data_2013027
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o688
_journal_page_last  o690
_publ_section_title
;
7-Methoxy-1H-indazole, a new inhibitor of neuronal nitric oxide synthase
;
loop_
_publ_author_name
  "Sopkov\'a-de Oliveira Santos, Jana"
  'Collot, Valerie'
  'Rault, Sylvain'
_chemical_name_common  '7-MI'
_chemical_formula_moiety  'C8 H8 N2 O'
_chemical_formula_sum  'C8 H8 N2 O'
_chemical_formula_weight  148.16
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  14.1297(5)
_cell_length_b  16.0074(7)
_cell_length_c  15.6990(10)
_cell_angle_alpha  90
_cell_angle_beta  102.533(4)
_cell_angle_gamma  90
_cell_volume  3466.2(3)
_cell_formula_units_Z  18
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.278
_diffrn_ambient_temperature  293(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 0.2087(2) 0.3827(2) 0.8152(2) 0.0659(10) Uani d . 1 . . C
  N2A 0.2716(2) 0.4343(2) 0.8667(2) 0.0747(9) Uani d . 1 . . N
  H2A 0.3326 0.4366 0.8676 0.090 Uiso calc R 1 . . H
  N3A 0.2263(3) 0.4823(2) 0.9168(2) 0.0808(9) Uani d . 1 . . N
  C4A 0.1345(3) 0.4597(3) 0.8969(3) 0.0869(12) Uani d . 1 . . C
  H4A 0.0864 0.4829 0.9216 0.104 Uiso calc R 1 . . H
  C5A 0.1181(3) 0.3962(2) 0.8335(2) 0.0723(10) Uani d . 1 . . C
  C6A 0.0379(3) 0.3482(3) 0.7901(3) 0.0931(13) Uani d . 1 . . C
  H6A -0.0235 0.3559 0.8011 0.112 Uiso calc R 1 . . H
  C7A 0.0544(3) 0.2901(3) 0.7314(3) 0.0939(14) Uani d . 1 . . C
  H7A 0.0028 0.2574 0.7027 0.113 Uiso calc R 1 . . H
  C8A 0.1455(3) 0.2778(2) 0.7126(3) 0.0840(12) Uani d . 1 . . C
  H8A 0.1528 0.2379 0.6714 0.101 Uiso calc R 1 . . H
  C9A 0.2242(3) 0.3233(2) 0.7536(3) 0.0712(10) Uani d . 1 . . C
  O10A 0.31709(19) 0.31719(17) 0.74411(19) 0.0853(8) Uani d . 1 . . O
  C11A 0.3365(3) 0.2588(3) 0.6814(3) 0.0939(13) Uani d . 1 . . C
  H11A 0.3272 0.2031 0.7006 0.141 Uiso calc R 1 . . H
  H12A 0.4022 0.2653 0.6753 0.141 Uiso calc R 1 . . H
  H13A 0.2931 0.2688 0.6262 0.141 Uiso calc R 1 . . H
  C1B 0.6990(2) 0.1344(2) 0.8818(2) 0.0640(9) Uani d . 1 . . C
  N2B 0.66845(19) 0.08728(19) 0.94318(19) 0.0705(8) Uani d . 1 . . N
  H2B 0.7062 0.0615 0.9854 0.085 Uiso calc R 1 . . H
  N3B 0.5701(2) 0.0867(2) 0.9283(2) 0.0744(8) Uani d . 1 . . N
  C4B 0.5398(3) 0.1327(3) 0.8583(3) 0.0745(10) Uani d . 1 . . C
  H4B 0.4748 0.1429 0.8337 0.089 Uiso calc R 1 . . H
  C5B 0.6176(3) 0.1645(2) 0.8248(2) 0.0713(10) Uani d . 1 . . C
  C6B 0.6302(4) 0.2146(3) 0.7553(3) 0.0938(13) Uani d . 1 . . C
  H6B 0.5771 0.2362 0.7158 0.113 Uiso calc R 1 . . H
  C7B 0.7214(5) 0.2305(3) 0.7471(4) 0.1104(17) Uani d . 1 . . C
  H7B 0.7301 0.2631 0.7003 0.133 Uiso calc R 1 . . H
  C8B 0.8029(4) 0.2011(3) 0.8047(4) 0.1020(15) Uani d . 1 . . C
  H8B 0.8643 0.2150 0.7969 0.122 Uiso calc R 1 . . H
  C9B 0.7931(3) 0.1512(3) 0.8736(3) 0.0828(12) Uani d . 1 . . C
  O10B 0.86536(19) 0.1177(2) 0.9360(2) 0.1086(10) Uani d . 1 . . O
  C11B 0.9628(3) 0.1340(4) 0.9307(4) 0.146(2) Uani d . 1 . . C
  H11B 0.9768 0.1055 0.8811 0.219 Uiso calc R 1 . . H
  H12B 1.0059 0.1145 0.9829 0.219 Uiso calc R 1 . . H
  H13B 0.9715 0.1930 0.9246 0.219 Uiso calc R 1 . . H
  C1C 0.2245(2) 0.0522(2) 0.6196(2) 0.0596(9) Uani d . 1 . . C
  N2C 0.13110(19) 0.05753(18) 0.62580(18) 0.0664(8) Uani d . 1 . . N
  H2C 0.1078 0.0345 0.6663 0.080 Uiso calc R 1 . . H
  N3C 0.0786(2) 0.1040(2) 0.5599(2) 0.0748(8) Uani d . 1 . . N
  C4C 0.1396(3) 0.1271(3) 0.5126(2) 0.0790(11) Uani d . 1 . . C
  H4C 0.1224 0.1597 0.4626 0.095 Uiso calc R 1 . . H
  C5C 0.2344(3) 0.0970(2) 0.5459(2) 0.0689(9) Uani d . 1 . . C
  C6C 0.3254(3) 0.1025(3) 0.5246(3) 0.0897(12) Uani d . 1 . . C
  H6C 0.3336 0.1321 0.4757 0.108 Uiso calc R 1 . . H
  C7C 0.4018(3) 0.0632(3) 0.5773(4) 0.0993(14) Uani d . 1 . . C
  H7C 0.4627 0.0660 0.5639 0.119 Uiso calc R 1 . . H
  C8C 0.3908(3) 0.0191(3) 0.6508(3) 0.0882(12) Uani d . 1 . . C
  H8C 0.4446 -0.0067 0.6855 0.106 Uiso calc R 1 . . H
  C9C 0.3030(2) 0.0125(2) 0.6734(3) 0.0687(9) Uani d . 1 . . C
  O10C 0.28336(17) -0.02998(17) 0.74296(18) 0.0832(8) Uani d . 1 . . O
  C11C 0.3636(3) -0.0667(3) 0.8038(3) 0.1031(14) Uani d . 1 . . C
  H11C 0.3956 -0.1065 0.7740 0.155 Uiso calc R 1 . . H
  H12C 0.3401 -0.0943 0.8494 0.155 Uiso calc R 1 . . H
  H13C 0.4085 -0.0237 0.8286 0.155 Uiso calc R 1 . . H
  C1D 0.3744(2) 0.0019(2) 0.0494(2) 0.0584(8) Uani d . 1 . . C
  N2D 0.47078(19) 0.00718(19) 0.05081(18) 0.0670(8) Uani d . 1 . . N
  H2D 0.4954 0.0378 0.0161 0.080 Uiso calc R 1 . . H
  N3D 0.5229(2) -0.0420(2) 0.1138(2) 0.0752(9) Uani d . 1 . . N
  C4D 0.4595(3) -0.0773(3) 0.1526(3) 0.0781(11) Uani d . 1 . . C
  H4D 0.4760 -0.1140 0.1995 0.094 Uiso calc R 1 . . H
  C5D 0.3639(3) -0.0532(2) 0.1150(2) 0.0656(9) Uani d . 1 . . C
  C6D 0.2699(3) -0.0701(3) 0.1274(3) 0.0841(12) Uani d . 1 . . C
  H6D 0.2602 -0.1069 0.1706 0.101 Uiso calc R 1 . . H
  C7D 0.1945(3) -0.0314(3) 0.0749(3) 0.0924(13) Uani d . 1 . . C
  H7D 0.1322 -0.0422 0.0826 0.111 Uiso calc R 1 . . H
  C8D 0.2061(3) 0.0240(3) 0.0094(3) 0.0840(12) Uani d . 1 . . C
  H8D 0.1519 0.0489 -0.0256 0.101 Uiso calc R 1 . . H
  C9D 0.2956(2) 0.0421(3) -0.0039(2) 0.0695(10) Uani d . 1 . . C
  O10D 0.31827(18) 0.09507(19) -0.06448(18) 0.0938(8) Uani d . 1 . . O
  C11D 0.2405(3) 0.1399(4) -0.1187(3) 0.1230(18) Uani d . 1 . . C
  H11D 0.1988 0.1014 -0.1561 0.184 Uiso calc R 1 . . H
  H12D 0.2663 0.1795 -0.1536 0.184 Uiso calc R 1 . . H
  H13D 0.2041 0.1688 -0.0828 0.184 Uiso calc R 1 . . H
  C1E 0.0900(2) 0.4343(2) 0.1973(2) 0.0625(9) Uani d . 1 . . C
  N2E 0.0620(2) 0.4817(2) 0.25877(19) 0.0727(8) Uani d . 1 . . N
  H2E 0.1010 0.5094 0.2985 0.087 Uiso calc R 1 . . H
  N3E -0.0352(2) 0.4797(2) 0.2496(2) 0.0755(9) Uani d . 1 . . N
  C4E -0.0689(3) 0.4316(3) 0.1828(3) 0.0739(10) Uani d . 1 . . C
  H4E -0.1343 0.4196 0.1622 0.089 Uiso calc R 1 . . H
  C5E 0.0062(3) 0.4002(2) 0.1457(2) 0.0653(9) Uani d . 1 . . C
  C6E 0.0131(3) 0.3483(3) 0.0745(2) 0.0796(11) Uani d . 1 . . C
  H6E -0.0416 0.3243 0.0393 0.096 Uiso calc R 1 . . H
  C7E 0.1029(3) 0.3350(3) 0.0597(3) 0.0889(12) Uani d . 1 . . C
  H7E 0.1090 0.3016 0.0128 0.107 Uiso calc R 1 . . H
  C8E 0.1867(3) 0.3692(3) 0.1117(3) 0.0841(12) Uani d . 1 . . C
  H8E 0.2467 0.3577 0.0991 0.101 Uiso calc R 1 . . H
  C9E 0.1814(3) 0.4195(3) 0.1813(3) 0.0737(11) Uani d . 1 . . C
  O10E 0.25551(19) 0.45844(18) 0.2381(2) 0.0953(9) Uani d . 1 . . O
  C11E 0.3526(3) 0.4398(4) 0.2296(4) 0.128(2) Uani d . 1 . . C
  H11E 0.3662 0.3818 0.2423 0.191 Uiso calc R 1 . . H
  H12E 0.3977 0.4735 0.2698 0.191 Uiso calc R 1 . . H
  H13E 0.3587 0.4516 0.1711 0.191 Uiso calc R 1 . . H
  C1F 0.8030(3) 0.1801(2) 0.4961(2) 0.0678(10) Uani d . 1 . . C
  N2F 0.8733(2) 0.1344(2) 0.5507(2) 0.0753(8) Uani d . 1 . . N
  H2F 0.9341 0.1361 0.5506 0.090 Uiso calc R 1 . . H
  N3F 0.8333(3) 0.0865(2) 0.6044(2) 0.0841(9) Uani d . 1 . . N
  C4F 0.7403(3) 0.1017(3) 0.5852(3) 0.0863(12) Uani d . 1 . . C
  H4F 0.6959 0.0760 0.6126 0.104 Uiso calc R 1 . . H
  C5F 0.7150(3) 0.1617(3) 0.5180(3) 0.0777(11) Uani d . 1 . . C
  C6F 0.6303(3) 0.2019(3) 0.4721(3) 0.0949(14) Uani d . 1 . . C
  H6F 0.5702 0.1911 0.4848 0.114 Uiso calc R 1 . . H
  C7F 0.6400(3) 0.2564(3) 0.4092(3) 0.1009(15) Uani d . 1 . . C
  H7F 0.5847 0.2832 0.3784 0.121 Uiso calc R 1 . . H
  C8F 0.7290(3) 0.2748(3) 0.3877(3) 0.0875(13) Uani d . 1 . . C
  H8F 0.7314 0.3135 0.3440 0.105 Uiso calc R 1 . . H
  C9F 0.8121(3) 0.2363(2) 0.4303(3) 0.0747(11) Uani d . 1 . . C
  O10F 0.9036(2) 0.24647(19) 0.41661(19) 0.0951(9) Uani d . 1 . . O
  C11F 0.9155(3) 0.3015(4) 0.3490(3) 0.1221(18) Uani d . 1 . . C
  H11F 0.8743 0.2841 0.2950 0.183 Uiso calc R 1 . . H
  H12F 0.9818 0.3006 0.3436 0.183 Uiso calc R 1 . . H
  H13F 0.8983 0.3572 0.3627 0.183 Uiso calc R 1 . . H
  C1G 0.3367(3) 0.4235(2) 0.5427(2) 0.0644(9) Uani d . 1 . . C
  N2G 0.3922(2) 0.4718(2) 0.6043(2) 0.0755(9) Uani d . 1 . . N
  H2G 0.3700 0.5049 0.6385 0.091 Uiso calc R 1 . . H
  N3G 0.4876(2) 0.4614(2) 0.6050(2) 0.0845(9) Uani d . 1 . . N
  C4G 0.4915(3) 0.4068(3) 0.5437(3) 0.0838(12) Uani d . 1 . . C
  H4G 0.5488 0.3884 0.5300 0.101 Uiso calc R 1 . . H
  C5G 0.3982(3) 0.3793(2) 0.5009(2) 0.0706(10) Uani d . 1 . . C
  C6G 0.3588(4) 0.3235(3) 0.4345(3) 0.0904(12) Uani d . 1 . . C
  H6G 0.3985 0.2931 0.4057 0.109 Uiso calc R 1 . . H
  C7G 0.2620(4) 0.3148(3) 0.4131(3) 0.1090(16) Uani d . 1 . . C
  H7G 0.2353 0.2783 0.3682 0.131 Uiso calc R 1 . . H
  C8G 0.1997(3) 0.3583(3) 0.4554(3) 0.0997(15) Uani d . 1 . . C
  H8G 0.1331 0.3498 0.4385 0.120 Uiso calc R 1 . . H
  C9G 0.2355(3) 0.4138(3) 0.5218(3) 0.0769(11) Uani d . 1 . . C
  O10G 0.18607(19) 0.4600(2) 0.5695(2) 0.0974(9) Uani d . 1 . . O
  C11G 0.0826(3) 0.4504(4) 0.5512(4) 0.136(2) Uani d . 1 . . C
  H11G 0.0564 0.4626 0.4908 0.204 Uiso calc R 1 . . H
  H12G 0.0555 0.4880 0.5871 0.204 Uiso calc R 1 . . H
  H13G 0.0667 0.3939 0.5635 0.204 Uiso calc R 1 . . H
  C1H 0.3774(3) 0.6832(2) 0.8382(2) 0.0703(10) Uani d . 1 . . C
  N2H 0.4141(2) 0.6364(2) 0.7806(2) 0.0753(8) Uani d . 1 . . N
  H2H 0.4743 0.6355 0.7779 0.090 Uiso calc R 1 . . H
  N3H 0.3435(3) 0.5915(2) 0.7278(2) 0.0794(9) Uani d . 1 . . N
  C4H 0.2627(3) 0.6105(3) 0.7530(3) 0.0818(11) Uani d . 1 . . C
  H4H 0.2023 0.5884 0.7276 0.098 Uiso calc R 1 . . H
  C5H 0.2784(3) 0.6677(3) 0.8223(2) 0.0735(10) Uani d . 1 . . C
  C6H 0.2226(3) 0.7085(3) 0.8739(3) 0.0934(14) Uani d . 1 . . C
  H6H 0.1560 0.7002 0.8643 0.112 Uiso calc R 1 . . H
  C7H 0.2687(4) 0.7603(3) 0.9381(3) 0.0951(14) Uani d . 1 . . C
  H7H 0.2327 0.7876 0.9727 0.114 Uiso calc R 1 . . H
  C8H 0.3691(4) 0.7740(3) 0.9538(3) 0.0866(12) Uani d . 1 . . C
  H8H 0.3978 0.8097 0.9987 0.104 Uiso calc R 1 . . H
  C9H 0.4255(3) 0.7364(2) 0.9051(3) 0.0749(10) Uani d . 1 . . C
  O10H 0.5226(2) 0.74407(19) 0.91276(19) 0.0964(9) Uani d . 1 . . O
  C11H 0.5735(4) 0.7918(4) 0.9847(3) 0.1197(17) Uani d . 1 . . C
  H11H 0.5526 0.8489 0.9780 0.180 Uiso calc R 1 . . H
  H12H 0.6418 0.7888 0.9869 0.180 Uiso calc R 1 . . H
  H13H 0.5604 0.7698 1.0379 0.180 Uiso calc R 1 . . H
  C1I 0.2637(2) 0.0685(2) 0.2889(2) 0.0626(9) Uani d . 1 . . C
  N2I 0.3612(2) 0.06746(19) 0.29795(18) 0.0695(8) Uani d . 1 . . N
  H2I 0.3991 0.0314 0.3286 0.083 Uiso calc R 1 . . H
  N3I 0.3916(2) 0.1302(2) 0.2527(2) 0.0836(9) Uani d . 1 . . N
  C4I 0.3121(3) 0.1707(3) 0.2157(3) 0.0869(12) Uani d . 1 . . C
  H4I 0.3115 0.2171 0.1799 0.104 Uiso calc R 1 . . H
  C5I 0.2283(3) 0.1361(3) 0.2361(2) 0.0751(10) Uani d . 1 . . C
  C6I 0.1287(3) 0.1522(3) 0.2155(3) 0.0955(13) Uani d . 1 . . C
  H6I 0.1033 0.1975 0.1809 0.115 Uiso calc R 1 . . H
  C7I 0.0709(3) 0.0993(4) 0.2481(3) 0.1013(14) Uani d . 1 . . C
  H7I 0.0044 0.1089 0.2348 0.122 Uiso calc R 1 . . H
  C8I 0.1064(3) 0.0308(3) 0.3007(3) 0.0846(12) Uani d . 1 . . C
  H8I 0.0634 -0.0035 0.3216 0.101 Uiso calc R 1 . . H
  C9I 0.2027(3) 0.0139(2) 0.3217(2) 0.0685(9) Uani d . 1 . . C
  O10I 0.24879(18) -0.05057(17) 0.37102(17) 0.0869(8) Uani d . 1 . . O
  C11I 0.1925(3) -0.1009(3) 0.4157(3) 0.1010(14) Uani d . 1 . . C
  H11I 0.1636 -0.0664 0.4531 0.151 Uiso calc R 1 . . H
  H12I 0.2333 -0.1419 0.4501 0.151 Uiso calc R 1 . . H
  H13I 0.1424 -0.1285 0.3740 0.151 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 0.061(2) 0.052(2) 0.073(2) -0.0132(18) -0.0093(19) 0.017(2)
  N2A 0.0588(18) 0.068(2) 0.089(2) -0.0086(17) -0.0024(17) 0.0021(19)
  N3A 0.086(2) 0.069(2) 0.084(2) -0.0134(18) 0.0124(18) -0.0064(19)
  C4A 0.075(3) 0.090(3) 0.094(3) -0.012(2) 0.015(2) 0.006(3)
  C5A 0.067(2) 0.070(3) 0.073(2) -0.017(2) -0.0001(19) 0.012(2)
  C6A 0.064(3) 0.101(3) 0.106(3) -0.023(2) 0.002(2) 0.008(3)
  C7A 0.079(3) 0.084(3) 0.105(4) -0.027(3) -0.012(3) 0.005(3)
  C8A 0.093(3) 0.062(3) 0.083(3) -0.012(2) -0.014(2) 0.003(2)
  C9A 0.070(3) 0.052(2) 0.079(3) -0.0040(19) -0.011(2) 0.013(2)
  O10A 0.0752(18) 0.0684(18) 0.105(2) -0.0020(14) 0.0032(15) -0.0129(16)
  C11A 0.108(3) 0.078(3) 0.093(3) 0.005(3) 0.016(3) -0.002(3)
  C1B 0.062(2) 0.060(2) 0.073(2) -0.0045(19) 0.0218(19) -0.008(2)
  N2B 0.0545(18) 0.073(2) 0.080(2) 0.0023(15) 0.0055(14) 0.0054(18)
  N3B 0.0608(19) 0.082(2) 0.080(2) -0.0014(16) 0.0139(15) 0.0049(19)
  C4B 0.063(2) 0.078(3) 0.079(3) 0.004(2) 0.007(2) 0.003(2)
  C5B 0.078(3) 0.065(2) 0.072(2) -0.003(2) 0.019(2) -0.002(2)
  C6B 0.128(4) 0.075(3) 0.082(3) 0.007(3) 0.030(3) 0.007(3)
  C7B 0.153(5) 0.091(4) 0.107(4) -0.017(4) 0.071(4) -0.005(3)
  C8B 0.106(4) 0.088(3) 0.130(4) -0.029(3) 0.065(4) -0.031(3)
  C9B 0.069(3) 0.077(3) 0.107(3) -0.009(2) 0.030(2) -0.022(3)
  O10B 0.0592(17) 0.117(3) 0.151(3) 0.0003(17) 0.0238(17) -0.021(2)
  C11B 0.062(3) 0.158(5) 0.226(6) -0.014(3) 0.046(3) -0.068(5)
  C1C 0.059(2) 0.056(2) 0.063(2) -0.0102(17) 0.0107(17) -0.0046(18)
  N2C 0.0602(18) 0.0639(18) 0.0706(19) -0.0061(15) 0.0048(15) 0.0098(16)
  N3C 0.0687(19) 0.072(2) 0.077(2) -0.0042(17) -0.0002(17) 0.0069(18)
  C4C 0.089(3) 0.076(3) 0.064(2) -0.012(2) 0.001(2) 0.006(2)
  C5C 0.076(3) 0.068(2) 0.063(2) -0.011(2) 0.0157(19) -0.005(2)
  C6C 0.101(3) 0.094(3) 0.082(3) -0.023(3) 0.037(3) -0.009(3)
  C7C 0.077(3) 0.107(4) 0.122(4) -0.007(3) 0.038(3) -0.007(3)
  C8C 0.066(3) 0.089(3) 0.108(3) 0.004(2) 0.014(2) 0.002(3)
  C9C 0.058(2) 0.063(2) 0.083(3) -0.0038(18) 0.012(2) 0.002(2)
  O10C 0.0694(16) 0.0814(19) 0.0928(18) 0.0025(14) 0.0042(14) 0.0222(17)
  C11C 0.093(3) 0.090(3) 0.111(3) 0.020(3) -0.012(2) 0.022(3)
  C1D 0.056(2) 0.060(2) 0.057(2) 0.0030(17) 0.0087(16) -0.0032(19)
  N2D 0.0623(19) 0.0666(19) 0.0687(18) 0.0027(15) 0.0065(15) 0.0106(17)
  N3D 0.071(2) 0.071(2) 0.077(2) 0.0084(18) 0.0010(17) 0.0079(18)
  C4D 0.094(3) 0.066(2) 0.069(2) 0.004(2) 0.007(2) 0.014(2)
  C5D 0.077(3) 0.059(2) 0.060(2) -0.0040(19) 0.0140(18) -0.001(2)
  C6D 0.093(3) 0.087(3) 0.079(3) -0.009(3) 0.034(2) 0.000(2)
  C7D 0.065(3) 0.119(4) 0.098(3) -0.003(3) 0.027(2) -0.007(3)
  C8D 0.061(2) 0.104(3) 0.084(3) 0.007(2) 0.011(2) -0.003(3)
  C9D 0.061(2) 0.078(3) 0.067(2) 0.001(2) 0.0079(19) 0.000(2)
  O10D 0.0797(17) 0.103(2) 0.0937(19) 0.0184(16) 0.0072(15) 0.0335(19)
  C11D 0.111(4) 0.119(4) 0.121(4) 0.028(3) -0.013(3) 0.043(3)
  C1E 0.061(2) 0.059(2) 0.068(2) 0.0045(18) 0.0154(18) 0.010(2)
  N2E 0.064(2) 0.075(2) 0.076(2) -0.0016(16) 0.0097(15) -0.0043(18)
  N3E 0.063(2) 0.082(2) 0.081(2) -0.0009(17) 0.0145(16) -0.011(2)
  C4E 0.057(2) 0.082(3) 0.080(3) -0.002(2) 0.010(2) -0.005(2)
  C5E 0.071(2) 0.065(2) 0.060(2) 0.0005(19) 0.0153(19) -0.0010(19)
  C6E 0.082(3) 0.082(3) 0.076(3) -0.001(2) 0.018(2) -0.003(2)
  C7E 0.105(4) 0.081(3) 0.086(3) 0.006(3) 0.030(3) -0.003(2)
  C8E 0.084(3) 0.078(3) 0.101(3) 0.021(2) 0.045(3) 0.018(3)
  C9E 0.061(2) 0.068(3) 0.093(3) 0.005(2) 0.018(2) 0.025(2)
  O10E 0.0626(17) 0.089(2) 0.133(2) -0.0035(15) 0.0184(16) 0.0163(19)
  C11E 0.057(3) 0.125(4) 0.200(6) 0.005(3) 0.027(3) 0.036(4)
  C1F 0.077(3) 0.055(2) 0.064(2) 0.0117(19) -0.001(2) -0.012(2)
  N2F 0.0712(19) 0.066(2) 0.082(2) 0.0118(17) 0.0015(17) -0.0001(18)
  N3F 0.083(2) 0.077(2) 0.088(2) 0.0151(19) 0.0100(19) 0.007(2)
  C4F 0.089(3) 0.083(3) 0.089(3) 0.013(2) 0.022(2) -0.007(3)
  C5F 0.080(3) 0.073(3) 0.077(3) 0.023(2) 0.009(2) -0.007(2)
  C6F 0.079(3) 0.107(4) 0.094(3) 0.035(3) 0.011(2) -0.003(3)
  C7F 0.091(4) 0.109(4) 0.094(3) 0.045(3) 0.002(3) -0.005(3)
  C8F 0.106(3) 0.073(3) 0.074(3) 0.023(3) -0.001(2) 0.000(2)
  C9F 0.084(3) 0.061(2) 0.072(3) 0.003(2) 0.001(2) -0.014(2)
  O10F 0.094(2) 0.093(2) 0.089(2) -0.0021(17) 0.0019(16) 0.0138(18)
  C11F 0.124(4) 0.126(4) 0.104(3) -0.035(3) -0.002(3) 0.027(4)
  C1G 0.062(2) 0.063(2) 0.066(2) -0.0048(19) 0.0095(19) 0.006(2)
  N2G 0.068(2) 0.079(2) 0.083(2) -0.0018(17) 0.0255(16) -0.0090(19)
  N3G 0.067(2) 0.092(3) 0.098(2) -0.0099(18) 0.0232(17) -0.021(2)
  C4G 0.073(3) 0.088(3) 0.098(3) -0.002(2) 0.034(2) -0.017(3)
  C5G 0.081(3) 0.060(2) 0.072(2) -0.008(2) 0.019(2) -0.002(2)
  C6G 0.108(3) 0.075(3) 0.086(3) 0.002(3) 0.015(3) -0.009(2)
  C7G 0.118(4) 0.086(3) 0.108(4) -0.006(3) -0.007(3) -0.011(3)
  C8G 0.072(3) 0.083(3) 0.125(4) -0.011(3) -0.019(3) 0.014(3)
  C9G 0.063(2) 0.072(3) 0.094(3) 0.002(2) 0.015(2) 0.023(2)
  O10G 0.0695(18) 0.105(2) 0.122(2) 0.0181(16) 0.0298(16) 0.023(2)
  C11G 0.062(3) 0.154(5) 0.196(6) 0.020(3) 0.038(3) 0.065(5)
  C1H 0.093(3) 0.060(2) 0.065(2) 0.022(2) 0.032(2) 0.008(2)
  N2H 0.084(2) 0.071(2) 0.0754(19) 0.0166(18) 0.0261(17) 0.0036(18)
  N3H 0.092(2) 0.075(2) 0.075(2) 0.011(2) 0.0256(19) 0.0019(18)
  C4H 0.083(3) 0.084(3) 0.081(3) 0.008(2) 0.023(2) 0.011(3)
  C5H 0.089(3) 0.070(3) 0.066(2) 0.019(2) 0.026(2) 0.012(2)
  C6H 0.096(3) 0.106(4) 0.087(3) 0.031(3) 0.039(3) 0.019(3)
  C7H 0.124(4) 0.094(3) 0.078(3) 0.039(3) 0.045(3) 0.011(3)
  C8H 0.124(4) 0.067(3) 0.074(3) 0.023(3) 0.034(3) 0.006(2)
  C9H 0.097(3) 0.064(2) 0.069(3) 0.016(2) 0.028(2) 0.007(2)
  O10H 0.101(2) 0.097(2) 0.097(2) -0.0003(18) 0.0344(18) -0.0164(18)
  C11H 0.129(4) 0.124(4) 0.108(4) -0.019(4) 0.029(3) -0.021(4)
  C1I 0.056(2) 0.066(2) 0.063(2) 0.0024(18) 0.0064(17) -0.0033(19)
  N2I 0.069(2) 0.066(2) 0.0726(19) 0.0042(16) 0.0141(15) 0.0128(16)
  N3I 0.081(2) 0.076(2) 0.095(2) -0.002(2) 0.0219(18) 0.017(2)
  C4I 0.097(3) 0.073(3) 0.093(3) -0.002(3) 0.024(2) 0.021(2)
  C5I 0.080(3) 0.067(2) 0.076(2) 0.006(2) 0.011(2) 0.008(2)
  C6I 0.084(3) 0.088(3) 0.108(3) 0.013(3) 0.007(2) 0.020(3)
  C7I 0.065(3) 0.116(4) 0.117(4) 0.019(3) 0.006(2) 0.009(3)
  C8I 0.070(3) 0.093(3) 0.091(3) -0.003(2) 0.017(2) 0.002(3)
  C9I 0.069(2) 0.068(2) 0.068(2) 0.003(2) 0.0135(18) 0.002(2)
  O10I 0.0880(17) 0.0794(19) 0.0952(19) 0.0033(15) 0.0238(15) 0.0269(17)
  C11I 0.120(3) 0.086(3) 0.103(3) -0.016(3) 0.036(3) 0.022(3)
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 N2A . 1.347(4) ?
  C1A C5A . 1.389(5) ?
  C1A C9A . 1.407(5) ?
  N2A N3A . 1.356(4) ?
  N2A H2A . 0.8600 ?
  N3A C4A . 1.317(5) ?
  C4A C5A . 1.406(5) ?
  C4A H4A . 0.9300 ?
  C5A C6A . 1.415(5) ?
  C6A C7A . 1.365(6) ?
  C6A H6A . 0.9300 ?
  C7A C8A . 1.396(6) ?
  C7A H7A . 0.9300 ?
  C8A C9A . 1.368(5) ?
  C8A H8A . 0.9300 ?
  C9A O10A . 1.357(4) ?
  O10A C11A . 1.426(5) ?
  C11A H11A . 0.9600 ?
  C11A H12A . 0.9600 ?
  C11A H13A . 0.9600 ?
  C1B N2B . 1.366(4) ?
  C1B C5B . 1.382(5) ?
  C1B C9B . 1.389(5) ?
  N2B N3B . 1.359(4) ?
  N2B H2B . 0.8600 ?
  N3B C4B . 1.314(4) ?
  C4B C5B . 1.412(5) ?
  C4B H4B . 0.9300 ?
  C5B C6B . 1.396(5) ?
  C6B C7B . 1.348(6) ?
  C6B H6B . 0.9300 ?
  C7B C8B . 1.383(7) ?
  C7B H7B . 0.9300 ?
  C8B C9B . 1.375(6) ?
  C8B H8B . 0.9300 ?
  C9B O10B . 1.362(5) ?
  O10B C11B . 1.421(5) ?
  C11B H11B . 0.9600 ?
  C11B H12B . 0.9600 ?
  C11B H13B . 0.9600 ?
  C1C N2C . 1.347(4) ?
  C1C C9C . 1.393(5) ?
  C1C C5C . 1.395(5) ?
  N2C N3C . 1.356(4) ?
  N2C H2C . 0.8600 ?
  N3C C4C . 1.307(4) ?
  C4C C5C . 1.413(5) ?
  C4C H4C . 0.9300 ?
  C5C C6C . 1.400(5) ?
  C6C C7C . 1.363(6) ?
  C6C H6C . 0.9300 ?
  C7C C8C . 1.390(6) ?
  C7C H7C . 0.9300 ?
  C8C C9C . 1.366(5) ?
  C8C H8C . 0.9300 ?
  C9C O10C . 1.366(4) ?
  O10C C11C . 1.439(4) ?
  C11C H11C . 0.9600 ?
  C11C H12C . 0.9600 ?
  C11C H13C . 0.9600 ?
  C1D N2D . 1.360(4) ?
  C1D C5D . 1.389(5) ?
  C1D C9D . 1.396(5) ?
  N2D N3D . 1.351(4) ?
  N2D H2D . 0.8600 ?
  N3D C4D . 1.315(5) ?
  C4D C5D . 1.406(5) ?
  C4D H4D . 0.9300 ?
  C5D C6D . 1.409(5) ?
  C6D C7D . 1.349(6) ?
  C6D H6D . 0.9300 ?
  C7D C8D . 1.395(6) ?
  C7D H7D . 0.9300 ?
  C8D C9D . 1.357(5) ?
  C8D H8D . 0.9300 ?
  C9D O10D . 1.363(4) ?
  O10D C11D . 1.429(5) ?
  C11D H11D . 0.9600 ?
  C11D H12D . 0.9600 ?
  C11D H13D . 0.9600 ?
  C1E N2E . 1.352(4) ?
  C1E C9E . 1.389(5) ?
  C1E C5E . 1.393(5) ?
  N2E N3E . 1.350(4) ?
  N2E H2E . 0.8600 ?
  N3E C4E . 1.306(5) ?
  C4E C5E . 1.409(5) ?
  C4E H4E . 0.9300 ?
  C5E C6E . 1.413(5) ?
  C6E C7E . 1.356(5) ?
  C6E H6E . 0.9300 ?
  C7E C8E . 1.395(6) ?
  C7E H7E . 0.9300 ?
  C8E C9E . 1.372(6) ?
  C8E H8E . 0.9300 ?
  C9E O10E . 1.369(5) ?
  O10E C11E . 1.438(5) ?
  C11E H11E . 0.9600 ?
  C11E H12E . 0.9600 ?
  C11E H13E . 0.9600 ?
  C1F N2F . 1.373(4) ?
  C1F C5F . 1.390(5) ?
  C1F C9F . 1.397(5) ?
  N2F N3F . 1.351(4) ?
  N2F H2F . 0.8600 ?
  N3F C4F . 1.305(5) ?
  C4F C5F . 1.414(6) ?
  C4F H4F . 0.9300 ?
  C5F C6F . 1.411(5) ?
  C6F C7F . 1.347(6) ?
  C6F H6F . 0.9300 ?
  C7F C8F . 1.402(6) ?
  C7F H7F . 0.9300 ?
  C8F C9F . 1.365(5) ?
  C8F H8F . 0.9300 ?
  C9F O10F . 1.366(5) ?
  O10F C11F . 1.417(5) ?
  C11F H11F . 0.9600 ?
  C11F H12F . 0.9600 ?
  C11F H13F . 0.9600 ?
  C1G N2G . 1.349(4) ?
  C1G C5G . 1.391(5) ?
  C1G C9G . 1.405(5) ?
  N2G N3G . 1.357(4) ?
  N2G H2G . 0.8600 ?
  N3G C4G . 1.309(5) ?
  C4G C5G . 1.413(5) ?
  C4G H4G . 0.9300 ?
  C5G C6G . 1.393(5) ?
  C6G C7G . 1.342(6) ?
  C6G H6G . 0.9300 ?
  C7G C8G . 1.399(7) ?
  C7G H7G . 0.9300 ?
  C8G C9G . 1.379(6) ?
  C8G H8G . 0.9300 ?
  C9G O10G . 1.350(5) ?
  O10G C11G . 1.436(5) ?
  C11G H11G . 0.9600 ?
  C11G H12G . 0.9600 ?
  C11G H13G . 0.9600 ?
  C1H N2H . 1.362(4) ?
  C1H C5H . 1.388(5) ?
  C1H C9H . 1.407(5) ?
  N2H N3H . 1.357(4) ?
  N2H H2H . 0.8600 ?
  N3H C4H . 1.322(4) ?
  C4H C5H . 1.403(5) ?
  C4H H4H . 0.9300 ?
  C5H C6H . 1.408(5) ?
  C6H C7H . 1.357(6) ?
  C6H H6H . 0.9300 ?
  C7H C8H . 1.403(6) ?
  C7H H7H . 0.9300 ?
  C8H C9H . 1.358(5) ?
  C8H H8H . 0.9300 ?
  C9H O10H . 1.356(5) ?
  O10H C11H . 1.423(5) ?
  C11H H11H . 0.9600 ?
  C11H H12H . 0.9600 ?
  C11H H13H . 0.9600 ?
  C1I N2I . 1.354(4) ?
  C1I C5I . 1.388(5) ?
  C1I C9I . 1.402(5) ?
  N2I N3I . 1.352(4) ?
  N2I H2I . 0.8600 ?
  N3I C4I . 1.318(5) ?
  C4I C5I . 1.405(5) ?
  C4I H4I . 0.9300 ?
  C5I C6I . 1.399(5) ?
  C6I C7I . 1.351(6) ?
  C6I H6I . 0.9300 ?
  C7I C8I . 1.399(6) ?
  C7I H7I . 0.9300 ?
  C8I C9I . 1.356(5) ?
  C8I H8I . 0.9300 ?
  C9I O10I . 1.367(4) ?
  O10I C11I . 1.420(5) ?
  C11I H11I . 0.9600 ?
  C11I H12I . 0.9600 ?
  C11I H13I . 0.9600 ?