#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:17:52 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179103 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/65/4306576.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_4306576
loop_
_publ_author_name
'Areg Zingiryan'
'Jian Zhang'
'Xianhui Bu'
_publ_contact_author_address
;
Department of Chemistry and Biochemistry
California State University, Long Beach
1250 Bellflower Boulevard, Long Beach, CA 90840
;
_publ_contact_author_name        'Xianhui Bu'
_publ_section_title
;
Cooperative Self-Assembly of Chirall-Malate and Achiral Succinate in the
Formation of a Three-Dimensional Homochiral Framework
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8607
_journal_page_last               8609
_journal_paper_doi               10.1021/ic801404p
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C14 H11 Mn N2 O9'
_chemical_formula_weight         406.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   21.6208(4)
_cell_length_b                   8.3474(2)
_cell_length_c                   11.6482(2)
_cell_measurement_reflns_used    2206
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.80
_cell_measurement_theta_min      2.57
_cell_volume                     2102.24(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10313
_diffrn_reflns_theta_full        24.57
_diffrn_reflns_theta_max         24.57
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_refine_diff_density_max         1.302
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.184
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0773
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1592P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2384
_reflns_number_gt                2704
_reflns_number_total             3509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801404p_si_001_2.cif
_cod_data_source_block           2
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4306576
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn -0.20746(4) 1.10124(12) 0.01101(8) 0.0202(3) Uani 1 1 d . . .
O1W O -0.1426(2) 1.2974(6) 0.0167(5) 0.0366(14) Uani 1 1 d . . .
O1 O -0.22250(19) 0.8404(5) 0.0039(5) 0.0252(10) Uani 1 1 d . . .
O2 O -0.18737(19) 0.5957(5) -0.0131(4) 0.0238(10) Uani 1 1 d . . .
O2W O -0.4191(8) 1.029(2) 0.2988(14) 0.080(5) Uiso 0.50 1 d P . .
O3 O 0.0157(4) 0.8207(19) -0.0131(9) 0.163(6) Uani 1 1 d . . .
O4 O 0.0314(5) 0.731(2) 0.1396(13) 0.247(11) Uani 1 1 d . . .
O4W O 0.0000 1.0000 0.382(2) 0.281(14) Uiso 1 2 d S . .
O5 O -0.11513(19) 0.9747(5) 0.0086(5) 0.0277(11) Uani 1 1 d . . .
H5O H -0.0804 1.0129 0.0023 0.042 Uiso 1 1 calc R . .
O6W O -0.4144(7) 1.0079(17) 0.5314(12) 0.068(4) Uiso 0.50 1 d P . .
N1 N -0.2119(3) 1.0963(9) 0.2048(4) 0.0320(15) Uani 1 1 d . . .
N2 N -0.2110(3) 1.1010(9) 0.8153(4) 0.0330(15) Uani 1 1 d . . .
C1 C -0.1597(4) 1.1043(16) 0.2664(6) 0.048(3) Uani 1 1 d . . .
H1A H -0.1224 1.1106 0.2269 0.057 Uiso 1 1 calc R . .
C2 C -0.1577(4) 1.1038(18) 0.3845(7) 0.058(3) Uani 1 1 d . . .
H2A H -0.1197 1.1111 0.4218 0.069 Uiso 1 1 calc R . .
C3 C -0.2113(4) 1.0927(12) 0.4483(6) 0.0391(19) Uani 1 1 d . . .
C4 C -0.2653(5) 1.0798(19) 0.3849(7) 0.071(4) Uani 1 1 d . . .
H4A H -0.3031 1.0726 0.4224 0.085 Uiso 1 1 calc R . .
C5 C -0.2634(4) 1.0776(16) 0.2649(7) 0.061(3) Uani 1 1 d . . .
H5A H -0.3002 1.0622 0.2253 0.074 Uiso 1 1 calc R . .
C6 C -0.1637(4) 1.1584(18) 0.7546(7) 0.074(5) Uani 1 1 d . . .
H6A H -0.1303 1.2033 0.7934 0.089 Uiso 1 1 calc R . .
C7 C -0.1625(5) 1.1535(18) 0.6367(8) 0.071(5) Uani 1 1 d . . .
H7A H -0.1280 1.1912 0.5975 0.085 Uiso 1 1 calc R . .
C8 C -0.2128(4) 1.0922(12) 0.5750(6) 0.0366(19) Uani 1 1 d . . .
C9 C -0.2602(4) 1.0436(13) 0.6376(6) 0.047(3) Uani 1 1 d . . .
H9A H -0.2952 1.0050 0.6004 0.057 Uiso 1 1 calc R . .
C10 C -0.2597(4) 1.0479(13) 0.7537(7) 0.050(3) Uani 1 1 d . . .
H10A H -0.2947 1.0127 0.7929 0.060 Uiso 1 1 calc R . .
C11 C -0.1780(3) 0.7426(9) -0.0041(6) 0.0229(14) Uani 1 1 d . . .
C12 C -0.1123(3) 0.8031(8) -0.0085(7) 0.0249(15) Uani 1 1 d . . .
H12A H -0.0945 0.7801 -0.0841 0.030 Uiso 1 1 calc R . .
C13 C -0.0732(4) 0.7260(11) 0.0834(8) 0.043(2) Uani 1 1 d . . .
H13A H -0.0789 0.6108 0.0809 0.051 Uiso 1 1 calc R . .
H13B H -0.0867 0.7635 0.1581 0.051 Uiso 1 1 calc R . .
C14 C -0.0030(5) 0.7660(11) 0.0673(12) 0.065(4) Uani 1 1 d . . .
O5W O -0.5080(11) 1.247(2) 0.2567(16) 0.271(9) Uiso 1 1 d . . .
O3W O -0.5000 1.0000 0.6855(16) 0.178(8) Uiso 1 2 d S . .
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'
Mn Mn 0.3368 0.7283 '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
O1W Mn1 O1 147.92(18) . . ?
O1W Mn1 N1 90.6(3) . . ?
O1 Mn1 N1 90.8(2) . . ?
O1W Mn1 O5 77.33(18) . . ?
O1 Mn1 O5 70.59(15) . . ?
N1 Mn1 O5 92.4(2) . . ?
O1W Mn1 O2 131.70(17) . 3_455 ?
O1 Mn1 O2 80.37(15) . 3_455 ?
N1 Mn1 O2 86.9(2) . 3_455 ?
O5 Mn1 O2 150.95(16) . 3_455 ?
O1W Mn1 N2 93.1(2) . 1_554 ?
O1 Mn1 N2 87.5(2) . 1_554 ?
N1 Mn1 N2 175.5(2) . 1_554 ?
O5 Mn1 N2 91.0(2) . 1_554 ?
O2 Mn1 N2 88.7(2) 3_455 1_554 ?
O1W Mn1 O1 77.93(16) . 3_455 ?
O1 Mn1 O1 133.94(7) . 3_455 ?
N1 Mn1 O1 93.3(2) . 3_455 ?
O5 Mn1 O1 154.66(15) . 3_455 ?
O2 Mn1 O1 54.13(14) 3_455 3_455 ?
N2 Mn1 O1 84.9(2) 1_554 3_455 ?
C11 O1 Mn1 121.9(4) . . ?
C11 O1 Mn1 86.6(4) . 3_445 ?
Mn1 O1 Mn1 151.30(19) . 3_445 ?
C11 O2 Mn1 98.1(4) . 3_445 ?
C12 O5 Mn1 120.2(3) . . ?
C12 O5 H5O 109.5 . . ?
Mn1 O5 H5O 129.0 . . ?
C5 N1 C1 115.5(6) . . ?
C5 N1 Mn1 124.5(5) . . ?
C1 N1 Mn1 119.9(5) . . ?
C6 N2 C10 115.8(6) . . ?
C6 N2 Mn1 120.2(5) . 1_556 ?
C10 N2 Mn1 123.9(5) . 1_556 ?
N1 C1 C2 124.2(7) . . ?
N1 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C1 C2 C3 120.7(7) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 C4 115.2(7) . . ?
C2 C3 C8 123.8(8) . . ?
C4 C3 C8 120.9(7) . . ?
C3 C4 C5 120.6(8) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
N1 C5 C4 123.5(8) . . ?
N1 C5 H5A 118.2 . . ?
C4 C5 H5A 118.2 . . ?
N2 C6 C7 122.2(9) . . ?
N2 C6 H6A 118.9 . . ?
C7 C6 H6A 118.9 . . ?
C6 C7 C8 120.6(9) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C9 C8 C7 115.5(7) . . ?
C9 C8 C3 124.7(8) . . ?
C7 C8 C3 119.7(8) . . ?
C8 C9 C10 122.5(8) . . ?
C8 C9 H9A 118.7 . . ?
C10 C9 H9A 118.7 . . ?
N2 C10 C9 123.1(8) . . ?
N2 C10 H10A 118.5 . . ?
C9 C10 H10A 118.5 . . ?
O2 C11 O1 121.1(6) . . ?
O2 C11 C12 118.6(6) . . ?
O1 C11 C12 120.2(6) . . ?
O5 C12 C13 110.4(7) . . ?
O5 C12 C11 106.6(5) . . ?
C13 C12 C11 111.2(6) . . ?
O5 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C12 C13 C14 111.5(7) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O3 C14 O4 118.6(13) . . ?
O3 C14 C13 122.5(9) . . ?
O4 C14 C13 118.8(12) . . ?
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
Mn1 O1W 2.157(5) . ?
Mn1 O1 2.203(4) . ?
Mn1 N1 2.260(5) . ?
Mn1 O5 2.259(4) . ?
Mn1 O2 2.275(4) 3_455 ?
Mn1 N2 2.281(5) 1_554 ?
Mn1 O1 2.512(4) 3_455 ?
O1 C11 1.265(8) . ?
O1 Mn1 2.512(4) 3_445 ?
O2 C11 1.248(8) . ?
O2 Mn1 2.275(4) 3_445 ?
O3 C14 1.117(13) . ?
O4 C14 1.160(13) . ?
O5 C12 1.447(8) . ?
O5 H5O 0.8200 . ?
N1 C5 1.324(11) . ?
N1 C1 1.339(10) . ?
N2 C6 1.333(11) . ?
N2 C10 1.350(11) . ?
N2 Mn1 2.281(5) 1_556 ?
C1 C2 1.376(10) . ?
C1 H1A 0.9300 . ?
C2 C3 1.380(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(12) . ?
C3 C8 1.476(9) . ?
C4 C5 1.397(11) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.375(12) . ?
C6 H6A 0.9300 . ?
C7 C8 1.400(13) . ?
C7 H7A 0.9300 . ?
C8 C9 1.321(11) . ?
C9 C10 1.353(11) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.509(9) . ?
C12 C13 1.508(10) . ?
C12 H12A 0.9800 . ?
C13 C14 1.566(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
