#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/49/2004914.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_2004914
loop_
_publ_author_name
'Schollmeyer, D.'
'Fischer, G.'
'Pindur, U.'
_publ_section_title
;Pyrrolo-Annellated Carbazoles as Potential Antitumour-Active Compounds:
 Dimethyl 4-Methoxy-9-methyl-9<i>H</i>-carbazole-1,2-dicarboxylate and
 5-Hydroxy-2-phenyl-10-methyl-1,2,3,10-tetrahydropyrrolo[3,4-<i>a</i>]carbazole-1,3-dione
 Methanol Solvate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1277
_journal_page_last               1280
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C18 H17 N1 O5'
_chemical_formula_sum            'C18 H17 N O5'
_chemical_formula_weight         327.34
_chemical_name_systematic
;
4-Methoxy-9-methyl-9H-carbazol-1,2-dimethyldicarboxalat
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.888(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.8415(3)
_cell_length_b                   24.411(3)
_cell_length_c                   19.3770(10)
_cell_measurement_reflns_used    75
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      70
_cell_measurement_theta_min      60
_cell_volume                     3219.0(5)
_computing_cell_refinement       'CELSIUS (Svenson, 1974)'
_computing_data_collection       'CAD-4 Software (Enraf Nonius, 1989)'
_computing_data_reduction        'CORINC (Dr\"ager & Gattow, 1971)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Enraf Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5416
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6818
_diffrn_reflns_theta_max         70.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%
'5 [corrected with a cubic spline function (CORINC; Dr\"ager & Gattow, 1971)]'
_diffrn_standards_interval_time  66.7
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'rectangular prism'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       colourless
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         .387
_refine_diff_density_min         -.278
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_method     'SHELX76 (Sheldrick, 1976)'
_refine_ls_goodness_of_fit_all   6.88
_refine_ls_hydrogen_treatment    'H-atom coordinates refined only'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         4182
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.06
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'calc w = 1/[\s^2^(Fo)+ 0.0002Fo^2^] '
_refine_ls_wR_factor_all         0.07
_reflns_number_observed          4182
_reflns_number_total             5236
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    na1206.cif
_[local]_cod_data_source_block   1
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_[local]_cod_chemical_formula_sum_orig 'C18 H17 N1 O5'
_cod_original_cell_volume        3219.1(3)
_cod_database_code               2004914
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_occupancy
_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_refinement_flags
_atom_site_disorder_group
_atom_site_type_symbol
C1 1 .4334(5) .68700(10) .8113(2) .0600(10) Uani d . . C
C2 1 .2739(5) .72080(10) .79100(10) .0600(10) Uani d . . C
C3 1 .2328(5) .73880(10) .72240(10) .0580(10) Uani d . . C
C4 1 .3505(4) .72340(10) .67220(10) .0527(10) Uani d . . C
C4A 1 .5155(4) .69040(10) .69140(10) .0526(10) Uani d . . C
C4B 1 .6659(5) .66900(10) .6524(2) .0580(10) Uani d . . C
C5 1 .7029(5) .67150(10) .5822(2) .0680(10) Uani d . . C
C6 1 .8624(6) .6438(2) .5629(2) .087(2) Uani d . . C
C7 1 .9879(6) .6147(2) .6121(3) .098(2) Uani d . . C
C8 1 .9576(6) .61300(10) .6802(2) .091(2) Uani d . . C
C8A 1 .7922(5) .63930(10) .7000(2) .0690(10) Uani d . . C
N9 1 .7260(4) .64180(10) .7653(2) .0710(10) Uani d . . N
C15 1 .8286(7) .6164(2) .8268(2) .101(2) Uani d . . C
C9A 1 .5554(5) .67320(10) .7603(2) .0590(10) Uani d . . C
O1 1 .3222(3) .73728(9) .60410(10) .0654(8) Uani d . . O
C10 1 .1528(5) .76970(10) .5815(2) .0710(10) Uani d . . C
C11 1 .1439(6) .7378(2) .8440(2) .0700(10) Uani d . . C
O2 1 .1598(5) .7233(2) .90200(10) .137(2) Uani d . . O
O3 1 .0022(4) .77150(10) .82000(10) .0920(10) Uani d . . O
C12 1 -0.1305(6) .7924(2) .8670(2) .096(2) Uani d . . C
C13 1 .4665(6) .6636(2) .8829(2) .0760(10) Uani d . . C
O4 1 .5754(4) .69500(10) .92600(10) .0920(10) Uani d . . O
O5 1 .4063(6) .61990(10) .89830(10) .124(2) Uani d . . O
C14 1 .6105(9) .6727(2) .9955(2) .141(3) Uani d . . C
C21 1 .1575(4) .93220(10) .70030(10) .0516(10) Uani d . . C
C22 1 .3130(4) .90130(10) .7327(2) .0534(10) Uani d . . C
C23 1 .3305(4) .89000(10) .8042(2) .0560(10) Uani d . . C
C24 1 .1946(5) .90980(10) .8451(2) .0570(10) Uani d . . C
C24A 1 .0370(4) .94080(10) .8148(2) .0550(10) Uani d . . C
C24B 1 -0.1263(5) .96670(10) .8431(2) .0650(10) Uani d . . C
C25 1 -0.1802(6) .97210(10) .9107(2) .0810(10) Uani d . . C
C26 1 -0.3518(7) 1.0017(2) .9183(3) .105(2) Uani d . . C
C27 1 -0.4610(6) 1.0245(2) .8621(3) .107(2) Uani d . . C
C28 1 -0.4103(5) 1.02040(10) .7961(3) .090(2) Uani d . . C
C28A 1 -0.2394(5) .99100(10) .7868(2) .0690(10) Uani d . . C
N29 1 -0.1523(4) .98180(10) .7261(2) .0657(10) Uani d . . N
C35 1 -0.2311(5) 1.00060(10) .6586(2) .0850(10) Uani d . . C
C29A 1 .0186(4) .95130(10) .7430(2) .0540(10) Uani d . . C
O21 1 .1978(4) .90210(10) .91460(10) .0744(9) Uani d . . O
C30 1 .3578(6) .8716(2) .9485(2) .0830(10) Uani d . . C
C31 1 .4631(5) .88010(10) .6891(2) .0560(10) Uani d . . C
O22 1 .4616(4) .88730(10) .62880(10) .0920(10) Uani d . . O
O23 1 .6044(3) .85160(10) .72540(10) .0806(9) Uani d . . C
C32 1 .7522(5) .8285(2) .6862(2) .0850(10) Uani d . . C
C33 1 .1470(5) .94540(10) .6244(2) .0630(10) Uani d . . C
O24 1 .2304(5) .98800(10) .60680(10) .0980(10) Uani d . . O
O25 1 .0532(4) .91230(10) .58290(10) .0813(9) Uani d . . O
C34 .6 .0680(10) .9176(3) .5097(3) .103(3) Uani d P 1 C
C34A .4 .282(2) .9966(5) .5385(5) .120(5) Uani d P 2 C
H3 1 .1060(5) .76280(10) .70980(10) .07 Uiso d R . H
H5 1 .5988(5) .69910(10) .5513(2) .07 Uiso d R . H
H6 1 .9002(6) .6479(2) .5132(2) .09 Uiso d R . H
H7 1 1.1138(6) .5960(2) .5996(3) .09 Uiso d R . H
H8 1 1.0315(6) .58560(10) .7125(2) .09 Uiso d R . H
H15A 1 .7215(7) .5961(2) .8479(2) .10 Uiso d R . H
H15B 1 .8941(7) .6408(2) .8646(2) .10 Uiso d R . H
H15C 1 .8618(7) .5847(2) .7986(2) .10 Uiso d R . H
H10A 1 .1465(5) .77690(10) .5272(2) .08 Uiso d R . H
H10B 1 .1713(5) .80680(10) .6077(2) .08 Uiso d R . H
H10C 1 .0373(5) .75260(10) .5988(2) .08 Uiso d R . H
H12A 1 -.0431(6) .7910(2) .9169(2) .10 Uiso d R . H
H12B 1 -0.2108(6) .7655(2) .8700(2) .10 Uiso d R . H
H12C 1 -0.1324(6) .8366(2) .8669(2) .10 Uiso d R . H
H14A 1 .7009(9) .7007(2) 1.0279(2) .12 Uiso d R . H
H14B 1 .6849(9) .6338(2) .9936(2) .12 Uiso d R . H
H14C 1 .4720(9) .6669(2) 1.0166(2) .12 Uiso d R . H
H23 1 .4343(4) .86380(10) .8211(2) .07 Uiso d R . H
H25 1 -.0919(6) .95330(10) .9538(2) .09 Uiso d R . H
H26 1 -0.3899(7) 1.0028(2) .9745(3) .10 Uiso d R . H
H27 1 -0.5976(6) 1.0425(2) .8682(3) .10 Uiso d R . H
H28 1 -0.4930(5) 1.03870(10) .7528(3) .10 Uiso d R . H
H35A 1 -0.1369(5) 1.01320(10) .6360(2) .08 Uiso d R . H
H35B 1 -0.3527(5) 1.01410(10) .6598(2) .08 Uiso d R . H
H35C 1 -0.2786(5) .96780(10) .6268(2) .08 Uiso d R . H
H30A 1 .3611(6) .8350(2) .9283(2) .09 Uiso d R . H
H30B 1 .5027(6) .8949(2) .9476(2) .09 Uiso d R . H
H30C 1 .3449(6) .8685(2) .9953(2) .09 Uiso d R . H
H32A 1 .6758(5) .8012(2) .6538(2) .09 Uiso d R . H
H32B 1 .7895(5) .8471(2) .6459(2) .09 Uiso d R . H
H32C 1 .8661(5) .8254(2) .7224(2) .09 Uiso d R . H
H34A .6 -.0180(10) .8863(3) .4814(3) .10 Uiso d R 1 H
H34B .6 .2210(10) .9130(3) .5007(3) .10 Uiso d R 1 H
H34C .6 .0170(10) .9575(3) .4923(3) .10 Uiso d R 1 H
H34D .4 .352(2) 1.0358(5) .5326(5) .10 Uiso d R 2 H
H34E .4 .150(2) .9940(5) .5029(5) .10 Uiso d R 2 H
H34F .4 .382(2) .9642(5) .5275(5) .10 Uiso d R 2 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
C1 0.067(2) 0.064(2) 0.050(2) -0.007(2) 0.007(2) 0.0040(10)
C2 0.062(2) 0.068(2) 0.049(2) -0.007(2) 0.0110(10) 0.0000(10)
C3 0.055(2) 0.066(2) 0.053(2) 0.005(2) 0.0080(10) 0.0000(10)
C4 0.055(2) 0.057(2) 0.046(2) -0.002(2) 0.0060(10) 0.0010(10)
C4A 0.055(2) 0.051(2) 0.053(2) -0.0010(10) 0.0070(10) 0.0000(10)
C4B 0.057(2) 0.048(2) 0.070(2) -0.0020(10) 0.012(2) -0.0040(10)
C5 0.068(2) 0.059(2) 0.079(2) -0.001(2) 0.025(2) -0.011(2)
C6 0.093(3) 0.072(2) 0.104(3) -0.003(2) 0.045(3) -0.014(2)
C7 0.079(3) 0.074(2) 0.148(4) 0.016(2) 0.043(3) -0.013(3)
C8 0.078(3) 0.067(2) 0.131(4) 0.021(2) 0.025(3) 0.006(2)
C8A 0.062(2) 0.051(2) 0.093(3) 0.005(2) 0.009(2) 0.000(2)
N9 0.067(2) 0.066(2) 0.080(2) 0.0170(10) 0.001(2) 0.0110(10)
C15 0.109(3) 0.099(3) 0.092(3) 0.026(3) -0.011(3) 0.014(2)
C9A 0.063(2) 0.055(2) 0.060(2) -0.002(2) 0.000(2) 0.0050(10)
O1 0.0670(10) 0.0820(10) 0.0480(10) 0.0160(10) 0.0110(10) 0.0080(10)
C10 0.070(2) 0.085(2) 0.055(2) 0.010(2) -0.003(2) 0.010(2)
C11 0.073(2) 0.087(2) 0.053(2) -0.005(2) 0.013(2) -0.004(2)
O2 0.138(3) 0.224(4) 0.053(2) 0.070(3) 0.030(2) 0.022(2)
O3 0.100(2) 0.111(2) 0.072(2) 0.028(2) 0.0420(10) 0.0100(10)
C12 0.104(3) 0.103(3) 0.092(3) 0.003(3) 0.058(3) -0.008(2)
C13 0.085(3) 0.082(2) 0.061(2) -0.007(2) 0.002(2) 0.009(2)
O4 0.109(2) 0.105(2) 0.0590(10) -0.027(2) -0.0110(10) 0.0130(10)
O5 0.193(4) 0.095(2) 0.081(2) -0.054(2) 0.003(2) 0.0230(10)
C14 0.182(6) 0.164(5) 0.067(3) -0.008(4) -0.031(3) 0.019(3)
C21 0.048(2) 0.050(2) 0.056(2) -0.0030(10) 0.0030(10) -0.0010(10)
C22 0.044(2) 0.057(2) 0.059(2) -0.0020(10) 0.0050(10) -0.0050(10)
C23 0.049(2) 0.060(2) 0.058(2) 0.0090(10) 0.0060(10) 0.0000(10)
C24 0.056(2) 0.060(2) 0.054(2) 0.000(2) 0.0120(10) 0.0000(10)
C24A 0.047(2) 0.051(2) 0.068(2) -0.0010(10) 0.0130(10) -0.0030(10)
C24B 0.056(2) 0.049(2) 0.094(2) -0.005(2) 0.028(2) -0.003(2)
C25 0.082(3) 0.062(2) 0.109(3) -0.002(2) 0.054(2) -0.002(2)
C26 0.101(3) 0.069(2) 0.159(4) 0.001(2) 0.082(3) 0.001(3)
C27 0.069(3) 0.072(3) 0.190(5) 0.008(2) 0.062(3) -0.006(3)
C28 0.052(2) 0.062(2) 0.159(4) 0.007(2) 0.028(2) 0.003(2)
C28A 0.047(2) 0.051(2) 0.113(3) -0.001(2) 0.018(2) 0.000(2)
N29 0.048(2) 0.0590(10) 0.089(2) 0.0070(10) 0.0020(10) 0.0030(10)
C35 0.053(2) 0.087(3) 0.111(3) 0.006(2) -0.014(2) 0.011(2)
C29A 0.044(2) 0.047(2) 0.070(2) -0.0010(10) 0.0030(10) -0.0010(10)
O21 0.074(2) 0.092(2) 0.0600(10) 0.0150(10) 0.0190(10) 0.0090(10)
C30 0.087(3) 0.102(3) 0.061(2) 0.008(2) 0.004(2) 0.015(2)
C31 0.049(2) 0.061(2) 0.059(2) -0.001(2) 0.006(2) -0.0070(10)
O22 0.081(2) 0.140(2) 0.0550(10) 0.031(2) 0.0140(10) -0.0040(10)
O23 0.065(2) 0.104(2) 0.075(2) 0.0330(10) 0.0200(10) 0.0010(10)
C32 0.060(2) 0.115(3) 0.084(2) 0.026(2) 0.023(2) -0.007(2)
C33 0.059(2) 0.064(2) 0.066(2) 0.000(2) 0.000(2) -0.001(2)
O24 0.132(3) 0.087(2) 0.076(2) -0.032(2) 0.011(2) 0.0080(10)
O25 0.085(2) 0.091(2) 0.0650(10) -0.0140(10) -0.0100(10) -0.0100(10)
C34 0.139(7) 0.106(5) 0.058(4) 0.003(5) -0.016(4) -0.007(3)
C34A 0.104(9) 0.180(10) 0.075(7) -0.022(8) 0.001(6) 0.059(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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
C13 C1 C2 121.9(3) yes
C11 C2 C1 118.5(3) yes
O1 C4 C3 125.6(2) yes
N9 C8A C4B 110.0(3) yes
N9 C8A C8 128.5(3) yes
C15 N9 C8A 123.5(3) yes
C9A N9 C8A 108.1(3) yes
C9A N9 C15 128.4(3) yes
N9 C9A C1 129.8(2) yes
N9 C9A C4A 108.2(3) yes
C10 O1 C4 117.8(2) yes
O2 C11 C2 125.1(3) yes
O3 C11 C2 113.6(3) yes
C12 O3 C11 119.0(3) yes
O4 C13 C1 113.0(3) yes
O5 C13 C1 123.4(3) yes
O5 C13 O4 123.6(3) yes
C14 O4 C13 113.7(3) yes
C33 C21 C22 120.9(2) yes
C31 C22 C21 118.0(2) yes
N29 C29A C21 129.9(2) yes
O21 C24 C23 125.6(2) yes
N29 C28A C24B 109.8(3) yes
N29 C28A C28 129.0(3) yes
C35 N29 C28A 124.4(3) yes
C29A N29 C28A 108.0(2) yes
N29 C29A C24A 108.5(2) yes
C30 O21 C24 117.6(2) yes
O22 C31 C22 125.0(3) yes
O23 C31 C22 112.8(2) yes
C32 O23 C31 115.9(2) yes
O24 C33 C21 118.0(2) yes
O25 C33 C21 117.1(2) yes
C34A O24 C33 122.8(5) yes
C34 O25 C33 119.1(3) yes
C29A N29 C35 127.6(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C13 1.495(5) yes
C2 C11 1.486(5) yes
C4 O1 1.356(3) yes
C4A C4B 1.436(4) yes
C8A N9 1.388(5) yes
N9 C15 1.458(5) yes
N9 C9A 1.392(4) yes
O1 C10 1.435(4) yes
C11 O2 1.173(4) yes
C11 O3 1.318(5) yes
O3 C12 1.443(5) yes
C13 O4 1.309(5) yes
C13 O5 1.193(5) yes
O4 C14 1.449(5) yes
C21 C29A 1.403(4) yes
C21 C33 1.499(4) yes
C22 C31 1.487(4) yes
C24 O21 1.358(4) yes
C24A C24B 1.439(4) yes
C28A N29 1.390(5) yes
N29 C35 1.438(5) yes
N29 C29A 1.395(4) yes
O21 C30 1.427(5) yes
C31 O22 1.182(4) yes
C31 O23 1.333(4) yes
O23 C32 1.441(4) yes
C33 O24 1.251(4) yes
C33 O25 1.268(4) yes
O24 C34A 1.420(10) yes
O25 C34 1.438(6) yes
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
_geom_torsion_publ_flag
C2 C1 C13 O5 92.4(4) yes
C9A C1 C13 O4 93.5(4) yes
C3 C2 C11 O3 -2.8(4) yes
C3 C4 O1 C10 -1.5(3) yes
C2 C3 C4 O1 178.4(3) yes
C23 C22 C31 O23 -0.1(3) yes
C2 C11 O3 C12 -178.0(4) yes
C1 C13 O4 C14 -179.4(4) yes
O5 C13 O4 C14 -2.2(5) yes
C1 C2 C11 O2 -3.1(4) yes
C22 C21 C33 O24 -88.8(4) yes
C23 C22 C31 O22 180.0(3) yes
C29A C21 C33 O25 -90.9(3) yes
C21 C22 C31 O23 179.7(3) yes
C22 C23 C24 O21 -179.2(3) yes
C23 C24 O21 C30 1.1(4) yes
C29A C21 C33 O24 89.0(4) yes
O25 C33 O24 C34A -19.7(7) yes
_journal_paper_doi 10.1107/S010827019501609X