data_2010315
_journal_name_full  'Acta Crystallographica'
_journal_year  1994
_journal_volume  C50
_journal_page_first  1919
_journal_page_last  1922
_publ_section_title
;
1,2-Dihydro-8-methyl-4(3H)-carbazolone Prepared by a
New Arynic Cyclization Reaction
;
loop_
_publ_author_name
  'Ianelli, Sandra'
  'Nardelli*, Mario'
  'Belletti, Daniele'
  "Caub\`ere, Caterine"
  "Caub\`ere, Paul"
  "Jamart-Gr\'egoire, Brigitte"
_chemical_formula_sum  'C13 H13 N O'
_chemical_formula_analytical  'C13 H13 N O'
_chemical_formula_weight  199.25
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x+1/2, -y+1/2, z+1/2'
  '-x, -y, -z'
  '-x-1/2, y-1/2, -z-1/2'
_cell_length_a  13.706(6)
_cell_length_b  9.908(4)
_cell_length_c  8.126(3)
_cell_angle_alpha  90.
_cell_angle_beta  105.29(3)
_cell_angle_gamma  90.
_cell_volume  1064.4(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.243
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0830
_refine_ls_wR_factor_obs  0.2314
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
  N1 0.3825(2) 0.1382(2) 0.1005(3) 0.0740(9) aniso . . N
  O1 0.0753(2) 0.3105(2) -0.1900(3) 0.1004(11) aniso . . O
  C1 0.2332(2) 0.2279(3) -0.0386(3) 0.0685(9) aniso . . C
  C2 0.1668(3) 0.3310(3) -0.1274(4) 0.0760(11) aniso . . C
  C3 0.2136(3) 0.4655(4) -0.1442(6) 0.0957(16) aniso . . C
  C4 0.3139(3) 0.4930(4) -0.0205(6) 0.0994(17) aniso . . C
  C5 0.3886(3) 0.3795(3) 0.0082(6) 0.0906(14) aniso . . C
  C6 0.3363(2) 0.2512(3) 0.0247(3) 0.0704(10) aniso . . C
  C7 0.3103(2) 0.0380(2) 0.0910(3) 0.0667(11) aniso . . C
  C8 0.2151(2) 0.0912(3) 0.0033(3) 0.0654(11) aniso . . C
  C9 0.1292(3) 0.0084(3) -0.0248(4) 0.0755(11) aniso . . C
  C10 0.1426(3) -0.1227(3) 0.0316(4) 0.0833(14) aniso . . C
  C11 0.2374(3) -0.1737(3) 0.1169(4) 0.0798(12) aniso . . C
  C12 0.3240(3) -0.0953(3) 0.1479(4) 0.0730(11) aniso . . C
  C13 0.4269(3) -0.1491(4) 0.2372(6) 0.0924(16) aniso . . C
  H1N 0.450(3)  0.136(3)  0.170(4)  0.075(9)  iso . N1 H
  H31 0.166(5)  0.531(5)  -0.151(7)  0.145(19) iso . C3 H
  H32 0.229(4)  0.462(6)  -0.268(7)  0.144(19) iso . C3 H
  H41 0.342(3)  0.582(5)  -0.054(5)  0.105(12) iso . C4 H
  H42 0.305(5)  0.499(7)  0.110(9)  0.19(3)  iso . C4 H
  H51 0.425(4)  0.373(5)  -0.094(7)  0.15(2)  iso . C5 H
  H52 0.451(3)  0.397(4)  0.101(5)  0.097(11) iso . C5 H
  H9 0.066(3)  0.044(4)  -0.094(4)  0.078(9)  iso . C9 H
  H10 0.082(3)  -0.180(4)  0.016(5)  0.105(12) iso . C10 H
  H11 0.242(3)  -0.281(4)  0.156(4)  0.079(9)  iso . C11 H
  H131 0.472(4)  -0.144(5)  0.169(7)  0.13(2)  iso . C13 H
  H132 0.420(4)  -0.235(5)  0.276(6)  0.128(16) iso . C13 H
  H133 0.450(4)  -0.102(6)  0.364(8)  0.153(19) iso . C13 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
  N1 0.0696(17) 0.0505(12) 0.0765(14) 0.0036(10) -0.0253(12) -0.0015(10)
  O1 0.0734(16) 0.0781(16) 0.1158(19) 0.0147(13) -0.0347(13) 0.0064(11)
  C1 0.0679(18) 0.0503(14) 0.0657(14) -0.0010(11) -0.0205(12) -0.0011(11)
  C2 0.074(2)  0.0613(16) 0.0713(16) 0.0071(12) -0.0178(14) 0.0027(13)
  C3 0.084(3)  0.069(2)  0.111(3)  0.0312(19) -0.016(2)  0.0051(16)
  C4 0.089(3)  0.0521(17) 0.135(3)  0.0162(18) -0.009(2)  -0.0032(16)
  C5 0.081(2)  0.0579(17) 0.107(3)  0.0138(16) -0.022(2)  -0.0106(15)
  C6 0.0706(19) 0.0509(15) 0.0691(15) 0.0023(11) -0.0181(13) -0.0041(11)
  C7 0.0703(18) 0.0457(13) 0.0643(14) -0.0033(10) -0.0170(12) -0.0003(11)
  C8 0.0656(18) 0.0483(14) 0.0634(14) -0.0050(10) -0.0165(12) -0.0003(10)
  C9 0.069(2)  0.0573(15) 0.0794(18) -0.0038(13) -0.0168(15) -0.0075(12)
  C10 0.085(2)  0.0562(16) 0.090(2)  -0.0061(14) -0.0091(17) -0.0155(14)
  C11 0.094(3)  0.0457(14) 0.0824(19) -0.0038(12) -0.0070(16) -0.0021(13)
  C12 0.083(2)  0.0474(14) 0.0702(16) -0.0004(11) -0.0124(14) 0.0044(12)
  C13 0.089(3)  0.0624(19) 0.105(3)  0.0173(18) -0.011(2)  0.0133(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
  N1 C6 1.352(3) no
  N1 C7 1.389(4) no
  N1 H1N 0.95(3) no
  O1 C2 1.239(4) no
  C1 C2 1.430(4) no
  C1 C6 1.389(4) no
  C1 C8 1.434(4) no
  C2 C3 1.501(5) no
  C3 C4 1.499(6) no
  C3 H31 0.92(5) no
  C3 H32 1.08(6) no
  C4 C5 1.497(5) no
  C4 H41 1.03(4) no
  C4 H42 1.10(7) no
  C5 C6 1.483(5) no
  C5 H51 1.08(6) no
  C5 H52 0.99(3) no
  C7 C8 1.414(4) no
  C7 C12 1.396(4) no
  C8 C9 1.403(4) no
  C9 C10 1.374(4) no
  C9 H9 0.96(3) no
  C10 C11 1.396(5) no
  C10 H10 0.98(4) no
  C11 C12 1.385(5) no
  C11 H11 1.11(3) no
  C12 C13 1.503(5) no
  C13 H131 0.94(6) no
  C13 H132 0.92(5) no
  C13 H133 1.10(5) no