#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:55:54 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179431 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/28/4332878.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_4332878
loop_
_publ_author_name
'Melton, Darren L.'
'VanDerveer, Donald G.'
'Hancock, Robert D.'
_publ_section_title
;
 Complexes of Greatly Enhanced Thermodynamic Stability and Metal Ion
 Size-Based Selectivity, Formed by the Highly Preorganized Non-Macrocyclic
 Ligand 1,10-Phenanthroline-2,9-dicarboxylic Acid. A Thermodynamic and
 Crystallographic Study
;
_journal_issue                   23
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9306
_journal_page_last               9314
_journal_paper_doi               10.1021/ic061010p
_journal_volume                  45
_journal_year                    2006
_chemical_formula_sum            'C14 H6 Ca N2 O8'
_chemical_formula_weight         370.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   44.007(9)
_cell_length_b                   18.945(4)
_cell_length_c                   7.2446(14)
_cell_measurement_temperature    183(2)
_cell_volume                     6040(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.1532
_diffrn_reflns_av_sigmaI/netI    0.1467
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7199
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.9128
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.56(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0882
_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)+(0.1048P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1937
_refine_ls_wR_factor_ref         0.2193
_reflns_number_gt                1669
_reflns_number_total             2629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic061010psup1.cif
_cod_data_source_block           ca_pda
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_sg_symbol_H-M      Fdd2
_cod_database_code               4332878
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'
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
Ca1 Ca -0.03195(4) 0.29405(11) 0.8104(3) 0.0331(5) Uani 1 1 d .
O1 O 0.04062(15) 0.1408(4) 0.0201(9) 0.0427(18) Uani 1 1 d .
O8A O 0.0037(3) 0.4259(9) 0.317(2) 0.043(4) Uani 0.50 1 d P
O8B O 0.0086(3) 0.4365(8) 0.452(2) 0.050(4) Uani 0.50 1 d P
O2 O 0.07088(16) 0.0996(4) -0.2017(10) 0.0441(17) Uani 1 1 d .
O3 O 0.01462(14) 0.2651(3) 0.5940(12) 0.0446(19) Uani 1 1 d .
O7 O 0.0136(3) 0.4757(8) 0.831(2) 0.055(4) Uani 0.50 1 d P
O5 O -0.03964(17) 0.1748(5) 0.7047(12) 0.059(2) Uani 1 1 d .
O6 O -0.03441(14) 0.3969(3) 1.0000(9) 0.0360(16) Uani 1 1 d .
O4 O 0.02297(14) 0.3303(3) 0.8440(10) 0.0379(17) Uani 1 1 d .
N1 N 0.08706(18) 0.1849(4) 0.2169(10) 0.0310(18) Uani 1 1 d .
N2 N 0.07312(14) 0.2498(4) 0.5310(9) 0.0244(15) Uani 1 1 d .
C1 C 0.0662(2) 0.1277(5) -0.0524(14) 0.034(2) Uani 1 1 d .
C2 C 0.0939(2) 0.1525(4) 0.0583(12) 0.030(2) Uani 1 1 d .
C3 C 0.1230(2) 0.1424(6) -0.0035(14) 0.038(2) Uani 1 1 d .
H3 H 0.1266 0.1201 -0.1205 0.045 Uiso 1 1 calc R
C4 C 0.1471(2) 0.1648(5) 0.1047(13) 0.035(2) Uani 1 1 d .
H4 H 0.1676 0.1579 0.0625 0.042 Uiso 1 1 calc R
C5 C 0.14177(19) 0.1975(5) 0.2754(11) 0.0249(19) Uani 1 1 d .
C6 C 0.1649(2) 0.2220(5) 0.3951(14) 0.036(2) Uani 1 1 d .
H6 H 0.1859 0.2174 0.3601 0.044 Uiso 1 1 calc R
C7 C 0.15745(19) 0.2526(4) 0.5617(12) 0.0285(19) Uani 1 1 d .
H7 H 0.1733 0.2668 0.6445 0.034 Uiso 1 1 calc R
C8 C 0.1267(2) 0.2635(5) 0.6131(12) 0.028(2) Uani 1 1 d .
C9 C 0.1181(2) 0.2964(5) 0.7758(13) 0.034(2) Uani 1 1 d .
H9 H 0.1332 0.3114 0.8630 0.041 Uiso 1 1 calc R
C10 C 0.08730(17) 0.3076(5) 0.8123(15) 0.029(2) Uani 1 1 d .
H10 H 0.0810 0.3320 0.9218 0.035 Uiso 1 1 calc R
C11 C 0.0661(2) 0.2827(5) 0.6872(13) 0.032(2) Uani 1 1 d .
C12 C 0.1032(2) 0.2409(5) 0.4971(13) 0.031(2) Uani 1 1 d .
C13 C 0.11067(19) 0.2062(5) 0.3194(15) 0.0315(19) Uani 1 1 d .
C14 C 0.0316(2) 0.2948(6) 0.7109(15) 0.042(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'
Ca Ca 0.2262 0.3064 '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
O6 Ca1 O5 160.4(3) . .
O6 Ca1 O3 84.6(2) . 6
O5 Ca1 O3 83.2(3) . 6
O6 Ca1 O1 94.3(2) . 6
O5 Ca1 O1 100.2(3) . 6
O3 Ca1 O1 170.7(2) 6 6
O6 Ca1 O4 76.5(2) . .
O5 Ca1 O4 114.8(2) . .
O3 Ca1 O4 75.3(2) 6 .
O1 Ca1 O4 95.4(2) 6 .
O6 Ca1 N1 89.0(2) . 6
O5 Ca1 N1 85.9(3) . 6
O3 Ca1 N1 126.0(2) 6 6
O1 Ca1 N1 63.1(2) 6 6
O4 Ca1 N1 153.4(2) . 6
O6 Ca1 N2 82.7(2) . 6
O5 Ca1 N2 78.1(3) . 6
O3 Ca1 N2 63.2(2) 6 6
O1 Ca1 N2 125.9(2) 6 6
O4 Ca1 N2 135.0(2) . 6
N1 Ca1 N2 62.8(2) 6 6
O6 Ca1 O3 123.2(2) . .
O5 Ca1 O3 74.1(2) . .
O3 Ca1 O3 99.25(10) 6 .
O1 Ca1 O3 73.6(2) 6 .
O4 Ca1 O3 50.9(2) . .
N1 Ca1 O3 127.8(3) 6 .
N2 Ca1 O3 148.8(2) 6 .
O6 Ca1 C14 100.6(3) . .
O5 Ca1 C14 93.5(3) . .
O3 Ca1 C14 84.9(3) 6 .
O1 Ca1 C14 86.2(3) 6 .
O4 Ca1 C14 25.2(3) . .
N1 Ca1 C14 148.7(3) 6 .
N2 Ca1 C14 147.6(3) 6 .
O3 Ca1 C14 25.9(3) . .
C1 O1 Ca1 126.1(6) . 6_554
C14 O3 Ca1 125.3(6) . 6_554
C14 O3 Ca1 88.3(7) . .
Ca1 O3 Ca1 146.2(3) 6_554 .
C14 O4 Ca1 94.2(6) . .
C2 N1 C13 116.2(8) . .
C2 N1 Ca1 120.9(6) . 6_554
C13 N1 Ca1 122.9(6) . 6_554
C11 N2 C12 116.0(8) . .
C11 N2 Ca1 121.4(6) . 6_554
C12 N2 Ca1 122.6(6) . 6_554
O2 C1 O1 127.1(9) . .
O2 C1 C2 117.4(9) . .
O1 C1 C2 115.4(8) . .
N1 C2 C3 123.7(9) . .
N1 C2 C1 114.3(8) . .
C3 C2 C1 122.0(9) . .
C2 C3 C4 119.2(9) . .
C3 C4 C5 120.4(9) . .
C4 C5 C13 114.3(8) . .
C4 C5 C6 124.4(8) . .
C13 C5 C6 121.3(8) . .
C7 C6 C5 120.2(8) . .
C6 C7 C8 121.2(8) . .
C9 C8 C12 116.4(8) . .
C9 C8 C7 123.3(8) . .
C12 C8 C7 120.2(8) . .
C8 C9 C10 119.6(9) . .
C11 C10 C9 118.6(9) . .
N2 C11 C10 124.3(9) . .
N2 C11 C14 113.0(9) . .
C10 C11 C14 122.6(9) . .
N2 C12 C8 125.1(8) . .
N2 C12 C13 115.4(8) . .
C8 C12 C13 119.5(8) . .
N1 C13 C5 126.1(9) . .
N1 C13 C12 116.3(8) . .
C5 C13 C12 117.5(8) . .
O4 C14 O3 125.6(10) . .
O4 C14 C11 118.1(10) . .
O3 C14 C11 116.3(10) . .
O4 C14 Ca1 60.6(5) . .
O3 C14 Ca1 65.8(5) . .
C11 C14 Ca1 168.1(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 O6 2.387(7) .
Ca1 O5 2.410(8) .
Ca1 O3 2.462(8) 6
Ca1 O1 2.468(7) 6
Ca1 O4 2.524(7) .
Ca1 N1 2.550(8) 6
Ca1 N2 2.555(7) 6
Ca1 O3 2.638(7) .
Ca1 C14 2.890(10) .
O1 C1 1.265(12) .
O1 Ca1 2.468(7) 6_554
O8A O8B 1.025(19) .
O2 C1 1.223(12) .
O3 C14 1.263(13) .
O3 Ca1 2.462(8) 6_554
O7 O7 1.51(3) 2_565
O4 C14 1.236(13) .
N1 C2 1.337(12) .
N1 C13 1.340(12) .
N1 Ca1 2.550(8) 6_554
N2 C11 1.328(11) .
N2 C12 1.357(11) .
N2 Ca1 2.555(7) 6_554
C1 C2 1.534(12) .
C2 C3 1.370(13) .
C3 C4 1.386(13) .
C4 C5 1.402(12) .
C5 C13 1.415(12) .
C5 C6 1.417(13) .
C6 C7 1.379(13) .
C7 C8 1.417(12) .
C8 C9 1.387(13) .
C8 C12 1.400(13) .
C9 C10 1.398(12) .
C10 C11 1.382(13) .
C11 C14 1.545(13) .
C12 C13 1.482(14) .
