#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/14/2011422.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_2011422
loop_
_publ_author_name
'Ramos Silva, M.'
'Matos Beja, A.'
'Paixao, J. A.'
'Alte da Veiga, L.'
'Sobral, A. J. F. N.'
'Rocha Gonsalves, A. M. d'A.'
_publ_section_title
;
 Benzyl 5-carboxy-4-ethyl-3-methylpyrrole-2-carboxylate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1263
_journal_page_last               1264
_journal_paper_doi               10.1107/S010827010000980X
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C16 H17 N O4'
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_weight         287.31
_chemical_name_systematic
;
 benzyl 2-carboxy-3-ethyl-4-methylpyrrole-5-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.938(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.195(6)
_cell_length_b                   5.2607(13)
_cell_length_c                   25.413(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.07
_cell_measurement_theta_min      6.01
_cell_volume                     2931.2(11)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .994
_diffrn_measured_fraction_theta_max .994
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .045
_diffrn_reflns_av_sigmaI/netI    .0591
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2638
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'colourless translucent'
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          .37
_exptl_crystal_size_mid          .37
_exptl_crystal_size_min          .10
_refine_diff_density_max         .16
_refine_diff_density_min         -.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .964
_refine_ls_R_factor_all          .138
_refine_ls_R_factor_gt           .041
_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)+(0.0669P)²+0.6191P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .129
_reflns_number_gt                1253
_reflns_number_total             2568
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1110.cif
_cod_data_source_block           I
_cod_original_cell_volume        2931.3(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2011422
_cod_database_fobs_code          2011422
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N1 .15075(8) .4042(4) .46155(7) .0524(6) Uani d . 1 . . N
H1 .1701 .3000 .4842 .063 Uiso calc R 1 . . H
O1 .07475(8) .0965(5) .50807(8) .0695(7) Uani d . 1 . . O
H1A .048(4) -.01(2) .517(3) .104 Uiso d P .53(8) . . H
O2 -.00716(8) .2519(4) .45602(8) .0662(6) Uani d . 1 . . O
H2 -.030(4) .16(2) .472(3) .099 Uiso d P .47(8) . . H
O3 .27747(9) .4599(5) .46634(9) .0950(8) Uani d . 1 . . O
O4 .26078(8) .7786(5) .40986(9) .0898(8) Uani d . 1 . . O
C2 .08877(10) .4190(5) .44821(9) .0483(6) Uani d . 1 . . C
C3 .07518(11) .6099(5) .41066(9) .0496(6) Uani d . 1 . . C
C5 .17672(10) .5810(6) .43316(9) .0511(7) Uani d . 1 . . C
C6 .04998(11) .2466(6) .47229(10) .0516(7) Uani d . 1 . . C
C7 .01351(11) .6876(6) .38249(11) .0635(8) Uani d . 1 . . C
H7A .0120 .8713 .3792 .076 Uiso calc R 1 . . H
H7B -.0173 .6361 .4036 .076 Uiso calc R 1 . . H
C8 -.00078(13) .5699(8) .32772(13) .0949(11) Uani d . 1 . . C
H8A .0300 .6179 .3069 .142 Uiso calc R 1 . . H
H8B -.0398 .6290 .3105 .142 Uiso calc R 1 . . H
H8C -.0016 .3882 .3309 .142 Uiso calc R 1 . . H
C9 .13762(12) .9259(6) .36351(11) .0662(8) Uani d . 1 . . C
H9A .1635 1.0546 .3818 .099 Uiso calc R 1 . . H
H9B .0983 .9973 .3507 .099 Uiso calc R 1 . . H
H9C .1554 .8627 .3340 .099 Uiso calc R 1 . . H
C10 .24292(11) .5948(6) .43876(10) .0578(7) Uani d . 1 . . C
C11 .32562(12) .8112(8) .40807(12) .0863(11) Uani d . 1 . . C
H11A .3484 .6684 .4252 .104 Uiso calc R 1 . . H
H11B .3404 .9655 .4266 .104 Uiso calc R 1 . . H
C12 .33374(11) .8269(6) .35103(11) .0594(8) Uani d . 1 . . C
C13 .36806(14) .6519(6) .32857(14) .0792(10) Uani d . 1 . . C
H13 .3869 .5202 .3493 .095 Uiso calc R 1 . . H
C14 .37483(16) .6693(7) .27582(16) .0903(11) Uani d . 1 . . C
H14 .3987 .5510 .2614 .108 Uiso calc R 1 . . H
C15 .34672(14) .8590(7) .24453(13) .0764(9) Uani d . 1 . . C
H15 .3512 .8693 .2088 .092 Uiso calc R 1 . . H
C16 .31222(13) 1.0324(7) .26582(12) .0739(9) Uani d . 1 . . C
H16 .2928 1.1613 .2446 .089 Uiso calc R 1 . . H
C17 .30587(13) 1.0183(6) .31852(13) .0685(8) Uani d . 1 . . C
H17 .2824 1.1394 .3327 .082 Uiso calc R 1 . . H
C4 .13078(10) .7118(5) .40117(9) .0504(7) Uani d . 1 . . C
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'
O O .0106 .0060 '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'
H H .0000 .0000 '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
C5 N1 C2 108.8(2) ?
C5 N1 H1 125.6 ?
C2 N1 H1 125.6 ?
C6 O1 H1A 111(5) ?
C6 O2 H2 117(5) ?
C10 O4 C11 119.3(2) yes
N1 C2 C3 108.3(2) ?
N1 C2 C6 120.0(2) ?
C3 C2 C6 131.6(2) ?
C2 C3 C4 107.0(2) ?
C2 C3 C7 127.6(2) ?
C4 C3 C7 125.2(2) ?
N1 C5 C4 108.5(2) ?
N1 C5 C10 119.2(2) ?
C4 C5 C10 132.3(2) ?
O1 C6 O2 123.2(2) ?
O1 C6 C2 118.3(2) ?
O2 C6 C2 118.5(2) ?
C3 C7 C8 111.9(2) ?
C3 C7 H7A 109.2 ?
C8 C7 H7A 109.2 ?
C3 C7 H7B 109.2 ?
C8 C7 H7B 109.2 ?
H7A C7 H7B 107.9 ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C4 C9 H9A 109.5 ?
C4 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C4 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
O3 C10 O4 123.1(2) yes
O3 C10 C5 125.2(3) yes
O4 C10 C5 111.7(3) yes
O4 C11 C12 107.8(2) yes
O4 C11 H11A 110.1 ?
C12 C11 H11A 110.1 ?
O4 C11 H11B 110.1 ?
C12 C11 H11B 110.1 ?
H11A C11 H11B 108.5 ?
C13 C12 C17 117.7(3) ?
C13 C12 C11 121.7(3) ?
C17 C12 C11 120.6(3) ?
C12 C13 C14 120.8(3) ?
C12 C13 H13 119.6 ?
C14 C13 H13 119.6 ?
C15 C14 C13 120.5(3) ?
C15 C14 H14 119.8 ?
C13 C14 H14 119.8 ?
C16 C15 C14 119.6(3) ?
C16 C15 H15 120.2 ?
C14 C15 H15 120.2 ?
C15 C16 C17 120.2(3) ?
C15 C16 H16 119.9 ?
C17 C16 H16 119.9 ?
C16 C17 C12 121.2(3) ?
C16 C17 H17 119.4 ?
C12 C17 H17 119.4 ?
C5 C4 C3 107.3(2) ?
C5 C4 C9 127.5(2) ?
C3 C4 C9 125.2(2) ?
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
N1 C5 . 1.359(3) yes
N1 C2 . 1.367(3) yes
N1 H1 . .8600 ?
O1 C6 . 1.264(3) ?
O1 H1A . .87(12) ?
O2 C6 . 1.272(3) ?
O2 H2 . .86(13) ?
O3 C10 . 1.190(3) yes
O4 C10 . 1.312(3) yes
O4 C11 . 1.457(3) yes
C2 C3 . 1.386(3) yes
C2 C6 . 1.450(3) ?
C3 C4 . 1.400(3) yes
C3 C7 . 1.499(3) ?
C5 C4 . 1.385(3) yes
C5 C10 . 1.456(3) ?
C7 C8 . 1.511(4) ?
C7 H7A . .9700 ?
C7 H7B . .9700 ?
C8 H8A . .9600 ?
C8 H8B . .9600 ?
C8 H8C . .9600 ?
C9 C4 . 1.501(3) ?
C9 H9A . .9600 ?
C9 H9B . .9600 ?
C9 H9C . .9600 ?
C11 C12 . 1.491(4) ?
C11 H11A . .9700 ?
C11 H11B . .9700 ?
C12 C13 . 1.374(4) ?
C12 C17 . 1.386(4) ?
C13 C14 . 1.375(5) ?
C13 H13 . .9300 ?
C14 C15 . 1.365(5) ?
C14 H14 . .9300 ?
C15 C16 . 1.357(4) ?
C15 H15 . .9300 ?
C16 C17 . 1.370(4) ?
C16 H16 . .9300 ?
C17 H17 . .9300 ?
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
N1 H1 O3 7_556 .86 2.09 2.942(3) 175
O1 H1A O2 5_556 .87(12) 1.77(13) 2.621(3) 168(8)
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
C5 N1 C2 C3 -.2(3) ?
C5 N1 C2 C6 178.9(2) ?
N1 C2 C3 C4 .2(3) ?
C6 C2 C3 C4 -178.7(3) ?
N1 C2 C3 C7 177.0(2) ?
C6 C2 C3 C7 -1.9(4) ?
C2 N1 C5 C4 .1(3) ?
C2 N1 C5 C10 -177.3(2) ?
N1 C2 C6 O1 4.7(4) ?
C3 C2 C6 O1 -176.5(3) ?
N1 C2 C6 O2 -174.6(2) ?
C3 C2 C6 O2 4.2(4) ?
C2 C3 C7 C8 -97.9(3) ?
C4 C3 C7 C8 78.4(4) ?
C11 O4 C10 O3 4.3(5) ?
C11 O4 C10 C5 -176.4(3) yes
N1 C5 C10 O3 .8(4) yes
C4 C5 C10 O3 -175.9(3) ?
N1 C5 C10 O4 -178.4(2) ?
C4 C5 C10 O4 4.8(4) ?
C10 O4 C11 C12 129.5(3) yes
O4 C11 C12 C13 -118.6(3) ?
O4 C11 C12 C17 60.5(4) ?
C17 C12 C13 C14 .7(4) ?
C11 C12 C13 C14 179.8(3) ?
C12 C13 C14 C15 -1.0(5) ?
C13 C14 C15 C16 .5(5) ?
C14 C15 C16 C17 .4(5) ?
C15 C16 C17 C12 -.7(5) ?
C13 C12 C17 C16 .1(4) ?
C11 C12 C17 C16 -179.0(3) ?
N1 C5 C4 C3 .0(3) ?
C10 C5 C4 C3 177.0(3) ?
N1 C5 C4 C9 179.2(2) ?
C10 C5 C4 C9 -3.8(5) yes
C2 C3 C4 C5 -.1(3) ?
C7 C3 C4 C5 -177.0(2) ?
C2 C3 C4 C9 -179.3(2) ?
C7 C3 C4 C9 3.7(4) yes
