#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/34/2203495.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_2203495
loop_
_publ_author_name
'Fallon, Gary D.'
'Langford, Steven J.'
'Lee, Marcia A.-P.'
_publ_section_title
;
 N,N'-Bis(2-carboxyethyl)-1,4,5,8-naphthalenetetracarboxylic
 diimine dimethylformamide disolvate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o542
_journal_page_last               o543
_journal_paper_doi               10.1107/S1600536804004350
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C20 H14 N2 O8, 2C3 H7 N O'
_chemical_formula_moiety         'C20 H14 N2 O8, 2C3 H7 N O'
_chemical_formula_sum            'C26 H28 N4 O10'
_chemical_formula_weight         556.52
_chemical_name_systematic
;
N,N'-Bis(2-carboxyethyl)-1,4,5,8-naphthalenetetracarboxylic diimine
dimethylformamide disolvate
;
_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
_cell_angle_alpha                111.9850(10)
_cell_angle_beta                 95.5780(10)
_cell_angle_gamma                94.0950(10)
_cell_formula_units_Z            1
_cell_length_a                   4.95190(10)
_cell_length_b                   10.8758(2)
_cell_length_c                   12.9078(3)
_cell_measurement_reflns_used    11976
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      3.1
_cell_volume                     637.17(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 1997--2000)'
_computing_data_reduction
'HKL Denzo (Otwinowski & Minor 1997) and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11976
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        '< 0.1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0504P)²+0.1167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2266
_reflns_number_total             3132
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6080.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2203495
_cod_database_fobs_code          2203495
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_type_symbol
C1 0.4386(3) 0.49628(13) 0.23584(12) 0.0214(3) Uani d . 1 C
C2 0.4498(3) 0.57134(13) 0.15918(11) 0.0202(3) Uani d . 1 C
H2A 0.3526 0.5146 0.0836 0.024 Uiso calc R 1 H
H2B 0.6426 0.5923 0.1511 0.024 Uiso calc R 1 H
C3 0.3198(3) 0.70013(13) 0.20541(12) 0.0206(3) Uani d . 1 C
H3A 0.1200 0.6786 0.1999 0.025 Uiso calc R 1 H
H3B 0.3925 0.7486 0.2860 0.025 Uiso calc R 1 H
N4 0.3746(2) 0.78706(11) 0.14326(9) 0.0187(3) Uani d . 1 N
C5 0.6107(3) 0.87750(13) 0.18261(11) 0.0180(3) Uani d . 1 C
C6 0.6592(2) 0.96879(13) 0.12316(11) 0.0169(3) Uani d . 1 C
C7 0.4761(2) 0.95622(12) 0.02825(11) 0.0150(3) Uani d . 1 C
C8 0.2454(2) 0.85935(12) -0.01183(11) 0.0163(3) Uani d . 1 C
C9 0.1893(3) 0.76971(13) 0.04845(11) 0.0190(3) Uani d . 1 C
O10 -0.0095(2) 0.68612(10) 0.01956(9) 0.0281(3) Uani d . 1 O
C11 0.0698(3) 0.84859(13) -0.10511(11) 0.0191(3) Uani d . 1 C
H11 -0.0844 0.7826 -0.1317 0.023 Uiso calc R 1 H
C12 0.8817(3) 1.06495(13) 0.16099(11) 0.0192(3) Uani d . 1 C
H12 1.0033 1.0729 0.2254 0.023 Uiso calc R 1 H
O13 0.7657(2) 0.88150(10) 0.26362(8) 0.0258(2) Uani d . 1 O
O14 0.5612(2) 0.38693(10) 0.20171(9) 0.0295(3) Uani d . 1 O
H14 0.5486 0.3485 0.2469 0.035 Uiso calc R 1 H
O15 0.3318(3) 0.53306(12) 0.32075(10) 0.0419(3) Uani d . 1 O
O16 0.4929(2) 0.25131(10) 0.33046(9) 0.0319(3) Uani d . 1 O
C17 0.3413(3) 0.29651(14) 0.40350(12) 0.0254(3) Uani d . 1 C
H17 0.2954 0.3843 0.4187 0.030 Uiso calc R 1 H
N18 0.2389(2) 0.23137(12) 0.46183(10) 0.0243(3) Uani d . 1 N
C19 0.3013(3) 0.09786(15) 0.44595(13) 0.0314(4) Uani d . 1 C
H19A 0.1389 0.0338 0.4078 0.047 Uiso calc R 1 H
H19B 0.3569 0.0938 0.5195 0.047 Uiso calc R 1 H
H19C 0.4503 0.0756 0.3998 0.047 Uiso calc R 1 H
C20 0.0541(3) 0.29017(18) 0.54327(14) 0.0368(4) Uani d . 1 C
H20A 0.0421 0.3829 0.5517 0.055 Uiso calc R 1 H
H20B 0.1234 0.2879 0.6162 0.055 Uiso calc R 1 H
H20C -0.1276 0.2393 0.5167 0.055 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 0.0016 '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_1
_geom_angle_site_symmetry_3
_geom_angle
O15 C1 O14 . . 123.37(13)
O15 C1 C2 . . 123.53(12)
O14 C1 C2 . . 113.09(11)
C1 C2 C3 . . 111.07(11)
C1 C2 H2A . . 109.4
C3 C2 H2A . . 109.4
C1 C2 H2B . . 109.4
C3 C2 H2B . . 109.4
H2A C2 H2B . . 108.0
N4 C3 C2 . . 111.71(11)
N4 C3 H3A . . 109.3
C2 C3 H3A . . 109.3
N4 C3 H3B . . 109.3
C2 C3 H3B . . 109.3
H3A C3 H3B . . 107.9
C5 N4 C9 . . 125.39(11)
C5 N4 C3 . . 117.02(11)
C9 N4 C3 . . 117.57(11)
O13 C5 N4 . . 120.55(12)
O13 C5 C6 . . 122.49(12)
N4 C5 C6 . . 116.94(11)
C12 C6 C7 . . 120.47(11)
C12 C6 C5 . . 119.99(12)
C7 C6 C5 . . 119.54(11)
C6 C7 C8 . . 121.69(11)
C6 C7 C7 . 2_675 119.23(14)
C8 C7 C7 . 2_675 119.08(15)
C11 C8 C7 . . 120.66(11)
C11 C8 C9 . . 119.80(11)
C7 C8 C9 . . 119.53(11)
O10 C9 N4 . . 120.51(12)
O10 C9 C8 . . 122.69(12)
N4 C9 C8 . . 116.78(11)
C8 C11 C12 . 2_675 120.09(12)
C8 C11 H11 . . 120.0
C12 C11 H11 2_675 . 120.0
C6 C12 C11 . 2_675 120.48(12)
C6 C12 H12 . . 119.8
C11 C12 H12 2_675 . 119.8
C1 O14 H14 . . 109.5
O16 C17 N18 . . 124.78(13)
O16 C17 H17 . . 117.6
N18 C17 H17 . . 117.6
C17 N18 C19 . . 121.57(12)
C17 N18 C20 . . 121.19(12)
C19 N18 C20 . . 117.23(12)
N18 C19 H19A . . 109.5
N18 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
N18 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
N18 C20 H20A . . 109.5
N18 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
N18 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O15 . 1.2065(17)
C1 O14 . 1.3189(16)
C1 C2 . 1.5025(18)
C2 C3 . 1.5198(18)
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 N4 . 1.4779(16)
C3 H3A . 0.9900
C3 H3B . 0.9900
N4 C5 . 1.3924(17)
N4 C9 . 1.3997(17)
C5 O13 . 1.2205(16)
C5 C6 . 1.4847(18)
C6 C12 . 1.3764(18)
C6 C7 . 1.4079(18)
C7 C8 . 1.4098(17)
C7 C7 2_675 1.420(2)
C8 C11 . 1.3769(18)
C8 C9 . 1.4847(18)
C9 O10 . 1.2175(16)
C11 C12 2_675 1.4041(18)
C11 H11 . 0.9500
C12 C11 2_675 1.4041(18)
C12 H12 . 0.9500
O14 H14 . 0.8400
O16 C17 . 1.2400(17)
C17 N18 . 1.3221(18)
C17 H17 . 0.9500
N18 C19 . 1.4490(18)
N18 C20 . 1.4556(19)
C19 H19A . 0.9800
C19 H19B . 0.9800
C19 H19C . 0.9800
C20 H20A . 0.9800
C20 H20B . 0.9800
C20 H20C . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O14 H14 O16 0.84 1.80 2.6315(14) 173
