#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:09:40 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179315 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/12/4321213.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_4321213
loop_
_publ_author_name
'Seth M. Cohen'
'Kenneth N. Raymond'
_publ_contact_author
;
      Kenneth N. Raymond
      Department of Chemistry
      University of California
      Berkeley
      CA 94720-1460
      USA
;
_publ_contact_author_email       raymond@garnet.berkeley.edu
_publ_contact_author_fax         '1 510 4865283'
_publ_contact_author_phone       '1 510 6427219'
_publ_section_title
;
 Catecholate/Salicylate Heteropodands: Demonstration of a Catecholate to
 Salicylate Coordination Change1
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3624
_journal_page_last               3631
_journal_paper_doi               10.1021/ic990608c
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C27 H30 Al Br Cl N4 O8'
_chemical_formula_weight         680.89
_chemical_name_common            'Triprotonated Aluminum Trencamsam'
_chemical_name_systematic
; 
Aluminum(III)[(2-hydroxy-benzoyl-2-aminoethyl)-
bis(2,3-dihydroxybenzoyl-2-aminoethyl)amine]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                109.1420(10)
_cell_angle_beta                 104.3270(10)
_cell_angle_gamma                103.6360(10)
_cell_formula_units_Z            2
_cell_length_a                   11.5475(4)
_cell_length_b                   12.1681(4)
_cell_length_c                   12.5094(4)
_cell_measurement_reflns_used    5034
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      1.84
_cell_volume                     1509.38(9)
_computing_cell_refinement       'Siemens SAINT'
_computing_data_collection       'Siemens SAINT'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_measurement_device       'Siemens SAINT'
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7209
_diffrn_reflns_theta_max         25.85
_diffrn_reflns_theta_min         1.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.534
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.8176
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       'Transparent blocks'
_exptl_crystal_F_000             698
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.167
_refine_ls_goodness_of_fit_obs   1.122
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         5033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_restrained_S_obs      1.122
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_obs          0.0450
_refine_ls_shift/esd_max         -1.018
_refine_ls_shift/esd_mean        0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0363P)²+2.5539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1208
_refine_ls_wR_factor_obs         0.1079
_reflns_number_observed          4408
_reflns_number_total             5034
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic990608c_2.cif
_cod_data_source_block           Al[TRENCAMSAM]H3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+2.5539P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+2.5539P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4321213
loop_
_symmetry_equiv_pos_as_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cl1 Cl 0.1329(13) 0.2201(9) 0.4461(12) 0.023(2) Uani 0.467(3) d P .
Br1 Br 0.1374(5) 0.2138(4) 0.4514(5) 0.0404(12) Uani 0.533(3) d P .
Al1 Al 0.60128(8) 0.19682(8) 0.82310(8) 0.0217(2) Uani 1 d . .
O11 O 0.4995(2) 0.0932(2) 0.6559(2) 0.0279(5) Uani 1 d . .
O12 O 0.6803(2) 0.3165(2) 0.7794(2) 0.0263(5) Uani 1 d . .
O32 O 0.7271(2) 0.1303(2) 0.8229(2) 0.0274(5) Uani 1 d . .
O31 O 0.5033(2) 0.0628(2) 0.8494(2) 0.0277(5) Uani 1 d . .
O21 O 0.4532(2) 0.2435(2) 0.8235(2) 0.0242(5) Uani 1 d . .
O22 O 0.6813(2) 0.2991(2) 0.9843(2) 0.0274(5) Uani 1 d . .
O33 O 0.9474(3) 0.0964(3) 0.8376(3) 0.0512(7) Uani 1 d . .
H33A H 0.9207(17) 0.1498(27) 0.8260(48) 0.077 Uiso 1 calc R .
O13 O 0.8104(4) 0.5235(4) 0.7691(4) 0.0355(12) Uani 0.533(3) d P .
O23 O 0.8386(4) 0.4211(5) 1.2139(4) 0.0356(14) Uani 0.467(3) d P .
N12 N 0.3448(3) 0.0655(3) 0.4913(3) 0.0343(7) Uani 1 d . .
H12A H 0.3175(3) 0.0920(3) 0.4376(3) 0.041 Uiso 1 calc R .
N1 N 0.2328(3) -0.0018(3) 0.6866(3) 0.0280(6) Uani 1 d . .
N22 N 0.3018(2) 0.2912(2) 0.8883(2) 0.0271(6) Uani 1 d . .
H22A H 0.2805(2) 0.3355(2) 0.9442(2) 0.033 Uiso 1 calc R .
N32 N 0.4180(3) -0.1283(3) 0.8304(3) 0.0349(7) Uani 1 d . .
H32A H 0.4254(3) -0.1982(3) 0.8259(3) 0.042 Uiso 1 calc R .
C24 C 0.5165(3) 0.3748(3) 1.0342(3) 0.0228(6) Uani 1 d . .
C23 C 0.4237(3) 0.3025(3) 0.9112(3) 0.0224(6) Uani 1 d . .
C29 C 0.6388(3) 0.3649(3) 1.0627(3) 0.0235(7) Uani 1 d . .
C19 C 0.6404(3) 0.3313(3) 0.6770(3) 0.0267(7) Uani 1 d . .
C13 C 0.4580(3) 0.1319(3) 0.5763(3) 0.0270(7) Uani 1 d . .
C25 C 0.4839(3) 0.4496(3) 1.1271(3) 0.0265(7) Uani 1 d . .
H25A H 0.4038(3) 0.4571(3) 1.1085(3) 0.032 Uiso 1 calc R .
C33 C 0.5190(3) -0.0390(3) 0.8434(3) 0.0264(7) Uani 1 d . .
C14 C 0.5328(3) 0.2469(3) 0.5754(3) 0.0284(7) Uani 1 d . .
C28 C 0.7233(3) 0.4292(3) 1.1841(3) 0.0308(7) Uani 1 d . .
C39 C 0.7365(3) 0.0304(3) 0.8399(3) 0.0242(7) Uani 1 d . .
C34 C 0.6402(3) -0.0575(3) 0.8496(3) 0.0263(7) Uani 1 d . .
C27 C 0.6880(3) 0.4998(3) 1.2727(3) 0.0333(8) Uani 1 d . .
H27A H 0.7447(3) 0.5401(3) 1.3523(3) 0.040 Uiso 1 calc R .
C11 C 0.1749(3) -0.0301(3) 0.5533(3) 0.0320(8) Uani 1 d . .
H11A H 0.0991(3) -0.1037(3) 0.5163(3) 0.038 Uiso 1 calc R .
H11B H 0.1488(3) 0.0381(3) 0.5463(3) 0.038 Uiso 1 calc R .
C31 C 0.2182(3) -0.1227(3) 0.7009(3) 0.0356(8) Uani 1 d . .
H31A H 0.2421(3) -0.1756(3) 0.6398(3) 0.043 Uiso 1 calc R .
H31B H 0.1288(3) -0.1637(3) 0.6844(3) 0.043 Uiso 1 calc R .
C26 C 0.5684(3) 0.5113(3) 1.2442(3) 0.0305(7) Uani 1 d . .
H26A H 0.5458(3) 0.5605(3) 1.3041(3) 0.037 Uiso 1 calc R .
C35 C 0.6630(4) -0.1609(3) 0.8662(3) 0.0375(8) Uani 1 d . .
H35A H 0.5997(4) -0.2185(3) 0.8733(3) 0.045 Uiso 1 calc R .
C12 C 0.2635(3) -0.0506(3) 0.4838(3) 0.0352(8) Uani 1 d . .
H12B H 0.3166(3) -0.0918(3) 0.5158(3) 0.042 Uiso 1 calc R .
H12C H 0.2135(3) -0.1047(3) 0.3996(3) 0.042 Uiso 1 calc R .
C17 C 0.6721(4) 0.4653(4) 0.5716(4) 0.0495(10) Uani 1 d . .
H17A H 0.7186(4) 0.5382(4) 0.5701(4) 0.059 Uiso 1 calc R .
C18 C 0.7091(3) 0.4421(3) 0.6732(3) 0.0359(8) Uani 1 d . .
C22 C 0.2027(3) 0.2067(3) 0.7720(3) 0.0287(7) Uani 1 d . .
H22B H 0.2322(3) 0.2141(3) 0.7077(3) 0.034 Uiso 1 calc R .
H22C H 0.1277(3) 0.2305(3) 0.7649(3) 0.034 Uiso 1 calc R .
C32 C 0.2948(3) -0.1132(3) 0.8234(4) 0.0374(8) Uani 1 d . .
H32B H 0.3090(3) -0.0329(3) 0.8847(4) 0.045 Uiso 1 calc R .
H32C H 0.2451(3) -0.1761(3) 0.8418(4) 0.045 Uiso 1 calc R .
C21 C 0.1664(3) 0.0712(3) 0.7561(3) 0.0305(7) Uani 1 d . .
H21A H 0.1865(3) 0.0695(3) 0.8355(3) 0.037 Uiso 1 calc R .
H21B H 0.0751(3) 0.0309(3) 0.7144(3) 0.037 Uiso 1 calc R .
C38 C 0.8535(3) 0.0103(3) 0.8465(3) 0.0321(8) Uani 1 d . .
C16 C 0.5658(4) 0.3807(4) 0.4712(4) 0.0522(11) Uani 1 d . .
H16A H 0.5416(4) 0.3973(4) 0.4031(4) 0.063 Uiso 1 calc R .
C15 C 0.4969(4) 0.2734(4) 0.4723(3) 0.0408(9) Uani 1 d . .
H15A H 0.4259(4) 0.2172(4) 0.4049(3) 0.049 Uiso 1 calc R .
C36 C 0.7776(4) -0.1769(4) 0.8719(4) 0.0469(10) Uani 1 d . .
H36A H 0.7914(4) -0.2458(4) 0.8820(4) 0.056 Uiso 1 calc R .
C37 C 0.8739(4) -0.0900(4) 0.8626(4) 0.0434(9) Uani 1 d . .
H37A H 0.9519(4) -0.1007(4) 0.8673(4) 0.052 Uiso 1 calc R .
H1A H 0.3150(33) 0.0443(31) 0.7147(29) 0.019(8) Uiso 1 d . .
O36 O 0.9388(3) 0.3158(2) 0.8016(3) 0.0398(6) Uani 1 d . .
O37 O 0.8378(3) 0.5585(3) 0.9966(3) 0.0544(9) Uani 1 d . .
O38 O -0.0363(5) 0.3465(4) 0.5987(4) 0.0788(13) Uani 1 d . .
O39 O 0.9442(4) 0.2933(5) 1.0815(4) 0.115(2) Uani 1 d . .
O40 O 1.0060(6) 0.3824(7) 1.3307(7) 0.066(2) Uani 0.50 d P .
H36C H 0.8574(51) 0.3184(45) 0.7949(43) 0.066(14) Uiso 1 d . .
H36B H 0.9507(50) 0.3321(49) 0.7421(50) 0.076(18) Uiso 1 d . .
H37A H 0.8898(72) 0.5762(81) 1.0200(75) 0.137(36) Uiso 1 d . .
H38A H -0.0053(72) 0.3458(72) 0.5629(68) 0.111(31) Uiso 1 d . .
H40A H 1.0265(25) 0.3169(26) 1.2837(25) 0.000(7) Uiso 1 d . .
H40B H 1.0136(29) 0.4371(30) 1.4171(31) 0.017(8) Uiso 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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
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
_geom_angle_publ_flag
O32 Al1 O22 91.84(11) . . ?
O32 Al1 O12 92.14(10) . . ?
O22 Al1 O12 91.74(11) . . ?
O32 Al1 O11 94.57(11) . . ?
O22 Al1 O11 173.27(11) . . ?
O12 Al1 O11 90.06(10) . . ?
O32 Al1 O21 171.04(10) . . ?
O22 Al1 O21 90.18(10) . . ?
O12 Al1 O21 96.52(10) . . ?
O11 Al1 O21 83.17(10) . . ?
O32 Al1 O31 90.21(10) . . ?
O22 Al1 O31 94.70(10) . . ?
O12 Al1 O31 173.07(11) . . ?
O11 Al1 O31 83.25(10) . . ?
O21 Al1 O31 80.93(9) . . ?
C13 O11 Al1 125.3(2) . . ?
C19 O12 Al1 128.5(2) . . ?
C39 O32 Al1 130.2(2) . . ?
C33 O31 Al1 130.3(2) . . ?
C23 O21 Al1 130.5(2) . . ?
C29 O22 Al1 130.7(2) . . ?
C13 N12 C12 123.4(3) . . ?
C21 N1 C31 110.9(3) . . ?
C21 N1 C11 109.2(3) . . ?
C31 N1 C11 109.0(3) . . ?
C23 N22 C22 122.5(3) . . ?
C33 N32 C32 123.0(3) . . ?
C29 C24 C25 119.1(3) . . ?
C29 C24 C23 119.5(3) . . ?
C25 C24 C23 121.2(3) . . ?
O21 C23 N22 117.1(3) . . ?
O21 C23 C24 122.6(3) . . ?
N22 C23 C24 120.2(3) . . ?
O22 C29 C24 125.1(3) . . ?
O22 C29 C28 116.7(3) . . ?
C24 C29 C28 118.2(3) . . ?
O12 C19 C14 124.5(3) . . ?
O12 C19 C18 117.2(3) . . ?
C14 C19 C18 118.2(3) . . ?
O11 C13 N12 118.8(3) . . ?
O11 C13 C14 122.0(3) . . ?
N12 C13 C14 119.2(3) . . ?
C26 C25 C24 121.2(3) . . ?
O31 C33 N32 116.2(3) . . ?
O31 C33 C34 122.4(3) . . ?
N32 C33 C34 121.5(3) . . ?
C19 C14 C15 119.9(3) . . ?
C19 C14 C13 119.9(3) . . ?
C15 C14 C13 120.2(3) . . ?
O23 C28 C27 119.1(4) . . ?
O23 C28 C29 119.7(4) . . ?
C27 C28 C29 121.2(3) . . ?
O32 C39 C34 125.8(3) . . ?
O32 C39 C38 116.3(3) . . ?
C34 C39 C38 117.9(3) . . ?
C39 C34 C35 119.7(3) . . ?
C39 C34 C33 119.0(3) . . ?
C35 C34 C33 121.3(3) . . ?
C28 C27 C26 120.5(3) . . ?
C12 C11 N1 114.1(3) . . ?
N1 C31 C32 116.4(3) . . ?
C25 C26 C27 119.7(3) . . ?
C36 C35 C34 120.5(3) . . ?
N12 C12 C11 112.1(3) . . ?
C18 C17 C16 120.6(4) . . ?
O13 C18 C17 120.4(4) . . ?
O13 C18 C19 119.0(3) . . ?
C17 C18 C19 120.7(4) . . ?
N22 C22 C21 112.6(3) . . ?
N32 C32 C31 113.9(3) . . ?
N1 C21 C22 114.1(3) . . ?
C37 C38 O33 120.6(3) . . ?
C37 C38 C39 121.6(3) . . ?
O33 C38 C39 117.8(3) . . ?
C15 C16 C17 120.2(4) . . ?
C16 C15 C14 120.5(4) . . ?
C35 C36 C37 120.2(3) . . ?
C38 C37 C36 120.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Al1 O32 1.823(2) . ?
Al1 O22 1.833(2) . ?
Al1 O12 1.843(2) . ?
Al1 O11 1.924(2) . ?
Al1 O21 1.925(2) . ?
Al1 O31 1.928(2) . ?
O11 C13 1.273(4) . ?
O12 C19 1.335(4) . ?
O32 C39 1.324(4) . ?
O31 C33 1.273(4) . ?
O21 C23 1.273(4) . ?
O22 C29 1.324(4) . ?
O33 C38 1.373(4) . ?
O13 C18 1.329(6) . ?
O23 C28 1.327(6) . ?
N12 C13 1.320(4) . ?
N12 C12 1.460(5) . ?
N1 C21 1.509(4) . ?
N1 C31 1.515(4) . ?
N1 C11 1.520(4) . ?
N22 C23 1.329(4) . ?
N22 C22 1.456(4) . ?
N32 C33 1.327(4) . ?
N32 C32 1.462(5) . ?
C24 C29 1.413(4) . ?
C24 C25 1.415(4) . ?
C24 C23 1.464(4) . ?
C29 C28 1.413(5) . ?
C19 C14 1.406(5) . ?
C19 C18 1.416(5) . ?
C13 C14 1.466(5) . ?
C25 C26 1.374(5) . ?
C33 C34 1.457(5) . ?
C14 C15 1.417(5) . ?
C28 C27 1.377(5) . ?
C39 C34 1.410(4) . ?
C39 C38 1.416(5) . ?
C34 C35 1.412(5) . ?
C27 C26 1.391(5) . ?
C11 C12 1.511(5) . ?
C31 C32 1.520(5) . ?
C35 C36 1.371(5) . ?
C17 C18 1.379(5) . ?
C17 C16 1.392(6) . ?
C22 C21 1.533(5) . ?
C38 C37 1.364(5) . ?
C16 C15 1.366(6) . ?
C36 C37 1.400(6) . ?
