#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/45/2204571.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_2204571
loop_
_publ_author_name
'Wei Xu'
'Yin-Xiang Lu'
'Zhen-Guang Zou'
'Chun-Ming Liu'
'Bi-Jian Lan'
'Hui Zhou'
_publ_section_title
;
 1,1,1-Tris[(pyrrol-1-yl)methyl]ethane: herring-bone packing of
 supramolecular assemblies in a homochiral crystal from chemically
 symmetric molecules
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2171
_journal_page_last               o2173
_journal_paper_doi               10.1107/S1600536804027011
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C17 H21 N3'
_chemical_formula_moiety         'C17 H21 N3'
_chemical_formula_sum            'C17 H21 N3'
_chemical_formula_weight         267.37
_chemical_name_systematic
;
1,1,1-Tris[(pyrrol-1-yl)methyl]ethane
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7625(14)
_cell_length_b                   11.2496(19)
_cell_length_c                   17.542(3)
_cell_measurement_reflns_used    2807
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.360
_cell_measurement_theta_min      2.248
_cell_volume                     1531.9(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7054
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        3.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_T_min  0.9527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.178
_refine_ls_abs_structure_details 'none, Friedel pairs merged'
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0570
_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)+(0.0751P)²+0.0401P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                1594
_reflns_number_total             1746
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6135.cif
_cod_data_source_block           I
_cod_original_cell_volume        1531.8(5)
_cod_database_code               2204571
_cod_database_fobs_code          2204571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_type_symbol
N1 0.4762(3) 0.22057(18) 0.08017(12) 0.0493(6) Uani d . 1 N
N3 0.0066(3) 0.36777(19) 0.18019(12) 0.0519(6) Uani d . 1 N
N2 0.4206(3) 0.59859(19) 0.08031(13) 0.0516(6) Uani d . 1 N
C1 0.2975(3) 0.3989(2) 0.11865(13) 0.0425(6) Uani d . 1 C
C2 0.4154(4) 0.3384(2) 0.05996(15) 0.0503(7) Uani d . 1 C
H2A 0.3536 0.3329 0.0120 0.060 Uiso calc R 1 H
H2B 0.5147 0.3890 0.0516 0.060 Uiso calc R 1 H
C3 0.3995(5) 0.1152(2) 0.06415(19) 0.0674(9) Uani d . 1 C
H3 0.2953 0.1049 0.0388 0.081 Uiso calc R 1 H
C4 0.5031(6) 0.0268(3) 0.0920(2) 0.0927(14) Uani d . 1 C
H4 0.4814 -0.0544 0.0893 0.111 Uiso calc R 1 H
C5 0.6459(6) 0.0798(3) 0.1251(2) 0.0863(12) Uani d . 1 C
H5 0.7378 0.0408 0.1481 0.104 Uiso calc R 1 H
C6 0.6269(4) 0.1989(3) 0.11764(18) 0.0653(8) Uani d . 1 C
H6 0.7037 0.2562 0.1351 0.078 Uiso calc R 1 H
C7 0.2652(3) 0.5279(2) 0.09090(18) 0.0532(7) Uani d . 1 C
H7A 0.2032 0.5248 0.0429 0.064 Uiso calc R 1 H
H7B 0.1917 0.5678 0.1276 0.064 Uiso calc R 1 H
C8 0.5097(5) 0.6093(2) 0.01356(17) 0.0640(7) Uani d . 1 C
H8 0.4809 0.5736 -0.0325 0.077 Uiso calc R 1 H
C9 0.6474(5) 0.6808(2) 0.0259(2) 0.0715(9) Uani d . 1 C
H9 0.7302 0.7026 -0.0098 0.086 Uiso calc R 1 H
C10 0.6416(4) 0.7159(2) 0.1029(2) 0.0701(9) Uani d . 1 C
H10 0.7199 0.7652 0.1276 0.084 Uiso calc R 1 H
C11 0.5016(4) 0.6647(2) 0.13430(18) 0.0632(8) Uani d . 1 C
H11 0.4663 0.6733 0.1847 0.076 Uiso calc R 1 H
C12 0.1220(3) 0.3341(2) 0.11952(16) 0.0507(6) Uani d . 1 C
H12A 0.0648 0.3486 0.0713 0.061 Uiso calc R 1 H
H12B 0.1431 0.2493 0.1231 0.061 Uiso calc R 1 H
C13 -0.0089(5) 0.3112(3) 0.2481(2) 0.0726(9) Uani d . 1 C
H13 0.0474 0.2414 0.2617 0.087 Uiso calc R 1 H
C14 -0.1189(5) 0.3724(4) 0.2927(2) 0.0877(12) Uani d . 1 C
H14 -0.1518 0.3527 0.3421 0.105 Uiso calc R 1 H
C15 -0.1748(4) 0.4716(4) 0.2506(2) 0.0833(11) Uani d . 1 C
H15 -0.2512 0.5299 0.2670 0.100 Uiso calc R 1 H
C16 -0.0972(4) 0.4662(3) 0.1824(2) 0.0636(8) Uani d . 1 C
H16 -0.1115 0.5206 0.1430 0.076 Uiso calc R 1 H
C17 0.3779(3) 0.3972(3) 0.19737(15) 0.0530(7) Uani d . 1 C
H17A 0.3075 0.4423 0.2319 0.079 Uiso calc R 1 H
H17B 0.4909 0.4317 0.1951 0.079 Uiso calc R 1 H
H17C 0.3862 0.3167 0.2150 0.079 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 0.0033 0.0000 '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 0.0000 '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
C3 N1 C6 108.7(3) y
C3 N1 C2 127.2(3) ?
C6 N1 C2 124.1(2) ?
C11 N2 C8 108.3(2) y
C11 N2 C7 126.4(2) ?
C8 N2 C7 125.3(3) ?
C13 N3 C16 107.6(3) y
C13 N3 C12 125.5(3) ?
C16 N3 C12 126.8(3) ?
C17 C1 C2 111.1(2) ?
C17 C1 C12 110.4(2) ?
C2 C1 C12 108.8(2) ?
C17 C1 C7 111.3(2) ?
C2 C1 C7 107.5(2) ?
C12 C1 C7 107.6(2) ?
N1 C2 C1 115.8(2) y
N1 C2 H2A 108.3 ?
C1 C2 H2A 108.3 ?
N1 C2 H2B 108.3 ?
C1 C2 H2B 108.3 ?
H2A C2 H2B 107.4 ?
N1 C3 C4 107.6(3) ?
N1 C3 H3 126.2 ?
C4 C3 H3 126.2 ?
C3 C4 C5 107.8(3) ?
C3 C4 H4 126.1 ?
C5 C4 H4 126.1 ?
C6 C5 C4 107.4(4) ?
C6 C5 H5 126.3 ?
C4 C5 H5 126.3 ?
C5 C6 N1 108.5(4) ?
C5 C6 H6 125.8 ?
N1 C6 H6 125.8 ?
N2 C7 C1 114.6(2) y
N2 C7 H7A 108.6 ?
C1 C7 H7A 108.6 ?
N2 C7 H7B 108.6 ?
C1 C7 H7B 108.6 ?
H7A C7 H7B 107.6 ?
C9 C8 N2 108.4(3) ?
C9 C8 H8 125.8 ?
N2 C8 H8 125.8 ?
C8 C9 C10 107.1(3) ?
C8 C9 H9 126.5 ?
C10 C9 H9 126.5 ?
C11 C10 C9 107.4(3) ?
C11 C10 H10 126.3 ?
C9 C10 H10 126.3 ?
C10 C11 N2 108.8(3) ?
C10 C11 H11 125.6 ?
N2 C11 H11 125.6 ?
N3 C12 C1 115.5(2) y
N3 C12 H12A 108.4 ?
C1 C12 H12A 108.4 ?
N3 C12 H12B 108.4 ?
C1 C12 H12B 108.4 ?
H12A C12 H12B 107.5 ?
C14 C13 N3 109.1(3) ?
C14 C13 H13 125.5 ?
N3 C13 H13 125.5 ?
C13 C14 C15 107.2(3) ?
C13 C14 H14 126.4 ?
C15 C14 H14 126.4 ?
C16 C15 C14 107.1(3) ?
C16 C15 H15 126.5 ?
C14 C15 H15 126.5 ?
C15 C16 N3 109.0(3) ?
C15 C16 H16 125.5 ?
N3 C16 H16 125.5 ?
C1 C17 H17A 109.5 ?
C1 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C1 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 1.356(4) ?
N1 C6 1.364(4) ?
N1 C2 1.451(3) y
N2 C11 1.359(4) ?
N2 C8 1.365(4) ?
N2 C7 1.457(3) y
N3 C13 1.355(4) ?
N3 C16 1.370(4) ?
N3 C12 1.442(3) y
C1 C17 1.516(3) ?
C1 C2 1.536(4) ?
C1 C12 1.545(3) ?
C1 C7 1.552(4) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.370(5) ?
C3 H3 0.9300 ?
C4 C5 1.386(6) y
C4 H4 0.9300 ?
C5 C6 1.353(5) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C9 1.355(4) ?
C8 H8 0.9300 ?
C9 C10 1.409(5) y
C9 H9 0.9300 ?
C10 C11 1.347(4) ?
C10 H10 0.9300 ?
C11 H11 0.9300 ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C14 1.348(5) ?
C13 H13 0.9300 ?
C14 C15 1.406(5) y
C14 H14 0.9300 ?
C15 C16 1.341(5) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
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
C3 N1 C2 C1 90.1(3) yes
C6 N1 C2 C1 -91.8(3) yes
C8 N2 C7 C1 92.3(3) yes
C11 N2 C7 C1 -87.8(3) yes
C13 N3 C12 C1 -94.5(3) yes
C16 N3 C12 C1 80.4(3) yes
C17 C1 C2 N1 51.4(3) yes
C17 C1 C7 N2 64.1(3) yes
C17 C1 C12 N3 48.2(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130274
