#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/54/1505449.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1505449
loop_
_publ_author_name
'Mei, Xuefeng'
'Liu, Shuanglong'
'Wolf, Christian'
_publ_section_title
;
 Template-controlled face-to-face stacking of olefinic and aromatic
 carboxylic acids in the solid state.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2729
_journal_page_last               2732
_journal_paper_doi               10.1021/ol071039c
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C24 H18 N2 O4'
_chemical_formula_sum            'C24 H18 N2 O4'
_chemical_formula_weight         398.13
_chemical_name_common            'fumaric acid and template'
_chemical_name_systematic
;
 1,8-dipyridyl naphthalene and fumaric acid
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.375(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5485(18)
_cell_length_b                   13.991(2)
_cell_length_c                   13.000(2)
_cell_measurement_reflns_used    2120
_cell_measurement_temperature    187(2)
_cell_measurement_theta_max      21.228
_cell_measurement_theta_min      2.378
_cell_volume                     1969.1(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      187(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'SMART platform CCD, Siemens/Bruker'
_diffrn_measurement_method       'omega scans'
_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  0.0850
_diffrn_reflns_av_sigmaI/netI    0.1072
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17488
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9551
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.895
_refine_ls_R_factor_all          0.1634
_refine_ls_R_factor_gt           0.0512
_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)+(0.0617P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                2107
_reflns_number_total             4632
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol071039csi20070508_035724.cif
_cod_data_source_block           d:\crysta~1\04037\work\p21onc
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_original_sg_symbol_H-M      P21/c
_cod_database_code               1505449
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.31079(13) 0.14454(11) 0.00074(12) 0.0385(4) Uani 1 1 d .
H1 H 0.2357 0.1598 -0.0216 0.046 Uiso 1 1 calc R
O2 O 0.26794(14) 0.09072(13) 0.14530(13) 0.0462(5) Uani 1 1 d .
O3 O 0.23731(14) -0.08409(13) -0.11040(12) 0.0449(5) Uani 1 1 d .
O4 O 0.28454(14) -0.02609(12) -0.25130(13) 0.0460(5) Uani 1 1 d .
H4 H 0.2092 -0.0118 -0.2754 0.055 Uiso 1 1 calc R
N1 N 0.07152(17) 0.18699(13) -0.07635(16) 0.0388(5) Uani 1 1 d .
N2 N 0.05214(17) 0.02845(14) -0.33124(15) 0.0394(5) Uani 1 1 d .
C1 C -0.32227(19) 0.16303(15) -0.23407(18) 0.0303(5) Uani 1 1 d .
C2 C -0.3898(2) 0.17891(16) -0.16728(19) 0.0356(6) Uani 1 1 d .
H2 H -0.3471 0.1901 -0.0914 0.043 Uiso 1 1 calc R
C3 C -0.5191(2) 0.17931(16) -0.20659(19) 0.0376(6) Uani 1 1 d .
H3 H -0.5630 0.1884 -0.1577 0.045 Uiso 1 1 calc R
C4 C -0.5808(2) 0.16655(15) -0.31529(19) 0.0357(6) Uani 1 1 d .
H4A H -0.6684 0.1701 -0.3428 0.043 Uiso 1 1 calc R
C5 C -0.5842(2) 0.13518(15) -0.50157(18) 0.0356(6) Uani 1 1 d .
H5 H -0.6717 0.1403 -0.5272 0.043 Uiso 1 1 calc R
C6 C -0.5276(2) 0.11576(16) -0.57393(19) 0.0384(6) Uani 1 1 d .
H6 H -0.5741 0.1102 -0.6500 0.046 Uiso 1 1 calc R
C7 C -0.3985(2) 0.10383(16) -0.53530(18) 0.0359(6) Uani 1 1 d .
H7 H -0.3589 0.0887 -0.5862 0.043 Uiso 1 1 calc R
C8 C -0.3281(2) 0.11329(14) -0.42656(18) 0.0298(5) Uani 1 1 d .
C9 C -0.38429(19) 0.14177(14) -0.34829(17) 0.0282(5) Uani 1 1 d .
C10 C -0.5172(2) 0.14809(14) -0.38859(18) 0.0317(5) Uani 1 1 d .
C11 C -0.1858(2) 0.17356(15) -0.18009(17) 0.0304(5) Uani 1 1 d .
C12 C -0.1245(2) 0.12694(15) -0.08150(17) 0.0336(6) Uani 1 1 d .
H12 H -0.1695 0.0893 -0.0475 0.040 Uiso 1 1 calc R
C13 C 0.0017(2) 0.13562(16) -0.03346(19) 0.0384(6) Uani 1 1 d .
H13 H 0.0415 0.1033 0.0339 0.046 Uiso 1 1 calc R
C14 C 0.0121(2) 0.23464(16) -0.16892(19) 0.0394(6) Uani 1 1 d .
H14 H 0.0594 0.2730 -0.1999 0.047 Uiso 1 1 calc R
C15 C -0.1142(2) 0.23111(15) -0.22191(18) 0.0339(6) Uani 1 1 d .
H15 H -0.1521 0.2677 -0.2865 0.041 Uiso 1 1 calc R
C16 C -0.1457(2) 0.01554(15) -0.31244(17) 0.0297(5) Uani 1 1 d .
H16 H -0.1957 -0.0137 -0.2768 0.036 Uiso 1 1 calc R
C17 C -0.0237(2) -0.00873(16) -0.28360(18) 0.0332(6) Uani 1 1 d .
H17 H 0.0090 -0.0544 -0.2268 0.040 Uiso 1 1 calc R
C18 C 0.0026(2) 0.09023(18) -0.4134(2) 0.0437(6) Uani 1 1 d .
H18 H 0.0538 0.1155 -0.4503 0.052 Uiso 1 1 calc R
C19 C -0.1197(2) 0.11912(16) -0.44724(18) 0.0367(6) Uani 1 1 d .
H19 H -0.1509 0.1631 -0.5061 0.044 Uiso 1 1 calc R
C20 C -0.1962(2) 0.08333(15) -0.39443(17) 0.0304(5) Uani 1 1 d .
C21 C 0.3399(2) 0.10255(16) 0.09703(18) 0.0321(5) Uani 1 1 d .
C22 C 0.4704(2) 0.07256(16) 0.14452(18) 0.0345(6) Uani 1 1 d .
H22 H 0.4932 0.0335 0.2082 0.041 Uiso 1 1 calc R
C23 C 0.4424(2) -0.09583(16) -0.10538(18) 0.0349(6) Uani 1 1 d .
H23 H 0.4655 -0.1332 -0.0404 0.042 Uiso 1 1 calc R
C24 C 0.3117(2) -0.06798(16) -0.15521(18) 0.0341(6) Uani 1 1 d .
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
_geom_angle_site_symmetry_1
C21 O1 H1 109.5 .
C24 O4 H4 109.5 .
C14 N1 C13 116.6(2) .
C18 N2 C17 116.9(2) .
C2 C1 C9 119.9(2) .
C2 C1 C11 115.2(2) .
C9 C1 C11 124.83(19) .
C1 C2 C3 122.6(2) .
C1 C2 H2 118.7 .
C3 C2 H2 118.7 .
C4 C3 C2 119.1(2) .
C4 C3 H3 120.4 .
C2 C3 H3 120.4 .
C3 C4 C10 121.2(2) .
C3 C4 H4A 119.4 .
C10 C4 H4A 119.4 .
C6 C5 C10 121.9(2) .
C6 C5 H5 119.1 .
C10 C5 H5 119.1 .
C5 C6 C7 119.1(2) .
C5 C6 H6 120.5 .
C7 C6 H6 120.5 .
C8 C7 C6 122.1(2) .
C8 C7 H7 119.0 .
C6 C7 H7 119.0 .
C7 C8 C9 120.3(2) .
C7 C8 C20 116.3(2) .
C9 C8 C20 123.15(19) .
C1 C9 C8 127.02(19) .
C1 C9 C10 116.6(2) .
C8 C9 C10 116.4(2) .
C5 C10 C4 119.9(2) .
C5 C10 C9 119.9(2) .
C4 C10 C9 120.2(2) .
C12 C11 C15 116.7(2) .
C12 C11 C1 120.1(2) .
C15 C11 C1 123.1(2) .
C13 C12 C11 119.7(2) .
C13 C12 H12 120.2 .
C11 C12 H12 120.2 .
N1 C13 C12 123.7(2) .
N1 C13 H13 118.2 .
C12 C13 H13 118.2 .
N1 C14 C15 123.6(2) .
N1 C14 H14 118.2 .
C15 C14 H14 118.2 .
C14 C15 C11 119.6(2) .
C14 C15 H15 120.2 .
C11 C15 H15 120.2 .
C17 C16 C20 119.7(2) .
C17 C16 H16 120.2 .
C20 C16 H16 120.2 .
N2 C17 C16 123.6(2) .
N2 C17 H17 118.2 .
C16 C17 H17 118.2 .
N2 C18 C19 123.2(2) .
N2 C18 H18 118.4 .
C19 C18 H18 118.4 .
C18 C19 C20 119.5(2) .
C18 C19 H19 120.3 .
C20 C19 H19 120.3 .
C19 C20 C16 117.0(2) .
C19 C20 C8 121.6(2) .
C16 C20 C8 121.33(19) .
O2 C21 O1 123.9(2) .
O2 C21 C22 121.8(2) .
O1 C21 C22 114.21(19) .
C23 C22 C21 125.1(2) 3_655
C23 C22 H22 117.5 3_655
C21 C22 H22 117.5 .
C22 C23 C24 124.7(2) 3_655
C22 C23 H23 117.7 3_655
C24 C23 H23 117.7 .
O3 C24 O4 124.3(2) .
O3 C24 C23 121.8(2) .
O4 C24 C23 113.9(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C21 1.316(2) .
O1 H1 0.8400 .
O2 C21 1.214(2) .
O3 C24 1.215(2) .
O4 C24 1.315(3) .
O4 H4 0.8400 .
N1 C14 1.337(3) .
N1 C13 1.338(3) .
N2 C18 1.338(3) .
N2 C17 1.341(3) .
C1 C2 1.372(3) .
C1 C9 1.437(3) .
C1 C11 1.492(3) .
C2 C3 1.400(3) .
C2 H2 0.9500 .
C3 C4 1.355(3) .
C3 H3 0.9500 .
C4 C10 1.415(3) .
C4 H4A 0.9500 .
C5 C6 1.347(3) .
C5 C10 1.413(3) .
C5 H5 0.9500 .
C6 C7 1.407(3) .
C6 H6 0.9500 .
C7 C8 1.370(3) .
C7 H7 0.9500 .
C8 C9 1.440(3) .
C8 C20 1.492(3) .
C9 C10 1.442(3) .
C11 C12 1.392(3) .
C11 C15 1.393(3) .
C12 C13 1.377(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.381(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C17 1.369(3) .
C16 C20 1.394(3) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C18 C19 1.385(3) .
C18 H18 0.9500 .
C19 C20 1.388(3) .
C19 H19 0.9500 .
C21 C22 1.476(3) .
C22 C23 1.318(3) 3_655
C22 H22 0.9500 .
C23 C22 1.318(3) 3_655
C23 C24 1.473(3) .
C23 H23 0.9500 .
