#------------------------------------------------------------------------------
#$Date: 2016-08-07 12:10:08 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185457 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/99/7039933.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_7039933
loop_
_publ_author_name
'Brady, Michael'
'Piombo, Sebastian D.'
'Hu, Chunhua'
'Buccella, Daniela'
_publ_section_title
;
 Structural and spectroscopic insight into the metal binding properties of
 the o-aminophenol-N,N,O-triacetic acid (APTRA) chelator: implications for
 design of metal indicators.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12458
_journal_page_last               12464
_journal_paper_doi               10.1039/c6dt01557c
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C12 H22 Ca2 Cl N O13'
_chemical_formula_weight         503.91
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-04-15 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                108.3734(10)
_cell_angle_beta                 104.9899(10)
_cell_angle_gamma                96.6152(11)
_cell_formula_units_Z            2
_cell_length_a                   8.4079(5)
_cell_length_b                   11.2214(7)
_cell_length_c                   12.0301(8)
_cell_measurement_reflns_used    3202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.57
_cell_volume                     1016.26(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_min         1.878
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5031
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0517P)²+0.0676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3777
_reflns_number_total             5031
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt01557c2.cif
_cod_data_source_block           16dab01b
_cod_depositor_comments
'Adding full bibliography for 7039931--7039934.cif.'
_cod_database_code               7039933
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.822
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ca1 Ca 0.80812(6) 0.42184(5) 0.33459(4) 0.01549(12) Uani 1 1 d . .
Ca2 Ca 0.75923(6) 0.25930(5) 0.62621(4) 0.01576(12) Uani 1 1 d . .
O1 O 0.9668(2) 0.57423(16) 0.29081(15) 0.0171(4) Uani 1 1 d . .
O2 O 1.0532(2) 0.64444(17) 0.15880(15) 0.0196(4) Uani 1 1 d . .
O3 O 0.6968(2) 0.41483(17) 0.12178(15) 0.0202(4) Uani 1 1 d . .
O4 O 0.7369(2) 0.27661(17) 0.42770(15) 0.0183(4) Uani 1 1 d . .
O5 O 0.6159(2) 0.08133(17) 0.40610(16) 0.0205(4) Uani 1 1 d . .
O6 O 0.5773(2) 0.52981(17) 0.33583(17) 0.0211(4) Uani 1 1 d . .
O7 O 0.3094(2) 0.52451(17) 0.33392(17) 0.0228(4) Uani 1 1 d . .
N1 N 0.5162(3) 0.2699(2) 0.21427(18) 0.0168(4) Uani 1 1 d . .
C1 C 0.9490(3) 0.5755(2) 0.1837(2) 0.0174(5) Uani 1 1 d . .
C2 C 0.7969(3) 0.4894(2) 0.0771(2) 0.0182(5) Uani 1 1 d . .
H2A H 0.7293 0.5424 0.0408 0.022 Uiso 1 1 calc R U
H2B H 0.8341 0.4318 0.0123 0.022 Uiso 1 1 calc R U
C3 C 0.5553(3) 0.3259(2) 0.0381(2) 0.0188(5) Uani 1 1 d . .
C4 C 0.4611(3) 0.2525(2) 0.0841(2) 0.0179(5) Uani 1 1 d . .
C5 C 0.3157(3) 0.1644(3) 0.0037(2) 0.0227(6) Uani 1 1 d . .
H5 H 0.2503 0.1158 0.0347 0.027 Uiso 1 1 calc R U
C6 C 0.2632(3) 0.1452(3) -0.1209(2) 0.0249(6) Uani 1 1 d . .
H6 H 0.1628 0.0846 -0.1747 0.030 Uiso 1 1 calc R U
C7 C 0.3589(3) 0.2156(3) -0.1657(2) 0.0242(6) Uani 1 1 d . .
H7 H 0.3248 0.2018 -0.2512 0.029 Uiso 1 1 calc R U
C8 C 0.5043(3) 0.3060(3) -0.0875(2) 0.0220(6) Uani 1 1 d . .
H8 H 0.5687 0.3541 -0.1193 0.026 Uiso 1 1 calc R U
C9 C 0.6363(3) 0.1680(2) 0.3636(2) 0.0167(5) Uani 1 1 d . .
C10 C 0.5347(3) 0.1453(2) 0.2308(2) 0.0185(5) Uani 1 1 d . .
H10A H 0.5923 0.0986 0.1740 0.022 Uiso 1 1 calc R U
H10B H 0.4217 0.0914 0.2100 0.022 Uiso 1 1 calc R U
C11 C 0.4306(3) 0.4717(3) 0.3177(2) 0.0187(5) Uani 1 1 d . .
C12 C 0.3969(3) 0.3260(2) 0.2765(2) 0.0192(5) Uani 1 1 d . .
H12A H 0.4050 0.3010 0.3493 0.023 Uiso 1 1 calc R U
H12B H 0.2805 0.2899 0.2192 0.023 Uiso 1 1 calc R U
O8 O 0.8908(2) 0.57287(17) 0.55214(16) 0.0170(4) Uani 1 1 d D .
H8A H 0.832(3) 0.544(3) 0.587(2) 0.026 Uiso 1 1 d D U
H8B H 0.874(4) 0.6459(14) 0.561(3) 0.026 Uiso 1 1 d D U
O9 O 0.8832(2) 0.24308(19) 0.19954(17) 0.0242(4) Uani 1 1 d D .
H9A H 0.941(3) 0.199(3) 0.230(3) 0.036 Uiso 1 1 d D U
H9B H 0.884(4) 0.219(3) 0.1265(13) 0.036 Uiso 1 1 d D U
O10 O 0.9796(2) 0.14482(18) 0.60252(17) 0.0213(4) Uani 1 1 d D .
H10C H 0.965(4) 0.0676(13) 0.596(3) 0.032 Uiso 1 1 d D U
H10D H 1.017(4) 0.146(3) 0.5441(19) 0.032 Uiso 1 1 d D U
O11 O 0.4637(2) 0.22918(18) 0.58936(18) 0.0243(4) Uani 1 1 d D .
H11A H 0.434(4) 0.3001(17) 0.606(3) 0.036 Uiso 1 1 d D U
H11B H 0.384(3) 0.172(2) 0.535(2) 0.036 Uiso 1 1 d D U
O12 O 0.6887(2) 0.09062(18) 0.70223(17) 0.0205(4) Uani 1 1 d D .
H12C H 0.745(3) 0.034(2) 0.688(3) 0.031 Uiso 1 1 d D U
H12D H 0.5888(17) 0.050(3) 0.675(3) 0.031 Uiso 1 1 d D U
Cl1 Cl 0.88945(8) 0.87270(6) 0.62726(6) 0.02187(15) Uani 1 1 d . .
O13 O 0.8870(3) 0.1834(2) 0.96209(18) 0.0323(5) Uani 1 1 d D .
H13A H 0.949(3) 0.239(3) 0.949(3) 0.048 Uiso 1 1 d D U
H13B H 0.800(3) 0.145(3) 0.902(2) 0.048 Uiso 1 1 d D U
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'
Cl Cl 0.1484 0.1585 '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'
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
O1 Ca1 O4 160.46(6) . .
O1 Ca1 O6 94.18(6) . .
O4 Ca1 O6 99.47(6) . .
O1 Ca1 O9 93.67(7) . .
O4 Ca1 O9 85.05(6) . .
O6 Ca1 O9 139.36(6) . .
O1 Ca1 O3 66.42(6) . .
O4 Ca1 O3 130.65(6) . .
O6 Ca1 O3 75.39(6) . .
O9 Ca1 O3 71.53(6) . .
O1 Ca1 O8 88.89(6) . .
O4 Ca1 O8 80.66(6) . .
O6 Ca1 O8 77.17(6) . .
O9 Ca1 O8 142.81(6) . .
O3 Ca1 O8 141.14(6) . .
O1 Ca1 O8 76.16(6) . 2_766
O4 Ca1 O8 84.70(6) . 2_766
O6 Ca1 O8 145.42(6) . 2_766
O9 Ca1 O8 75.01(6) . 2_766
O3 Ca1 O8 126.99(6) . 2_766
O8 Ca1 O8 69.63(7) . 2_766
O1 Ca1 N1 132.12(6) . .
O4 Ca1 N1 66.82(6) . .
O6 Ca1 N1 66.44(6) . .
O9 Ca1 N1 78.95(7) . .
O3 Ca1 N1 66.40(6) . .
O8 Ca1 N1 124.78(6) . .
O8 Ca1 N1 142.77(6) 2_766 .
O1 Ca1 Ca1 80.88(4) . 2_766
O4 Ca1 Ca1 81.10(4) . 2_766
O6 Ca1 Ca1 111.80(5) . 2_766
O9 Ca1 Ca1 108.81(5) . 2_766
O3 Ca1 Ca1 147.12(5) . 2_766
O8 Ca1 Ca1 35.14(4) . 2_766
O8 Ca1 Ca1 34.49(4) 2_766 2_766
N1 Ca1 Ca1 146.45(5) . 2_766
O11 Ca2 O10 142.58(7) . .
O11 Ca2 O4 92.76(6) . .
O10 Ca2 O4 88.07(6) . .
O11 Ca2 O12 74.93(6) . .
O10 Ca2 O12 79.04(6) . .
O4 Ca2 O12 136.74(6) . .
O11 Ca2 O2 118.49(7) . 2_766
O10 Ca2 O2 82.02(6) . 2_766
O4 Ca2 O2 139.31(6) . 2_766
O12 Ca2 O2 79.81(6) . 2_766
O11 Ca2 O7 73.18(6) . 2_666
O10 Ca2 O7 143.37(6) . 2_666
O4 Ca2 O7 80.78(6) . 2_666
O12 Ca2 O7 131.22(6) . 2_666
O2 Ca2 O7 84.09(6) 2_766 2_666
O11 Ca2 O1 144.51(6) . 2_766
O10 Ca2 O1 72.90(6) . 2_766
O4 Ca2 O1 86.71(6) . 2_766
O12 Ca2 O1 126.90(6) . 2_766
O2 Ca2 O1 52.64(5) 2_766 2_766
O7 Ca2 O1 71.71(6) 2_666 2_766
O11 Ca2 O5 73.00(6) . .
O10 Ca2 O5 78.44(6) . .
O4 Ca2 O5 51.79(6) . .
O12 Ca2 O5 85.06(6) . .
O2 Ca2 O5 157.23(6) 2_766 .
O7 Ca2 O5 118.65(6) 2_666 .
O1 Ca2 O5 129.96(6) 2_766 .
C1 O1 Ca1 124.29(15) . .
C1 O1 Ca2 90.28(14) . 2_766
Ca1 O1 Ca2 143.66(7) . 2_766
C1 O2 Ca2 93.69(14) . 2_766
C3 O3 C2 118.23(18) . .
C3 O3 Ca1 121.85(14) . .
C2 O3 Ca1 119.02(13) . .
C9 O4 Ca1 120.97(15) . .
C9 O4 Ca2 96.06(14) . .
Ca1 O4 Ca2 142.44(8) . .
C9 O5 Ca2 86.98(14) . .
C11 O6 Ca1 122.13(16) . .
C11 O7 Ca2 138.72(16) . 2_666
C4 N1 C12 111.15(19) . .
C4 N1 C10 110.83(19) . .
C12 N1 C10 109.76(19) . .
C4 N1 Ca1 113.42(14) . .
C12 N1 Ca1 106.32(14) . .
C10 N1 Ca1 105.09(14) . .
O2 C1 O1 123.4(2) . .
O2 C1 C2 116.8(2) . .
O1 C1 C2 119.9(2) . .
O2 C1 Ca2 60.07(13) . 2_766
O1 C1 Ca2 63.31(12) . 2_766
C2 C1 Ca2 176.81(17) . 2_766
O3 C2 C1 108.85(19) . .
O3 C2 H2A 109.9 . .
C1 C2 H2A 109.9 . .
O3 C2 H2B 109.9 . .
C1 C2 H2B 109.9 . .
H2A C2 H2B 108.3 . .
O3 C3 C8 123.2(2) . .
O3 C3 C4 117.0(2) . .
C8 C3 C4 119.8(2) . .
C5 C4 C3 118.9(2) . .
C5 C4 N1 120.9(2) . .
C3 C4 N1 120.1(2) . .
C4 C5 C6 121.5(2) . .
C4 C5 H5 119.2 . .
C6 C5 H5 119.2 . .
C7 C6 C5 119.1(2) . .
C7 C6 H6 120.5 . .
C5 C6 H6 120.5 . .
C6 C7 C8 120.9(2) . .
C6 C7 H7 119.5 . .
C8 C7 H7 119.5 . .
C7 C8 C3 119.7(2) . .
C7 C8 H8 120.1 . .
C3 C8 H8 120.1 . .
O5 C9 O4 122.5(2) . .
O5 C9 C10 119.2(2) . .
O4 C9 C10 118.3(2) . .
N1 C10 C9 110.7(2) . .
N1 C10 H10A 109.5 . .
C9 C10 H10A 109.5 . .
N1 C10 H10B 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
O6 C11 O7 125.4(2) . .
O6 C11 C12 117.6(2) . .
O7 C11 C12 117.0(2) . .
N1 C12 C11 112.8(2) . .
N1 C12 H12A 109.0 . .
C11 C12 H12A 109.0 . .
N1 C12 H12B 109.0 . .
C11 C12 H12B 109.0 . .
H12A C12 H12B 107.8 . .
Ca1 O8 Ca1 110.37(7) . 2_766
Ca1 O8 H8A 108(2) . .
Ca1 O8 H8A 106(2) 2_766 .
Ca1 O8 H8B 115(2) . .
Ca1 O8 H8B 112(2) 2_766 .
H8A O8 H8B 105(3) . .
Ca1 O9 H9A 119(2) . .
Ca1 O9 H9B 136(2) . .
H9A O9 H9B 104(3) . .
Ca2 O10 H10C 120(2) . .
Ca2 O10 H10D 116(2) . .
H10C O10 H10D 104(3) . .
Ca2 O11 H11A 111(2) . .
Ca2 O11 H11B 131(2) . .
H11A O11 H11B 109(3) . .
Ca2 O12 H12C 112(2) . .
Ca2 O12 H12D 117(2) . .
H12C O12 H12D 105(3) . .
H13A O13 H13B 113(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 O1 2.3212(17) .
Ca1 O4 2.3541(17) .
Ca1 O6 2.4044(18) .
Ca1 O9 2.4146(19) .
Ca1 O3 2.4602(17) .
Ca1 O8 2.4892(18) .
Ca1 O8 2.5297(18) 2_766
Ca1 N1 2.582(2) .
Ca1 Ca1 4.1206(10) 2_766
Ca2 O11 2.3721(19) .
Ca2 O10 2.3991(19) .
Ca2 O4 2.4177(17) .
Ca2 O12 2.4257(19) .
Ca2 O2 2.4656(17) 2_766
Ca2 O7 2.4862(18) 2_666
Ca2 O1 2.5367(17) 2_766
Ca2 O5 2.6293(18) .
O1 C1 1.263(3) .
O1 Ca2 2.5366(17) 2_766
O2 C1 1.258(3) .
O2 Ca2 2.4656(17) 2_766
O3 C3 1.378(3) .
O3 C2 1.433(3) .
O4 C9 1.276(3) .
O5 C9 1.248(3) .
O6 C11 1.256(3) .
O7 C11 1.264(3) .
O7 Ca2 2.4862(18) 2_666
N1 C4 1.455(3) .
N1 C12 1.483(3) .
N1 C10 1.493(3) .
C1 C2 1.517(3) .
C1 Ca2 2.839(3) 2_766
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C8 1.395(3) .
C3 C4 1.405(3) .
C4 C5 1.384(3) .
C5 C6 1.386(4) .
C5 H5 0.9500 .
C6 C7 1.381(4) .
C6 H6 0.9500 .
C7 C8 1.388(4) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C10 1.528(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.519(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
O8 Ca1 2.5297(18) 2_766
O8 H8A 0.833(10) .
O8 H8B 0.826(10) .
O9 H9A 0.828(10) .
O9 H9B 0.837(10) .
O10 H10C 0.837(10) .
O10 H10D 0.844(10) .
O11 H11A 0.843(10) .
O11 H11B 0.835(10) .
O12 H12C 0.836(10) .
O12 H12D 0.833(10) .
O13 H13A 0.844(10) .
O13 H13B 0.836(10) .
