#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223369.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_2223369
loop_
_publ_author_name
'Monroe, Thomas Blake'
'Moazami, Yasamin'
'Jones, Daniel S.'
'Ogle, Craig A.'
_publ_section_title
;
Methyl 5,6-dimethoxy-1H-indole-2-carboxylate
;
_journal_coeditor_code FJ2241
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o2353
_journal_volume 65
_journal_year 2009
_chemical_formula_iupac 'C12 H13 N1 O4'
_chemical_formula_moiety 'C12 H13 N1 O4'
_chemical_formula_sum 'C12 H13 N O4'
_chemical_formula_weight 235.23
_chemical_name_systematic
;
Methyl 5,6-dimethoxy-1H-indole-2-carboxylate
;
_space_group_IT_number 61
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall '-P 2ac 2ab'
_symmetry_space_group_name_H-M 'P b c a'
_audit_creation_method 'WinGX routine CIF_UPDATE'
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 8
_cell_length_a 17.0768(19)
_cell_length_b 7.7232(11)
_cell_length_c 17.678(2)
_cell_measurement_reflns_used 25
_cell_measurement_temperature 295(2)
_cell_measurement_theta_max 43.03
_cell_measurement_theta_min 10.03
_cell_volume 2331.5(5)
_computing_cell_refinement 'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection 'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;ORTEP-3 for Windows (Farrugia, 1997) and Mercury
(Macrae et al., 2006)
;
_computing_publication_material 'WinGX (Farrugia, 1999)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 295(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device '\k-geometry diffractometer'
_diffrn_measurement_device_type 'Enraf--Nonius CAD-4'
_diffrn_measurement_method 'Non-profiled \w/2\q'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0302
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 9909
_diffrn_reflns_theta_full 67.41
_diffrn_reflns_theta_max 67.41
_diffrn_reflns_theta_min 5
_diffrn_standards_decay_% 1
_diffrn_standards_interval_count 171
_diffrn_standards_interval_time 57
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 0.85
_exptl_absorpt_correction_type none
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.34
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 992
_exptl_crystal_size_max 0.36
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.21
_refine_diff_density_max 0.143
_refine_diff_density_min -0.117
_refine_ls_extinction_coef 0.0047(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref 1.019
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 162
_refine_ls_number_reflns 2098
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.019
_refine_ls_R_factor_gt 0.0345
_refine_ls_shift/su_max 0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.2248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_ref 0.1015
_reflns_number_gt 1522
_reflns_number_total 2098
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file fj2241.cif
_[local]_cod_data_source_block I
_cod_database_code 2223369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
N N 0.05760(8) 0.76815(19) 0.51504(7) 0.0509(3) Uani d . 1
O O1 0.07015(8) 1.05091(17) 0.41553(7) 0.0727(4) Uani d . 1
O O2 0.17099(7) 0.92154(18) 0.35786(7) 0.0722(4) Uani d . 1
O O3 0.00702(6) 0.30330(14) 0.69682(6) 0.0564(3) Uani d . 1
O O4 0.12332(7) 0.14080(15) 0.64271(7) 0.0656(4) Uani d . 1
C C2 0.11320(9) 0.7786(2) 0.45863(8) 0.0516(4) Uani d . 1
C C3 0.15832(9) 0.6316(2) 0.46040(8) 0.0530(4) Uani d . 1
H H3 0.2001 0.6062 0.4285 0.064 Uiso calc R 1
C C4 0.15041(8) 0.3618(2) 0.54858(8) 0.0495(4) Uani d . 1
H H4 0.1918 0.2997 0.5277 0.059 Uiso calc R 1
C C5 0.10882(9) 0.2958(2) 0.60783(8) 0.0476(4) Uani d . 1
C C6 0.04402(8) 0.3882(2) 0.63953(8) 0.0453(4) Uani d . 1
C C7 0.02331(8) 0.5479(2) 0.61286(8) 0.0459(4) Uani d . 1
H H7 -0.018 0.6096 0.634 0.055 Uiso calc R 1
C C8 0.06679(8) 0.6150(2) 0.55251(8) 0.0448(4) Uani d . 1
C C9 0.12971(8) 0.5256(2) 0.51953(8) 0.0466(4) Uani d . 1
C C10 0.11447(10) 0.9300(2) 0.41017(9) 0.0556(4) Uani d . 1
C C11 0.17434(13) 1.0657(4) 0.30566(12) 0.0936(8) Uani d . 1
H H11A 0.1271 1.0693 0.2763 0.14 Uiso calc R 1
H H11B 0.2184 1.0517 0.2725 0.14 Uiso calc R 1
H H11C 0.1797 1.1718 0.3335 0.14 Uiso calc R 1
C C12 0.18869(10) 0.0457(2) 0.61719(11) 0.0661(5) Uani d . 1
H H12A 0.1826 0.0201 0.5644 0.099 Uiso calc R 1
H H12B 0.1925 -0.0604 0.6452 0.099 Uiso calc R 1
H H12C 0.2354 0.1128 0.6246 0.099 Uiso calc R 1
C C13 -0.05334(10) 0.3942(2) 0.73565(10) 0.0622(5) Uani d . 1
H H13A -0.0324 0.4989 0.7568 0.093 Uiso calc R 1
H H13B -0.0737 0.3228 0.7755 0.093 Uiso calc R 1
H H13C -0.0946 0.4221 0.7009 0.093 Uiso calc R 1
H H1 0.0202(10) 0.852(2) 0.5251(10) 0.064(5) Uiso d . 1
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
N 0.0517(7) 0.0518(8) 0.0492(7) -0.0002(6) 0.0024(6) 0.0013(6)
O1 0.0850(9) 0.0656(9) 0.0676(8) 0.0067(7) 0.0120(7) 0.0111(6)
O2 0.0623(7) 0.0919(10) 0.0624(7) 0.0005(7) 0.0096(6) 0.0236(7)
O3 0.0601(6) 0.0515(7) 0.0576(6) 0.0056(5) 0.0185(5) 0.0030(5)
O4 0.0607(7) 0.0554(7) 0.0806(8) 0.0140(6) 0.0226(6) 0.0125(6)
C2 0.0472(8) 0.0623(10) 0.0454(8) -0.0074(8) -0.0004(7) 0.0008(7)
C3 0.0422(8) 0.0693(11) 0.0475(8) -0.0042(8) 0.0021(6) 0.0007(8)
C4 0.0390(7) 0.0577(10) 0.0517(8) 0.0014(7) 0.0033(6) -0.0050(8)
C5 0.0442(8) 0.0465(9) 0.0520(8) 0.0006(6) 0.0013(6) -0.0026(7)
C6 0.0437(7) 0.0482(9) 0.0438(7) -0.0035(7) 0.0026(6) -0.0036(7)
C7 0.0435(8) 0.0486(9) 0.0457(8) 0.0003(7) 0.0029(6) -0.0069(7)
C8 0.0431(7) 0.0474(8) 0.0438(7) -0.0037(6) -0.0037(6) -0.0030(7)
C9 0.0375(7) 0.0583(10) 0.0441(7) -0.0041(7) -0.0016(6) -0.0028(7)
C10 0.0522(9) 0.0675(11) 0.0470(8) -0.0070(9) -0.0033(7) 0.0026(8)
C11 0.0829(14) 0.124(2) 0.0739(12) -0.0071(13) 0.0069(11) 0.0451(13)
C12 0.0582(10) 0.0595(11) 0.0806(12) 0.0141(9) 0.0098(9) 0.0036(9)
C13 0.0647(10) 0.0622(10) 0.0598(10) 0.0076(9) 0.0219(8) 0.0008(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 4
0 -2 1
0 2 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N C2 108.82(14)
C8 N H1 126.2(11)
C2 N H1 125.0(11)
C10 O2 C11 115.57(16)
C6 O3 C13 117.19(12)
C5 O4 C12 117.03(13)
C3 C2 N 108.74(14)
C3 C2 C10 132.24(14)
N C2 C10 119.01(15)
C2 C3 C9 107.56(14)
C2 C3 H3 126.2
C9 C3 H3 126.2
C5 C4 C9 118.94(14)
C5 C4 H4 120.5
C9 C4 H4 120.5
C4 C5 O4 125.31(14)
C4 C5 C6 121.15(15)
O4 C5 C6 113.54(13)
O3 C6 C7 124.82(13)
O3 C6 C5 114.20(13)
C7 C6 C5 120.98(14)
C6 C7 C8 117.36(13)
C6 C7 H7 121.3
C8 C7 H7 121.3
N C8 C7 129.03(14)
N C8 C9 108.22(13)
C7 C8 C9 122.74(14)
C8 C9 C4 118.80(14)
C8 C9 C3 106.66(14)
C4 C9 C3 134.55(14)
O1 C10 O2 123.01(16)
O1 C10 C2 124.67(15)
O2 C10 C2 112.32(16)
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O4 C12 H12A 109.5
O4 C12 H12B 109.5
H12A C12 H12B 109.5
O4 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C8 1.365(2)
N C2 1.3792(19)
N H1 0.926(19)
O1 C10 1.206(2)
O2 C10 1.338(2)
O2 C11 1.447(2)
O3 C6 1.3619(18)
O3 C13 1.4235(19)
O4 C5 1.3695(19)
O4 C12 1.410(2)
C2 C3 1.373(2)
C2 C10 1.449(2)
C3 C9 1.415(2)
C3 H3 0.93
C4 C5 1.364(2)
C4 C9 1.410(2)
C4 H4 0.93
C5 C6 1.431(2)
C6 C7 1.367(2)
C7 C8 1.399(2)
C7 H7 0.93
C8 C9 1.404(2)
C11 H11A 0.96
C11 H11B 0.96
C11 H11C 0.96
C12 H12A 0.96
C12 H12B 0.96
C12 H12C 0.96
C13 H13A 0.96
C13 H13B 0.96
C13 H13C 0.96
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
N H1 O1 5_576 0.926(19) 2.011(19) 2.867(2) 152.9(16)