#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:12:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179656 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/09/4510983.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_4510983
loop_
_publ_author_name
'Zhang, Gao'
'Yao, Shi-Yan'
'Guo, Dong-Wei'
'Tian, Yun-Qi'
_publ_section_title
;
 Noncentrosymmetric and Homochiral Metal−Organic Frameworks of
 (S)-2-(1H-Imidazole1-yl) Propionic Acid
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2355
_journal_paper_doi               10.1021/cg1001368
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         Mn(C6H7N2O2)2
_chemical_formula_sum            'C12 H14 Mn N4 O4'
_chemical_formula_weight         333.21
_chemical_name_common            'manganese 2-(1H-imidazole-yl) propinate'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                   15.215(2)
_cell_length_b                   5.0455(7)
_cell_length_c                   16.937(2)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      none
_cell_measurement_theta_min      none'
_cell_volume                     1300.2(3)
_computing_cell_refinement       'Bruker SAINT'
_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  'Bruker SMART 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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5929
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_T_max  0.9033
_exptl_absorpt_correction_T_min  0.5747
_exptl_absorpt_correction_type   'empirical used sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'quadrate sheet'
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.61(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0261
_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)+(0.0417P)²+0.2107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0683
_reflns_number_gt                1928
_reflns_number_total             2102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1.CIF
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4510983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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
Mn1 Mn 0.62682(2) 1.50213(10) 0.52970(8) 0.01997(12) Uani 1 1 d .
O1 O 0.61351(12) 1.1560(5) 0.45338(14) 0.0258(5) Uani 1 1 d .
O2 O 0.54722(14) 0.7622(4) 0.45006(19) 0.0280(8) Uani 1 1 d .
O3 O 0.20791(14) 1.2613(4) 0.61015(18) 0.0245(7) Uani 1 1 d .
O4 O 0.13971(12) 1.6551(5) 0.60735(14) 0.0248(5) Uani 1 1 d .
N1 N 0.38615(16) 1.0048(4) 0.41767(16) 0.0211(5) Uani 1 1 d .
N2 N 0.25506(15) 0.9154(5) 0.46860(16) 0.0237(5) Uani 1 1 d .
N3 N 0.49770(15) 1.4260(5) 0.59043(17) 0.0239(5) Uani 1 1 d .
N4 N 0.36746(15) 1.5115(4) 0.64286(17) 0.0208(5) Uani 1 1 d .
C1 C 0.54975(18) 1.0084(6) 0.44026(19) 0.0205(6) Uani 1 1 d .
C2 C 0.4855(2) 1.1890(9) 0.3165(2) 0.0364(9) Uani 1 1 d .
H2A H 0.4359 1.2754 0.2928 0.055 Uiso 1 1 calc R
H2B H 0.4946 1.0202 0.2917 0.055 Uiso 1 1 calc R
H2C H 0.5369 1.2969 0.3098 0.055 Uiso 1 1 calc R
C3 C 0.46828(17) 1.1486(7) 0.40378(17) 0.0209(7) Uani 1 1 d .
H3A H 0.4629 1.3237 0.4284 0.025 Uiso 1 1 calc R
C4 C 0.3571(2) 0.7747(6) 0.3829(3) 0.0263(9) Uani 1 1 d .
H4A H 0.3865 0.6745 0.3452 0.032 Uiso 1 1 calc R
C5 C 0.2770(3) 0.7227(7) 0.4145(3) 0.0268(11) Uani 1 1 d .
H5A H 0.2420 0.5780 0.4016 0.032 Uiso 1 1 calc R
C6 C 0.32289(17) 1.0801(6) 0.46863(19) 0.0222(6) Uani 1 1 d .
H6A H 0.3264 1.2305 0.5002 0.027 Uiso 1 1 calc R
C7 C 0.4784(3) 1.2369(6) 0.6467(3) 0.0290(12) Uani 1 1 d .
H7A H 0.5149 1.0966 0.6607 0.035 Uiso 1 1 calc R
C8 C 0.42953(18) 1.5862(6) 0.59034(19) 0.0241(6) Uani 1 1 d .
H8A H 0.4246 1.7340 0.5578 0.029 Uiso 1 1 calc R
C9 C 0.3990(2) 1.2857(7) 0.6785(3) 0.0277(9) Uani 1 1 d .
H9A H 0.3708 1.1860 0.7172 0.033 Uiso 1 1 calc R
C10 C 0.28394(17) 1.6480(7) 0.65627(18) 0.0217(7) Uani 1 1 d .
H10A H 0.2883 1.8220 0.6308 0.026 Uiso 1 1 calc R
C11 C 0.2677(2) 1.6967(8) 0.7440(2) 0.0343(9) Uani 1 1 d .
H11A H 0.3175 1.7857 0.7664 0.051 Uiso 1 1 calc R
H11C H 0.2591 1.5301 0.7703 0.051 Uiso 1 1 calc R
H11D H 0.2162 1.8047 0.7503 0.051 Uiso 1 1 calc R
C12 C 0.20460(18) 1.5061(5) 0.6200(2) 0.0201(6) 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'
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
O4 Mn1 O1 179.25(13) 3_585 .
O4 Mn1 O2 86.97(9) 3_585 1_565
O1 Mn1 O2 93.56(10) . 1_565
O4 Mn1 N2 93.02(8) 3_585 3_575
O1 Mn1 N2 87.47(9) . 3_575
O2 Mn1 N2 94.81(11) 1_565 3_575
O4 Mn1 N3 86.46(10) 3_585 .
O1 Mn1 N3 93.05(9) . .
O2 Mn1 N3 84.44(10) 1_565 .
N2 Mn1 N3 179.11(11) 3_575 .
O4 Mn1 O3 93.07(10) 3_585 3_575
O1 Mn1 O3 86.41(9) . 3_575
O2 Mn1 O3 179.80(15) 1_565 3_575
N2 Mn1 O3 85.00(10) 3_575 3_575
N3 Mn1 O3 95.75(10) . 3_575
C1 O1 Mn1 131.1(2) . .
C1 O2 Mn1 130.1(2) . 1_545
C12 O3 Mn1 129.7(2) . 3_475
C12 O4 Mn1 130.3(2) . 3_485
C6 N1 C4 106.4(3) . .
C6 N1 C3 125.0(3) . .
C4 N1 C3 128.6(3) . .
C6 N2 C5 104.8(3) . .
C6 N2 Mn1 124.0(2) . 3_475
C5 N2 Mn1 130.3(2) . 3_475
C8 N3 C7 104.9(3) . .
C8 N3 Mn1 125.7(2) . .
C7 N3 Mn1 128.3(2) . .
C8 N4 C9 106.1(3) . .
C8 N4 C10 125.3(3) . .
C9 N4 C10 128.6(3) . .
O1 C1 O2 126.4(3) . .
O1 C1 C3 114.9(3) . .
O2 C1 C3 118.6(3) . .
C3 C2 H2A 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C3 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 C2 111.8(3) . .
N1 C3 C1 113.0(3) . .
C2 C3 C1 108.1(3) . .
N1 C3 H3A 107.9 . .
C2 C3 H3A 107.9 . .
C1 C3 H3A 107.9 . .
C5 C4 N1 106.5(3) . .
C5 C4 H4A 126.8 . .
N1 C4 H4A 126.8 . .
C4 C5 N2 110.1(3) . .
C4 C5 H5A 125.0 . .
N2 C5 H5A 125.0 . .
N2 C6 N1 112.3(3) . .
N2 C6 H6A 123.9 . .
N1 C6 H6A 123.9 . .
C9 C7 N3 109.9(3) . .
C9 C7 H7A 125.0 . .
N3 C7 H7A 125.0 . .
N3 C8 N4 112.3(3) . .
N3 C8 H8A 123.9 . .
N4 C8 H8A 123.9 . .
C7 C9 N4 106.8(3) . .
C7 C9 H9A 126.6 . .
N4 C9 H9A 126.6 . .
N4 C10 C11 111.6(3) . .
N4 C10 C12 113.7(3) . .
C11 C10 C12 109.8(3) . .
N4 C10 H10A 107.2 . .
C11 C10 H10A 107.2 . .
C12 C10 H10A 107.2 . .
C10 C11 H11A 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
C10 C11 H11D 109.5 . .
H11A C11 H11D 109.5 . .
H11C C11 H11D 109.5 . .
O3 C12 O4 126.9(3) . .
O3 C12 C10 119.0(3) . .
O4 C12 C10 114.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O4 2.182(3) 3_585
Mn1 O1 2.182(3) .
Mn1 O2 2.238(3) 1_565
Mn1 N2 2.248(2) 3_575
Mn1 N3 2.250(3) .
Mn1 O3 2.269(3) 3_575
O1 C1 1.243(4) .
O2 C1 1.253(3) .
O2 Mn1 2.238(3) 1_545
O3 C12 1.247(3) .
O3 Mn1 2.269(3) 3_475
O4 C12 1.259(4) .
O4 Mn1 2.182(3) 3_485
N1 C6 1.347(4) .
N1 C4 1.375(4) .
N1 C3 1.464(4) .
N2 C6 1.325(4) .
N2 C5 1.376(5) .
N2 Mn1 2.248(2) 3_475
N3 C8 1.315(4) .
N3 C7 1.381(4) .
N4 C8 1.351(4) .
N4 C9 1.376(4) .
N4 C10 1.463(4) .
C1 C3 1.555(4) .
C2 C3 1.515(5) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 H3A 0.9800 .
C4 C5 1.357(5) .
C4 H4A 0.9300 .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C7 C9 1.346(6) .
C7 H7A 0.9300 .
C8 H8A 0.9300 .
C9 H9A 0.9300 .
C10 C11 1.526(5) .
C10 C12 1.532(4) .
C10 H10A 0.9800 .
C11 H11A 0.9600 .
C11 H11C 0.9600 .
C11 H11D 0.9600 .
