data_2010395
_journal_name_full  'Acta Crystallographica'
_journal_year  1995
_journal_volume  C51
_journal_page_first  135
_journal_page_last  139
_publ_section_title
;
(13-Methyl-1,4,7,8,13,13b-hexahydro[1',2']oxazepino[2',3':1,2]-
pyrido[3,4-b]indol-1-yl)methanol and its unusual packing style
;
loop_
_publ_author_name
  'Ohishi, H.'
  'Sakamoto, Y.'
  'Harusawa, S.'
  'Yoneda, R.'
  'Kurihara, T.'
_chemical_formula_moiety  'C17 H20 N2 O2'
_chemical_formula_sum  'C17 H20 N2 O2'
_chemical_formula_weight  284.359
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P c'
_symmetry_space_group_name_Hall  'P -2yc'
_cell_length_a  18.499(4)
_cell_length_b  6.2149(9)
_cell_length_c  26.450(10)
_cell_angle_alpha  90.
_cell_angle_beta  103.16(3)
_cell_angle_gamma  90.
_cell_volume  2961.0(10)
_cell_formula_units_Z  8
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.2757
; empirical (North, Phillips & Mathews, 1968)
;
_refine_ls_R_factor_obs  0.0615
_refine_ls_wR_factor_obs  0.0675
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
  C1A .9428(3) .2564(8) .3598(2)
  C2A .9883(3) .0971(8) .4011(2)
  C3A .9693(3) -.0007(9) .4393(2)
  C4A .8930(3) .0020(10)
  .4538(2)
  O5A .8397(2) .1181(6) .41550(10)
  N6A .8368(2) .0175(7) .36560(10)
  C7A .7570(3) -.0460(9) .3458(2)
  C8A .7562(3) -.1820(10)
  .2968(2)
  C9A .8012(2) -.0687(8) .2650(2)
  C10A .8027(3) -.1090(9) .2115(2)
  C11A .7659(3) -.2632(9) .1738(2)
  C12A .7761(4) -.2670(10)
  .1262(3)
  C13A .8293(3) -.1050(10)
  .1121(2)
  C14A .8658(3) .0460(10)
  .1482(2)
  C15A .8518(3) .0404(8) .1991(2)
  N16A .8787(2) .1659(6) .2394(2)
  C17A .8504(2) .0960(8) .2789(2)
  C18A .8645(2) .1903(7) .3354(2)
  C19A .9248(4) .3630(10)
  .2396(2)
  C20A .9440(3) .4801(7) .3855(2)
  O21A .9246(2) .6266(5) .34580(10)
  C1B .0252(2) .2531(7) .6218(2)
  C2B -.0174(3) .4002(9) .5824(2)
  C3B .0028(3) .4930(9) .5417(2)
  C4B .0740(4) .5000(10)
  .5321(2)
  O5B .1298(2) .3813(6) .5682(2)
  N6B .1336(2) .4813(7) .6183(2)
  C7B .2101(3) .5330(10)
  .6401(2)
  C8B .2159(3) .6687(9) .6877(2)
  C9B .1684(3) .5719(9) .7218(2)
  C10B .1670(3) .6110(8) .7734(2)
  C11B .1996(3) .7640(10)
  .8089(3)
  C12B .1847(3) .7440(9) .8605(2)
  C13B .1413(3) .5980(10)
  .8720(2)
  C14B .1058(3) .4443(9) .8366(2)
  C15B .1189(3) .4559(9) .7883(2)
  N16B .0920(2) .3246(7) .74340(10)
  C17B .1236(3) .3991(7) .7019(2)
  C18B .1092(3) .3150(8) .6498(2)
  C19B .0499(3) .1340(8) .7490(2)
  C20B .0230(3) .0320(9) .5974(2)
  O21B .0517(2) -.1269(6) .63950(10)
  C1C .5396(3) .4937(8) .0947(2)
  C2C .6091(3) .3420(9) .1034(2)
  C3C .6475(3) .2500(9) .1425(2)
  C4C .6294(3) .2380(10)
  .1926(2)
  O5C .5605(2) .3619(7) .19820(10)
  N6C .4988(3) .2570(9) .1612(2)
  C7C .4418(3) .2130(10)
  .1893(2)
  C8C .3837(3) .0660(10)
  .1510(2)
  C9C .3688(3) .1793(8) .1010(2)
  C10C .3049(3) .1523(8) .0575(2)
  C11C .2440(3) -.0040(10)
  .0501(2)
  C12C .1940(3) .0150(10)
  .0028(2)
  C13C .1988(3) .1640(10)
  -.0308(2)
  C14C .2574(3) .3101(9) -.0240(2)
  C15C .3088(3) .2993(8) .0214(2)
  N16C .3683(3) .4200(7) .0392(2)
  C17C .4072(3) .3453(9) .0881(2)
  C18C .4777(3) .4294(8) .1235(2)
  C19C .3860(4) .6150(10)
  .0130(2)
  C20C .5699(3) .7214(8) .1131(3)
  O21C .5136(2) .8715(5) .0919(2)
  C1D .4292(2) -.0070(9) .3884(2)
  C2D .3652(3) -.1540(8) .3823(2)
  C3D .3269(3) -.2560(9) .3359(3)
  C4D .3442(4) -.2500(10)
  .2820(3)
  O5D .4061(2) -.1436(6) .28420(10)
  N6D .4658(2) -.2381(6) .3235(2)
  C7D .5237(3) -.3180(10)
  .2955(2)
  C8D .5794(3) -.4400(9) .3310(2)
  C9D .6048(3) -.3323(9) .3834(2)
  C10D .6657(3) -.3745(8) .4234(2)
  C11D .7217(3) -.5190(10)
  .4343(2)
  C12D .7775(4) -.5020(10)
  .4804(3)
  C13D .7762(3) -.3280(10)
  .5200(2)
  C14D .7168(3) -.1740(10)
  .5096(3)
  C15D .6633(3) -.2020(9) .4623(2)
  N16D .5985(2) -.0714(7) .4438(2)
  C17D .5650(3) -.1553(8) .3962(2)
  C18D .4946(3) -.0673(8) .3624(2)
  C19D .5854(3) .1216(8) .4707(2)
  C20D .4006(3) .2140(9) .3728(2)
  O21D .4593(2) .3691(7) .3871(2)
  H1A .970(3) .270(10)
  .330(2)
  H2A 1.039(3) .070(9) .398(2)
  H3A 1.010(3) -.091(9) .464(2)
  H4A .872(3) -.160(10)
  .454(2)
  H5A .897(3) .060(10)
  .489(2)
  H6A .741(3) -.130(10)
  .373(2)
  H7A .722(3) .089(9) .333(2)
  H8A .776(3) -.330(10)
  .310(2)
  H9A .704(3) -.200(9) .277(2)
  H10A .728(3) -.360(9) .188(2)
  H11A .751(3) -.399(9) .100(2)
  H12A .838(3) -.100(9) .069(2)
  H13A .902(3) .159(9) .137(2)
  H14A .975(3) .310(9) .233(2)
  H15A .933(3) .441(9) .275(2)
  H16A .899(3) .470(10)
  .212(2)
  H17A .833(3) .330(9) .338(2)
  H18A .997(3) .511(9) .408(2)
  H19A .878(3) .732(9) .353(2)
  H20A .908(3) .470(10)
  .410(2)
  H1B -.002(3) .250(10)
  .654(2)
  H2B -.070(3) .420(10)
  .584(2)
  H3B -.035(3) .600(10)
  .517(2)
  H4B .071(3) .430(9) .496(2)
  H5B .093(3) .660(10)
  .530(2)
  H6B .244(3) .390(9) .648(2)
  H7B .231(3) .621(9) .611(2)
  H8B .267(3) .680(9) .709(2)
  H9B .199(3) .820(10)
  .677(2)
  H10B .233(3) .890(9) .797(2)
  H11B .213(3) .831(9) .893(2)
  H12B .072(3) .330(9) .849(2)
  H13B .131(3) .590(9) .912(2)
  H14B .074(3) .060(10)
  .784(2)
  H15B .052(3) .020(10)
  .718(2)
  H16B -.002(3) .170(9) .750(2)
  H17B .143(3) .180(9) .651(2)
  H18B .055(3) .029(9) .570(2)
  H19B -.032(3) -.020(9) .578(2)
  H20B .010(3) -.230(10)
  .638(2)
  H1C .510(3) .480(10)
  .054(2)
  H2C .630(3) .322(9) .069(2)
  H3C .691(3) .179(9) .137(2)
  H4C .624(3) .071(9) .203(2)
  H5C .677(3) .310(10)
  .219(2)
  H6C .415(3) .350(9) .199(2)
  H7C .463(3) .140(10)
  .224(2)
  H8C .411(3) -.100(9) .147(2)
  H9C .335(3) .040(9) .164(2)
  H10C .239(3) -.119(9) .079(2)
  H11C .146(3) -.090(10)
  -.007(2)
  H12C .156(3) .160(10)
  -.063(2)
  H13C .252(3) .430(9) -.051(2)
  H14C .401(3) .590(9) -.020(2)
  H15C .426(3) .712(9) .039(2)
  H16C .335(3) .708(9) .003(2)
  H17C .469(3) .580(10)
  .144(2)
  H18C .620(3) .760(10)
  .100(2)
  H19C .583(3) .729(9) .155(2)
  H20C .499(3) .982(9) .123(2)
  H1D .453(3) -.010(10)
  .429(2)
  H2D .350(3) -.200(10)
  .417(2)
  H3D .279(4) -.330(9) .337(2)
  H4D .356(3) -.429(9) .270(2)
  H5D .303(3) -.190(9) .254(2)
  H6D .493(3) -.400(9) .264(2)
  H7D .541(3) -.179(9) .278(2)
  H8D .561(3) -.600(9) .336(2)
  H9D .631(3) -.450(9) .317(2)
  H10D .697(3) -.670(10)
  .422(2)
  H11D .822(3) -.620(9) .485(2)
  H12D .818(3) -.310(10)
  .556(2)
  H13D .714(3) -.040(10)
  .535(2)
  H14D .573(3) .070(9) .506(2)
  H15D .633(3) .200(10)
  .481(2)
  H16D .540(3) .210(10)
  .450(2)
  H17D .512(3) .079(9) .345(2)
  H18D .378(3) .220(9) .331(2)
  H19D .359(3) .260(9) .394(2)
  H20D .480(3) .460(9) .419(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
  C1A C2A 1.569(7) yes
  C1A C18A 1.503(7) yes
  C1A C20A 1.545(7) yes
  C2A C3A 1.294(7) yes
  C3A C4A 1.545(8) yes
  C4A O5A 1.437(7) yes
  O5A N6A 1.450(6) yes
  N6A C7A 1.502(7) yes
  N6A C18A 1.497(6) yes
  C7A C8A 1.545(8) yes
  C8A C9A 1.488(7) yes
  C9A C10A 1.444(7) yes
  C9A C17A 1.363(7) yes
  C10A C11A 1.438(7) yes
  C10A C15A 1.389(7) yes
  C11A C12A 1.315(9) yes
  C12A C13A 1.510(10)
  yes
  C13A C14A 1.398(9) yes
  C14A C15A 1.428(8) yes
  C15A N16A 1.323(6) yes
  N16A C17A 1.343(6) yes
  N16A C19A 1.492(7) yes
  C17A C18A 1.571(7) yes
  C20A O21A 1.374(6) yes
  C1B C2B 1.473(7) yes
  C1B C18B 1.608(7) yes
  C1B C20B 1.515(7) yes
  C2B C3B 1.347(8) yes
  C3B C4B 1.398(9) yes
  C4B O5B 1.440(8) yes
  O5B N6B 1.451(6) yes
  N6B C7B 1.438(7) yes
  N6B C18B 1.462(7) yes
  C7B C8B 1.499(8) yes
  C8B C9B 1.519(8) yes
  C9B C10B 1.392(7) yes
  C9B C17B 1.385(7) yes
  C10B C11B 1.375(8) yes
  C10B C15B 1.427(7) yes
  C11B C12B 1.458(8) yes
  C12B C13B 1.293(8) yes
  C13B C14B 1.393(8) yes
  C14B C15B 1.355(7) yes
  C15B N16B 1.433(7) yes
  N16B C17B 1.433(6) yes
  N16B C19B 1.444(7) yes
  C17B C18B 1.441(7) yes
  C20B O21B 1.493(7) yes
  C1C C2C 1.568(8) yes
  C1C C18C 1.565(8) yes
  C1C C20C 1.559(8) yes
  C2C C3C 1.252(8) yes
  C3C C4C 1.441(9) yes
  C4C O5C 1.525(7) yes
  O5C N6C 1.475(7) yes
  N6C C7C 1.448(8) yes
  N6C C18C 1.455(7) yes
  C7C C8C 1.588(8) yes
  C8C C9C 1.468(8) yes
  C9C C10C 1.459(7) yes
  C9C C17C 1.340(8) yes
  C10C C11C 1.467(8) yes
  C10C C15C 1.335(7) yes
  C11C C12C 1.381(8) yes
  C12C C13C 1.300(9) yes
  C13C C14C 1.394(8) yes
  C14C C15C 1.353(7) yes
  C15C N16C 1.327(7) yes
  N16C C17C 1.408(7) yes
  N16C C19C 1.470(8) yes
  C17C C18C 1.515(8) yes
  C20C O21C 1.415(7) yes
  C1D C2D 1.475(8) yes
  C1D C18D 1.567(7) yes
  C1D C20D 1.496(7) yes
  C2D C3D 1.419(8) yes
  C3D C4D 1.531(9) yes
  C4D O5D 1.312(8) yes
  O5D N6D 1.457(6) yes
  N6D C7D 1.518(7) yes
  N6D C18D 1.490(6) yes
  C7D C8D 1.441(8) yes
  C8D C9D 1.514(8) yes
  C9D C10D 1.384(8) yes
  C9D C17D 1.407(7) yes
  C10D C11D 1.352(8) yes
  C10D C15D 1.494(8) yes
  C11D C12D 1.420(10)
  yes
  C12D C13D 1.500(10)
  yes
  C13D C14D 1.436(9) yes
  C14D C15D 1.418(9) yes
  C15D N16D 1.438(7) yes
  N16D C17D 1.373(6) yes
  N16D C19D 1.443(7) yes
  C17D C18D 1.505(7) yes
  C20D O21D 1.437(7) yes