#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:08:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180413 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/82/7208227.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_7208227
loop_
_publ_author_name
'Yan, Dongpeng'
'Delori, Amit'
'Lloyd, Gareth O.'
'Patel, Bhavnita'
'Friščić, Tomislav'
'Day, Graeme M.'
'Bučar, Dejan-Krešimir'
'Jones, William'
'Lu, Jun'
'Wei, Min'
'Evans, David G.'
'Duan, Xue'
_publ_section_title
;
 Modification of luminescent properties of a coumarin derivative by
 formation of multi-component crystals
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              5121
_journal_paper_doi               10.1039/c2ce25217a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C12 H10 N2, 2(C10 H6 O4)'
_chemical_formula_sum            'C32 H22 N2 O8'
_chemical_formula_weight         562.52
_chemical_name_systematic
'coumarin-3-carboxylic acid+4,4'-bipyridylethene'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.9180(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.2227(4)
_cell_length_b                   5.02570(10)
_cell_length_c                   16.3150(5)
_cell_measurement_reflns_used    5288
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.00
_cell_volume                     1306.09(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8761
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.79
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.4609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                1884
_reflns_number_total             2288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25217a.txt
_cod_data_source_block           wj1108
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7208227
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60677(11) -0.0909(3) 0.61484(10) 0.0352(4) Uani 1 1 d . . .
H1 H 0.5487 -0.0589 0.6126 0.042 Uiso 1 1 calc R . .
C2 C 0.64708(12) -0.2891(3) 0.66576(10) 0.0398(4) Uani 1 1 d . . .
H2 H 0.6165 -0.3956 0.6977 0.048 Uiso 1 1 calc R . .
C3 C 0.73227(12) -0.3328(3) 0.67037(10) 0.0426(5) Uani 1 1 d . . .
H3 H 0.7597 -0.4686 0.7060 0.051 Uiso 1 1 calc R . .
C4 C 0.77779(11) -0.1821(3) 0.62404(10) 0.0396(4) Uani 1 1 d . . .
H4 H 0.8362 -0.2114 0.6278 0.048 Uiso 1 1 calc R . .
C5 C 0.73637(10) 0.0130(3) 0.57175(9) 0.0312(4) Uani 1 1 d . . .
C6 C 0.74781(10) 0.3399(3) 0.46568(11) 0.0372(4) Uani 1 1 d . . .
C7 C 0.65944(9) 0.4043(3) 0.46232(9) 0.0293(4) Uani 1 1 d . . .
C8 C 0.61480(9) 0.2698(3) 0.51010(9) 0.0294(4) Uani 1 1 d . . .
H8 H 0.5572 0.3124 0.5066 0.035 Uiso 1 1 calc R . .
C9 C 0.65140(9) 0.0635(3) 0.56637(9) 0.0293(4) Uani 1 1 d . . .
C10 C 0.61727(10) 0.6174(3) 0.40485(9) 0.0317(4) Uani 1 1 d . . .
C1' C 0.0229(7) 0.486(2) 0.7177(5) 0.0592(18) Uani 0.65 1 d P A 1
H1' H -0.0074 0.6086 0.7449 0.071 Uiso 0.65 1 calc PR A 1
C2' C -0.0165(2) 0.3969(7) 0.6391(2) 0.0460(11) Uani 0.65 1 d P A 1
H2' H -0.0691 0.4668 0.6120 0.055 Uiso 0.65 1 calc PR A 1
C3' C 0.02504(19) 0.1996(7) 0.60211(18) 0.0317(7) Uani 0.65 1 d P A 1
C4' C 0.1017(2) 0.1176(7) 0.6464(2) 0.0374(8) Uani 0.65 1 d P A 1
H4' H 0.1327 -0.0169 0.6247 0.045 Uiso 0.65 1 calc PR A 1
C5' C 0.1334(3) 0.2349(14) 0.7238(4) 0.0406(11) Uani 0.65 1 d P A 1
H5' H 0.1861 0.1737 0.7534 0.049 Uiso 0.65 1 calc PR A 1
C6' C -0.01399(16) 0.1009(6) 0.51975(16) 0.0363(6) Uani 0.65 1 d P . 1
H6' H -0.0634 0.1883 0.4922 0.044 Uiso 0.65 1 calc PR . 1
C1" C 0.0211(11) 0.487(3) 0.7045(11) 0.0338(7) Uiso 0.35 1 d P B 2
H1" H -0.0134 0.6310 0.7153 0.041 Uiso 0.35 1 calc PR B 2
C2" C 0.0013(5) 0.3178(16) 0.6321(5) 0.0338(7) Uiso 0.35 1 d P B 2
H2" H -0.0516 0.3448 0.5964 0.041 Uiso 0.35 1 calc PR B 2
C3" C 0.0517(5) 0.1205(13) 0.6096(5) 0.0338(7) Uiso 0.35 1 d P B 2
C4" C 0.1256(5) 0.0693(15) 0.6639(5) 0.0338(7) Uiso 0.35 1 d P B 2
H4" H 0.1607 -0.0705 0.6515 0.041 Uiso 0.35 1 calc PR B 2
C5" C 0.1500(8) 0.212(3) 0.7345(8) 0.0338(7) Uiso 0.35 1 d P B 2
H5" H 0.2027 0.1767 0.7694 0.041 Uiso 0.35 1 calc PR B 2
C6" C 0.0303(3) -0.0285(11) 0.5321(3) 0.0338(7) Uiso 0.35 1 d P . 2
H6" H 0.0631 -0.1821 0.5269 0.041 Uiso 0.35 1 calc PR . 2
N1' N 0.09669(9) 0.4180(3) 0.75737(8) 0.0422(7) Uani 0.65 1 d P A 1
N1" N 0.09669(9) 0.4180(3) 0.75737(8) 0.0338(7) Uiso 0.35 1 d P B 2
O1 O 0.54102(7) 0.6273(3) 0.38632(8) 0.0496(4) Uani 1 1 d . . .
O2 O 0.66798(7) 0.7843(2) 0.37870(7) 0.0387(3) Uani 1 1 d . . .
H2A H 0.6407 0.8803 0.3409 0.046 Uiso 1 1 calc R . .
O3 O 0.79399(8) 0.4248(3) 0.42265(10) 0.0639(5) Uani 1 1 d . . .
O4 O 0.78305(7) 0.1545(2) 0.52526(7) 0.0373(3) 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
C2 C1 C9 120.15(16) .
C2 C1 H1 119.9 .
C9 C1 H1 119.9 .
C1 C2 C3 120.05(16) .
C1 C2 H2 120.0 .
C3 C2 H2 120.0 .
C4 C3 C2 120.97(16) .
C4 C3 H3 119.5 .
C2 C3 H3 119.5 .
C3 C4 C5 118.56(16) .
C3 C4 H4 120.7 .
C5 C4 H4 120.7 .
O4 C5 C4 116.99(14) .
O4 C5 C9 121.16(14) .
C4 C5 C9 121.86(15) .
O3 C6 O4 115.38(14) .
O3 C6 C7 128.13(16) .
O4 C6 C7 116.48(14) .
C8 C7 C6 120.01(14) .
C8 C7 C10 119.34(14) .
C6 C7 C10 120.65(14) .
C7 C8 C9 122.09(14) .
C7 C8 H8 119.0 .
C9 C8 H8 119.0 .
C5 C9 C1 118.41(14) .
C5 C9 C8 117.24(14) .
C1 C9 C8 124.35(14) .
O1 C10 O2 124.60(15) .
O1 C10 C7 120.37(15) .
O2 C10 C7 115.02(13) .
N1' C1' C2' 126.6(8) .
N1' C1' H1' 116.7 .
C2' C1' H1' 116.7 .
C1' C2' C3' 116.7(5) .
C1' C2' H2' 121.7 .
C3' C2' H2' 121.6 .
C4' C3' C2' 116.5(3) .
C4' C3' C6' 124.9(3) .
C2' C3' C6' 118.5(3) .
C3' C4' C5' 119.2(3) .
C3' C4' H4' 120.4 .
C5' C4' H4' 120.4 .
N1' C5' C4' 124.7(3) .
N1' C5' H5' 117.6 .
C4' C5' H5' 117.6 .
C6' C6' C3' 125.3(3) 3_556
C6' C6' H6' 117.3 3_556
C3' C6' H6' 117.3 .
C2" C1" H1" 123.5 .
C3" C2" C1" 126.2(9) .
C3" C2" H2" 116.9 .
C1" C2" H2" 116.9 .
C4" C3" C2" 116.9(7) .
C4" C3" C6" 120.0(7) .
C2" C3" C6" 123.1(8) .
C5" C4" C3" 121.9(8) .
C5" C4" H4" 119.1 .
C3" C4" H4" 119.1 .
C4" C5" H5" 119.7 .
C6" C6" C3" 126.5(7) 3_556
C6" C6" H6" 116.7 3_556
C3" C6" H6" 116.7 .
C5' N1' C1' 116.0(5) .
C10 O2 H2A 109.5 .
C5 O4 C6 122.60(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.380(2) .
C1 C9 1.403(2) .
C1 H1 0.9500 .
C2 C3 1.387(3) .
C2 H2 0.9500 .
C3 C4 1.379(2) .
C3 H3 0.9500 .
C4 C5 1.387(2) .
C4 H4 0.9500 .
C5 O4 1.3681(19) .
C5 C9 1.388(2) .
C6 O3 1.198(2) .
C6 O4 1.389(2) .
C6 C7 1.460(2) .
C7 C8 1.343(2) .
C7 C10 1.501(2) .
C8 C9 1.437(2) .
C8 H8 0.9500 .
C10 O1 1.2175(19) .
C10 O2 1.3019(19) .
C1' N1' 1.294(10) .
C1' C2' 1.393(10) .
C1' H1' 0.9500 .
C2' C3' 1.399(4) .
C2' H2' 0.9500 .
C3' C4' 1.377(4) .
C3' C6' 1.460(4) .
C4' C5' 1.400(7) .
C4' H4' 0.9500 .
C5' N1' 1.275(7) .
C5' H5' 0.9500 .
C6' C6' 1.327(5) 3_556
C6' H6' 0.9500 .
C1" C2" 1.44(2) .
C1" H1" 0.9500 .
C2" C3" 1.378(9) .
C2" H2" 0.9500 .
C3" C4" 1.374(9) .
C3" C6" 1.455(10) .
C4" C5" 1.351(17) .
C4" H4" 0.9500 .
C5" H5" 0.9500 .
C6" C6" 1.325(10) 3_556
C6" H6" 0.9500 .
O2 H2A 0.8400 .
