#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/30/2013081.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_2013081
loop_
_publ_author_name
'Paixão, José António'
'Ramos Silva, Manuela'
'Matos Beja, Ana'
'Sobral, Abílio J. F. N.'
'Lopes, Susana H.'
'Rocha Gonsalves, A. M. d'A.'
_publ_section_title
;
 Ethyl 3,5-dimethyl-4-phenyl-1H-pyrrole-2-carboxylate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o721
_journal_page_last               o723
_journal_paper_doi               10.1107/S0108270102020656
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C15 H17 N O2'
_chemical_formula_sum            'C15 H17 N O2'
_chemical_formula_weight         243.30
_chemical_name_systematic
;
Ethyl 3,5-dimethyl-4-phenyl-1H-pyrrole-2-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 102.887(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3160(13)
_cell_length_b                   6.744(2)
_cell_length_c                   18.4091(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      13.31
_cell_volume                     1369.5(5)
_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 0.960
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Enraf-Nonius MACH3'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_sigmaI/netI    0.019
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5053
_diffrn_reflns_theta_full        72.32
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         4.00
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.062
_refine_ls_R_factor_gt           0.054
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0953P)²+0.3261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.158
_refine_ls_wR_factor_ref         0.169
_reflns_number_gt                2215
_reflns_number_total             2606
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln1155.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013081
_cod_database_fobs_code          2013081
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
O1 0.08411(13) 0.7753(2) 0.01941(7) 0.0628(4) Uani d . 1 . . O
N1 0.07943(13) 1.0948(2) 0.11493(8) 0.0480(4) Uani d . 1 . . N
H1 0.026(2) 1.109(4) 0.0729(14) 0.074(7) Uiso d . 1 . . H
O2 0.24911(13) 0.6564(2) 0.09765(7) 0.0655(4) Uani d . 1 . . O
C2 0.16045(14) 0.9405(3) 0.13282(9) 0.0459(4) Uani d . 1 . . C
C6 0.15884(16) 0.7862(3) 0.07809(9) 0.0487(4) Uani d . 1 . . C
C3 0.23092(14) 0.9768(3) 0.20347(9) 0.0466(4) Uani d . 1 . . C
C4 0.19098(14) 1.1596(3) 0.22732(9) 0.0450(4) Uani d . 1 . . C
C5 0.09618(14) 1.2275(3) 0.17099(9) 0.0467(4) Uani d . 1 . . C
C10 0.24644(15) 1.2691(3) 0.29571(9) 0.0476(4) Uani d . 1 . . C
C9 0.3244(2) 0.8422(3) 0.24883(11) 0.0649(6) Uani d . 1 . . C
H9A 0.3081 0.7079 0.2323 0.097 Uiso calc R 1 . . H
H9B 0.3215 0.8522 0.3004 0.097 Uiso calc R 1 . . H
H9C 0.4034 0.8802 0.2428 0.097 Uiso calc R 1 . . H
C16 0.02067(19) 1.4105(3) 0.16556(12) 0.0627(5) Uani d . 1 . . C
H16A -0.0030 1.4514 0.1144 0.094 Uiso calc R 1 . . H
H16B 0.0668 1.5142 0.1945 0.094 Uiso calc R 1 . . H
H16C -0.0504 1.3836 0.1843 0.094 Uiso calc R 1 . . H
C11 0.17869(18) 1.3577(3) 0.34084(11) 0.0628(5) Uani d . 1 . . C
H11 0.0950 1.3409 0.3301 0.075 Uiso calc R 1 . . H
C15 0.37183(16) 1.2952(3) 0.31516(11) 0.0587(5) Uani d . 1 . . C
H15 0.4198 1.2357 0.2864 0.070 Uiso calc R 1 . . H
C14 0.42634(19) 1.4074(4) 0.37624(12) 0.0684(6) Uani d . 1 . . C
H14 0.5101 1.4232 0.3880 0.082 Uiso calc R 1 . . H
C13 0.3578(2) 1.4948(4) 0.41925(12) 0.0742(7) Uani d . 1 . . C
H13 0.3944 1.5704 0.4604 0.089 Uiso calc R 1 . . H
C12 0.2339(2) 1.4706(4) 0.40152(12) 0.0762(7) Uani d . 1 . . C
H12 0.1868 1.5309 0.4307 0.091 Uiso calc R 1 . . H
C7 0.2565(2) 0.4987(4) 0.04539(13) 0.0735(6) Uani d . 1 . . C
H7A 0.2629 0.5537 -0.0023 0.088 Uiso calc R 1 . . H
H7B 0.1846 0.4161 0.0377 0.088 Uiso calc R 1 . . H
C8 0.3634(3) 0.3826(5) 0.0771(2) 0.1202(12) Uani d . 1 . . C
H8A 0.4338 0.4662 0.0848 0.180 Uiso calc R 1 . . H
H8B 0.3717 0.2773 0.0435 0.180 Uiso calc R 1 . . H
H8C 0.3555 0.3276 0.1238 0.180 Uiso calc R 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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'
N N 0.0311 0.0180 '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 110.27(14) yes
C5 N1 H1 123.5(17) ?
C2 N1 H1 126.2(17) ?
C6 O2 C7 117.20(15) ?
N1 C2 C3 107.67(15) yes
N1 C2 C6 118.22(15) ?
C3 C2 C6 134.08(16) ?
O1 C6 O2 122.66(17) ?
O1 C6 C2 124.09(16) ?
O2 C6 C2 113.24(14) ?
C2 C3 C4 106.73(15) yes
C2 C3 C9 127.02(17) ?
C4 C3 C9 126.08(16) ?
C5 C4 C3 107.56(15) yes
C5 C4 C10 125.57(16) ?
C3 C4 C10 126.62(15) ?
N1 C5 C4 107.76(15) yes
N1 C5 C16 121.19(15) ?
C4 C5 C16 131.05(17) ?
C11 C10 C15 117.31(17) ?
C11 C10 C4 122.77(16) ?
C15 C10 C4 119.84(16) ?
C3 C9 H9A 109.5 ?
C3 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C3 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C5 C16 H16A 109.5 ?
C5 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C5 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C12 C11 C10 120.81(19) ?
C12 C11 H11 119.6 ?
C10 C11 H11 119.6 ?
C14 C15 C10 121.47(19) ?
C14 C15 H15 119.3 ?
C10 C15 H15 119.3 ?
C13 C14 C15 120.13(19) ?
C13 C14 H14 119.9 ?
C15 C14 H14 119.9 ?
C14 C13 C12 119.6(2) ?
C14 C13 H13 120.2 ?
C12 C13 H13 120.2 ?
C13 C12 C11 120.7(2) ?
C13 C12 H12 119.7 ?
C11 C12 H12 119.7 ?
O2 C7 C8 107.2(2) ?
O2 C7 H7A 110.3 ?
C8 C7 H7A 110.3 ?
O2 C7 H7B 110.3 ?
C8 C7 H7B 110.3 ?
H7A C7 H7B 108.5 ?
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 ?
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
O1 C6 . 1.216(2) yes
N1 C5 . 1.347(2) ?
N1 C2 . 1.377(2) ?
N1 H1 . 0.88(3) ?
O2 C6 . 1.332(2) yes
O2 C7 . 1.449(2) ?
C2 C3 . 1.387(2) yes
C2 C6 . 1.446(2) ?
C3 C4 . 1.416(3) yes
C3 C9 . 1.498(2) ?
C4 C5 . 1.393(2) yes
C4 C10 . 1.474(2) ?
C5 C16 . 1.491(3) ?
C10 C11 . 1.385(3) ?
C10 C15 . 1.395(2) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C11 C12 . 1.380(3) ?
C11 H11 . 0.9300 ?
C15 C14 . 1.382(3) ?
C15 H15 . 0.9300 ?
C14 C13 . 1.360(3) ?
C14 H14 . 0.9300 ?
C13 C12 . 1.377(3) ?
C13 H13 . 0.9300 ?
C12 H12 . 0.9300 ?
C7 C8 . 1.450(4) yes
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
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 O1 3_575 0.88(3) 2.02(3) 2.875(2) 164(2)
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
C5 N1 C2 C3 0.40(19)
C5 N1 C2 C6 -177.95(15)
C7 O2 C6 O1 0.5(3)
C7 O2 C6 C2 -178.64(17)
N1 C2 C6 O1 -6.1(3)
C3 C2 C6 O1 176.09(19)
N1 C2 C6 O2 173.02(15)
C3 C2 C6 O2 -4.8(3)
N1 C2 C3 C4 -0.80(19)
C6 C2 C3 C4 177.18(18)
N1 C2 C3 C9 174.65(18)
C6 C2 C3 C9 -7.4(3)
C2 C3 C4 C5 0.91(19)
C9 C3 C4 C5 -174.60(18)
C2 C3 C4 C10 -173.60(16)
C9 C3 C4 C10 10.9(3)
C2 N1 C5 C4 0.18(19)
C2 N1 C5 C16 179.43(16)
C3 C4 C5 N1 -0.67(19)
C10 C4 C5 N1 173.91(15)
C3 C4 C5 C16 -179.82(19)
C10 C4 C5 C16 -5.2(3)
C5 C4 C10 C11 49.1(3)
C3 C4 C10 C11 -137.3(2)
C5 C4 C10 C15 -127.6(2)
C3 C4 C10 C15 45.9(3)
C15 C10 C11 C12 1.4(3)
C4 C10 C11 C12 -175.4(2)
C11 C10 C15 C14 -1.0(3)
C4 C10 C15 C14 175.90(19)
C10 C15 C14 C13 0.3(4)
C15 C14 C13 C12 0.0(4)
C14 C13 C12 C11 0.4(4)
C10 C11 C12 C13 -1.1(4)
C6 O2 C7 C8 177.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4407496
