#------------------------------------------------------------------------------
#$Date: 2015-06-05 07:12:56 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138217 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/36/4123616.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_4123616
loop_
_publ_author_name
'Tominaka, Satoshi'
'Coudert, François-Xavier'
'Dao, Thang D.'
'Nagao, Tadaaki'
'Cheetham, Anthony K.'
_publ_section_title
;
 Insulator-to-Proton-Conductor Transition in a Dense Metal-Organic
 Framework.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6428
_journal_page_last               6431
_journal_paper_doi               10.1021/jacs.5b02777
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C8 Li2 O16 Zr, 2(C2 H8 N)'
_chemical_formula_sum            'C12 H16 Li2 N2 O16 Zr'
_chemical_formula_weight         549.37
_chemical_name_common            dma2[Li2Zr(ox)4]
_chemical_name_systematic        'Lithium Zirconium Oxalate Dimethylammonium'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.834(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.0091(8)
_cell_length_b                   16.6385(9)
_cell_length_c                   15.3534(7)
_cell_measurement_reflns_used    7476
_cell_measurement_temperature    120.00(14)
_cell_measurement_theta_max      67.5110
_cell_measurement_theta_min      3.9130
_cell_volume                     4089.2(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.00(14)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0079189000
_diffrn_orient_matrix_UB_12      -0.0306215000
_diffrn_orient_matrix_UB_13      0.0942376000
_diffrn_orient_matrix_UB_21      0.0950318000
_diffrn_orient_matrix_UB_22      -0.0145888000
_diffrn_orient_matrix_UB_23      0.0046349000
_diffrn_orient_matrix_UB_31      0.0131734000
_diffrn_orient_matrix_UB_32      0.0861290000
_diffrn_orient_matrix_UB_33      0.0341650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21297
_diffrn_reflns_theta_full        67.86
_diffrn_reflns_theta_max         67.86
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.206
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_correction_T_min  0.251
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.6843
_exptl_crystal_size_mid          0.0519
_exptl_crystal_size_min          0.0467
_refine_diff_density_max         1.022
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0659P)²+1.6469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                3110
_reflns_number_total             3697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b02777_si_002.cif
_cod_data_source_block           PhaseI_120K
_cod_depositor_comments
'Adding full bibliography for 4123615--4123618.cif.'
_cod_original_cell_volume        4089.2(3)
_cod_database_code               4123616
_chemical_oxdiff_formula         'Li2 Zr C12 O16 N2 H16'
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N22(H22A,H22B), N1(H1D,H1E)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C29(H29A,H29B,H29C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x, -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_posn
Li2 Li 0.1948(2) 0.5450(2) 0.8826(2) 0.0153(7) Uani 1 1 d .
Li3 Li -0.1955(2) -0.0501(2) 0.8683(2) 0.0142(6) Uani 1 1 d .
C5 C -0.14752(13) 0.36618(13) 0.86121(14) 0.0133(4) Uani 1 1 d .
C8 C -0.12460(11) 0.36281(11) 0.95941(12) 0.0137(4) Uani 1 1 d .
C9 C -0.12800(13) 0.11505(13) 0.84565(14) 0.0133(4) Uani 1 1 d .
C10 C 0.13354(13) 0.38001(13) 0.88607(14) 0.0137(5) Uani 1 1 d .
C11 C 0.12296(12) 0.36279(12) 0.78798(12) 0.0140(4) Uani 1 1 d .
C13 C -0.08704(11) 0.12532(11) 0.75545(12) 0.0128(4) Uani 1 1 d .
C19 C 0.08949(11) 0.13408(11) 0.99874(12) 0.0125(4) Uani 1 1 d .
C24 C 0.13674(13) 0.12688(13) 0.91203(14) 0.0136(4) Uani 1 1 d .
O1 O 0.03412(8) 0.19023(8) 0.99782(8) 0.0124(3) Uani 1 1 d .
O2 O -0.03467(8) 0.18443(8) 0.75313(8) 0.0131(3) Uani 1 1 d .
O3 O -0.09593(8) 0.32615(8) 0.81426(8) 0.0154(3) Uani 1 1 d .
O4 O -0.10184(8) 0.16675(8) 0.90199(9) 0.0161(3) Uani 1 1 d .
O5 O 0.06331(8) 0.31349(8) 0.76930(8) 0.0141(3) Uani 1 1 d .
O6 O 0.09070(8) 0.33111(8) 0.93335(8) 0.0162(3) Uani 1 1 d .
O7 O -0.06567(8) 0.31314(8) 0.97818(8) 0.0152(3) Uani 1 1 d .
O8 O 0.10346(8) 0.16864(8) 0.85050(9) 0.0162(3) Uani 1 1 d .
O9 O 0.10455(9) 0.08970(9) 1.06014(9) 0.0207(3) Uani 1 1 d .
O10 O -0.17948(9) 0.06268(9) 0.85840(10) 0.0193(3) Uani 1 1 d .
O11 O 0.17044(9) 0.39469(9) 0.73715(9) 0.0228(3) Uani 1 1 d .
O12 O -0.16177(10) 0.40582(10) 1.00970(9) 0.0266(4) Uani 1 1 d .
O13 O -0.20738(9) 0.40404(9) 0.83380(9) 0.0190(3) Uani 1 1 d .
O14 O 0.17823(9) 0.43349(9) 0.91391(9) 0.0181(3) Uani 1 1 d .
O15 O -0.10342(9) 0.08088(9) 0.69479(9) 0.0205(3) Uani 1 1 d .
O17 O 0.19791(9) 0.08363(9) 0.90684(10) 0.0201(4) Uani 1 1 d .
Zr1 Zr -0.000556(8) 0.249649(8) 0.874164(7) 0.00688(11) Uani 1 1 d .
C25 C -0.17174(14) 0.28761(14) 0.61785(15) 0.0258(5) Uani 1 1 d .
H25A H -0.2001 0.3032 0.5650 0.039 Uiso 1 1 calc GR
H25B H -0.2062 0.2999 0.6668 0.039 Uiso 1 1 calc GR
H25C H -0.1608 0.2309 0.6166 0.039 Uiso 1 1 calc GR
C29 C -0.10286(16) 0.42013(13) 0.61941(15) 0.0289(5) Uani 1 1 d .
H29A H -0.1259 0.4335 0.5632 0.043 Uiso 1 1 calc GR
H29B H -0.0497 0.4460 0.6270 0.043 Uiso 1 1 calc GR
H29C H -0.1401 0.4380 0.6639 0.043 Uiso 1 1 calc GR
N22 N -0.09197(11) 0.33188(10) 0.62586(10) 0.0180(4) Uani 1 1 d .
H22A H -0.0575 0.3154 0.5836 0.022 Uiso 1 1 calc R
H22B H -0.0676 0.3200 0.6775 0.022 Uiso 1 1 calc R
C1 C 0.09939(18) 0.07181(15) 0.62798(17) 0.0369(6) Uani 1 1 d .
H1A H 0.1354 0.0543 0.5823 0.055 Uiso 1 1 calc GR
H1B H 0.0462 0.0456 0.6220 0.055 Uiso 1 1 calc GR
H1C H 0.1241 0.0585 0.6835 0.055 Uiso 1 1 calc GR
C2 C 0.16664(14) 0.20517(14) 0.63304(14) 0.0256(5) Uani 1 1 d .
H2A H 0.2031 0.1929 0.5858 0.038 Uiso 1 1 calc GR
H2B H 0.1932 0.1902 0.6871 0.038 Uiso 1 1 calc GR
H2C H 0.1550 0.2618 0.6334 0.038 Uiso 1 1 calc GR
N1 N 0.08767(11) 0.15995(11) 0.62205(11) 0.0204(4) Uani 1 1 d .
H1D H 0.0647 0.1720 0.5698 0.024 Uiso 1 1 calc R
H1E H 0.0518 0.1756 0.6633 0.024 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 0.0181 0.0091 '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'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -0.1862 2.2449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10 0 0 0.0179 10.0002 0.0003 -0.0004 -0.0792 0.9503 0.1317
-10 0 0 0.0339 -10.0002 -0.0003 0.0004 0.0792 -0.9503 -0.1317
0 0 -10 0.3262 -0.0014 0.0002 -10.0002 -0.9424 -0.0465 -0.3417
0 0 10 0.3572 0.0014 -0.0002 10.0002 0.9424 0.0465 0.3417
1 11 0 0.0224 1.0002 10.9999 -0.0002 -0.3448 -0.0654 0.9606
-1 -11 0 0.0244 -1.0002 -10.9999 0.0002 0.3448 0.0654 -0.9606
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
O12 Li2 O13 112.23(17) 5_567 6_665
O12 Li2 O14 98.85(16) 5_567 .
O12 Li2 O15 100.29(16) 5_567 4_456
O13 Li2 O15 103.39(16) 6_665 4_456
O14 Li2 O13 128.98(19) . 6_665
O14 Li2 O15 109.79(17) . 4_456
O10 Li3 O9 106.36(17) . 5_557
O10 Li3 O11 112.17(17) . 4_446
O11 Li3 O9 98.79(16) 4_446 5_557
O17 Li3 O9 113.37(17) 6 5_557
O17 Li3 O10 115.98(18) 6 .
O17 Li3 O11 108.89(17) 6 4_446
O3 C5 C8 112.41(17) . .
O13 C5 C8 122.00(19) . .
O13 C5 O3 125.58(19) . .
O7 C8 C5 113.89(16) . .
O12 C8 C5 119.12(17) . .
O12 C8 O7 126.99(18) . .
O4 C9 C13 112.91(17) . .
O10 C9 C13 121.26(19) . .
O10 C9 O4 125.8(2) . .
O6 C10 C11 112.33(18) . .
O14 C10 C11 122.42(19) . .
O14 C10 O6 125.2(2) . .
O5 C11 C10 114.01(17) . .
O11 C11 C10 118.96(18) . .
O11 C11 O5 127.02(18) . .
O2 C13 C9 113.04(16) . .
O15 C13 C9 121.89(18) . .
O15 C13 O2 125.06(18) . .
O1 C19 C24 113.09(16) . .
O9 C19 C24 121.71(17) . .
O9 C19 O1 125.20(18) . .
O8 C24 C19 112.91(17) . .
O17 C24 C19 120.39(19) . .
O17 C24 O8 126.7(2) . .
C19 O1 Zr1 119.97(11) . .
C13 O2 Zr1 120.12(11) . .
C5 O3 Zr1 121.06(12) . .
C9 O4 Zr1 121.90(13) . .
C11 O5 Zr1 119.79(12) . .
C10 O6 Zr1 120.95(13) . .
C8 O7 Zr1 120.17(12) . .
C24 O8 Zr1 121.55(13) . .
C19 O9 Li3 141.95(17) . 5_557
C9 O10 Li3 144.31(18) . .
C11 O11 Li3 153.26(17) . 4_456
C8 O12 Li2 159.92(18) . 5_567
C5 O13 Li2 136.78(17) . 6_565
C10 O14 Li2 134.12(17) . .
C13 O15 Li2 143.09(16) . 4_446
C24 O17 Li3 157.04(19) . 6_655
O1 Zr1 O2 124.00(6) . .
O3 Zr1 O1 142.27(5) . .
O3 Zr1 O2 76.67(5) . .
O3 Zr1 O5 74.86(5) . .
O3 Zr1 O6 105.88(6) . .
O3 Zr1 O7 71.85(5) . .
O4 Zr1 O1 74.08(5) . .
O4 Zr1 O2 71.25(5) . .
O4 Zr1 O3 86.19(5) . .
O4 Zr1 O5 143.85(5) . .
O4 Zr1 O6 143.96(5) . .
O4 Zr1 O7 78.39(5) . .
O4 Zr1 O8 102.38(6) . .
O5 Zr1 O1 137.30(5) . .
O5 Zr1 O2 74.52(5) . .
O6 Zr1 O1 76.18(5) . .
O6 Zr1 O2 144.08(5) . .
O6 Zr1 O5 71.85(5) . .
O6 Zr1 O7 73.72(5) . .
O7 Zr1 O1 72.84(5) . .
O7 Zr1 O2 137.23(5) . .
O7 Zr1 O5 122.22(6) . .
O8 Zr1 O1 71.48(5) . .
O8 Zr1 O2 74.71(5) . .
O8 Zr1 O3 145.44(5) . .
O8 Zr1 O5 79.13(5) . .
O8 Zr1 O6 86.84(5) . .
O8 Zr1 O7 142.49(5) . .
C25 N22 C29 112.81(17) . .
C2 N1 C1 112.92(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li2 O12 1.926(4) 5_567
Li2 O13 1.941(3) 6_665
Li2 O14 1.935(4) .
Li2 O15 1.964(3) 4_456
Li3 O9 1.927(3) 5_557
Li3 O10 1.900(4) .
Li3 O11 1.909(3) 4_446
Li3 O17 1.898(4) 6
C5 C8 1.548(3) .
C5 O3 1.289(3) .
C5 O13 1.217(3) .
C8 O7 1.284(2) .
C8 O12 1.215(2) .
C9 C13 1.550(3) .
C9 O4 1.286(3) .
C9 O10 1.217(3) .
C10 C11 1.540(3) .
C10 O6 1.294(3) .
C10 O14 1.215(3) .
C11 O5 1.288(2) .
C11 O11 1.219(2) .
C13 O2 1.293(2) .
C13 O15 1.215(2) .
C19 C24 1.545(3) .
C19 O1 1.288(2) .
C19 O9 1.219(2) .
C24 O8 1.282(3) .
C24 O17 1.219(3) .
O1 Zr1 2.2044(12) .
O2 Zr1 2.2135(12) .
O3 Zr1 2.1809(13) .
O4 Zr1 2.1758(13) .
O5 Zr1 2.1940(13) .
O6 Zr1 2.1814(13) .
O7 Zr1 2.1913(13) .
O8 Zr1 2.1769(13) .
O9 Li3 1.927(3) 5_557
O11 Li3 1.909(4) 4_456
O12 Li2 1.926(4) 5_567
O13 Li2 1.941(3) 6_565
O15 Li2 1.964(3) 4_446
O17 Li3 1.899(4) 6_655
C25 N22 1.478(3) .
C29 N22 1.482(3) .
C1 N1 1.481(3) .
C2 N1 1.479(3) .
