#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/21/2202199.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_2202199
loop_
_publ_author_name
'Dale, Sophie H.'
'Elsegood, Mark R. J.'
_publ_section_title
;
 Trimesic acid bis(N,N-dimethylformamide) solvate at 150K
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o127
_journal_page_last               o128
_journal_paper_doi               10.1107/S160053680300076X
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C15 H20 N2 O8'
_chemical_formula_moiety         'C15 H20 N2 O8'
_chemical_formula_sum            'C15 H20 N2 O8'
_chemical_formula_weight         356.33
_chemical_name_systematic
;
Trimesic acid bis(N,N-dimethylformamide) solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   'Geom except OH coords freely refined'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'All non-H atoms found by direct methods'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.719(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6529(18)
_cell_length_b                   14.4143(16)
_cell_length_c                   7.2310(8)
_cell_measurement_reflns_used    1416
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.45
_cell_volume                     1735.6(3)
_computing_cell_refinement       'SAINT (Siemens, 1994)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0740
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8644
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.219
_refine_ls_extinction_coef       0.0005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0514
_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)+(0.0475P)²+0.6362P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                1664
_reflns_number_total             3064
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6132.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202199
_cod_database_fobs_code          2202199
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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 0.33564(17) 0.6428(2) -0.0696(4) 0.0220(7) Uani d . 1 . . C
C2 0.27185(17) 0.6966(2) -0.0084(4) 0.0208(7) Uani d . 1 . . C
H2 0.2242 0.6673 0.0326 0.025 Uiso calc R 1 . . H
C3 0.27729(17) 0.7922(2) -0.0067(4) 0.0206(7) Uani d . 1 . . C
C4 0.34667(17) 0.8353(2) -0.0695(4) 0.0234(7) Uani d . 1 . . C
H4 0.3502 0.9010 -0.0704 0.028 Uiso calc R 1 . . H
C5 0.41113(18) 0.7819(2) -0.1313(4) 0.0223(7) Uani d . 1 . . C
C6 0.40506(17) 0.6859(2) -0.1303(4) 0.0220(7) Uani d . 1 . . C
H6 0.4488 0.6493 -0.1715 0.026 Uiso calc R 1 . . H
C7 0.33008(18) 0.5389(2) -0.0747(4) 0.0251(8) Uani d . 1 . . C
O1 0.38163(13) 0.48977(15) -0.1405(3) 0.0345(6) Uani d . 1 . . O
O2 0.26379(13) 0.50821(15) -0.0014(3) 0.0316(6) Uani d . 1 . . O
H2A 0.260(2) 0.455(3) -0.019(5) 0.047 Uiso d . 1 . . H
C8 0.21036(18) 0.8513(2) 0.0593(4) 0.0238(8) Uani d . 1 . . C
O3 0.14420(13) 0.80494(16) 0.0989(3) 0.0328(6) Uani d . 1 . . O
H3 0.105(2) 0.839(3) 0.135(5) 0.049 Uiso d . 1 . . H
O4 0.21653(13) 0.93499(15) 0.0756(3) 0.0319(6) Uani d . 1 . . O
C9 0.48552(19) 0.8249(2) -0.2024(4) 0.0270(8) Uani d . 1 . . C
O5 0.48175(14) 0.91764(16) -0.2115(3) 0.0375(6) Uani d . 1 . . O
H5 0.527(2) 0.936(3) -0.252(5) 0.056 Uiso d . 1 . . H
O6 0.54328(13) 0.78065(16) -0.2484(3) 0.0418(7) Uani d . 1 . . O
O7 0.23200(13) 0.33931(16) -0.0409(3) 0.0399(7) Uani d . 1 . . O
C10 0.2856(2) 0.2795(2) -0.0544(5) 0.0332(9) Uani d . 1 . . C
H10 0.3399 0.2995 -0.0583 0.040 Uiso calc R 1 . . H
N1 0.27062(16) 0.18998(18) -0.0638(4) 0.0321(7) Uani d . 1 . . N
C11 0.3350(2) 0.1219(2) -0.0824(5) 0.0428(10) Uani d . 1 . . C
H11A 0.3861 0.1542 -0.0996 0.064 Uiso calc R 1 . . H
H11B 0.3238 0.0822 -0.1897 0.064 Uiso calc R 1 . . H
H11C 0.3382 0.0837 0.0295 0.064 Uiso calc R 1 . . H
C12 0.1889(2) 0.1561(3) -0.0598(6) 0.0538(11) Uani d . 1 . . C
H12A 0.1556 0.1995 0.0100 0.081 Uiso calc R 1 . . H
H12B 0.1878 0.0951 -0.0002 0.081 Uiso calc R 1 . . H
H12C 0.1678 0.1508 -0.1866 0.081 Uiso calc R 1 . . H
O8 0.02931(13) 0.91508(17) 0.2006(3) 0.0419(7) Uani d . 1 . . O
C13 0.0486(2) 0.9956(3) 0.2403(5) 0.0366(9) Uani d . 1 . . C
H13 0.1039 1.0114 0.2333 0.044 Uiso calc R 1 . . H
N2 -0.00169(16) 1.0615(2) 0.2917(4) 0.0336(7) Uani d . 1 . . N
C14 -0.0872(2) 1.0426(3) 0.3040(6) 0.0569(12) Uani d . 1 . . C
H14A -0.1149 1.0677 0.1947 0.085 Uiso calc R 1 . . H
H14B -0.1084 1.0718 0.4156 0.085 Uiso calc R 1 . . H
H14C -0.0958 0.9754 0.3100 0.085 Uiso calc R 1 . . H
C15 0.0248(3) 1.1553(3) 0.3322(6) 0.0626(13) Uani d . 1 . . C
H15A 0.0836 1.1580 0.3287 0.094 Uiso calc R 1 . . H
H15B 0.0066 1.1732 0.4555 0.094 Uiso calc R 1 . . H
H15C 0.0021 1.1979 0.2398 0.094 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
C6 C1 C2 119.5(3)
C6 C1 C7 119.3(3)
C2 C1 C7 121.1(3)
C3 C2 C1 120.6(3)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 119.8(3)
C2 C3 C8 121.7(3)
C4 C3 C8 118.6(3)
C3 C4 C5 120.2(3)
C3 C4 H4 119.9
C5 C4 H4 119.9
C6 C5 C4 119.4(3)
C6 C5 C9 118.6(3)
C4 C5 C9 122.0(3)
C1 C6 C5 120.6(3)
C1 C6 H6 119.7
C5 C6 H6 119.7
O1 C7 O2 124.4(3)
O1 C7 C1 123.2(3)
O2 C7 C1 112.3(3)
C7 O2 H2A 109(3)
O4 C8 O3 123.3(3)
O4 C8 C3 122.4(3)
O3 C8 C3 114.3(3)
C8 O3 H3 115(2)
O6 C9 O5 123.5(3)
O6 C9 C5 123.3(3)
O5 C9 C5 113.2(3)
C9 O5 H5 106(3)
O7 C10 N1 123.2(3)
O7 C10 H10 118.4
N1 C10 H10 118.4
C10 N1 C12 120.5(3)
C10 N1 C11 121.7(3)
C12 N1 C11 117.9(3)
N1 C11 H11A 109.5
N1 C11 H11B 109.5
H11A C11 H11B 109.5
N1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N1 C12 H12A 109.5
N1 C12 H12B 109.5
H12A C12 H12B 109.5
N1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O8 C13 N2 125.1(3)
O8 C13 H13 117.5
N2 C13 H13 117.5
C13 N2 C15 122.2(3)
C13 N2 C14 120.5(3)
C15 N2 C14 117.3(3)
N2 C14 H14A 109.5
N2 C14 H14B 109.5
H14A C14 H14B 109.5
N2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N2 C15 H15A 109.5
N2 C15 H15B 109.5
H15A C15 H15B 109.5
N2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 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
C1 C6 . 1.388(4) ?
C1 C2 . 1.392(4) ?
C1 C7 . 1.500(4) ?
C2 C3 . 1.382(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.393(4) ?
C3 C8 . 1.486(4) ?
C4 C5 . 1.398(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.388(4) ?
C5 C9 . 1.483(4) ?
C6 H6 . 0.9500 ?
C7 O1 . 1.215(4) ?
C7 O2 . 1.308(4) ?
O2 H2A . 0.79(4) ?
C8 O4 . 1.217(4) ?
C8 O3 . 1.323(4) ?
O3 H3 . 0.85(4) ?
C9 O6 . 1.204(4) ?
C9 O5 . 1.340(4) ?
O5 H5 . 0.86(4) ?
O7 C10 . 1.245(4) ?
C10 N1 . 1.316(4) ?
C10 H10 . 0.9500 ?
N1 C12 . 1.447(4) ?
N1 C11 . 1.460(4) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
O8 C13 . 1.238(4) ?
C13 N2 . 1.323(4) ?
C13 H13 . 0.9500 ?
N2 C15 . 1.451(5) ?
N2 C14 . 1.453(4) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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
O2 H2A O7 . 0.79(4) 1.73(4) 2.507(3) 168(4)
O3 H3 O8 . 0.85(4) 1.75(4) 2.599(3) 176(4)
O5 H5 O1 2_654 0.86(4) 1.88(4) 2.732(3) 171(4)
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
C6 C1 C2 C3 -0.4(5)
C7 C1 C2 C3 -179.1(3)
C1 C2 C3 C4 1.0(5)
C1 C2 C3 C8 -179.5(3)
C2 C3 C4 C5 -1.0(5)
C8 C3 C4 C5 179.5(3)
C3 C4 C5 C6 0.4(4)
C3 C4 C5 C9 178.9(3)
C2 C1 C6 C5 -0.3(5)
C7 C1 C6 C5 178.4(3)
C4 C5 C6 C1 0.3(5)
C9 C5 C6 C1 -178.3(3)
C6 C1 C7 O1 -4.7(5)
C2 C1 C7 O1 174.0(3)
C6 C1 C7 O2 175.5(3)
C2 C1 C7 O2 -5.8(4)
C2 C3 C8 O4 174.0(3)
C4 C3 C8 O4 -6.5(5)
C2 C3 C8 O3 -5.8(4)
C4 C3 C8 O3 173.6(3)
C6 C5 C9 O6 -5.0(5)
C4 C5 C9 O6 176.5(3)
C6 C5 C9 O5 174.6(3)
C4 C5 C9 O5 -4.0(4)
O7 C10 N1 C12 0.5(5)
O7 C10 N1 C11 179.1(3)
O8 C13 N2 C15 -178.5(4)
O8 C13 N2 C14 -0.5(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131938
