#------------------------------------------------------------------------------
#$Date: 2019-11-28 16:39:24 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/83/7238329.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_7238329
loop_
_publ_author_name
'Yao, Ru-Xin'
'Hao, Zheng-Ming'
'Guo, Cai-Hong'
'Zhang, Xian-Ming'
_publ_section_title
;
 Enantiomers of conformation-flexible
 cyclopentane-1,2,3,4-tetracarboxylate in metal--organic frameworks
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4416
_journal_paper_doi               10.1039/c0ce00144a
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C19 H18 Mn2 N2 O10'
_chemical_formula_weight         544.23
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                90.1950(10)
_cell_angle_beta                 99.3210(10)
_cell_angle_gamma                104.2720(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8282(4)
_cell_length_b                   9.3941(4)
_cell_length_c                   13.1958(6)
_cell_measurement_reflns_used    2974
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.41
_cell_volume                     1045.51(8)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SAINT (Bruker, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker Apex CCD Diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6488
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    1.269
_exptl_absorpt_correction_T_max  0.9277
_exptl_absorpt_correction_T_min  0.7854
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0406
_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)+(0.0651P)²+0.4415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                3670
_reflns_number_total             4388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00144a.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7238329
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Mn1 Mn 0.30585(4) 0.77285(4) 0.54184(3) 0.02680(13) Uani 1 1 d .
Mn2 Mn 0.08476(5) 0.74033(4) 0.75331(3) 0.02744(13) Uani 1 1 d .
O1 O -0.0910(2) 0.4815(2) 0.28361(16) 0.0380(5) Uani 1 1 d .
O2 O -0.3027(2) 0.41941(19) 0.36050(16) 0.0356(4) Uani 1 1 d .
O3 O 0.0506(2) 0.7073(3) 0.50891(16) 0.0436(5) Uani 1 1 d .
O4 O -0.0923(2) 0.7421(2) 0.62521(14) 0.0374(5) Uani 1 1 d .
O5 O -0.4480(2) 0.7967(2) 0.54970(15) 0.0336(4) Uani 1 1 d .
O6 O -0.3272(2) 1.0339(2) 0.54620(15) 0.0344(4) Uani 1 1 d .
O7 O -0.2842(2) 1.12277(19) 0.31297(15) 0.0341(4) Uani 1 1 d .
O8 O -0.1842(4) 1.0004(2) 0.2142(2) 0.0618(7) Uani 1 1 d .
O1W O 0.2577(3) 0.6416(2) 0.39592(17) 0.0470(5) Uani 1 1 d .
H14A H 0.1615 0.6104 0.4035 0.056 Uiso 1 1 d R
H15A H 0.2593 0.6909 0.3420 0.056 Uiso 1 1 d R
O2W O 0.3817(3) 0.4392(2) 0.32479(19) 0.0488(6) Uani 1 1 d .
H16A H 0.2889 0.4014 0.3370 0.059 Uiso 1 1 d R
H17A H 0.4193 0.3695 0.3072 0.059 Uiso 1 1 d R
N1 N 0.1659(3) 0.6954(3) 0.91830(19) 0.0423(6) Uani 1 1 d .
N2 N -0.0891(3) 0.7918(3) 0.8489(2) 0.0455(6) Uani 1 1 d .
C1 C -0.1927(3) 0.6745(3) 0.34258(19) 0.0254(5) Uani 1 1 d .
H1A H -0.0918 0.7358 0.3285 0.031 Uiso 1 1 calc R
C2 C -0.2157(3) 0.7135(3) 0.45072(18) 0.0230(5) Uani 1 1 d .
H2A H -0.3077 0.6419 0.4685 0.028 Uiso 1 1 calc R
C3 C -0.2534(3) 0.8648(3) 0.44061(19) 0.0235(5) Uani 1 1 d .
H3A H -0.1534 0.9409 0.4471 0.028 Uiso 1 1 calc R
C4 C -0.3458(3) 0.8611(3) 0.32798(19) 0.0255(5) Uani 1 1 d .
H4A H -0.4576 0.8562 0.3294 0.031 Uiso 1 1 calc R
C5 C -0.3309(3) 0.7193(3) 0.2751(2) 0.0307(6) Uani 1 1 d .
H5A H -0.4281 0.6425 0.2712 0.037 Uiso 1 1 calc R
H5B H -0.3085 0.7378 0.2061 0.037 Uiso 1 1 calc R
C6 C -0.1955(3) 0.5127(3) 0.32820(19) 0.0272(5) Uani 1 1 d .
C7 C -0.0738(3) 0.7210(3) 0.53385(19) 0.0257(5) Uani 1 1 d .
C8 C -0.3497(3) 0.9013(3) 0.51888(19) 0.0258(5) Uani 1 1 d .
C9 C -0.2705(3) 1.0006(3) 0.2789(2) 0.0296(6) Uani 1 1 d .
C10 C 0.2896(5) 0.6377(4) 0.9470(3) 0.0615(10) Uani 1 1 d .
H6A H 0.3512 0.6250 0.8985 0.074 Uiso 1 1 calc R
C11 C 0.3293(6) 0.5963(5) 1.0461(4) 0.0830(14) Uani 1 1 d .
H7A H 0.4164 0.5571 1.0641 0.100 Uiso 1 1 calc R
C12 C 0.2388(7) 0.6138(6) 1.1168(3) 0.0863(15) Uani 1 1 d .
H8A H 0.2634 0.5868 1.1840 0.104 Uiso 1 1 calc R
C13 C 0.1113(6) 0.6716(5) 1.0884(3) 0.0702(12) Uani 1 1 d .
H9A H 0.0476 0.6827 1.1361 0.084 Uiso 1 1 calc R
C14 C 0.0770(4) 0.7138(4) 0.9877(2) 0.0468(8) Uani 1 1 d .
C15 C -0.0566(4) 0.7793(4) 0.9509(2) 0.0465(8) Uani 1 1 d .
C16 C -0.1418(5) 0.8298(5) 1.0165(3) 0.0661(11) Uani 1 1 d .
H10A H -0.1174 0.8219 1.0872 0.079 Uiso 1 1 calc R
C17 C -0.2610(6) 0.8907(6) 0.9764(4) 0.0836(15) Uani 1 1 d .
H11A H -0.3199 0.9231 1.0199 0.100 Uiso 1 1 calc R
C18 C -0.2958(5) 0.9051(6) 0.8726(4) 0.0810(14) Uani 1 1 d .
H12A H -0.3770 0.9472 0.8442 0.097 Uiso 1 1 calc R
C19 C -0.2052(5) 0.8546(5) 0.8121(3) 0.0627(10) Uani 1 1 d .
H13A H -0.2263 0.8648 0.7415 0.075 Uiso 1 1 calc R
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
O5 Mn1 O6 88.52(7) 1_655 2_576
O5 Mn1 O3 166.74(8) 1_655 .
O6 Mn1 O3 95.10(8) 2_576 .
O5 Mn1 O7 104.71(8) 1_655 2_576
O6 Mn1 O7 96.60(7) 2_576 2_576
O3 Mn1 O7 87.57(8) . 2_576
O5 Mn1 O1W 90.35(8) 1_655 .
O6 Mn1 O1W 88.17(8) 2_576 .
O3 Mn1 O1W 77.05(8) . .
O7 Mn1 O1W 164.27(8) 2_576 .
O5 Mn1 O2 87.75(7) 1_655 2_566
O6 Mn1 O2 175.54(8) 2_576 2_566
O3 Mn1 O2 89.08(8) . 2_566
O7 Mn1 O2 82.00(7) 2_576 2_566
O1W Mn1 O2 94.29(8) . 2_566
O4 Mn2 O1 92.80(8) . 2_566
O4 Mn2 O7 96.08(8) . 2_576
O1 Mn2 O7 103.65(7) 2_566 2_576
O4 Mn2 N1 152.65(9) . .
O1 Mn2 N1 86.64(9) 2_566 .
O7 Mn2 N1 110.63(9) 2_576 .
O4 Mn2 N2 85.58(9) . .
O1 Mn2 N2 122.40(9) 2_566 .
O7 Mn2 N2 133.82(9) 2_576 .
N1 Mn2 N2 71.92(10) . .
O4 Mn2 O8 98.65(9) . 2_576
O1 Mn2 O8 157.27(9) 2_566 2_576
O7 Mn2 O8 55.80(7) 2_576 2_576
N1 Mn2 O8 91.92(9) . 2_576
N2 Mn2 O8 78.26(9) . 2_576
C6 O1 Mn2 123.48(17) . 2_566
C6 O2 Mn1 134.15(16) . 2_566
C7 O3 Mn1 146.02(19) . .
C7 O4 Mn2 122.65(16) . .
C8 O5 Mn1 127.48(15) . 1_455
C8 O6 Mn1 130.95(17) . 2_576
C9 O7 Mn1 139.60(17) . 2_576
C9 O7 Mn2 95.43(16) . 2_576
Mn1 O7 Mn2 110.29(8) 2_576 2_576
C9 O8 Mn2 88.40(17) . 2_576
Mn1 O1W H14A 89.4 . .
Mn1 O1W H15A 115.2 . .
H14A O1W H15A 107.7 . .
H16A O2W H17A 107.7 . .
C14 N1 C10 119.0(3) . .
C14 N1 Mn2 118.1(2) . .
C10 N1 Mn2 122.5(2) . .
C19 N2 C15 118.3(3) . .
C19 N2 Mn2 123.6(2) . .
C15 N2 Mn2 117.2(2) . .
C6 C1 C2 112.4(2) . .
C6 C1 C5 113.7(2) . .
C2 C1 C5 101.90(19) . .
C6 C1 H1A 109.5 . .
C2 C1 H1A 109.5 . .
C5 C1 H1A 109.5 . .
C7 C2 C1 114.84(19) . .
C7 C2 C3 110.5(2) . .
C1 C2 C3 103.88(18) . .
C7 C2 H2A 109.1 . .
C1 C2 H2A 109.1 . .
C3 C2 H2A 109.1 . .
C8 C3 C2 114.92(19) . .
C8 C3 C4 110.95(19) . .
C2 C3 C4 104.66(19) . .
C8 C3 H3A 108.7 . .
C2 C3 H3A 108.7 . .
C4 C3 H3A 108.7 . .
C9 C4 C5 113.7(2) . .
C9 C4 C3 107.7(2) . .
C5 C4 C3 105.35(18) . .
C9 C4 H4A 110.0 . .
C5 C4 H4A 110.0 . .
C3 C4 H4A 110.0 . .
C1 C5 C4 105.5(2) . .
C1 C5 H5A 110.6 . .
C4 C5 H5A 110.6 . .
C1 C5 H5B 110.6 . .
C4 C5 H5B 110.6 . .
H5A C5 H5B 108.8 . .
O2 C6 O1 124.4(2) . .
O2 C6 C1 117.7(2) . .
O1 C6 C1 117.9(2) . .
O3 C7 O4 124.5(2) . .
O3 C7 C2 118.8(2) . .
O4 C7 C2 116.6(2) . .
O6 C8 O5 124.7(2) . .
O6 C8 C3 117.6(2) . .
O5 C8 C3 117.7(2) . .
O8 C9 O7 119.1(3) . .
O8 C9 C4 121.9(2) . .
O7 C9 C4 118.6(2) . .
N1 C10 C11 122.4(4) . .
N1 C10 H6A 118.8 . .
C11 C10 H6A 118.8 . .
C12 C11 C10 118.8(4) . .
C12 C11 H7A 120.6 . .
C10 C11 H7A 120.6 . .
C11 C12 C13 119.5(4) . .
C11 C12 H8A 120.3 . .
C13 C12 H8A 120.3 . .
C12 C13 C14 119.7(4) . .
C12 C13 H9A 120.1 . .
C14 C13 H9A 120.1 . .
N1 C14 C13 120.5(4) . .
N1 C14 C15 116.1(3) . .
C13 C14 C15 123.4(4) . .
N2 C15 C16 121.1(4) . .
N2 C15 C14 115.9(3) . .
C16 C15 C14 123.0(3) . .
C17 C16 C15 119.2(4) . .
C17 C16 H10A 120.4 . .
C15 C16 H10A 120.4 . .
C16 C17 C18 120.7(4) . .
C16 C17 H11A 119.7 . .
C18 C17 H11A 119.7 . .
C17 C18 C19 117.1(4) . .
C17 C18 H12A 121.5 . .
C19 C18 H12A 121.5 . .
N2 C19 C18 123.7(4) . .
N2 C19 H13A 118.2 . .
C18 C19 H13A 118.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O5 2.1143(18) 1_655
Mn1 O6 2.1444(19) 2_576
Mn1 O3 2.1547(19) .
Mn1 O7 2.2060(19) 2_576
Mn1 O1W 2.207(2) .
Mn1 O2 2.2195(19) 2_566
Mn2 O4 2.1118(19) .
Mn2 O1 2.1549(19) 2_566
Mn2 O7 2.216(2) 2_576
Mn2 N1 2.254(3) .
Mn2 N2 2.273(3) .
Mn2 O8 2.388(2) 2_576
O1 C6 1.261(3) .
O1 Mn2 2.1549(19) 2_566
O2 C6 1.253(3) .
O2 Mn1 2.2195(19) 2_566
O3 C7 1.232(3) .
O4 C7 1.264(3) .
O5 C8 1.258(3) .
O5 Mn1 2.1143(18) 1_455
O6 C8 1.254(3) .
O6 Mn1 2.1444(19) 2_576
O7 C9 1.272(3) .
O7 Mn1 2.2060(19) 2_576
O7 Mn2 2.216(2) 2_576
O8 C9 1.234(3) .
O8 Mn2 2.388(2) 2_576
O1W H14A 0.8500 .
O1W H15A 0.8500 .
O2W H16A 0.8501 .
O2W H17A 0.8500 .
N1 C14 1.336(4) .
N1 C10 1.338(4) .
N2 C19 1.332(4) .
N2 C15 1.341(4) .
C1 C6 1.525(3) .
C1 C2 1.529(3) .
C1 C5 1.537(3) .
C1 H1A 0.9800 .
C2 C7 1.513(3) .
C2 C3 1.539(3) .
C2 H2A 0.9800 .
C3 C8 1.528(3) .
C3 C4 1.571(3) .
C3 H3A 0.9800 .
C4 C9 1.515(3) .
C4 C5 1.545(3) .
C4 H4A 0.9800 .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C10 C11 1.380(5) .
C10 H6A 0.9300 .
C11 C12 1.356(7) .
C11 H7A 0.9300 .
C12 C13 1.367(7) .
C12 H8A 0.9300 .
C13 C14 1.395(5) .
C13 H9A 0.9300 .
C14 C15 1.477(5) .
C15 C16 1.388(5) .
C16 C17 1.354(6) .
C16 H10A 0.9300 .
C17 C18 1.370(7) .
C17 H11A 0.9300 .
C18 C19 1.376(5) .
C18 H12A 0.9300 .
C19 H13A 0.9300 .
