#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/17/8101773.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101773
loop_
_publ_author_name
'Ramos Silva, M.'
'Matos Beja, A.'
'Paixão, J. A.'
'Cabral, A. M. T. D. V.'
'Barradas, F. I. F.'
'Paliteiro, C.'
'Sobral, A. J. F. N.'
_publ_section_title
;
Crystal structure of 2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrole, 
C₂₄H₂₄N₄O₄
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              273
_journal_page_last               274
_journal_volume                  220
_journal_year                    2005
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.13
_chemical_name_systematic
; 
 2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrole
;
_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                 104.26(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.660(6)
_cell_length_b                   13.8928(13)
_cell_length_c                   13.448(8)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.27
_cell_measurement_theta_min      4.69
_cell_volume                     2292.4(18)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    PLATON
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Enraf-Nonius Mach3'
_diffrn_measurement_method       'ω-2θ, profile fit'
_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  0.0907
_diffrn_reflns_av_sigmaI/netI    0.4631
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4419
_diffrn_reflns_theta_full        25.47
_diffrn_reflns_theta_max         25.47
_diffrn_reflns_theta_min         2.93
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.3948
_refine_ls_R_factor_gt           0.0747
_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)+(0.0693P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1994
_reflns_number_gt                1108
_reflns_number_total             4227
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1524.cff
_cod_data_source_block           fib
_cod_original_cell_volume        2292.3(17)
_cod_original_sg_symbol_H-M      'P 1 2(1)/c 1'
_cod_database_code               8101773
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3712(3) 0.2589(4) 0.2079(3) 0.0533(13) Uani 1 4 e d . . .
C10 C 0.5828(5) 0.3789(4) 0.0495(5) 0.0605(17) Uani 1 4 e d . . .
C12 C 0.5392(5) 0.3411(4) 0.2058(4) 0.0680(17) Uani 1 4 e d . . .
H12 H 0.5574 0.3411 0.2772 0.082 Uiso 1 4 e calc R . .
C3 C 0.2741(4) 0.1508(5) 0.2644(4) 0.0649(18) Uani 1 4 e d . . .
H3 H 0.2435 0.0930 0.2780 0.078 Uiso 1 4 e calc R . .
C9 C 0.4879(6) 0.3400(5) -0.0042(5) 0.0758(19) Uani 1 4 e d . . .
H9 H 0.4711 0.3390 -0.0755 0.091 Uiso 1 4 e calc R . .
O1 O 0.6371(5) 0.4082(5) -0.0984(5) 0.145(3) Uani 1 4 e d . . .
C11 C 0.6097(5) 0.3806(4) 0.1539(5) 0.0740(19) Uani 1 4 e d . . .
H11 H 0.6750 0.4082 0.1897 0.089 Uiso 1 4 e calc R . .
C8 C 0.4161(4) 0.3018(5) 0.0476(4) 0.0716(19) Uani 1 4 e d . . .
H8 H 0.3500 0.2762 0.0112 0.086 Uiso 1 4 e calc R . .
C2 C 0.2523(4) 0.2422(5) 0.3002(4) 0.0604(17) Uani 1 4 e d . . .
H2 H 0.2050 0.2548 0.3417 0.072 Uiso 1 4 e calc R . .
C4 C 0.3478(4) 0.1617(5) 0.2065(4) 0.0538(16) Uani 1 4 e d . . .
C1 C 0.3116(5) 0.3081(5) 0.2642(4) 0.0596(17) Uani 1 4 e d . . .
O2 O 0.7445(5) 0.4483(5) 0.0426(5) 0.145(3) Uani 1 4 e d . . .
N2 N 0.6604(6) 0.4150(5) -0.0063(6) 0.093(2) Uani 1 4 e d . . .
C5 C 0.3995(5) 0.0907(4) 0.1519(5) 0.089(2) Uani 1 4 e d . . .
H5A H 0.3775 0.1029 0.0795 0.134 Uiso 1 4 e calc R . .
H5B H 0.3773 0.0270 0.1657 0.134 Uiso 1 4 e calc R . .
H5C H 0.4773 0.0959 0.1751 0.134 Uiso 1 4 e calc R . .
C7 C 0.4424(4) 0.3017(4) 0.1530(4) 0.0497(15) Uani 1 4 e d . . .
C6 C 0.3184(5) 0.4126(5) 0.2803(5) 0.103(3) Uani 1 4 e d . . .
H6A H 0.2668 0.4321 0.3180 0.154 Uiso 1 4 e calc R . .
H6B H 0.3023 0.4447 0.2150 0.154 Uiso 1 4 e calc R . .
H6C H 0.3907 0.4295 0.3182 0.154 Uiso 1 4 e calc R . .
O3 O 0.3863(4) 0.6027(4) 0.4819(4) 0.1121(19) Uani 1 4 e d . . .
N4 N 0.2991(5) 0.6325(4) 0.4886(5) 0.0805(18) Uani 1 4 e d . . .
C18 C -0.0374(5) 0.6142(5) 0.0455(5) 0.097(2) Uani 1 4 e d . . .
H18A H -0.0920 0.5896 -0.0115 0.145 Uiso 1 4 e calc R . .
H18B H -0.0462 0.5855 0.1078 0.145 Uiso 1 4 e calc R . .
H18C H 0.0336 0.5989 0.0364 0.145 Uiso 1 4 e calc R . .
C22 C 0.2230(5) 0.6661(4) 0.3934(5) 0.0530(16) Uani 1 4 e d . . .
C19 C 0.0833(5) 0.7351(4) 0.2231(4) 0.0469(15) Uani 1 4 e d . . .
C14 C -0.1125(5) 0.7841(6) -0.0132(4) 0.0691(19) Uani 1 4 e d . . .
H14 H -0.1608 0.7687 -0.0753 0.083 Uiso 1 4 e calc R . .
C13 C -0.0490(5) 0.7210(5) 0.0512(5) 0.0583(17) Uani 1 4 e d . . .
C17 C 0.0328(6) 0.9461(4) 0.1943(5) 0.105(2) Uani 1 4 e d . . .
H17A H 0.1106 0.9418 0.2065 0.157 Uiso 1 4 e calc R . .
H17B H 0.0121 0.9374 0.2577 0.157 Uiso 1 4 e calc R . .
H17C H 0.0089 1.0082 0.1663 0.157 Uiso 1 4 e calc R . .
C21 C 0.1253(5) 0.7009(4) 0.4010(4) 0.0665(18) Uani 1 4 e d . . .
H21 H 0.1069 0.7014 0.4639 0.080 Uiso 1 4 e calc R . .
C24 C 0.1808(5) 0.6983(4) 0.2170(4) 0.0659(18) Uani 1 4 e d . . .
H24 H 0.1990 0.6968 0.1541 0.079 Uiso 1 4 e calc R . .
N3 N 0.0100(4) 0.7737(4) 0.1335(3) 0.0529(13) Uani 1 4 e d . . .
C16 C -0.0188(5) 0.8699(5) 0.1203(5) 0.0645(18) Uani 1 4 e d . . .
C23 C 0.2525(5) 0.6635(4) 0.3027(5) 0.0712(19) Uani 1 4 e d . . .
H23 H 0.3197 0.6387 0.2991 0.085 Uiso 1 4 e calc R . .
C20 C 0.0536(4) 0.7356(4) 0.3139(4) 0.0692(19) Uani 1 4 e d . . .
H20 H -0.0143 0.7591 0.3171 0.083 Uiso 1 4 e calc R . .
O4 O 0.2716(4) 0.6345(4) 0.5676(4) 0.122(2) Uani 1 4 e d . . .
C15 C -0.0933(5) 0.8769(5) 0.0291(6) 0.073(2) Uani 1 4 e d . . .
H15 H -0.1262 0.9334 -0.0005 0.088 Uiso 1 4 e calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 110.4(5) . . ?
C1 N1 C7 125.4(5) . . ?
C4 N1 C7 124.1(5) . . ?
C9 C10 C11 121.5(6) . . ?
C9 C10 N2 118.8(7) . . ?
C11 C10 N2 119.6(7) . . ?
C7 C12 C11 120.4(6) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C4 C3 C2 108.3(5) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C10 C9 C8 119.5(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C10 C11 C12 119.2(6) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C1 C2 C3 108.4(5) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
C3 C4 N1 106.0(5) . . ?
C3 C4 C5 131.3(6) . . ?
N1 C4 C5 122.7(5) . . ?
C2 C1 N1 106.9(6) . . ?
C2 C1 C6 129.6(6) . . ?
N1 C1 C6 123.5(6) . . ?
O2 N2 O1 123.6(8) . . ?
O2 N2 C10 117.9(8) . . ?
O1 N2 C10 118.4(8) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 C7 C8 119.5(5) . . ?
C12 C7 N1 119.8(5) . . ?
C8 C7 N1 120.7(5) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 N4 O3 123.2(7) . . ?
O4 N4 C22 119.5(6) . . ?
O3 N4 C22 117.3(7) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C22 C23 122.3(6) . . ?
C21 C22 N4 117.4(6) . . ?
C23 C22 N4 120.3(6) . . ?
C24 C19 C20 120.7(5) . . ?
C24 C19 N3 120.1(5) . . ?
C20 C19 N3 119.2(5) . . ?
C13 C14 C15 108.6(6) . . ?
C13 C14 H14 125.7 . . ?
C15 C14 H14 125.7 . . ?
C14 C13 N3 106.8(6) . . ?
C14 C13 C18 131.4(7) . . ?
N3 C13 C18 121.8(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 C20 118.8(5) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C19 C24 C23 120.5(5) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C13 N3 C16 109.6(6) . . ?
C13 N3 C19 125.8(5) . . ?
C16 N3 C19 124.4(5) . . ?
C15 C16 N3 106.8(6) . . ?
C15 C16 C17 130.3(7) . . ?
N3 C16 C17 122.8(6) . . ?
C22 C23 C24 118.3(5) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C19 C20 C21 119.3(5) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C15 C14 108.2(6) . . ?
C16 C15 H15 125.9 . . ?
C14 C15 H15 125.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.375(6) . ?
N1 C4 1.381(7) . ?
N1 C7 1.428(6) . ?
C10 C9 1.353(7) . ?
C10 C11 1.360(7) . ?
C10 N2 1.464(8) . ?
C12 C7 1.371(7) . ?
C12 C11 1.376(7) . ?
C12 H12 0.9300 . ?
C3 C4 1.363(6) . ?
C3 C2 1.408(7) . ?
C3 H3 0.9300 . ?
C9 C8 1.380(7) . ?
C9 H9 0.9300 . ?
O1 N2 1.204(7) . ?
C11 H11 0.9300 . ?
C8 C7 1.373(6) . ?
C8 H8 0.9300 . ?
C2 C1 1.347(7) . ?
C2 H2 0.9300 . ?
C4 C5 1.476(7) . ?
C1 C6 1.468(8) . ?
O2 N2 1.198(7) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
O3 N4 1.203(6) . ?
N4 O4 1.197(6) . ?
N4 C22 1.476(7) . ?
C18 C13 1.494(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C22 C21 1.355(6) . ?
C22 C23 1.361(7) . ?
C19 C24 1.357(6) . ?
C19 C20 1.363(6) . ?
C19 N3 1.431(6) . ?
C14 C13 1.350(7) . ?
C14 C15 1.406(8) . ?
C14 H14 0.9300 . ?
C13 N3 1.383(6) . ?
C17 C16 1.489(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 C20 1.381(7) . ?
C21 H21 0.9300 . ?
C24 C23 1.368(7) . ?
C24 H24 0.9300 . ?
N3 C16 1.384(7) . ?
C16 C15 1.354(7) . ?
C23 H23 0.9300 . ?
C20 H20 0.9300 . ?
C15 H15 0.9300 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C10 C9 C8 0.5(10) . . . . ?
N2 C10 C9 C8 177.1(6) . . . . ?
C9 C10 C11 C12 0.6(10) . . . . ?
N2 C10 C11 C12 -176.0(5) . . . . ?
C7 C12 C11 C10 -0.9(9) . . . . ?
C10 C9 C8 C7 -1.4(9) . . . . ?
C4 C3 C2 C1 0.3(7) . . . . ?
C2 C3 C4 N1 0.5(6) . . . . ?
C2 C3 C4 C5 179.3(6) . . . . ?
C1 N1 C4 C3 -1.1(6) . . . . ?
C7 N1 C4 C3 -177.6(5) . . . . ?
C1 N1 C4 C5 180.0(5) . . . . ?
C7 N1 C4 C5 3.5(8) . . . . ?
C3 C2 C1 N1 -0.9(6) . . . . ?
C3 C2 C1 C6 -179.4(6) . . . . ?
C4 N1 C1 C2 1.3(6) . . . . ?
C7 N1 C1 C2 177.7(5) . . . . ?
C4 N1 C1 C6 179.8(5) . . . . ?
C7 N1 C1 C6 -3.7(9) . . . . ?
C9 C10 N2 O2 -179.3(7) . . . . ?
C11 C10 N2 O2 -2.6(10) . . . . ?
C9 C10 N2 O1 -0.4(10) . . . . ?
C11 C10 N2 O1 176.3(7) . . . . ?
C11 C12 C7 C8 0.1(8) . . . . ?
C11 C12 C7 N1 178.5(5) . . . . ?
C9 C8 C7 C12 1.1(9) . . . . ?
C9 C8 C7 N1 -177.3(5) . . . . ?
C1 N1 C7 C12 71.1(7) . . . . ?
C4 N1 C7 C12 -112.9(6) . . . . ?
C1 N1 C7 C8 -110.5(6) . . . . ?
C4 N1 C7 C8 65.5(7) . . . . ?
O4 N4 C22 C21 2.0(9) . . . . ?
O3 N4 C22 C21 -179.1(6) . . . . ?
O4 N4 C22 C23 -179.4(6) . . . . ?
O3 N4 C22 C23 -0.5(9) . . . . ?
C15 C14 C13 N3 -0.2(6) . . . . ?
C15 C14 C13 C18 179.1(6) . . . . ?
C23 C22 C21 C20 -0.5(9) . . . . ?
N4 C22 C21 C20 178.0(5) . . . . ?
C20 C19 C24 C23 -1.9(9) . . . . ?
N3 C19 C24 C23 178.4(5) . . . . ?
C14 C13 N3 C16 1.0(6) . . . . ?
C18 C13 N3 C16 -178.4(5) . . . . ?
C14 C13 N3 C19 176.3(5) . . . . ?
C18 C13 N3 C19 -3.0(8) . . . . ?
C24 C19 N3 C13 71.6(7) . . . . ?
C20 C19 N3 C13 -108.2(6) . . . . ?
C24 C19 N3 C16 -113.7(6) . . . . ?
C20 C19 N3 C16 66.5(7) . . . . ?
C13 N3 C16 C15 -1.5(6) . . . . ?
C19 N3 C16 C15 -176.9(5) . . . . ?
C13 N3 C16 C17 -178.0(5) . . . . ?
C19 N3 C16 C17 6.6(9) . . . . ?
C21 C22 C23 C24 0.7(9) . . . . ?
N4 C22 C23 C24 -177.9(5) . . . . ?
C19 C24 C23 C22 0.6(9) . . . . ?
C24 C19 C20 C21 2.0(9) . . . . ?
N3 C19 C20 C21 -178.2(5) . . . . ?
C22 C21 C20 C19 -0.8(9) . . . . ?
N3 C16 C15 C14 1.3(7) . . . . ?
C17 C16 C15 C14 177.5(6) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 404016
