#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/35/2013581.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_2013581
loop_
_publ_author_name
'Munro, Orde Q.'
'Camp, Greville L.'
_publ_section_title
;
 Self-recognition in a flexible bis(pyrrole) Schiff base derivative:
 formation of a one-dimensional hydrogen-bonded polymer
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o672
_journal_page_last               o675
_journal_paper_doi               10.1107/S0108270103023230
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C13 H16 N4'
_chemical_formula_moiety         'C13 H16 N4'
_chemical_formula_sum            'C13 H16 N4'
_chemical_formula_weight         228.3
_chemical_name_systematic
;
N,N'-bis(pyrrol-2-ylmethylene)propane-1,2-diamine
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.469(3)
_cell_length_b                   20.644(4)
_cell_length_c                   7.997(4)
_cell_measurement_reflns_used    826
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      4
_cell_volume                     2553.8(15)
_computing_cell_refinement       CrysAlisCCD
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, Year?)'
_computing_data_reduction        'CrysAlisRED (Oxford Diffraction, Year?)'
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur2 CCD area-detector'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            23402
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         31.87
_diffrn_reflns_theta_min         4.16
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0575P)²+0.6559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.123
_reflns_number_gt                3367
_reflns_number_total             4144
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1708.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2554.0(14)
_cod_database_code               2013581
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
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
C1 -0.10106(7) 0.63907(5) -0.90905(14) 0.0221(2) Uani d . 1 . . C
H1A -0.1031 0.6118 -1.0046 0.026 Uiso calc R 1 . . H
C2 -0.16703(7) 0.67885(6) -0.85429(15) 0.0228(2) Uani d . 1 . . C
H2 -0.2226 0.6833 -0.9037 0.027 Uiso calc R 1 . . H
C3 -0.13650(7) 0.71161(5) -0.71119(14) 0.0197(2) Uani d . 1 . . C
H3 -0.1674 0.7428 -0.6475 0.024 Uiso calc R 1 . . H
C4 -0.05301(7) 0.68995(5) -0.68053(13) 0.0166(2) Uani d . 1 . . C
C5 0.00268(7) 0.70402(5) -0.53978(13) 0.01671(19) Uani d . 1 . . C
H5 -0.0111 0.7396 -0.4695 0.02 Uiso calc R 1 . . H
C6 0.11919(7) 0.68795(5) -0.35662(12) 0.0178(2) Uani d . 1 . . C
H6A 0.1031 0.7323 -0.3214 0.021 Uiso calc R 1 . . H
H6B 0.1817 0.6878 -0.383 0.021 Uiso calc R 1 . . H
C7 0.10141(7) 0.64064(5) -0.21366(13) 0.0197(2) Uani d . 1 . . C
H7A 0.0423 0.648 -0.17 0.024 Uiso calc R 1 . . H
H7B 0.1043 0.5957 -0.2565 0.024 Uiso calc R 1 . . H
C8 0.16671(7) 0.64896(5) -0.07220(12) 0.0181(2) Uani d . 1 . . C
H8A 0.2242 0.6339 -0.1104 0.022 Uiso calc R 1 . . H
H8B 0.1715 0.6955 -0.0437 0.022 Uiso calc R 1 . . H
C9 0.18122(6) 0.55911(5) 0.10468(13) 0.0175(2) Uani d . 1 . . C
H9 0.2242 0.5456 0.0274 0.021 Uiso calc R 1 . . H
C10 0.16340(7) 0.51857(5) 0.24798(12) 0.0170(2) Uani d . 1 . . C
C11 0.18834(7) 0.45494(5) 0.27627(14) 0.0209(2) Uani d . 1 . . C
H11 0.2237 0.4292 0.2054 0.025 Uiso calc R 1 . . H
C12 0.15141(7) 0.43535(5) 0.43018(15) 0.0223(2) Uani d . 1 . . C
H12 0.1564 0.3939 0.4808 0.027 Uiso calc R 1 . . H
C13 0.10686(7) 0.48781(5) 0.49267(14) 0.0208(2) Uani d . 1 . . C
H13 0.0766 0.489 0.596 0.025 Uiso calc R 1 . . H
N1 -0.03241(6) 0.64556(4) -0.80283(11) 0.01793(18) Uani d . 1 . . N
N2 0.06989(6) 0.67017(4) -0.50660(10) 0.01746(18) Uani d . 1 . . N
N3 0.14145(6) 0.61245(4) 0.07761(10) 0.01782(18) Uani d . 1 . . N
N4 0.11336(6) 0.53797(5) 0.38170(11) 0.01789(18) Uani d . 1 . . N
H1 0.0212(9) 0.6300(7) -0.8218(18) 0.021 Uiso d . 1 . . H
H4 0.0972(9) 0.5786(7) 0.4009(17) 0.021 Uiso d . 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 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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'
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
N1 C1 C2 108.59(10) ?
N1 C1 H1A 125.7 ?
C2 C1 H1A 125.7 ?
C1 C2 C3 107.16(10) ?
C1 C2 H2 126.4 ?
C3 C2 H2 126.4 ?
C4 C3 C2 107.47(10) ?
C4 C3 H3 126.3 ?
C2 C3 H3 126.3 ?
N1 C4 C3 107.70(9) ?
N1 C4 C5 123.24(9) ?
C3 C4 C5 128.79(10) ?
N2 C5 C4 122.34(9) ?
N2 C5 H5 118.8 ?
C4 C5 H5 118.8 ?
N2 C6 C7 110.97(9) ?
N2 C6 H6A 109.4 ?
C7 C6 H6A 109.4 ?
N2 C6 H6B 109.4 ?
C7 C6 H6B 109.4 ?
H6A C6 H6B 108 ?
C8 C7 C6 111.31(9) ?
C8 C7 H7A 109.4 ?
C6 C7 H7A 109.4 ?
C8 C7 H7B 109.4 ?
C6 C7 H7B 109.4 ?
H7A C7 H7B 108 ?
N3 C8 C7 111.77(9) ?
N3 C8 H8A 109.3 ?
C7 C8 H8A 109.3 ?
N3 C8 H8B 109.3 ?
C7 C8 H8B 109.3 ?
H8A C8 H8B 107.9 ?
N3 C9 C10 122.72(10) ?
N3 C9 H9 118.6 ?
C10 C9 H9 118.6 ?
N4 C10 C11 107.73(9) ?
N4 C10 C9 123.60(9) ?
C11 C10 C9 128.63(10) ?
C10 C11 C12 107.46(10) ?
C10 C11 H11 126.3 ?
C12 C11 H11 126.3 ?
C13 C12 C11 107.01(10) ?
C13 C12 H12 126.5 ?
C11 C12 H12 126.5 ?
N4 C13 C12 108.85(10) ?
N4 C13 H13 125.6 ?
C12 C13 H13 125.6 ?
C1 N1 C4 109.08(9) y
C1 N1 H1 125.1(9) ?
C4 N1 H1 124.7(9) ?
C5 N2 C6 117.04(9) y
C9 N3 C8 116.85(9) y
C13 N4 C10 108.93(9) y
C13 N4 H4 125.6(9) ?
C10 N4 H4 124.5(9) ?
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
C1 N1 . 1.3665(14) y
C1 C2 . 1.3811(17) ?
C1 H1A . 0.95 ?
C2 C3 . 1.4108(17) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3886(14) ?
C3 H3 . 0.95 ?
C4 N1 . 1.3776(14) y
C4 C5 . 1.4469(15) ?
C5 N2 . 1.2806(13) y
C5 H5 . 0.95 ?
C6 N2 . 1.4680(14) y
C6 C7 . 1.5287(15) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.5264(15) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 N3 . 1.4684(14) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 N3 . 1.2798(14) y
C9 C10 . 1.4457(15) ?
C9 H9 . 0.95 ?
C10 N4 . 1.3796(14) y
C10 C11 . 1.3875(15) ?
C11 C12 . 1.4160(16) ?
C11 H11 . 0.95 ?
C12 C13 . 1.3776(16) ?
C12 H12 . 0.95 ?
C13 N4 . 1.3675(14) y
C13 H13 . 0.95 ?
N1 H1 . 0.903(15) ?
N4 H4 . 0.888(15) ?
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
_geom_hbond_publ_flag
N1 H1 N3 1_554 0.902(14) 2.059(14) 2.935(2) 163.5(13) y
N4 H4 N2 1_556 0.889(14) 2.073(14) 2.949(2) 168.4(12) y
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
N1 C1 C2 C3 1.13(13)
C1 C2 C3 C4 -1.11(12)
C2 C3 C4 N1 0.67(12)
C2 C3 C4 C5 -173.42(10)
N1 C4 C5 N2 -9.46(16)
C3 C4 C5 N2 163.79(11)
N2 C6 C7 C8 166.96(9)
C6 C7 C8 N3 169.72(9)
N3 C9 C10 N4 -11.13(16)
N3 C9 C10 C11 166.20(11)
N4 C10 C11 C12 0.72(12)
C9 C10 C11 C12 -176.95(10)
C10 C11 C12 C13 -1.30(12)
C11 C12 C13 N4 1.41(12)
C2 C1 N1 C4 -0.74(12)
C3 C4 N1 C1 0.03(12)
C5 C4 N1 C1 174.52(10)
C4 C5 N2 C6 -177.76(9)
C7 C6 N2 C5 103.56(11)
C10 C9 N3 C8 179.49(9)
C7 C8 N3 C9 102.49(11)
C12 C13 N4 C10 -0.98(12)
C11 C10 N4 C13 0.15(12)
C9 C10 N4 C13 177.96(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652374
