#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215511.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_2215511
loop_
_publ_author_name
'Kang, Si-Shun'
'Wang, Hai-Ying'
'Li, Hai-Lin'
'Zeng, Hai-Su'
'Wang, Hai-Bo'
_publ_section_title
;
 2-tert-Butyl 4-ethyl
 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
;
_journal_coeditor_code           HB2539
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4186
_journal_page_last               o4186
_journal_paper_doi               10.1107/S1600536807047186
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H21 N O4'
_chemical_formula_moiety         'C14 H21 N O4'
_chemical_formula_sum            'C14 H21 N O4'
_chemical_formula_weight         267.32
_chemical_name_systematic
;
2-tert-Butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.46(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.570(4)
_cell_length_b                   7.1420(14)
_cell_length_c                   12.431(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1476.0(7)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1578
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0753
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.05P)²+2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1766
_reflns_number_gt                920
_reflns_number_total             1578
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2539.cif
_cod_data_source_block           I
_cod_original_cell_volume        1476.0(5)
_cod_original_sg_symbol_Hall     '-C 2y '
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2215511
_cod_database_fobs_code          2215511
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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 N1 0.1275(2) 0.0000 0.0227(3) 0.0429(9) Uani d S 1
H H1 0.0763 0.0000 -0.0214 0.051 Uiso calc SR 1
O O1 0.32742(17) 0.0000 -0.0354(3) 0.0565(9) Uani d S 1
O O2 0.39992(18) 0.0000 0.1619(3) 0.0745(12) Uani d S 1
O O3 0.04155(18) 0.0000 0.1558(3) 0.0615(10) Uani d S 1
O O4 0.15571(17) 0.0000 0.3287(2) 0.0527(9) Uani d S 1
C C1 0.3784(3) 0.0000 -0.1789(4) 0.0621(14) Uani d S 1
H H1A 0.4260 0.0000 -0.1911 0.093 Uiso d SR 1
H H1B 0.3471 -0.1098 -0.2152 0.093 Uiso d R 1
C C2 0.4002(2) 0.0000 -0.0504(4) 0.0473(11) Uani d S 1
H H2A 0.4323 -0.1087 -0.0142 0.057 Uiso d R 1
C C3 0.3360(3) 0.0000 0.0753(4) 0.0480(11) Uani d S 1
C C4 0.2571(2) 0.0000 0.0810(4) 0.0449(11) Uani d S 1
C C5 0.2468(2) 0.0000 0.1835(4) 0.0487(11) Uani d S 1
C C6 0.1645(2) 0.0000 0.1481(4) 0.0430(10) Uani d S 1
C C7 0.1821(2) 0.0000 -0.0197(4) 0.0420(10) Uani d S 1
C C8 0.1544(3) 0.0000 -0.1516(4) 0.0532(12) Uani d S 1
H H8A 0.0969 0.0000 -0.1966 0.080 Uiso d SR 1
H H8B 0.1760 0.1098 -0.1712 0.080 Uiso d R 1
C C9 0.3123(3) 0.0000 0.3113(4) 0.0628(14) Uani d S 1
H H9A 0.3645 0.0000 0.3130 0.094 Uiso d SR 1
H H9B 0.3066 0.1098 0.3514 0.094 Uiso d R 1
C C10 0.1142(3) 0.0000 0.2074(4) 0.0475(12) Uani d S 1
C C12 0.0679(2) 0.1808(6) 0.3897(3) 0.0838(13) Uani d . 1
H H12A 0.1018 0.2865 0.3976 0.126 Uiso calc R 1
H H12B 0.0483 0.1882 0.4492 0.126 Uiso calc R 1
H H12C 0.0232 0.1809 0.3110 0.126 Uiso calc R 1
C C13 0.1879(3) 0.0000 0.5340(4) 0.0783(18) Uani d S 1
H H13A 0.2211 -0.1066 0.5408 0.117 Uiso d R 1
H H13C 0.1698 0.0000 0.5952 0.117 Uiso d SR 1
C C11 0.1162(3) 0.0000 0.4075(4) 0.0581(13) Uani d S 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C7 N1 C6 . . 111.0(3)
C7 N1 H1 . . 124.5
C6 N1 H1 . . 124.5
C3 O1 C2 . . 116.8(3)
C10 O4 C11 . . 122.7(3)
C2 C1 H1A . . 110.2
C2 C1 H1B . . 109.1
H1A C1 H1B . . 109.5
O1 C2 C1 . . 108.8(4)
O1 C2 H2A . . 111.2
C1 C2 H2A . . 108.8
O2 C3 O1 . . 123.5(4)
O2 C3 C4 . . 123.8(4)
O1 C3 C4 . . 112.6(4)
C5 C4 C7 . . 109.7(4)
C5 C4 C3 . . 126.0(4)
C7 C4 C3 . . 124.2(4)
C4 C5 C6 . . 107.1(4)
C4 C5 C9 . . 126.7(4)
C6 C5 C9 . . 126.2(4)
N1 C6 C5 . . 106.2(4)
N1 C6 C10 . . 117.9(4)
C5 C6 C10 . . 135.9(4)
N1 C7 C4 . . 105.9(3)
N1 C7 C8 . . 119.1(4)
C4 C7 C8 . . 135.0(4)
C7 C8 H8A . . 113.1
C7 C8 H8B . . 107.7
H8A C8 H8B . . 109.5
C5 C9 H9A . . 110.8
C5 C9 H9B . . 108.8
H9A C9 H9B . . 109.5
O3 C10 O4 . . 122.6(4)
O3 C10 C6 . . 124.0(4)
O4 C10 C6 . . 113.4(4)
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
C11 C13 H13A . . 108.6
C11 C13 H13C . . 111.1
H13A C13 H13C . . 111.7
O4 C11 C12 . 6 109.8(3)
O4 C11 C12 . . 109.8(3)
C12 C11 C12 6 . 115.0(4)
O4 C11 C13 . . 102.7(4)
C12 C11 C13 6 . 109.4(3)
C12 C11 C13 . . 109.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C7 . 1.335(5)
N1 C6 . 1.395(5)
N1 H1 . 0.8600
O1 C3 . 1.312(5)
O1 C2 . 1.444(5)
O2 C3 . 1.195(5)
O3 C10 . 1.208(5)
O4 C10 . 1.353(5)
O4 C11 . 1.463(5)
C1 C2 . 1.464(6)
C1 H1A . 0.9600
C1 H1B . 0.9601
C2 H2A . 0.9600
C3 C4 . 1.500(6)
C4 C5 . 1.370(6)
C4 C7 . 1.397(5)
C5 C6 . 1.389(6)
C5 C9 . 1.511(6)
C6 C10 . 1.425(6)
C7 C8 . 1.483(5)
C8 H8A . 0.9601
C8 H8B . 0.9600
C9 H9A . 0.9600
C9 H9B . 0.9600
C12 C11 . 1.531(5)
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 C11 . 1.542(6)
C13 H13A . 0.9601
C13 H13C . 0.9589
C11 C12 6 1.531(5)
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 2_555 0.86 2.08 2.928(5) 169
C9 H9A O2 . 0.96 2.25 2.965(7) 131
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_site_symmetry_4
_geom_torsion
C3 O1 C2 C1 . 180.0
C2 O1 C3 O2 . 0.0
C2 O1 C3 C4 . 180.0
O2 C3 C4 C5 . 0.0
O1 C3 C4 C5 . 180.0
O2 C3 C4 C7 . 180.0
O1 C3 C4 C7 . 0.0
C7 C4 C5 C6 . 0.0
C3 C4 C5 C6 . 180.0
C7 C4 C5 C9 . 180.0
C3 C4 C5 C9 . 0.0
C7 N1 C6 C5 . 0.0
C7 N1 C6 C10 . 180.0
C4 C5 C6 N1 . 0.0
C9 C5 C6 N1 . 180.0
C4 C5 C6 C10 . 180.0
C9 C5 C6 C10 . 0.0
C6 N1 C7 C4 . 0.0
C6 N1 C7 C8 . 180.0
C5 C4 C7 N1 . 0.0
C3 C4 C7 N1 . 180.0
C5 C4 C7 C8 . 180.0
C3 C4 C7 C8 . 0.0
C11 O4 C10 O3 . 0.0
C11 O4 C10 C6 . 180.0
N1 C6 C10 O3 . 0.0
C5 C6 C10 O3 . 180.0
N1 C6 C10 O4 . 180.0
C5 C6 C10 O4 . 0.0
C10 O4 C11 C12 6 63.7(3)
C10 O4 C11 C12 . -63.7(3)
C10 O4 C11 C13 . 180.0
