#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:08:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180413 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/82/7208226.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_7208226
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 H12 N2, 2(C10 H6 O4)'
_chemical_formula_sum            'C32 H24 N2 O8'
_chemical_formula_weight         564.53
_chemical_name_systematic
'coumarin-3-carboxylic acid+4,4'-bipyridylethane'
_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                 103.209(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.3933(6)
_cell_length_b                   4.8921(2)
_cell_length_c                   16.5326(8)
_cell_measurement_reflns_used    7038
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1290.80(10)
_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 0.995
_diffrn_measured_fraction_theta_max 0.975
_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  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8351
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.72
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.837
_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    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0445
_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)+(0.0599P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                1678
_reflns_number_total             2884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25217a.txt
_cod_data_source_block           wj1113
_cod_original_cell_volume        1290.80(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7208226
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
C1 C 0.26928(9) 1.3640(4) 0.33104(9) 0.0379(4) Uani 1 1 d .
H1 H 0.2424 1.5047 0.2950 0.045 Uiso 1 1 calc R
C2 C 0.22411(9) 1.2155(4) 0.37661(9) 0.0350(4) Uani 1 1 d .
H2 H 0.1664 1.2524 0.3721 0.042 Uiso 1 1 calc R
C3 C 0.26390(9) 1.0135(3) 0.42852(9) 0.0300(4) Uani 1 1 d .
C4 C 0.25038(9) 0.6689(4) 0.53074(9) 0.0350(4) Uani 1 1 d .
C5 C 0.33940(8) 0.6029(3) 0.53907(8) 0.0287(4) Uani 1 1 d .
C6 C 0.38397(9) 0.7392(3) 0.49276(9) 0.0305(4) Uani 1 1 d .
H6 H 0.4412 0.6924 0.4979 0.037 Uiso 1 1 calc R
C7 C 0.34836(9) 0.9512(3) 0.43629(8) 0.0289(4) Uani 1 1 d .
C8 C 0.39286(9) 1.1037(3) 0.38848(9) 0.0331(4) Uani 1 1 d .
H8 H 0.4502 1.0638 0.3916 0.040 Uiso 1 1 calc R
C9 C 0.35432(10) 1.3096(4) 0.33736(9) 0.0372(4) Uani 1 1 d .
H9 H 0.3852 1.4148 0.3064 0.045 Uiso 1 1 calc R
C10 C 0.38181(9) 0.3855(4) 0.59759(9) 0.0324(4) Uani 1 1 d .
C11 C 0.64582(10) 0.2600(4) 0.22395(10) 0.0460(5) Uani 1 1 d .
H11 H 0.7039 0.2671 0.2497 0.055 Uiso 1 1 calc R
C12 C 0.61622(10) 0.4218(4) 0.15542(10) 0.0443(5) Uani 1 1 d .
H12 H 0.6536 0.5371 0.1350 0.053 Uiso 1 1 calc R
C13 C 0.53232(9) 0.4166(3) 0.11638(8) 0.0323(4) Uani 1 1 d .
C14 C 0.48161(10) 0.2437(4) 0.15024(10) 0.0405(4) Uani 1 1 d .
H14 H 0.4233 0.2333 0.1260 0.049 Uiso 1 1 calc R
C15 C 0.51574(9) 0.0880(4) 0.21862(9) 0.0412(4) Uani 1 1 d .
H15 H 0.4799 -0.0294 0.2405 0.049 Uiso 1 1 calc R
C16 C 0.49875(9) 0.5823(4) 0.03930(8) 0.0375(4) Uani 1 1 d .
H16B H 0.5326 0.7505 0.0408 0.045 Uiso 1 1 calc R
H16A H 0.4403 0.6373 0.0377 0.045 Uiso 1 1 calc R
N1 N 0.59697(8) 0.0943(3) 0.25578(7) 0.0372(4) Uani 1 1 d .
O1 O 0.45777(6) 0.3618(3) 0.61362(7) 0.0488(4) Uani 1 1 d .
O2 O 0.33176(6) 0.2294(3) 0.62800(7) 0.0421(3) Uani 1 1 d .
H2A H 0.3601 0.1300 0.6655 0.104(9) Uiso 1 1 calc R
O3 O 0.20228(7) 0.5708(3) 0.56743(8) 0.0545(4) Uani 1 1 d .
O4 O 0.21702(6) 0.8704(2) 0.47363(6) 0.0340(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
_geom_angle_site_symmetry_3
C2 C1 C9 120.63(15) . .
C2 C1 H1 119.7 . .
C9 C1 H1 119.7 . .
C3 C2 C1 118.92(14) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 O4 117.39(12) . .
C2 C3 C7 122.34(14) . .
O4 C3 C7 120.27(14) . .
O3 C4 O4 115.21(13) . .
O3 C4 C5 128.16(15) . .
O4 C4 C5 116.63(13) . .
C6 C5 C4 119.54(14) . .
C6 C5 C10 119.07(13) . .
C4 C5 C10 121.38(13) . .
C5 C6 C7 122.44(13) . .
C5 C6 H6 118.8 . .
C7 C6 H6 118.8 . .
C3 C7 C8 117.65(14) . .
C3 C7 C6 117.90(13) . .
C8 C7 C6 124.45(13) . .
C9 C8 C7 120.70(14) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C8 C9 C1 119.74(15) . .
C8 C9 H9 120.1 . .
C1 C9 H9 120.1 . .
O1 C10 O2 124.27(15) . .
O1 C10 C5 120.57(14) . .
O2 C10 C5 115.16(13) . .
N1 C11 C12 123.06(15) . .
N1 C11 H11 118.5 . .
C12 C11 H11 118.5 . .
C11 C12 C13 120.06(15) . .
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 . .
C12 C13 C14 116.53(14) . .
C12 C13 C16 121.26(14) . .
C14 C13 C16 122.17(14) . .
C15 C14 C13 120.06(14) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
N1 C15 C14 122.89(15) . .
N1 C15 H15 118.6 . .
C14 C15 H15 118.6 . .
C13 C16 C16 111.00(17) . 3_665
C13 C16 H16B 109.4 . .
C16 C16 H16B 109.4 3_665 .
C13 C16 H16A 109.4 . .
C16 C16 H16A 109.4 3_665 .
H16B C16 H16A 108.0 . .
C11 N1 C15 117.40(14) . .
C10 O2 H2A 109.5 . .
C3 O4 C4 123.17(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.378(2) .
C1 C9 1.399(2) .
C1 H1 0.9500 .
C2 C3 1.372(2) .
C2 H2 0.9500 .
C3 O4 1.3780(17) .
C3 C7 1.395(2) .
C4 O3 1.1995(18) .
C4 O4 1.3878(19) .
C4 C5 1.470(2) .
C5 C6 1.349(2) .
C5 C10 1.498(2) .
C6 C7 1.428(2) .
C6 H6 0.9500 .
C7 C8 1.406(2) .
C8 C9 1.373(2) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 O1 1.2180(16) .
C10 O2 1.3026(18) .
C11 N1 1.330(2) .
C11 C12 1.376(2) .
C11 H11 0.9500 .
C12 C13 1.380(2) .
C12 H12 0.9500 .
C13 C14 1.390(2) .
C13 C16 1.505(2) .
C14 C15 1.372(2) .
C14 H14 0.9500 .
C15 N1 1.3334(19) .
C15 H15 0.9500 .
C16 C16 1.537(3) 3_665
C16 H16B 0.9900 .
C16 H16A 0.9900 .
O2 H2A 0.8400 .
