#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012046.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012046
loop_
_publ_author_name
'Kubicki, Maciej'
'Codding, Penelope W.'
_publ_section_title
;
 Form II of monoclinic methyl β-carboline-3-carboxylate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              728
_journal_page_last               729
_journal_paper_doi               10.1107/S0108270101003171
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23
_chemical_name_systematic
;
Methyl β-carboline-3-carboxylate.
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.388(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.6550(5)
_cell_length_b                   20.8077(8)
_cell_length_c                   11.0793(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38
_cell_measurement_theta_min      10
_cell_volume                     2173.99(18)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'ENPROC (Rettig, 1978)'
_computing_molecular_graphics    'Stereochemical Workstation (Siemens, 1989)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CAD4-F four-circle diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  Ni-filter
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .0191
_diffrn_reflns_av_sigmaI/netI    .0357
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8604
_diffrn_reflns_theta_full        69.86
_diffrn_reflns_theta_max         69.86
_diffrn_reflns_theta_min         4.25
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  33
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .784
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .2
_refine_diff_density_max         .152
_refine_diff_density_min         -.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          .0492
_refine_ls_R_factor_gt           .0391
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.1443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0988
_reflns_number_gt                3280
_reflns_number_total             4113
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1458.cif
_cod_data_source_block           BCCM
_cod_original_cell_volume        2173.99(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012046
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'
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_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N9A C1AA C1A 130.70(10) ?
N9A C1AA C4AA 109.30(10) ?
C1A C1AA C4AA 120.00(10) ?
N2A C1A C1AA 121.70(10) ?
N2A C1A H1A 116.0(10) ?
C1AA C1A H1A 122.0(10) ?
C1A N2A C3A 118.00(10) y
N2A C3A C4A 124.40(10) ?
N2A C3A C31A 114.70(10) ?
C4A C3A C31A 121.00(10) ?
O31A C31A O32A 123.10(10) ?
O31A C31A C3A 125.10(10) ?
O32A C31A C3A 111.80(10) ?
C31A O32A C32A 116.80(10) ?
O32A C32A H32A 107(2) ?
O32A C32A H32B 109(2) ?
H32A C32A H32B 115(3) ?
O32A C32A H32C 108(2) ?
H32A C32A H32C 108(2) ?
H32B C32A H32C 109(2) ?
O32A C32A H32D 107(2) ?
H32D C32A H32E 115(3) ?
O32A C32A H32F 105(2) ?
H32D C32A H32F 118(3) ?
H32E C32A H32F 102(3) ?
C3A C4A C4AA 117.70(10) ?
C3A C4A H4A 118.7(9) ?
C4AA C4A H4A 123.6(9) ?
C4A C4AA C1AA 118.30(10) ?
C4A C4AA C4BA 135.10(10) ?
C1AA C4AA C4BA 106.60(10) ?
C5A C4BA C8AA 119.70(10) ?
C5A C4BA C4AA 134.30(10) ?
C8AA C4BA C4AA 106.00(10) ?
C6A C5A C4BA 118.90(10) ?
C6A C5A H5A 121.0(10) ?
C4BA C5A H5A 120.0(10) ?
C5A C6A C7A 120.8(2) ?
C5A C6A H6A 119.0(10) ?
C7A C6A H6A 120.0(10) ?
C8A C7A C6A 121.7(2) ?
C8A C7A H7A 119.0(10) ?
C6A C7A H7A 120.0(10) ?
C7A C8A C8AA 117.7(2) ?
C7A C8A H8A 123.0(10) ?
C8AA C8A H8A 119.0(10) ?
N9A C8AA C8A 129.50(10) ?
N9A C8AA C4BA 109.30(10) ?
C8A C8AA C4BA 121.20(10) ?
C1AA N9A C8AA 108.80(10) y
C1AA N9A H9A 125.0(10) ?
C8AA N9A H9A 125.0(10) ?
N9B C1AB C1B 130.60(10) ?
N9B C1AB C4AB 109.50(10) ?
C1B C1AB C4AB 119.80(10) ?
N2B C1B C1AB 121.70(10) ?
N2B C1B H1B 117.0(10) ?
C1AB C1B H1B 121.0(10) ?
C1B N2B C3B 118.20(10) y
N2B C3B C4B 124.00(10) ?
N2B C3B C31B 114.80(10) ?
C4B C3B C31B 121.20(10) ?
O31B C31B O32B 122.60(10) ?
O31B C31B C3B 125.00(10) ?
O32B C31B C3B 112.40(10) ?
C31B O32B C32B 116.70(10) ?
O32B C32B H32G 109.0(10) ?
O32B C32B H32H 108.0(10) ?
H32G C32B H32H 109(2) ?
O32B C32B H32I 108.0(10) ?
H32G C32B H32I 117(2) ?
H32H C32B H32I 105(2) ?
C3B C4B C4AB 117.80(10) ?
C3B C4B H4B 120.9(9) ?
C4AB C4B H4B 122.2(9) ?
C4B C4AB C1AB 118.30(10) ?
C4B C4AB C4BB 135.20(10) ?
C1AB C4AB C4BB 106.50(10) ?
C5B C4BB C8AB 119.80(10) ?
C5B C4BB C4AB 134.10(10) ?
C8AB C4BB C4AB 106.10(10) ?
C6B C5B C4BB 118.7(2) ?
C6B C5B H5B 121.0(10) ?
C4BB C5B H5B 120.0(10) ?
C5B C6B C7B 120.6(2) ?
C5B C6B H6B 120.0(10) ?
C7B C6B H6B 119.0(10) ?
C8B C7B C6B 122.1(2) ?
C8B C7B H7B 122.0(10) ?
C6B C7B H7B 116.0(10) ?
C7B C8B C8AB 117.6(2) ?
C7B C8B H8B 126.0(10) ?
C8AB C8B H8B 116.0(10) ?
N9B C8AB C8B 129.70(10) ?
N9B C8AB C4BB 109.30(10) ?
C8B C8AB C4BB 121.0(2) ?
C1AB N9B C8AB 108.60(10) y
C1AB N9B H9B 125.0(10) ?
C8AB N9B H9B 126.0(10) ?
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) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N9A H9A O31B 1_655 .88(2) 2.06(2) 2.840(2) 146(2)
N9A H9A N2B 1_655 .88(2) 2.73(2) 3.492(2) 145.0(10)
N9B H9B O31A 1_556 .88(2) 2.05(2) 2.835(2) 147(2)
N9B H9B N2A 1_556 .88(2) 2.72(2) 3.476(2) 144.0(10)
C6A H6A O32B 2_656 .97(2) 2.58(2) 3.431(2) 147.0(10)
C6B H6B O31B 4_666 .96(2) 2.61(2) 3.473(2) 150.0(10)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N9A C1AA C1A N2A -179.50(10)
C4AA C1AA C1A N2A .9(2)
C1AA C1A N2A C3A .6(2)
C1A N2A C3A C4A -1.4(2)
C1A N2A C3A C31A 178.40(10)
N2A C3A C31A O31A -5.2(2)
C4A C3A C31A O31A 174.60(10)
N2A C3A C31A O32A 175.60(10)
C4A C3A C31A O32A -4.6(2)
O31A C31A O32A C32A -.7(2)
C3A C31A O32A C32A 178.50(10)
N2A C3A C4A C4AA .6(2)
C31A C3A C4A C4AA -179.20(10)
C3A C4A C4AA C1AA 1.0(2)
C3A C4A C4AA C4BA -179.00(10)
N9A C1AA C4AA C4A 178.60(10)
C1A C1AA C4AA C4A -1.7(2)
N9A C1AA C4AA C4BA -1.4(2)
C1A C1AA C4AA C4BA 178.30(10)
C4A C4AA C4BA C5A 2.7(3)
C1AA C4AA C4BA C5A -177.3(2)
C4A C4AA C4BA C8AA -178.60(10)
C1AA C4AA C4BA C8AA 1.40(10)
C8AA C4BA C5A C6A .5(2)
C4AA C4BA C5A C6A 179.0(2)
C4BA C5A C6A C7A 1.2(3)
C5A C6A C7A C8A -1.6(3)
C6A C7A C8A C8AA .3(3)
C7A C8A C8AA N9A -178.3(2)
C7A C8A C8AA C4BA 1.3(3)
C5A C4BA C8AA N9A 178.00(10)
C4AA C4BA C8AA N9A -1.0(2)
C5A C4BA C8AA C8A -1.7(2)
C4AA C4BA C8AA C8A 179.30(10)
C1A C1AA N9A C8AA -178.9(2)
C4AA C1AA N9A C8AA .8(2)
C8A C8AA N9A C1AA 179.8(2)
C4BA C8AA N9A C1AA .1(2)
N9B C1AB C1B N2B -179.4(2)
C4AB C1AB C1B N2B -.9(3)
C1AB C1B N2B C3B -1.2(2)
C1B N2B C3B C4B 1.4(2)
C1B N2B C3B C31B -179.20(10)
N2B C3B C31B O31B -2.5(2)
C4B C3B C31B O31B 176.90(10)
N2B C3B C31B O32B 177.90(10)
C4B C3B C31B O32B -2.6(2)
O31B C31B O32B C32B -2.4(2)
C3B C31B O32B C32B 177.10(10)
N2B C3B C4B C4AB .7(2)
C31B C3B C4B C4AB -178.70(10)
C3B C4B C4AB C1AB -2.7(2)
C3B C4B C4AB C4BB 178.10(10)
N9B C1AB C4AB C4B -178.30(10)
C1B C1AB C4AB C4B 2.9(2)
N9B C1AB C4AB C4BB 1.1(2)
C1B C1AB C4AB C4BB -177.70(10)
C4B C4AB C4BB C5B -2.7(3)
C1AB C4AB C4BB C5B 178.1(2)
C4B C4AB C4BB C8AB 178.4(2)
C1AB C4AB C4BB C8AB -.9(2)
C8AB C4BB C5B C6B .0(2)
C4AB C4BB C5B C6B -178.9(2)
C4BB C5B C6B C7B -1.5(3)
C5B C6B C7B C8B 1.4(3)
C6B C7B C8B C8AB .2(3)
C7B C8B C8AB N9B 178.8(2)
C7B C8B C8AB C4BB -1.8(3)
C5B C4BB C8AB N9B -178.70(10)
C4AB C4BB C8AB N9B .4(2)
C5B C4BB C8AB C8B 1.7(2)
C4AB C4BB C8AB C8B -179.10(10)
C1B C1AB N9B C8AB 177.8(2)
C4AB C1AB N9B C8AB -.9(2)
C8B C8AB N9B C1AB 179.8(2)
C4BB C8AB N9B C1AB .3(2)
