data_2012046 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 728 _journal_page_last 729 _publ_section_title ; Form II of monoclinic methyl \b-carboline-3-carboxylate ; loop_ _publ_author_name 'Kubicki, Maciej' 'Codding, Penelope W.' _chemical_formula_moiety 'C13 H10 N2 O2' _chemical_formula_sum 'C13 H10 N2 O2' _chemical_formula_weight 226.23 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 9.6550(5) _cell_length_b 20.8077(8) _cell_length_c 11.0793(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.388(5) _cell_angle_gamma 90.00 _cell_volume 2173.99(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.382 _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 C1AA .77699(15) .49647(7) .50226(13) .0521(3) Uani d . 1 . . C C1A .73661(17) .45891(7) .39661(15) .0592(4) Uani d . 1 . . C H1A .7903(18) .4230(8) .3806(16) .074(5) Uiso d . 1 . . H N2A .62048(14) .47172(6) .31164(11) .0592(3) Uani d . 1 . . N C3A .54165(15) .52333(7) .32979(13) .0522(3) Uani d . 1 . . C C31A .41510(16) .53548(7) .22854(14) .0561(4) Uani d . 1 . . C O31A .38630(13) .50624(6) .13295(10) .0748(3) Uani d . 1 . . O O32A .33677(12) .58386(5) .25567(10) .0683(3) Uani d . 1 . . O C32A .2134(2) .60102(11) .1633(2) .0745(5) Uani d . 1 . . C H32A .176(3) .6431(16) .191(3) .049(5) Uiso d P .50 . . H H32B .145(3) .5643(16) .152(3) .049(5) Uiso d P .50 . . H H32C .245(3) .6096(17) .079(3) .049(5) Uiso d P .50 . . H H32D .195(4) .5658(19) .105(3) .066(6) Uiso d P .50 . . H H32E .231(4) .6424(18) .128(3) .066(6) Uiso d P .50 . . H H32F .134(4) .6128(19) .213(3) .066(6) Uiso d P .50 . . H C4A .57249(15) .56282(7) .43218(13) .0501(3) Uani d . 1 . . C H4A .5096(16) .5994(7) .4373(13) .058(4) Uiso d . 1 . . H C4AA .69294(14) .54895(6) .52184(13) .0488(3) Uani d . 1 . . C C4BA .75996(15) .57647(6) .63938(13) .0511(3) Uani d . 1 . . C C5A .72662(18) .62666(7) .71074(15) .0623(4) Uani d . 1 . . C H5A .6412(19) .6526(8) .6803(15) .078(5) Uiso d . 1 . . H C6A .8158(2) .63965(8) .82222(16) .0718(5) Uani d . 1 . . C H6A .7921(19) .6744(9) .8724(17) .087(6) Uiso d . 1 . . H C7A .9394(2) .60391(9) .86258(17) .0751(5) Uani d . 1 . . C H7A .997(2) .6125(9) .9405(17) .083(5) Uiso d . 1 . . H C8A .97481(18) .55386(8) .79472(16) .0683(4) Uani d . 1 . . C H8A 1.057(2) .5279(9) .8212(16) .082(5) Uiso d . 1 . . H C8AA .88343(15) .53972(7) .68287(14) .0540(3) Uani d . 1 . . C N9A .89173(13) .49179(6) .59924(12) .0584(3) Uani d . 1 . . N H9A .952(2) .4592(9) .6120(17) .083(6) Uiso d . 1 . . H C1AB .37615(17) .38237(7) .93274(14) .0574(4) Uani d . 1 . . C C1B .26108(19) .42080(8) .87921(16) .0661(4) Uani d . 1 . . C H1B .2412(18) .4608(8) .9178(16) .076(5) Uiso d . 1 . . H N2B .17707(14) .40581(6) .77217(12) .0615(3) Uani d . 1 . . N C3B .20684(15) .35219(7) .71339(13) .0521(3) Uani d . 1 . . C C31B .10855(16) .33938(7) .59329(14) .0549(3) Uani d . 1 . . C O31B .00621(12) .37134(5) .54957(11) .0717(3) Uani d . 1 . . O O32B .14493(12) .28749(5) .53749(10) .0681(3) Uani d . 1 . . O C32B .0522(2) .26920(11) .42285(18) .0763(5) Uani d . 1 . . C H32G .090(2) .2303(11) .390(2) .113(4) Uiso d . 1 . . H H32H -.039(3) .2599(11) .440(2) .113(4) Uiso d . 1 . . H H32I .037(2) .3055(11) .371(2) .113(4) Uiso d . 1 . . H C4B .31840(15) .31121(7) .75957(13) .0527(3) Uani d . 1 . . C H4B .3351(16) .2737(7) .7120(14) .058(4) Uiso d . 1 . . H C4AB .40378(15) .32572(7) .87352(13) .0521(3) Uani d . 1 . . C C4BB .52446(15) .29591(7) .95351(13) .0539(3) Uani d . 1 . . C C5B .59907(17) .23912(8) .94830(16) .0646(4) Uani d . 1 . . C H5B .5732(18) .2105(8) .8750(16) .073(5) Uiso d . 1 . . H C6B .7106(2) .22462(10) 1.04429(19) .0798(5) Uani d . 1 . . C H6B .765(2) .1860(9) 1.0412(17) .094(6) Uiso d . 1 . . H C7B .7502(2) .26656(11) 1.14316(18) .0859(6) Uani d . 1 . . C H7B .829(2) .2531(10) 1.2069(19) .107(7) Uiso d . 1 . . H C8B .6794(2) .32285(10) 1.15115(16) .0756(5) Uani d . 1 . . C H8B .701(2) .3536(9) 1.2174(18) .095(6) Uiso d . 1 . . H C8AB .56401(17) .33713(8) 1.05600(14) .0592(4) Uani d . 1 . . C N9B .47373(15) .38910(7) 1.04178(12) .0655(4) Uani d . 1 . . N H9B .4765(19) .4214(9) 1.0940(17) .078(6) Uiso d . 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 C1AA .0498(8) .0507(7) .0550(8) -.0004(6) .0093(6) .0031(6) C1A .0596(9) .0541(8) .0627(9) .0065(7) .0107(7) -.0044(7) N2A .0617(8) .0574(7) .0568(7) .0010(6) .0091(6) -.0052(6) C3A .0510(8) .0530(8) .0507(8) -.0036(6) .0069(6) .0012(6) C31A .0578(9) .0561(8) .0519(8) -.0064(7) .0062(7) .0001(7) O31A .0799(8) .0788(8) .0568(6) .0035(6) -.0052(6) -.0121(6) O32A .0611(7) .0725(7) .0620(6) .0106(5) -.0078(5) -.0064(5) C32A .0649(11) .0762(13) .0712(12) .0074(10) -.0101(9) .0060(10) C4A .0467(7) .0496(7) .0518(8) -.0008(6) .0053(6) .0013(6) C4AA .0478(7) .0472(7) .0505(7) -.0022(6) .0083(6) .0014(6) C4BA .0484(7) .0480(7) .0533(8) -.0013(6) .0031(6) .0019(6) C5A .0604(9) .0566(9) .0629(9) .0064(7) -.0022(7) -.0054(7) C6A .0790(12) .0642(10) .0629(10) .0047(9) -.0054(9) -.0119(8) C7A .0756(12) .0741(11) .0612(10) .0015(9) -.0171(9) -.0047(9) C8A .0580(9) .0679(10) .0688(10) .0072(8) -.0090(8) .0044(8) C8AA .0496(8) .0508(8) .0580(8) .0002(6) .0036(7) .0043(6) N9A .0505(7) .0574(7) .0634(8) .0088(6) .0035(6) .0018(6) C1AB .0616(9) .0582(8) .0508(8) -.0006(7) .0088(7) -.0017(6) C1B .0742(11) .0581(9) .0634(10) .0097(8) .0091(8) -.0062(7) N2B .0622(8) .0562(7) .0634(8) .0061(6) .0072(6) .0007(6) C3B .0513(8) .0487(7) .0546(8) -.0009(6) .0078(6) .0031(6) C31B .0519(8) .0486(7) .0616(9) -.0005(6) .0066(7) .0059(6) O31B .0585(6) .0648(7) .0809(8) .0101(5) -.0090(6) -.0046(5) O32B .0704(7) .0660(7) .0587(6) .0117(5) -.0069(5) -.0064(5) C32B .0745(11) .0843(13) .0614(10) .0016(10) -.0045(9) -.0105(9) C4B .0534(8) .0492(8) .0532(8) -.0007(6) .0062(7) -.0007(6) C4AB .0511(8) .0516(8) .0525(8) -.0016(6) .0090(6) .0013(6) C4BB .0501(8) .0591(8) .0502(8) -.0024(6) .0053(6) .0007(6) C5B .0543(9) .0669(9) .0667(10) .0050(7) .0003(7) -.0073(8) C6B .0629(10) .0817(12) .0843(13) .0152(9) -.0075(9) -.0040(10) C7B .0743(12) .0966(14) .0715(12) .0089(11) -.0180(10) -.0029(10) C8B .0768(12) .0856(12) .0561(10) -.0032(10) -.0043(9) -.0084(9) C8AB .0606(9) .0656(9) .0501(8) -.0043(7) .0087(7) -.0013(7) N9B .0742(9) .0650(8) .0537(7) .0030(7) .0057(7) -.0105(6) 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 C1AA N9A . 1.371(2) y C1AA C1A . 1.392(2) ? C1AA C4AA . 1.405(2) ? C1A N2A . 1.327(2) y C1A H1A . .95(2) ? N2A C3A . 1.356(2) y C3A C4A . 1.380(2) ? C3A C31A . 1.492(2) ? C31A O31A . 1.201(2) y C31A O32A . 1.332(2) ? O32A C32A . 1.439(2) ? C32A H32A . 1.02(3) ? C32A H32B . 1.00(3) ? C32A H32C . 1.06(3) ? C32A H32D . .97(4) ? C32A H32E . .98(4) ? C32A H32F . 1.07(4) ? C4A C4AA . 1.388(2) ? C4A H4A . .98(2) ? C4AA C4BA . 1.443(2) ? C4BA C5A . 1.389(2) ? C4BA C8AA . 1.411(2) ? C5A C6A . 1.372(2) ? C5A H5A . .98(2) ? C6A C7A . 1.396(2) ? C6A H6A . .97(2) ? C7A C8A . 1.370(3) ? C7A H7A . .94(2) ? C8A C8AA . 1.390(2) ? C8A H8A . .95(2) ? C8AA N9A . 1.375(2) y N9A H9A . .88(2) ? C1AB N9B . 1.370(2) y C1AB C1B . 1.394(2) ? C1AB C4AB . 1.402(2) ? C1B N2B . 1.322(2) y C1B H1B . .97(2) ? N2B C3B . 1.353(2) y C3B C4B . 1.383(2) ? C3B C31B . 1.483(2) ? C31B O31B . 1.203(2) y C31B O32B . 1.328(2) ? O32B C32B . 1.439(2) ? C32B H32G . .99(2) ? C32B H32H . .96(2) ? C32B H32I . .94(2) ? C4B C4AB . 1.385(2) ? C4B H4B . .98(2) ? C4AB C4BB . 1.444(2) ? C4BB C5B . 1.392(2) ? C4BB C8AB . 1.409(2) ? C5B C6B . 1.375(2) ? C5B H5B . 1.00(2) ? C6B C7B . 1.389(3) ? C6B H6B . .96(2) ? C7B C8B . 1.369(3) ? C7B H7B . .96(2) ? C8B C8AB . 1.392(2) ? C8B H8B . .96(2) ? C8AB N9B . 1.377(2) y N9B H9B . .88(2) ?