -0.0007(11)
  C11B 0.0228(19) 0.0246(16) 0.041(2) -0.0010(14) 0.0016(15) -0.0006(14)
  C12B 0.0196(18) 0.0286(17) 0.041(2) -0.0030(14) 0.0031(16) -0.0016(15)
  C13B 0.0207(18) 0.0241(16) 0.0283(18) -0.0039(14) 0.0000(15) 0.0064(14)
  C14B 0.027(2) 0.0359(18) 0.037(2) -0.0034(15) -0.0005(16) 0.0014(16)
  C15B 0.038(2) 0.038(2) 0.041(2) -0.0138(17) -0.0058(18) 0.0030(17)
  C16B 0.025(2) 0.041(2) 0.047(2) -0.0068(17) -0.0095(17) 0.0201(18)
  C17B 0.026(2) 0.0285(18) 0.063(2) 0.0029(15) 0.0014(18) 0.0115(17)
  C18B 0.0253(19) 0.0253(17) 0.043(2) -0.0045(14) 0.0004(16) -0.0013(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  C1A N7A . 1.396(3) ?
  C1A C6A . 1.400(3) ?
  C1A C2A . 1.413(3) ?
  C2A C3A . 1.384(3) ?
  C2A N21A . 1.465(3) ?
  N21A O22A . 1.228(3) ?
  N21A O21A . 1.228(3) ?
  C3A C4A . 1.389(3) ?
  C4A C5A . 1.379(3) ?
  C4A C41A . 1.485(4) ?
  C41A F41A . 1.340(3) ?
  C41A F42A . 1.341(3) ?
  C41A F43A . 1.345(3) ?
  C5A C6A . 1.376(3) ?
  N7A C8A . 1.469(3) ?
  N7A C12A . 1.475(3) ?
  C8A C9A . 1.512(3) ?
  C9A N10A . 1.473(3) ?
  N10A C13A . 1.425(3) ?
  N10A C11A . 1.454(3) ?
  C11A C12A . 1.519(3) ?
  C13A C14A . 1.391(4) ?
  C13A C18A . 1.397(4) ?
  C14A C15A . 1.385(4) ?
  C15A C16A . 1.391(4) ?
  C16A C17A . 1.367(4) ?
  C17A C18A . 1.393(4) ?
  C3A H3A . 0.95 ?
  C5A H5A . 0.95 ?
  C6A H6A . 0.95 ?
  C8A H81A . 0.99 ?
  C8A H82A . 0.99 ?
  C9A H91A . 0.99 ?
  C9A H92A . 0.99 ?
  C11A H10A . 0.99 ?
  C11A H11A . 0.99 ?
  C12A H12A . 0.99 ?
  C12A H13A . 0.99 ?
  C14A H14A . 0.95 ?
  C15A H15A . 0.95 ?
  C16A H16A . 0.95 ?
  C17A H17A . 0.95 ?
  C18A H18A . 0.95 ?
  C1B N7B . 1.383(3) ?
  C1B C6B . 1.400(4) ?
  C1B C2B . 1.408(4) ?
  C2B C3B . 1.383(4) ?
  C2B N21B . 1.472(3) ?
  N21B O22B . 1.223(3) ?
  N21B O21B . 1.224(3) ?
  C3B C4B . 1.376(4) ?
  C4B C5B . 1.377(4) ?
  C4B C41B . 1.485(4) ?
  C41B F41B . 1.335(3) ?
  C41B F43B . 1.339(4) ?
  C41B F42B . 1.351(3) ?
  C5B C6B . 1.381(4) ?
  N7B C12B . 1.464(3) ?
  N7B C8B . 1.465(3) ?
  C8B C9B . 1.522(3) ?
  C9B N10B . 1.456(3) ?
  N10B C13B . 1.431(3) ?
  N10B C11B . 1.474(3) ?
  C11B C12B . 1.511(3) ?
  C13B C14B . 1.382(4) ?
  C13B C18B . 1.394(4) ?
  C14B C15B . 1.388(4) ?
  C15B C16B . 1.376(4) ?
  C16B C17B . 1.387(4) ?
  C17B C18B . 1.376(4) ?
  C3B H3B . 0.95 ?
  C5B H5B . 0.95 ?
  C6B H6B . 0.95 ?
  C8B H81B . 0.99 ?
  C8B H82B . 0.99 ?
  C9B H91B . 0.99 ?
  C9B H92B . 0.99 ?
  C11B H10B . 0.99 ?
  C11B H11B . 0.99 ?
  C12B H12B . 0.99 ?
  C12B H13B . 0.99 ?
  C14B H14B . 0.95 ?
  C15B H15B . 0.95 ?
  C16B H16B . 0.95 ?
  C17B H17B . 0.95 ?
  C18B H18B . 0.95 ?