#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/21/1512130.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_1512130
loop_
_publ_author_name
'Liu, Xiaogang'
'Cole, Jacqueline M.'
'Waddell, Paul G.'
'Lin, Tze-Chia'
'McKechnie, Scott'
_publ_section_title
;
 Molecular Origins of Optoelectronic Properties in Coumarins 343, 314T,
 445, and 522B
;
_journal_issue                   27
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              14130
_journal_paper_doi               10.1021/jp400614e
_journal_volume                  117
_journal_year                    2013
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_chemical_name_common            'Coumarin 343'
_chemical_name_systematic
; 
 11-oxo-2,3,5,6,7,11-hexahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carboxylic acid 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.707(3)
_cell_length_b                   13.875(5)
_cell_length_c                   23.418(8)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.9
_cell_measurement_theta_min      1.7
_cell_volume                     2504.2(16)
_computing_cell_refinement
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_data_collection
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_data_reduction
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_diffrn_measurement_method       'profile data from ω-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  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8873
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 Scaled and merged with Sortav 
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0694
_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)+(0.0915P)²+2.0899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.1873
_reflns_number_gt                2318
_reflns_number_total             2841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp400614e_si_002.cif
_cod_data_source_block           coumarin343_120k
_cod_original_cell_volume        2504.1(15)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1512130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.0651(3) 1.01465(17) 0.38302(9) 0.0265(5) Uani 1 1 d .
C2 C 0.1346(3) 1.11246(16) 0.47112(9) 0.0244(5) Uani 1 1 d .
C3 C 0.1424(3) 1.02280(16) 0.44055(9) 0.0243(5) Uani 1 1 d .
C4 C 0.2243(3) 0.94490(16) 0.46536(9) 0.0252(5) Uani 1 1 d .
H4 H 0.2287 0.8855 0.4452 0.030 Uiso 1 1 calc R
C5 C 0.3867(3) 0.87346(16) 0.54688(9) 0.0259(5) Uani 1 1 d .
H5 H 0.3939 0.8129 0.5281 0.031 Uiso 1 1 calc R
C6 C 0.4594(3) 0.88384(16) 0.59995(10) 0.0258(5) Uani 1 1 d .
C7 C 0.4490(3) 0.97493(16) 0.62857(9) 0.0236(5) Uani 1 1 d .
C8 C 0.3631(3) 1.05442(16) 0.60212(9) 0.0245(5) Uani 1 1 d .
C9 C 0.2931(3) 1.03986(15) 0.54899(9) 0.0231(5) Uani 1 1 d .
C10 C 0.3009(3) 0.95111(16) 0.51934(9) 0.0241(5) Uani 1 1 d .
C11 C 0.5951(3) 0.90476(18) 0.71329(10) 0.0314(5) Uani 1 1 d .
H11A H 0.5672 0.9128 0.7543 0.038 Uiso 1 1 calc R
H11B H 0.7230 0.9060 0.7093 0.038 Uiso 1 1 calc R
C12 C 0.5397(3) 1.07957(18) 0.70947(10) 0.0297(5) Uani 1 1 d .
H12A H 0.6559 1.0835 0.7273 0.036 Uiso 1 1 calc R
H12B H 0.4521 1.0849 0.7402 0.036 Uiso 1 1 calc R
C13 C 0.5511(3) 0.80075(17) 0.62873(10) 0.0291(5) Uani 1 1 d .
H13A H 0.6762 0.8023 0.6191 0.035 Uiso 1 1 calc R
H13B H 0.5025 0.7390 0.6149 0.035 Uiso 1 1 calc R
C14 C 0.5280(3) 0.80817(19) 0.69325(10) 0.0342(6) Uani 1 1 d .
H14A H 0.4037 0.8016 0.7032 0.041 Uiso 1 1 calc R
H14B H 0.5928 0.7557 0.7124 0.041 Uiso 1 1 calc R
C15 C 0.5175(3) 1.16351(17) 0.66837(9) 0.0286(5) Uani 1 1 d .
H15A H 0.6191 1.1673 0.6426 0.034 Uiso 1 1 calc R
H15B H 0.5100 1.2246 0.6900 0.034 Uiso 1 1 calc R
C16 C 0.3522(3) 1.14931(16) 0.63324(9) 0.0278(5) Uani 1 1 d .
H16A H 0.2497 1.1496 0.6587 0.033 Uiso 1 1 calc R
H16B H 0.3395 1.2026 0.6054 0.033 Uiso 1 1 calc R
H3O H -0.006(4) 1.143(2) 0.3909(13) 0.039(8) Uiso 1 1 d .
N1 N 0.5212(2) 0.98549(14) 0.68126(8) 0.0273(4) Uani 1 1 d .
O1 O 0.20945(19) 1.11777(11) 0.52422(6) 0.0257(4) Uani 1 1 d .
O2 O 0.0658(2) 1.18779(12) 0.45416(7) 0.0310(4) Uani 1 1 d .
O3 O -0.0131(2) 1.09347(13) 0.36208(7) 0.0313(4) Uani 1 1 d .
O4 O 0.0728(2) 0.94074(13) 0.35452(7) 0.0324(4) 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
O4 C1 O3 120.3(2)
O4 C1 C3 122.8(2)
O3 C1 C3 116.9(2)
O2 C2 O1 115.17(19)
O2 C2 C3 126.1(2)
O1 C2 C3 118.69(19)
C4 C3 C2 119.2(2)
C4 C3 C1 120.6(2)
C2 C3 C1 120.24(19)
C3 C4 C10 121.7(2)
C3 C4 H4 119.1
C10 C4 H4 119.1
C6 C5 C10 121.5(2)
C6 C5 H5 119.2
C10 C5 H5 119.2
C5 C6 C7 119.6(2)
C5 C6 C13 121.0(2)
C7 C6 C13 119.4(2)
N1 C7 C8 120.0(2)
N1 C7 C6 119.7(2)
C8 C7 C6 120.3(2)
C9 C8 C7 117.5(2)
C9 C8 C16 123.1(2)
C7 C8 C16 119.41(19)
C8 C9 O1 116.61(19)
C8 C9 C10 123.8(2)
O1 C9 C10 119.54(19)
C4 C10 C9 118.7(2)
C4 C10 C5 124.1(2)
C9 C10 C5 117.22(19)
N1 C11 C14 112.73(19)
N1 C11 H11A 109.0
C14 C11 H11A 109.0
N1 C11 H11B 109.0
C14 C11 H11B 109.0
H11A C11 H11B 107.8
N1 C12 C15 112.63(18)
N1 C12 H12A 109.1
C15 C12 H12A 109.1
N1 C12 H12B 109.1
C15 C12 H12B 109.1
H12A C12 H12B 107.8
C6 C13 C14 109.63(19)
C6 C13 H13A 109.7
C14 C13 H13A 109.7
C6 C13 H13B 109.7
C14 C13 H13B 109.7
H13A C13 H13B 108.2
C11 C14 C13 109.12(19)
C11 C14 H14A 109.9
C13 C14 H14A 109.9
C11 C14 H14B 109.9
C13 C14 H14B 109.9
H14A C14 H14B 108.3
C12 C15 C16 109.62(19)
C12 C15 H15A 109.7
C16 C15 H15A 109.7
C12 C15 H15B 109.7
C16 C15 H15B 109.7
H15A C15 H15B 108.2
C8 C16 C15 109.03(19)
C8 C16 H16A 109.9
C15 C16 H16A 109.9
C8 C16 H16B 109.9
C15 C16 H16B 109.9
H16A C16 H16B 108.3
C7 N1 C11 122.8(2)
C7 N1 C12 122.85(19)
C11 N1 C12 114.31(18)
C2 O1 C9 122.19(17)
C1 O3 H3O 107.5(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O4 1.225(3)
C1 O3 1.341(3)
C1 C3 1.478(3)
C2 O2 1.237(3)
C2 O1 1.373(3)
C2 C3 1.437(3)
C3 C4 1.380(3)
C4 C10 1.398(3)
C4 H4 0.9500
C5 C6 1.371(3)
C5 C10 1.419(3)
C5 H5 0.9500
C6 C7 1.433(3)
C6 C13 1.511(3)
C7 N1 1.362(3)
C7 C8 1.428(3)
C8 C9 1.371(3)
C8 C16 1.507(3)
C9 O1 1.386(3)
C9 C10 1.415(3)
C11 N1 1.463(3)
C11 C14 1.511(4)
C11 H11A 0.9900
C11 H11B 0.9900
C12 N1 1.470(3)
C12 C15 1.521(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.525(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.529(3)
C15 H15A 0.9900
C15 H15B 0.9900
C16 H16A 0.9900
C16 H16B 0.9900
O3 H3O 0.97(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3O O2 0.97(3) 1.70(3) 2.595(2) 153(3)
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
O2 C2 C3 C4 180.0(2)
O1 C2 C3 C4 0.1(3)
O2 C2 C3 C1 0.6(3)
O1 C2 C3 C1 -179.31(18)
O4 C1 C3 C4 -1.6(3)
O3 C1 C3 C4 179.58(19)
O4 C1 C3 C2 177.8(2)
O3 C1 C3 C2 -1.0(3)
C2 C3 C4 C10 -0.4(3)
C1 C3 C4 C10 178.98(19)
C10 C5 C6 C7 0.0(3)
C10 C5 C6 C13 -179.72(19)
C5 C6 C7 N1 -179.9(2)
C13 C6 C7 N1 -0.2(3)
C5 C6 C7 C8 0.2(3)
C13 C6 C7 C8 179.93(19)
N1 C7 C8 C9 179.84(19)
C6 C7 C8 C9 -0.3(3)
N1 C7 C8 C16 -0.5(3)
C6 C7 C8 C16 179.38(19)
C7 C8 C9 O1 179.64(18)
C16 C8 C9 O1 0.0(3)
C7 C8 C9 C10 0.2(3)
C16 C8 C9 C10 -179.5(2)
C3 C4 C10 C9 0.2(3)
C3 C4 C10 C5 -180.0(2)
C8 C9 C10 C4 179.83(19)
O1 C9 C10 C4 0.4(3)
C8 C9 C10 C5 0.0(3)
O1 C9 C10 C5 -179.42(18)
C6 C5 C10 C4 -179.9(2)
C6 C5 C10 C9 -0.1(3)
C5 C6 C13 C14 -148.0(2)
C7 C6 C13 C14 32.3(3)
N1 C11 C14 C13 51.9(3)
C6 C13 C14 C11 -56.8(3)
N1 C12 C15 C16 49.4(2)
C9 C8 C16 C15 -146.0(2)
C7 C8 C16 C15 34.3(3)
C12 C15 C16 C8 -57.5(2)
C8 C7 N1 C11 173.5(2)
C6 C7 N1 C11 -6.4(3)
C8 C7 N1 C12 -9.8(3)
C6 C7 N1 C12 170.3(2)
C14 C11 N1 C7 -20.6(3)
C14 C11 N1 C12 162.39(19)
C15 C12 N1 C7 -15.8(3)
C15 C12 N1 C11 161.16(19)
O2 C2 O1 C9 -179.38(18)
C3 C2 O1 C9 0.5(3)
C8 C9 O1 C2 179.78(18)
C10 C9 O1 C2 -0.8(3)
