#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/12/2231253.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_2231253
loop_
_publ_author_name
'Lu, Gui-Fen'
'Lin, Wen-Sheng'
'Zhu, Wei-Hua'
'Ou, Zhong-Ping'
_publ_section_title
;
 Dimethyl 3,5-diethyl-1H-pyrrole-2,4-dicarboxylate
;
_journal_coeditor_code           PK2335
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2097
_journal_paper_doi               10.1107/S1600536811028352
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H17 N O4'
_chemical_formula_moiety         'C12 H17 N O4'
_chemical_formula_sum            'C12 H17 N O4'
_chemical_formula_weight         239.27
_chemical_name_common            2,4-Dimethoxycarbonyl-3,5-diethylpyrrole
_chemical_name_systematic
;
Dimethyl 3,5-diethyl-1H-pyrrole-2,4-dicarboxylate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.467(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4697(7)
_cell_length_b                   14.616(2)
_cell_length_c                   19.784(3)
_cell_measurement_reflns_used    3745
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.79
_cell_volume                     1292.4(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6296
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.157
_refine_ls_extinction_coef       0.110(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.1775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                1977
_reflns_number_total             2285
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2335.cif
_cod_data_source_block           I
_cod_original_cell_volume        1292.4(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231253
_cod_database_fobs_code          2231253
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_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
_atom_site_symmetry_multiplicity
C C1 1.0716(4) -0.06793(13) 0.67868(10) 0.0771(5) Uani d . 1 1
H H1A 1.1839 -0.0662 0.7202 0.116 Uiso calc R 1 1
H H1B 1.2038 -0.0808 0.6419 0.116 Uiso calc R 1 1
H H1C 0.9220 -0.1149 0.6812 0.116 Uiso calc R 1 1
C C2 0.7645(3) 0.02789(10) 0.61180(6) 0.0485(4) Uani d . 1 1
C C3 0.6201(3) 0.11655(9) 0.60495(6) 0.0429(3) Uani d . 1 1
C C4 0.6275(3) 0.19623(9) 0.64214(6) 0.0428(3) Uani d . 1 1
C C5 0.4354(3) 0.25896(9) 0.60761(6) 0.0440(3) Uani d . 1 1
C C6 0.3161(3) 0.21461(9) 0.55064(6) 0.0422(3) Uani d . 1 1
C C7 0.1103(3) 0.24441(10) 0.49502(7) 0.0504(4) Uani d . 1 1
H H7A -0.0305 0.2888 0.5126 0.060 Uiso calc R 1 1
H H7B -0.0030 0.1920 0.4789 0.060 Uiso calc R 1 1
C C8 0.2772(4) 0.28646(14) 0.43641(8) 0.0753(5) Uani d . 1 1
H H8A 0.1370 0.3043 0.4018 0.113 Uiso calc R 1 1
H H8B 0.4146 0.2425 0.4184 0.113 Uiso calc R 1 1
H H8C 0.3857 0.3393 0.4519 0.113 Uiso calc R 1 1
C C9 0.3744(3) 0.35270(11) 0.62967(7) 0.0548(4) Uani d . 1 1
C C10 0.1230(6) 0.49089(14) 0.60468(13) 0.1063(8) Uani d . 1 1
H H10A 0.0056 0.5182 0.5692 0.159 Uiso calc R 1 1
H H10B 0.2992 0.5270 0.6126 0.159 Uiso calc R 1 1
H H10C 0.0071 0.4882 0.6453 0.159 Uiso calc R 1 1
C C11 0.8015(3) 0.21297(11) 0.70625(7) 0.0530(4) Uani d . 1 1
H H11A 0.8638 0.2765 0.7077 0.064 Uiso calc R 1 1
H H11B 0.9803 0.1754 0.7062 0.064 Uiso calc R 1 1
C C12 0.6215(4) 0.19160(16) 0.76897(8) 0.0802(6) Uani d . 1 1
H H12A 0.7415 0.2033 0.8085 0.120 Uiso calc R 1 1
H H12B 0.5628 0.1284 0.7683 0.120 Uiso calc R 1 1
H H12C 0.4463 0.2296 0.7698 0.120 Uiso calc R 1 1
N N1 0.4307(2) 0.12986(7) 0.55029(5) 0.0439(3) Uani d D 1 1
H H1N 0.3918 0.0897 0.5207 0.053 Uiso d RD 1 1
O O1 0.2088(3) 0.39946(8) 0.58509(7) 0.0858(4) Uani d . 1 1
O O2 0.4557(3) 0.38626(9) 0.68180(7) 0.0867(4) Uani d . 1 1
O O3 0.9285(3) 0.01959(7) 0.66768(5) 0.0619(3) Uani d . 1 1
O O4 0.7364(3) -0.03336(7) 0.57103(5) 0.0725(4) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O3 C1 H1A 109.5
O3 C1 H1B 109.5
H1A C1 H1B 109.5
O3 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O4 C2 O3 122.75(13)
O4 C2 C3 123.61(12)
O3 C2 C3 113.64(12)
C4 C3 N1 108.11(12)
C4 C3 C2 134.03(12)
N1 C3 C2 117.86(11)
C3 C4 C5 106.00(11)
C3 C4 C11 126.77(13)
C5 C4 C11 127.23(12)
C6 C5 C4 108.15(12)
C6 C5 C9 127.00(13)
C4 C5 C9 124.85(12)
N1 C6 C5 106.78(11)
N1 C6 C7 119.92(12)
C5 C6 C7 133.28(13)
C6 C7 C8 112.23(12)
C6 C7 H7A 109.2
C8 C7 H7A 109.2
C6 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
O2 C9 O1 121.51(15)
O2 C9 C5 125.79(15)
O1 C9 C5 112.69(13)
O1 C10 H10A 109.5
O1 C10 H10B 109.5
H10A C10 H10B 109.5
O1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C4 C11 C12 112.50(12)
C4 C11 H11A 109.1
C12 C11 H11A 109.1
C4 C11 H11B 109.1
C12 C11 H11B 109.1
H11A C11 H11B 107.8
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C6 N1 C3 110.97(11)
C6 N1 H1N 124.6
C3 N1 H1N 124.4
C9 O1 C10 116.33(15)
C2 O3 C1 116.55(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O3 1.446(2)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 O4 1.2109(17)
C2 O3 1.3270(16)
C2 C3 1.453(2)
C3 C4 1.3779(19)
C3 N1 1.3816(16)
C4 C5 1.4266(19)
C4 C11 1.5024(18)
C5 C6 1.4017(17)
C5 C9 1.464(2)
C6 N1 1.3404(17)
C6 C7 1.4935(18)
C7 C8 1.514(2)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 O2 1.1959(18)
C9 O1 1.335(2)
C10 O1 1.444(2)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.517(2)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
N1 H1N 0.8457
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 H1N O4 3_656 0.85 2.07 2.8773(15) 159.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656869
