#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/04/2240431.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_2240431
loop_
_publ_author_name
'Alshawi, Jasim'
'Yousif, Muoayed'
'Zangana, Karzan H.'
'Vitorica Yrezabal, Inigo J.'
'Winpenny, Richard'
'Al-Jeboori, Mohamad J.'
_publ_section_title
;
 Crystal structure of diethyl
 2,2'-[((1E,1'E)-{[(1R,4R)-cyclohexane-1,4-diyl]bis(azanylylidene)}bis(methanylylidene))bis(1H-pyrrole-2,1-diyl)]diacetate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o165
_journal_page_last               o166
_journal_paper_doi               10.1107/S2056989015002674
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C24 H32 N4 O4'
_chemical_formula_moiety         'C24 H32 N4 O4'
_chemical_formula_sum            'C24 H32 N4 O4'
_chemical_formula_weight         440.54
_chemical_name_systematic
;Diethyl
2,2'-[((1E,1'E)-{[(1R,4R)-cyclohexane-1,4-diyl]bis(azanylylidene)}bis(methanylylidene))bis(1H-pyrrole-2,1-diyl)]diacetate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                115.166(9)
_cell_angle_beta                 92.105(7)
_cell_angle_gamma                113.288(8)
_cell_formula_units_Z            1
_cell_length_a                   8.5531(6)
_cell_length_b                   8.8379(7)
_cell_length_c                   9.6492(9)
_cell_measurement_reflns_used    1515
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      3.27
_cell_volume                     587.68(11)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.37
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_device_type
'Agilent SuperNova (single source at offset, Atlas)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4657
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         29.44
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0363P)²+0.1039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                1827
_reflns_number_total             2734
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5080sup1.cf
_cod_data_source_block           I
_cod_original_cell_volume        587.68(10)
_cod_database_code               2240431
_cod_database_fobs_code          2240431
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
O O13 0.46898(16) 0.46998(17) 0.19574(15) 0.0317(3) Uani d 1
O O16 0.63475(17) 0.71083(17) 0.43494(15) 0.0338(4) Uani d 1
N N1 0.67517(19) 0.9650(2) 0.32094(18) 0.0274(4) Uani d 1
N N7 0.87176(19) 0.7539(2) 0.17968(18) 0.0313(4) Uani d 1
C C12 0.5599(2) 0.6517(3) 0.3013(2) 0.0270(4) Uani d 1
C C6 0.9477(2) 0.9265(3) 0.2821(2) 0.0297(5) Uani d 1
H H6 1.0695 0.9854 0.3163 0.036 Uiso calc 1
C C5 0.8559(2) 1.0361(2) 0.3483(2) 0.0275(4) Uani d 1
C C10 0.9066(2) 0.4733(2) 0.1181(2) 0.0311(5) Uani d 1
H H10A 0.7851 0.3992 0.0575 0.037 Uiso calc 1
H H10B 0.9087 0.4935 0.2252 0.037 Uiso calc 1
C C11 0.5474(2) 0.7689(2) 0.2290(2) 0.0279(4) Uani d 1
H H11A 0.5653 0.7192 0.1233 0.033 Uiso calc 1
H H11B 0.4302 0.7597 0.2201 0.033 Uiso calc 1
C C2 0.6355(3) 1.1083(3) 0.4039(2) 0.0317(5) Uani d 1
H H2 0.5229 1.0970 0.4061 0.038 Uiso calc 1
C C9 1.0097(2) 0.3654(3) 0.0461(2) 0.0307(5) Uani d 1
H H9A 0.9545 0.2438 0.0420 0.037 Uiso calc 1
H H9B 1.1280 0.4334 0.1127 0.037 Uiso calc 1
C C8 0.9819(2) 0.6620(2) 0.1201(2) 0.0304(5) Uani d 1
H H8 1.1007 0.7412 0.1897 0.036 Uiso calc 1
C C4 0.9269(3) 1.2260(3) 0.4484(2) 0.0340(5) Uani d 1
H H4 1.0459 1.3098 0.4864 0.041 Uiso calc 1
C C3 0.7880(3) 1.2712(3) 0.4833(2) 0.0377(5) Uani d 1
H H3 0.7980 1.3898 0.5483 0.045 Uiso calc 1
C C14 0.4577(3) 0.3383(3) 0.2513(2) 0.0400(5) Uani d 1
H H14A 0.4025 0.3576 0.3392 0.048 Uiso calc 1
H H14B 0.5743 0.3562 0.2869 0.048 Uiso calc 1
C C15 0.3512(3) 0.1451(3) 0.1175(3) 0.0544(7) Uani d 1
H H15A 0.4111 0.1242 0.0342 0.082 Uiso calc 1
H H15B 0.2388 0.1314 0.0787 0.082 Uiso calc 1
H H15C 0.3349 0.0551 0.1534 0.082 Uiso calc 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_site_symmetry_3
_geom_angle
C12 O13 C14 . 116.15(15)
C5 N1 C11 . 126.32(15)
C2 N1 C5 . 108.70(15)
C2 N1 C11 . 124.84(15)
C6 N7 C8 . 117.71(15)
O13 C12 C11 . 109.47(16)
O16 C12 O13 . 124.75(19)
O16 C12 C11 . 125.74(17)
N7 C6 C5 . 123.74(17)
N1 C5 C6 . 124.91(15)
C4 C5 N1 . 107.27(16)
C4 C5 C6 . 127.83(17)
C8 C10 C9 . 111.74(14)
N1 C11 C12 . 112.58(15)
N1 C2 C3 . 108.91(17)
C10 C9 C8 2_765 111.47(17)
N7 C8 C10 . 109.64(14)
N7 C8 C9 2_765 109.49(17)
C10 C8 C9 2_765 110.20(15)
C5 C4 C3 . 107.99(18)
C2 C3 C4 . 107.14(17)
O13 C14 C15 . 107.88(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O13 C12 . 1.336(2)
O13 C14 . 1.448(2)
O16 C12 . 1.203(2)
N1 C5 . 1.384(2)
N1 C11 . 1.452(2)
N1 C2 . 1.363(2)
N7 C6 . 1.270(2)
N7 C8 . 1.458(2)
C12 C11 . 1.506(3)
C6 C5 . 1.441(2)
C5 C4 . 1.375(2)
C10 C9 . 1.522(2)
C10 C8 . 1.522(3)
C2 C3 . 1.365(3)
C9 C8 2_765 1.526(3)
C8 C9 2_765 1.526(3)
C4 C3 . 1.405(3)
C14 C15 . 1.490(3)
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
C14 H14A O16 2_666 0.97 2.50 3.317(3) 142 yes
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_site_symmetry_4
_geom_torsion
O13 C12 C11 N1 . -166.07(14)
O16 C12 C11 N1 . 16.3(3)
N1 C5 C4 C3 . 0.4(2)
N1 C2 C3 C4 . -0.3(2)
N7 C6 C5 N1 . 6.4(3)
N7 C6 C5 C4 . -173.7(2)
C12 O13 C14 C15 . 179.68(16)
C6 N7 C8 C10 . 134.27(18)
C6 N7 C8 C9 2_765 -104.71(19)
C6 C5 C4 C3 . -179.5(2)
C5 N1 C11 C12 . 64.5(2)
C5 N1 C2 C3 . 0.6(2)
C5 C4 C3 C2 . 0.0(2)
C11 N1 C5 C6 . 3.5(3)
C11 N1 C5 C4 . -176.36(17)
C11 N1 C2 C3 . 176.43(17)
C2 N1 C5 C6 . 179.33(19)
C2 N1 C5 C4 . -0.6(2)
C2 N1 C11 C12 . -110.7(2)
C9 C10 C8 N7 . 176.06(15)
C9 C10 C8 C9 2_765 55.5(2)
C8 N7 C6 C5 . 178.46(18)
C8 C10 C9 C8 2_765 -56.2(2)
C14 O13 C12 O16 . 2.0(3)
C14 O13 C12 C11 . -175.70(15)
