#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/29/2012942.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_2012942
loop_
_publ_author_name
'Ramos Silva, Manuela'
'Matos Beja, Ana'
'Paixao, Jose Antonio'
'Sobral, Abilio J. F. N.'
'Lopes, Susana H.'
'Rocha Gonsalves, A. M. d'A.'
_publ_section_title
;
 Ethyl 4-dodecyl-3,5-dimethyl-1H-pyrrole-2-carboxylate:
 intermolecular interactions in an amphiphilic pyrrole
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o572
_journal_page_last               o574
_journal_paper_doi               10.1107/S0108270102013653
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C21 H37 N O2'
_chemical_formula_moiety         'C21 H37 N O2'
_chemical_formula_sum            'C21 H37 N O2'
_chemical_formula_weight         335.52
_chemical_name_systematic
;
Ethyl 4-dodecyl-3,5-dimethyl-1H-pyrrole-2-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.79(7)
_cell_angle_beta                 94.06(8)
_cell_angle_gamma                99.93(9)
_cell_formula_units_Z            2
_cell_length_a                   5.4778(6)
_cell_length_b                   9.8774(10)
_cell_length_c                   20.4090(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      21.68
_cell_volume                     1069.6(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_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           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8228
_diffrn_reflns_theta_full        72.41
_diffrn_reflns_theta_max         72.42
_diffrn_reflns_theta_min         4.41
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.8120
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    1.042
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.178
_refine_ls_extinction_coef       0.0043(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0647P)²+0.1001P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1563
_reflns_number_gt                2953
_reflns_number_total             4238
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln1145.cif
_cod_data_source_block           I
_cod_database_code               2012942
_cod_database_fobs_code          2012942
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 1.0100(2) -0.14476(12) 0.08837(6) 0.0788(4) Uani d . 1 . . O
O2 0.6962(3) -0.12250(13) 0.01766(6) 0.0896(4) Uani d . 1 . . O
N1 0.6976(3) 0.14459(14) 0.08465(7) 0.0689(4) Uani d . 1 . . N
H1 0.578(3) 0.1216(19) 0.0519(10) 0.083 Uiso d . 1 . . H
C1 0.8588(3) 0.06328(17) 0.10478(8) 0.0665(4) Uani d . 1 . . C
C2 1.0068(3) 0.13898(17) 0.16073(8) 0.0674(4) Uani d . 1 . . C
C3 0.9304(3) 0.26928(17) 0.17390(8) 0.0677(4) Uani d . 1 . . C
C4 0.7386(3) 0.26943(16) 0.12589(8) 0.0676(4) Uani d . 1 . . C
C5 0.8446(3) -0.07390(17) 0.06595(8) 0.0694(4) Uani d . 1 . . C
C6 0.9986(4) -0.28412(19) 0.05197(10) 0.0864(5) Uani d . 1 . . C
H6A 1.0303 -0.2803 0.0061 0.104 Uiso calc R 1 . . H
H6B 0.8350 -0.3403 0.0523 0.104 Uiso calc R 1 . . H
C7 1.1922(5) -0.3456(2) 0.08564(14) 0.1121(8) Uani d . 1 . . C
H7A 1.3536 -0.2909 0.0837 0.168 Uiso calc R 1 . . H
H7B 1.1863 -0.4394 0.0636 0.168 Uiso calc R 1 . . H
H7C 1.1617 -0.3461 0.1314 0.168 Uiso calc R 1 . . H
C8 1.2096(3) 0.0935(2) 0.20041(10) 0.0858(5) Uani d . 1 . . C
H8A 1.1370 0.0268 0.2265 0.129 Uiso calc R 1 . . H
H8B 1.3073 0.1729 0.2295 0.129 Uiso calc R 1 . . H
H8C 1.3142 0.0516 0.1707 0.129 Uiso calc R 1 . . H
C9 0.5878(4) 0.37766(19) 0.11528(10) 0.0843(5) Uani d . 1 . . C
H9A 0.5813 0.3891 0.0694 0.127 Uiso calc R 1 . . H
H9B 0.6629 0.4645 0.1429 0.127 Uiso calc R 1 . . H
H9C 0.4219 0.3490 0.1267 0.127 Uiso calc R 1 . . H
C10 1.0316(3) 0.38638(19) 0.23060(9) 0.0769(5) Uani d . 1 . . C
H10A 1.0354 0.4743 0.2147 0.092 Uiso calc R 1 . . H
H10B 1.2018 0.3802 0.2445 0.092 Uiso calc R 1 . . H
C11 0.8836(3) 0.3869(2) 0.29048(9) 0.0803(5) Uani d . 1 . . C
H11A 0.8898 0.3020 0.3085 0.096 Uiso calc R 1 . . H
H11B 0.7109 0.3866 0.2762 0.096 Uiso calc R 1 . . H
C12 0.9780(3) 0.5112(2) 0.34502(9) 0.0824(5) Uani d . 1 . . C
H12A 1.1366 0.5001 0.3657 0.099 Uiso calc R 1 . . H
H12B 1.0076 0.5944 0.3248 0.099 Uiso calc R 1 . . H
C13 0.8075(3) 0.5328(2) 0.39818(9) 0.0806(5) Uani d . 1 . . C
H13A 0.7975 0.4556 0.4227 0.097 Uiso calc R 1 . . H
H13B 0.6421 0.5298 0.3769 0.097 Uiso calc R 1 . . H
C14 0.8810(3) 0.6665(2) 0.44707(9) 0.0839(5) Uani d . 1 . . C
H14A 1.0367 0.6640 0.4722 0.101 Uiso calc R 1 . . H
H14B 0.9121 0.7428 0.4222 0.101 Uiso calc R 1 . . H
C15 0.6970(4) 0.6979(2) 0.49536(10) 0.0911(6) Uani d . 1 . . C
H15A 0.5364 0.6898 0.4703 0.109 Uiso calc R 1 . . H
H15B 0.6802 0.6270 0.5236 0.109 Uiso calc R 1 . . H
C16 0.7559(4) 0.8371(2) 0.53899(10) 0.0910(6) Uani d . 1 . . C
H16A 0.7830 0.9078 0.5108 0.109 Uiso calc R 1 . . H
H16B 0.9115 0.8429 0.5660 0.109 Uiso calc R 1 . . H
C17 0.5643(4) 0.8721(2) 0.58458(11) 0.0942(6) Uani d . 1 . . C
H17A 0.4063 0.8611 0.5578 0.113 Uiso calc R 1 . . H
H17B 0.5442 0.8046 0.6146 0.113 Uiso calc R 1 . . H
C18 0.6178(4) 1.0149(2) 0.62554(10) 0.0870(5) Uani d . 1 . . C
H18A 0.6370 1.0824 0.5955 0.104 Uiso calc R 1 . . H
H18B 0.7762 1.0260 0.6521 0.104 Uiso calc R 1 . . H
C19 0.4271(3) 1.0498(2) 0.67136(10) 0.0839(5) Uani d . 1 . . C
H19A 0.2706 1.0432 0.6446 0.101 Uiso calc R 1 . . H
H19B 0.4020 0.9799 0.7001 0.101 Uiso calc R 1 . . H
C20 0.4885(4) 1.1908(2) 0.71444(11) 0.0944(6) Uani d . 1 . . C
H20A 0.6489 1.1993 0.7397 0.113 Uiso calc R 1 . . H
H20B 0.5051 1.2611 0.6858 0.113 Uiso calc R 1 . . H
C21 0.3023(5) 1.2212(3) 0.76213(14) 0.1170(8) Uani d . 1 . . C
H21A 0.1426 1.2135 0.7379 0.175 Uiso calc R 1 . . H
H21B 0.3540 1.3140 0.7867 0.175 Uiso calc R 1 . . H
H21C 0.2909 1.1555 0.7925 0.175 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_publ_flag
C5 O1 C6 115.78(15) ?
C4 N1 C1 109.95(15) ?
C4 N1 H1 122.5(13) ?
C1 N1 H1 127.5(12) ?
N1 C1 C2 107.78(15) ?
N1 C1 C5 117.84(16) yes
C2 C1 C5 134.38(17) ?
C1 C2 C3 106.83(16) ?
C1 C2 C8 127.29(17) yes
C3 C2 C8 125.87(17) yes
C4 C3 C2 107.68(16) ?
C4 C3 C10 125.42(17) ?
C2 C3 C10 126.89(17) ?
N1 C4 C3 107.76(16) ?
N1 C4 C9 120.97(16) yes
C3 C4 C9 131.27(16) yes
O2 C5 O1 122.00(16) yes
O2 C5 C1 124.14(18) ?
O1 C5 C1 113.85(16) ?
O1 C6 C7 107.22(19) yes
O1 C6 H6A 110.3 ?
C7 C6 H6A 110.3 ?
O1 C6 H6B 110.3 ?
C7 C6 H6B 110.3 ?
H6A C6 H6B 108.5 ?
C6 C7 H7A 109.5 ?
C6 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C2 C8 H8A 109.5 ?
C2 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C2 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C4 C9 H9A 109.5 ?
C4 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C4 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C3 C10 C11 114.20(15) ?
C3 C10 H10A 108.7 ?
C11 C10 H10A 108.7 ?
C3 C10 H10B 108.7 ?
C11 C10 H10B 108.7 ?
H10A C10 H10B 107.6 ?
C10 C11 C12 113.31(15) ?
C10 C11 H11A 108.9 ?
C12 C11 H11A 108.9 ?
C10 C11 H11B 108.9 ?
C12 C11 H11B 108.9 ?
H11A C11 H11B 107.7 ?
C13 C12 C11 115.06(16) ?
C13 C12 H12A 108.5 ?
C11 C12 H12A 108.5 ?
C13 C12 H12B 108.5 ?
C11 C12 H12B 108.5 ?
H12A C12 H12B 107.5 ?
C12 C13 C14 115.56(16) ?
C12 C13 H13A 108.4 ?
C14 C13 H13A 108.4 ?
C12 C13 H13B 108.4 ?
C14 C13 H13B 108.4 ?
H13A C13 H13B 107.5 ?
C15 C14 C13 116.19(17) ?
C15 C14 H14A 108.2 ?
C13 C14 H14A 108.2 ?
C15 C14 H14B 108.2 ?
C13 C14 H14B 108.2 ?
H14A C14 H14B 107.4 ?
C16 C15 C14 116.44(17) ?
C16 C15 H15A 108.2 ?
C14 C15 H15A 108.2 ?
C16 C15 H15B 108.2 ?
C14 C15 H15B 108.2 ?
H15A C15 H15B 107.3 ?
C15 C16 C17 116.48(18) ?
C15 C16 H16A 108.2 ?
C17 C16 H16A 108.2 ?
C15 C16 H16B 108.2 ?
C17 C16 H16B 108.2 ?
H16A C16 H16B 107.3 ?
C18 C17 C16 116.28(18) ?
C18 C17 H17A 108.2 ?
C16 C17 H17A 108.2 ?
C18 C17 H17B 108.2 ?
C16 C17 H17B 108.2 ?
H17A C17 H17B 107.4 ?
C17 C18 C19 116.35(18) ?
C17 C18 H18A 108.2 ?
C19 C18 H18A 108.2 ?
C17 C18 H18B 108.2 ?
C19 C18 H18B 108.2 ?
H18A C18 H18B 107.4 ?
C20 C19 C18 115.83(18) ?
C20 C19 H19A 108.3 ?
C18 C19 H19A 108.3 ?
C20 C19 H19B 108.3 ?
C18 C19 H19B 108.3 ?
H19A C19 H19B 107.4 ?
C21 C20 C19 115.10(19) ?
C21 C20 H20A 108.5 ?
C19 C20 H20A 108.5 ?
C21 C20 H20B 108.5 ?
C19 C20 H20B 108.5 ?
H20A C20 H20B 107.5 ?
C20 C21 H21A 109.5 ?
C20 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C20 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.334(2) ?
O1 C6 . 1.450(2) ?
O2 C5 . 1.212(2) ?
N1 C4 . 1.356(2) yes
N1 C1 . 1.374(2) yes
N1 H1 . 0.875(19) ?
C1 C2 . 1.385(3) yes
C1 C5 . 1.448(2) ?
C2 C3 . 1.414(2) yes
C2 C8 . 1.499(3) ?
C3 C4 . 1.385(3) yes
C3 C10 . 1.504(3) ?
C4 C9 . 1.491(3) ?
C6 C7 . 1.487(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
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 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.513(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.515(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.495(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.503(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.496(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.489(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.501(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.495(3) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.499(3) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.499(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 C21 . 1.495(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 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
N1 H1 O2 2_655 0.875(19) 1.996(19) 2.850(3) 164.9(18)
C6 H6A Cg 2_755 0.97 3.18 4.119(2) 164
C8 H8C Cg 1_655 0.96 3.18 3.872(2) 130
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_publ_flag
C4 N1 C1 C2 0.10(18) ?
C4 N1 C1 C5 -179.21(13) ?
N1 C1 C2 C3 -0.10(17) yes
C5 C1 C2 C3 179.05(17) ?
N1 C1 C2 C8 179.87(15) yes
C5 C1 C2 C8 -1.0(3) ?
C1 C2 C3 C4 0.07(17) ?
C8 C2 C3 C4 -179.90(15) ?
C1 C2 C3 C10 178.49(15) ?
C8 C2 C3 C10 -1.5(3) ?
C1 N1 C4 C3 -0.05(18) ?
C1 N1 C4 C9 -179.84(15) yes
C2 C3 C4 N1 -0.01(18) ?
C10 C3 C4 N1 -178.46(14) ?
C2 C3 C4 C9 179.74(17) yes
C10 C3 C4 C9 1.3(3) yes
C6 O1 C5 O2 -0.9(2) ?
C6 O1 C5 C1 178.55(14) ?
N1 C1 C5 O2 -1.6(3) yes
C2 C1 C5 O2 179.36(17) ?
N1 C1 C5 O1 179.02(14) yes
C2 C1 C5 O1 -0.1(3) ?
C5 O1 C6 C7 -178.67(16) yes
C4 C3 C10 C11 83.1(2) ?
C2 C3 C10 C11 -95.1(2) ?
C3 C10 C11 C12 -175.98(17) ?
C10 C11 C12 C13 167.42(18) yes
C11 C12 C13 C14 -171.63(18) yes
C12 C13 C14 C15 172.76(18) yes
C13 C14 C15 C16 -173.58(19) ?
C14 C15 C16 C17 176.47(19) ?
C15 C16 C17 C18 -176.7(2) ?
C16 C17 C18 C19 -179.71(19) ?
C17 C18 C19 C20 177.30(19) ?
C18 C19 C20 C21 -177.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21134756
