#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:08:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180413 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/82/7208228.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_7208228
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         'C10 H5 O4, C5 H8 N3'
_chemical_formula_sum            'C15 H13 N3 O4'
_chemical_formula_weight         299.28
_chemical_name_systematic
'coumarin-3-carboxylic acid+pyridine-2,6-diamine'
_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                 90.383(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8797(2)
_cell_length_b                   12.9776(5)
_cell_length_c                   7.3847(6)
_cell_measurement_reflns_used    3814
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      1.00
_cell_volume                     1330.14(12)
_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 0.995
_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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7181
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.23
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.008
_exptl_absorpt_correction_T_min  0.885
_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    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0343
_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)+(0.0312P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                1614
_reflns_number_total             2398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25217a.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7208228
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
C1 C 0.03855(12) 0.01870(13) 0.2609(2) 0.0412(4) Uani 1 1 d
C2 C -0.01905(12) 0.09887(13) 0.1991(2) 0.0393(4) Uani 1 1 d
C3 C 0.01196(11) 0.19945(13) 0.2111(2) 0.0348(4) Uani 1 1 d
C4 C 0.10170(10) 0.21908(10) 0.28602(18) 0.0263(3) Uani 1 1 d
C5 C 0.21910(10) 0.35013(11) 0.36815(17) 0.0274(3) Uani 1 1 d
C6 C 0.28232(10) 0.26853(10) 0.43388(17) 0.0236(3) Uani 1 1 d
C7 C 0.25329(10) 0.16960(11) 0.42134(17) 0.0257(3) Uani 1 1 d
C8 C 0.16156(10) 0.14094(10) 0.34819(17) 0.0257(3) Uani 1 1 d
C9 C 0.12791(12) 0.03947(12) 0.33475(19) 0.0355(4) Uani 1 1 d
C10 C 0.38045(11) 0.29296(11) 0.51509(17) 0.0278(4) Uani 1 1 d
C11 C 0.22730(11) 0.75109(13) 0.61041(19) 0.0335(4) Uani 1 1 d
C12 C 0.27050(11) 0.65692(12) 0.63876(18) 0.0326(4) Uani 1 1 d
C13 C 0.35940(11) 0.65483(11) 0.72514(18) 0.0285(4) Uani 1 1 d
C14 C 0.35898(10) 0.83849(11) 0.74815(17) 0.0258(3) Uani 1 1 d
C15 C 0.26912(11) 0.84207(12) 0.66438(18) 0.0313(4) Uani 1 1 d
H1 H 0.0144(11) -0.0533(12) 0.2554(17) 0.054(5) Uiso 1 1 d
H2 H -0.0812(11) 0.0817(10) 0.1453(18) 0.044(4) Uiso 1 1 d
H3 H -0.0252(11) 0.2556(11) 0.1665(18) 0.041(4) Uiso 1 1 d
H7 H 0.2979(9) 0.1186(9) 0.4642(16) 0.025(4) Uiso 1 1 d
H9 H 0.1688(10) -0.0157(11) 0.3780(17) 0.041(4) Uiso 1 1 d
H11 H 0.1649(11) 0.7533(11) 0.5482(18) 0.039(4) Uiso 1 1 d
H12 H 0.2424(10) 0.5948(10) 0.5973(16) 0.031(4) Uiso 1 1 d
H15 H 0.2390(11) 0.9050(11) 0.6470(18) 0.041(4) Uiso 1 1 d
H1A H 0.3897(11) 0.5101(13) 0.705(2) 0.063(6) Uiso 1 1 d
H2A H 0.4641(12) 0.9097(11) 0.8673(19) 0.047(5) Uiso 1 1 d
H3A H 0.4641(12) 0.7414(10) 0.8361(19) 0.041(4) Uiso 1 1 d
H1B H 0.4646(12) 0.5714(11) 0.814(2) 0.042(5) Uiso 1 1 d
H2B H 0.3751(11) 0.9780(12) 0.8237(19) 0.056(6) Uiso 1 1 d
N1 N 0.40711(11) 0.56735(10) 0.76848(19) 0.0382(4) Uani 1 1 d
N2 N 0.40870(10) 0.92161(10) 0.80378(16) 0.0317(3) Uani 1 1 d
N3 N 0.40111(9) 0.74515(8) 0.77470(15) 0.0258(3) Uani 1 1 d
O1 O 0.42941(7) 0.21649(8) 0.56471(13) 0.0377(3) Uani 1 1 d
O2 O 0.40584(7) 0.38504(7) 0.52893(12) 0.0390(3) Uani 1 1 d
O3 O 0.23312(7) 0.44203(7) 0.36553(14) 0.0418(3) Uani 1 1 d
O4 O 0.13015(7) 0.32033(7) 0.29702(12) 0.0300(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
C9 C1 C2 119.91(16)
C9 C1 H1 120.2(9)
C2 C1 H1 119.9(9)
C3 C2 C1 120.68(16)
C3 C2 H2 121.3(8)
C1 C2 H2 118.0(9)
C2 C3 C4 118.72(16)
C2 C3 H3 122.4(9)
C4 C3 H3 118.9(9)
O4 C4 C3 117.21(13)
O4 C4 C8 120.54(12)
C3 C4 C8 122.24(14)
O3 C5 O4 114.23(12)
O3 C5 C6 128.76(13)
O4 C5 C6 117.01(12)
C7 C6 C5 119.35(13)
C7 C6 C10 119.53(12)
C5 C6 C10 121.12(12)
C6 C7 C8 122.60(13)
C6 C7 H7 116.3(7)
C8 C7 H7 121.1(7)
C4 C8 C9 117.73(13)
C4 C8 C7 117.71(13)
C9 C8 C7 124.57(14)
C1 C9 C8 120.72(16)
C1 C9 H9 120.7(8)
C8 C9 H9 118.5(8)
O2 C10 O1 125.43(13)
O2 C10 C6 118.94(13)
O1 C10 C6 115.63(12)
C15 C11 C12 122.42(15)
C15 C11 H11 118.8(9)
C12 C11 H11 118.8(9)
C11 C12 C13 118.23(15)
C11 C12 H12 121.9(8)
C13 C12 H12 119.8(8)
N1 C13 N3 117.02(14)
N1 C13 C12 123.97(15)
N3 C13 C12 118.98(14)
N2 C14 N3 116.87(13)
N2 C14 C15 124.55(14)
N3 C14 C15 118.57(14)
C11 C15 C14 118.48(15)
C11 C15 H15 121.9(9)
C14 C15 H15 119.6(9)
C13 N1 H1A 115.9(10)
C13 N1 H1B 119.3(10)
H1A N1 H1B 119.4(14)
C14 N2 H2A 116.8(9)
C14 N2 H2B 116.5(10)
H2A N2 H2B 120.0(14)
C13 N3 C14 123.29(13)
C13 N3 H3A 117.3(8)
C14 N3 H3A 119.4(8)
C4 O4 C5 122.77(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9 1.378(2)
C1 C2 1.388(2)
C1 H1 0.994(15)
C2 C3 1.377(2)
C2 H2 0.973(15)
C3 C4 1.383(2)
C3 H3 0.950(14)
C4 O4 1.3743(15)
C4 C8 1.3871(19)
C5 O3 1.2086(15)
C5 O4 1.3931(16)
C5 C6 1.4565(19)
C6 C7 1.3487(18)
C6 C10 1.5179(19)
C7 C8 1.4290(19)
C7 H7 0.959(13)
C8 C9 1.4005(19)
C9 H9 0.966(14)
C10 O2 1.2498(15)
C10 O1 1.2560(16)
C11 C15 1.374(2)
C11 C12 1.377(2)
C11 H11 0.978(15)
C12 C13 1.385(2)
C12 H12 0.946(13)
C13 N1 1.3517(18)
C13 N3 1.3565(17)
C14 N2 1.3434(17)
C14 N3 1.3587(16)
C14 C15 1.3893(19)
C15 H15 0.926(14)
N1 H1A 0.909(16)
N1 H1B 0.867(15)
N2 H2A 0.911(16)
N2 H2B 0.881(16)
N3 H3A 0.984(16)
