#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/61/2216182.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_2216182
loop_
_publ_author_name
'Santos, Ana C.'
'Marques, Ana T.'
'Ramos Silva, Manuela'
'Matos Beja, Ana'
'Sobral, Abilio J.F.N.'
_publ_section_title
;
 1-(4-Acetylphenyl)-2,5-dimethyl-1H-pyrrole
;
_journal_coeditor_code           ZL2069
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4233
_journal_page_last               o4233
_journal_paper_doi               10.1107/S1600536807047800
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H15 N O'
_chemical_formula_moiety         'C14 H15 N O'
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27
_chemical_name_systematic
;
1-(4-Acetylphenyl)-2,5-dimethyl-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                 100.043(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9476(13)
_cell_length_b                   7.4005(6)
_cell_length_c                   14.8518(14)
_cell_measurement_reflns_used    1357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.17
_cell_measurement_theta_min      2.79
_cell_volume                     1184.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX 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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8847
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0463
_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)+(0.0559P)²+0.009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                1461
_reflns_number_total             2945
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2069.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216182
_cod_database_fobs_code          2216182
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
O O1 0.02792(13) -0.15368(19) 0.36051(9) 0.0795(4) Uani d . 1
N N1 0.31347(12) 0.52600(19) 0.56347(9) 0.0533(4) Uani d . 1
C C1 0.37686(15) 0.6603(2) 0.52528(12) 0.0557(5) Uani d . 1
C C2 0.43942(17) 0.7583(3) 0.59568(13) 0.0686(5) Uani d . 1
H H2 0.4906 0.8567 0.5905 0.082 Uiso calc R 1
C C3 0.41374(17) 0.6856(3) 0.67830(13) 0.0709(6) Uani d . 1
H H3 0.4447 0.7284 0.7367 0.085 Uiso calc R 1
C C4 0.33637(16) 0.5430(3) 0.65807(12) 0.0598(5) Uani d . 1
C C5 0.37593(17) 0.6748(3) 0.42511(12) 0.0690(5) Uani d . 1
H H5A 0.4332 0.7669 0.4139 0.103 Uiso calc R 1
H H5B 0.2940 0.7057 0.3945 0.103 Uiso calc R 1
H H5C 0.4000 0.5612 0.4024 0.103 Uiso calc R 1
C C6 0.27643(18) 0.4236(3) 0.71888(13) 0.0768(6) Uani d . 1
H H6A 0.3174 0.3084 0.7248 0.115 Uiso calc R 1
H H6B 0.1906 0.4071 0.6928 0.115 Uiso calc R 1
H H6C 0.2828 0.4785 0.7781 0.115 Uiso calc R 1
C C7 0.23376(15) 0.3954(2) 0.51268(11) 0.0498(4) Uani d . 1
C C8 0.25979(16) 0.2123(3) 0.52272(12) 0.0571(5) Uani d . 1
H H8 0.3294 0.1734 0.5632 0.069 Uiso calc R 1
C C9 0.18239(15) 0.0885(2) 0.47270(12) 0.0563(5) Uani d . 1
H H9 0.2006 -0.0339 0.4797 0.068 Uiso calc R 1
C C10 0.07785(15) 0.1421(2) 0.41203(10) 0.0484(4) Uani d . 1
C C11 0.05271(15) 0.3253(2) 0.40330(11) 0.0566(5) Uani d . 1
H H11 -0.0173 0.3642 0.3632 0.068 Uiso calc R 1
C C12 0.12968(15) 0.4513(2) 0.45298(11) 0.0560(5) Uani d . 1
H H12 0.1114 0.5738 0.4462 0.067 Uiso calc R 1
C C13 -0.00238(17) 0.0043(3) 0.35785(11) 0.0563(5) Uani d . 1
C C14 -0.12147(16) 0.0631(3) 0.30037(13) 0.0713(6) Uani d . 1
H H14A -0.1657 -0.0409 0.2731 0.107 Uiso calc R 1
H H14B -0.1042 0.1428 0.2531 0.107 Uiso calc R 1
H H14C -0.1711 0.1252 0.3379 0.107 Uiso calc R 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
C1 N1 C4 109.47(15)
C1 N1 C7 124.90(14)
C4 N1 C7 125.60(14)
C2 C1 N1 106.80(16)
C2 C1 C5 130.24(17)
N1 C1 C5 122.86(16)
C1 C2 C3 108.41(18)
C1 C2 H2 125.8
C3 C2 H2 125.8
C4 C3 C2 108.41(17)
C4 C3 H3 125.8
C2 C3 H3 125.8
C3 C4 N1 106.91(16)
C3 C4 C6 130.57(17)
N1 C4 C6 122.46(17)
C1 C5 H5A 109.5
C1 C5 H5B 109.5
H5A C5 H5B 109.5
C1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C12 C7 C8 119.55(17)
C12 C7 N1 119.81(16)
C8 C7 N1 120.64(15)
C9 C8 C7 119.81(16)
C9 C8 H8 120.1
C7 C8 H8 120.1
C8 C9 C10 121.48(17)
C8 C9 H9 119.3
C10 C9 H9 119.3
C11 C10 C9 117.98(17)
C11 C10 C13 122.10(16)
C9 C10 C13 119.92(16)
C12 C11 C10 121.20(16)
C12 C11 H11 119.4
C10 C11 H11 119.4
C7 C12 C11 119.97(16)
C7 C12 H12 120.0
C11 C12 H12 120.0
O1 C13 C10 120.68(17)
O1 C13 C14 120.36(18)
C10 C13 C14 118.96(17)
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.214(2)
N1 C1 1.389(2)
N1 C4 1.389(2)
N1 C7 1.427(2)
C1 C2 1.356(2)
C1 C5 1.490(2)
C2 C3 1.412(2)
C2 H2 0.9300
C3 C4 1.353(2)
C3 H3 0.9300
C4 C6 1.495(3)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C12 1.380(2)
C7 C8 1.387(2)
C8 C9 1.375(2)
C8 H8 0.9300
C9 C10 1.385(2)
C9 H9 0.9300
C10 C11 1.385(2)
C10 C13 1.487(2)
C11 C12 1.381(2)
C11 H11 0.9300
C12 H12 0.9300
C13 C14 1.493(2)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 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
C12 H12 O1 1_565 0.93 2.47 3.338(2) 155
C14 H14B O1 2_555 0.96 2.51 3.465(2) 172
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
C4 N1 C1 C2 0.61(18)
C7 N1 C1 C2 178.52(15)
C4 N1 C1 C5 177.38(15)
C7 N1 C1 C5 -4.7(2)
N1 C1 C2 C3 -0.6(2)
C5 C1 C2 C3 -177.04(17)
C1 C2 C3 C4 0.4(2)
C2 C3 C4 N1 0.0(2)
C2 C3 C4 C6 -177.10(18)
C1 N1 C4 C3 -0.38(18)
C7 N1 C4 C3 -178.27(15)
C1 N1 C4 C6 177.01(16)
C7 N1 C4 C6 -0.9(3)
C1 N1 C7 C12 -60.9(2)
C4 N1 C7 C12 116.66(18)
C1 N1 C7 C8 119.11(18)
C4 N1 C7 C8 -63.3(2)
C12 C7 C8 C9 0.5(2)
N1 C7 C8 C9 -179.52(14)
C7 C8 C9 C10 -0.1(2)
C8 C9 C10 C11 -0.3(2)
C8 C9 C10 C13 178.87(14)
C9 C10 C11 C12 0.4(2)
C13 C10 C11 C12 -178.77(14)
C8 C7 C12 C11 -0.4(2)
N1 C7 C12 C11 179.61(14)
C10 C11 C12 C7 -0.1(2)
C11 C10 C13 O1 173.12(16)
C9 C10 C13 O1 -6.0(2)
C11 C10 C13 C14 -7.2(2)
C9 C10 C13 C14 173.60(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 456043
