#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/52/2235273.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_2235273
loop_
_publ_author_name
'Cai, Hong-Xin'
'Zhang, Zhao-Po'
_publ_section_title
;
 2-tert-Butyl 4-methyl
 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
;
_journal_coeditor_code           VM2170
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1697
_journal_paper_doi               10.1107/S1600536812020120
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H19 N O4'
_chemical_formula_moiety         'C13 H19 N O4'
_chemical_formula_sum            'C13 H19 N O4'
_chemical_formula_weight         253.29
_chemical_name_systematic
;
2-tert-Butyl 4-methyl 3,5-dimethyl-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                 106.420(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.788(4)
_cell_length_b                   17.045(6)
_cell_length_c                   7.229(2)
_cell_measurement_reflns_used    1135
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.51
_cell_measurement_theta_min      2.99
_cell_volume                     1393.3(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7149
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0705
_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)+(0.1445P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2057
_refine_ls_wR_factor_ref         0.2500
_reflns_number_gt                1334
_reflns_number_total             2458
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            vm2170.cif
_cod_data_source_block           I
_cod_original_cell_volume        1393.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235273
_cod_database_fobs_code          2235273
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 1.1539(4) 0.4652(3) 1.0373(8) 0.1274(19) Uani d . 1 1
H H1B 1.0961 0.5063 1.0193 0.191 Uiso calc R 1 1
H H1C 1.1953 0.4696 0.9409 0.191 Uiso calc R 1 1
H H1D 1.2091 0.4699 1.1630 0.191 Uiso calc R 1 1
C C2 1.1615(3) 0.3246(2) 1.0408(5) 0.0768(11) Uani d . 1 1
C C3 1.0936(3) 0.25230(19) 1.0199(4) 0.0587(9) Uani d . 1 1
C C4 0.9687(3) 0.24090(18) 0.9753(4) 0.0554(8) Uani d . 1 1
C C5 0.9521(2) 0.16057(19) 0.9724(4) 0.0586(9) Uani d . 1 1
C C6 1.1478(3) 0.1795(2) 1.0403(5) 0.0657(9) Uani d . 1 1
C C7 0.8755(3) 0.30226(19) 0.9401(5) 0.0692(10) Uani d . 1 1
H H7A 0.7992 0.2778 0.9138 0.104 Uiso calc R 1 1
H H7B 0.8788 0.3337 0.8315 0.104 Uiso calc R 1 1
H H7C 0.8881 0.3350 1.0521 0.104 Uiso calc R 1 1
C C8 1.2746(3) 0.1548(3) 1.0879(7) 0.0978(14) Uani d . 1 1
H H8A 1.2792 0.0986 1.0897 0.147 Uiso calc R 1 1
H H8B 1.3167 0.1750 1.2123 0.147 Uiso calc R 1 1
H H8C 1.3092 0.1750 0.9923 0.147 Uiso calc R 1 1
C C9 0.8486(3) 0.1108(2) 0.9370(5) 0.0632(9) Uani d . 1 1
C C10 0.6297(3) 0.1201(2) 0.8529(6) 0.0735(11) Uani d . 1 1
C C11 0.6041(4) 0.0676(3) 0.6820(8) 0.131(2) Uani d . 1 1
H H11A 0.6540 0.0222 0.7116 0.197 Uiso calc R 1 1
H H11B 0.6189 0.0952 0.5753 0.197 Uiso calc R 1 1
H H11C 0.5227 0.0517 0.6488 0.197 Uiso calc R 1 1
C C12 0.6181(4) 0.0814(3) 1.0336(7) 0.1063(15) Uani d . 1 1
H H12A 0.6657 0.0348 1.0584 0.159 Uiso calc R 1 1
H H12B 0.5368 0.0677 1.0175 0.159 Uiso calc R 1 1
H H12C 0.6443 0.1169 1.1403 0.159 Uiso calc R 1 1
C C13 0.5522(3) 0.1940(3) 0.8125(8) 0.1084(16) Uani d . 1 1
H H13A 0.5697 0.2261 0.9261 0.163 Uiso calc R 1 1
H H13B 0.4703 0.1790 0.7776 0.163 Uiso calc R 1 1
H H13C 0.5680 0.2229 0.7086 0.163 Uiso calc R 1 1
O O1 1.0949(2) 0.38906(15) 1.0199(4) 0.0925(9) Uani d . 1 1
O O2 1.2657(3) 0.32986(18) 1.0728(6) 0.1295(13) Uani d . 1 1
O O3 0.74888(17) 0.15373(14) 0.8891(3) 0.0713(8) Uani d . 1 1
O O4 0.85058(19) 0.03974(15) 0.9488(4) 0.0876(9) Uani d . 1 1
N N1 1.0615(2) 0.12471(17) 1.0127(4) 0.0674(8) Uani d . 1 1
H H1A 1.0730 0.0748 1.0192 0.081 Uiso calc R 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
O1 C1 H1B 109.5
O1 C1 H1C 109.5
H1B C1 H1C 109.5
O1 C1 H1D 109.5
H1B C1 H1D 109.5
H1C C1 H1D 109.5
O2 C2 O1 120.2(4)
O2 C2 C3 126.4(4)
O1 C2 C3 113.4(3)
C6 C3 C4 108.5(3)
C6 C3 C2 121.7(3)
C4 C3 C2 129.8(3)
C5 C4 C3 105.7(3)
C5 C4 C7 126.9(3)
C3 C4 C7 127.4(3)
N1 C5 C4 108.4(3)
N1 C5 C9 117.9(3)
C4 C5 C9 133.7(3)
N1 C6 C3 107.3(3)
N1 C6 C8 120.0(3)
C3 C6 C8 132.6(3)
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O4 C9 O3 124.0(3)
O4 C9 C5 125.0(3)
O3 C9 C5 111.0(3)
O3 C10 C11 110.0(3)
O3 C10 C12 109.5(3)
C11 C10 C12 114.2(4)
O3 C10 C13 101.7(3)
C11 C10 C13 111.4(4)
C12 C10 C13 109.3(3)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C2 O1 C1 118.1(3)
C9 O3 C10 123.8(3)
C6 N1 C5 110.1(3)
C6 N1 H1A 124.9
C5 N1 H1A 124.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.461(5)
C1 H1B 0.9600
C1 H1C 0.9600
C1 H1D 0.9600
C2 O2 1.188(4)
C2 O1 1.334(4)
C2 C3 1.454(5)
C3 C6 1.385(5)
C3 C4 1.429(4)
C4 C5 1.383(4)
C4 C7 1.486(4)
C5 N1 1.382(4)
C5 C9 1.448(4)
C6 N1 1.354(4)
C6 C8 1.496(5)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 O4 1.215(4)
C9 O3 1.344(4)
C10 O3 1.470(4)
C10 C11 1.486(6)
C10 C12 1.504(6)
C10 C13 1.534(5)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
N1 H1A 0.8600
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 H1A O4 3_757 0.86 2.14 2.974(4) 164.8
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
O2 C2 C3 C6 1.3(6)
O1 C2 C3 C6 -178.8(3)
O2 C2 C3 C4 -177.7(4)
O1 C2 C3 C4 2.2(5)
C6 C3 C4 C5 0.6(4)
C2 C3 C4 C5 179.7(3)
C6 C3 C4 C7 -179.6(3)
C2 C3 C4 C7 -0.6(6)
C3 C4 C5 N1 -0.2(3)
C7 C4 C5 N1 -179.9(3)
C3 C4 C5 C9 180.0(3)
C7 C4 C5 C9 0.2(6)
C4 C3 C6 N1 -0.8(4)
C2 C3 C6 N1 -180.0(3)
C4 C3 C6 C8 -179.3(4)
C2 C3 C6 C8 1.5(6)
N1 C5 C9 O4 3.7(5)
C4 C5 C9 O4 -176.5(4)
N1 C5 C9 O3 -176.4(3)
C4 C5 C9 O3 3.4(5)
O2 C2 O1 C1 0.1(6)
C3 C2 O1 C1 -179.8(3)
O4 C9 O3 C10 2.7(5)
C5 C9 O3 C10 -177.2(3)
C11 C10 O3 C9 -63.7(5)
C12 C10 O3 C9 62.6(4)
C13 C10 O3 C9 178.1(3)
C3 C6 N1 C5 0.7(4)
C8 C6 N1 C5 179.4(3)
C4 C5 N1 C6 -0.4(4)
C9 C5 N1 C6 179.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26515766
