#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:25:37 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179630 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/94/4509420.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509420
loop_
_publ_author_name
'Song, Jun-Ling'
'Yi, Fei-Yan'
'Mao, Jiang-Gao'
_publ_section_title
;
 New Types of Luminescent Lanthanide Squarato-Aminophosphonates
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3273
_journal_paper_doi               10.1021/cg900010z
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C13 H9 La N O8 P'
_chemical_formula_weight         477.09
_chemical_name_systematic
; 
 ? 
;
_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                   11.088(3)
_cell_length_b                   9.669(3)
_cell_length_c                   28.537(7)
_cell_measurement_temperature    293(2)
_cell_volume                     3059.4(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       'narrow frame method'
_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  0.0713
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20889
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        <1%
_exptl_absorpt_coefficient_mu    2.940
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.8856
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.610
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0228P)²+14.6208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                2883
_reflns_number_total             3506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg900010zsup1.cif
_cod_data_source_block           La
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3059.5(14)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4509420
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
La1 La 0.93577(3) 0.80624(4) -0.046683(12) 0.02403(12) Uani 1 1 d .
P1 P 1.12102(14) 0.83013(18) 0.06620(5) 0.0258(3) Uani 1 1 d .
N1 N 0.9226(4) 0.7101(6) 0.10630(17) 0.0267(11) Uani 1 1 d .
C1 C 0.9355(7) 0.8546(8) 0.2156(2) 0.0465(19) Uani 1 1 d .
H1A H 0.9871 0.9234 0.2049 0.056 Uiso 1 1 calc R
C2 C 0.9348(8) 0.8186(8) 0.2631(2) 0.049(2) Uani 1 1 d .
H2A H 0.9842 0.8660 0.2840 0.059 Uiso 1 1 calc R
C3 C 0.8635(6) 0.7163(8) 0.2790(2) 0.0397(17) Uani 1 1 d .
C4 C 0.7861(8) 0.6510(11) 0.2487(3) 0.068(3) Uani 1 1 d .
H4A H 0.7352 0.5815 0.2595 0.082 Uiso 1 1 calc R
C5 C 0.7842(8) 0.6892(11) 0.2020(2) 0.065(3) Uani 1 1 d .
H5A H 0.7302 0.6465 0.1817 0.078 Uiso 1 1 calc R
C6 C 0.8605(6) 0.7886(7) 0.1852(2) 0.0321(15) Uani 1 1 d .
C7 C 0.8702(7) 0.6714(8) 0.3291(2) 0.0413(18) Uani 1 1 d .
C8 C 0.8599(6) 0.8205(7) 0.13272(19) 0.0299(14) Uani 1 1 d .
H8A H 0.7773 0.8282 0.1218 0.036 Uiso 1 1 calc R
H8B H 0.8997 0.9083 0.1272 0.036 Uiso 1 1 calc R
C9 C 1.0548(5) 0.7069(7) 0.1068(2) 0.0291(14) Uani 1 1 d .
H9A H 1.0819 0.6146 0.0987 0.035 Uiso 1 1 calc R
H9B H 1.0829 0.7273 0.1382 0.035 Uiso 1 1 calc R
C10 C 0.8614(6) 0.6225(7) 0.0798(2) 0.0276(14) Uani 1 1 d .
C11 C 0.7354(6) 0.6054(7) 0.0674(2) 0.0303(14) Uani 1 1 d .
C12 C 0.7668(6) 0.4875(7) 0.0378(2) 0.0349(16) Uani 1 1 d .
C13 C 0.8933(5) 0.5002(7) 0.0533(2) 0.0267(13) Uani 1 1 d .
O1 O 0.8065(6) 0.5594(7) 0.33774(18) 0.0643(18) Uani 1 1 d .
H1B H 0.8295 0.5242 0.3623 0.096 Uiso 1 1 calc R
O2 O 0.9307(5) 0.7300(6) 0.35846(16) 0.0447(12) Uani 1 1 d .
O3 O 0.6411(4) 0.6640(5) 0.08024(16) 0.0387(12) Uani 1 1 d .
O4 O 0.7084(4) 0.4069(5) 0.01274(18) 0.0469(13) Uani 1 1 d .
O5 O 0.9884(4) 0.4320(5) 0.04952(16) 0.0371(11) Uani 1 1 d .
O11 O 1.2521(4) 0.7961(5) 0.06458(17) 0.0450(13) Uani 1 1 d .
O12 O 1.1017(4) 0.9753(5) 0.08598(16) 0.0378(11) Uani 1 1 d .
O13 O 1.0528(4) 0.8163(6) 0.02093(15) 0.0471(14) 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 '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
O11 La1 O13 133.59(18) 4_465 .
O11 La1 O12 96.86(17) 4_465 5_775
O13 La1 O12 116.24(18) . 5_775
O11 La1 O5 83.87(17) 4_465 5_765
O13 La1 O5 82.84(18) . 5_765
O12 La1 O5 149.36(16) 5_775 5_765
O11 La1 O3 140.16(17) 4_465 4_565
O13 La1 O3 78.69(16) . 4_565
O12 La1 O3 82.98(16) 5_775 4_565
O5 La1 O3 77.42(16) 5_765 4_565
O11 La1 O4 75.92(17) 4_465 8_765
O13 La1 O4 77.30(17) . 8_765
O12 La1 O4 82.34(16) 5_775 8_765
O5 La1 O4 126.93(16) 5_765 8_765
O3 La1 O4 142.51(17) 4_565 8_765
O11 La1 O2 73.09(16) 4_465 7_575
O13 La1 O2 147.01(17) . 7_575
O12 La1 O2 69.51(16) 5_775 7_575
O5 La1 O2 81.60(16) 5_765 7_575
O3 La1 O2 69.62(15) 4_565 7_575
O4 La1 O2 134.61(16) 8_765 7_575
O11 P1 O13 116.4(3) . .
O11 P1 O12 110.6(3) . .
O13 P1 O12 109.2(3) . .
O11 P1 C9 105.6(3) . .
O13 P1 C9 106.6(3) . .
O12 P1 C9 108.0(3) . .
C10 N1 C9 120.3(5) . .
C10 N1 C8 120.8(5) . .
C9 N1 C8 118.7(5) . .
C6 C1 C2 119.9(7) . .
C6 C1 H1A 120.1 . .
C2 C1 H1A 120.1 . .
C3 C2 C1 120.8(7) . .
C3 C2 H2A 119.6 . .
C1 C2 H2A 119.6 . .
C2 C3 C4 119.6(7) . .
C2 C3 C7 120.4(7) . .
C4 C3 C7 120.0(7) . .
C3 C4 C5 119.6(8) . .
C3 C4 H4A 120.2 . .
C5 C4 H4A 120.2 . .
C6 C5 C4 121.1(7) . .
C6 C5 H5A 119.5 . .
C4 C5 H5A 119.5 . .
C1 C6 C5 118.9(6) . .
C1 C6 C8 122.2(6) . .
C5 C6 C8 118.9(6) . .
O2 C7 O1 123.5(6) . .
O2 C7 C3 123.5(7) . .
O1 C7 C3 113.0(7) . .
N1 C8 C6 110.6(5) . .
N1 C8 H8A 109.5 . .
C6 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
N1 C9 P1 112.6(4) . .
N1 C9 H9A 109.1 . .
P1 C9 H9A 109.1 . .
N1 C9 H9B 109.1 . .
P1 C9 H9B 109.1 . .
H9A C9 H9B 107.8 . .
N1 C10 C13 134.1(6) . .
N1 C10 C11 135.0(6) . .
C13 C10 C11 90.8(5) . .
O3 C11 C10 133.2(6) . .
O3 C11 C12 136.6(6) . .
C10 C11 C12 90.0(5) . .
O4 C12 C11 134.4(6) . .
O4 C12 C13 136.2(7) . .
C11 C12 C13 89.3(5) . .
O5 C13 C10 133.1(6) . .
O5 C13 C12 137.1(6) . .
C10 C13 C12 89.5(5) . .
C7 O1 H1B 109.5 . .
C7 O2 La1 129.5(5) . 7_576
C11 O3 La1 135.1(4) . 4_465
C12 O4 La1 163.7(5) . 8_755
C13 O5 La1 142.0(4) . 5_765
P1 O11 La1 163.0(3) . 4_565
P1 O12 La1 130.7(3) . 5_775
P1 O13 La1 175.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
La1 O11 2.321(5) 4_465
La1 O13 2.327(4) .
La1 O12 2.427(5) 5_775
La1 O5 2.454(5) 5_765
La1 O3 2.486(4) 4_565
La1 O4 2.525(5) 8_765
La1 O2 2.730(5) 7_575
P1 O11 1.491(5) .
P1 O13 1.503(5) .
P1 O12 1.528(5) .
P1 C9 1.817(7) .
N1 C10 1.323(8) .
N1 C9 1.466(7) .
N1 C8 1.480(8) .
C1 C6 1.362(9) .
C1 C2 1.399(9) .
C1 H1A 0.9300 .
C2 C3 1.345(10) .
C2 H2A 0.9300 .
C3 C4 1.372(10) .
C3 C7 1.497(9) .
C4 C5 1.384(10) .
C4 H4A 0.9300 .
C5 C6 1.368(11) .
C5 H5A 0.9300 .
C6 C8 1.529(8) .
C7 O2 1.213(9) .
C7 O1 1.317(9) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C13 1.447(9) .
C10 C11 1.451(9) .
C11 O3 1.245(8) .
C11 C12 1.459(10) .
C12 O4 1.241(8) .
C12 C13 1.476(9) .
C13 O5 1.248(7) .
O1 H1B 0.8200 .
O2 La1 2.730(5) 7_576
O3 La1 2.486(4) 4_465
O4 La1 2.525(5) 8_755
O5 La1 2.454(5) 5_765
O11 La1 2.321(5) 4_565
O12 La1 2.427(5) 5_775
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
_geom_hbond_site_symmetry_A
O1 H1B O12 0.82 1.73 2.537(7) 169.0 3_745
