#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:33:44 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179485 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/82/4338276.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_4338276
loop_
_publ_author_name
'Lin, Lang'
'Yu, Rongmin'
'Wu, Xiao-Yuan'
'Yang, Wen-Bin'
'Zhang, Jian'
'Guo, Xiang-Guang'
'Lin, Zu-Jin'
'Lu, Can-Zhong'
_publ_section_title
;
 Enantioselective inclusion of alcohols by solvent-controlled assembled
 flexible metal-organic frameworks.
;
_journal_issue                   10
_journal_name_full               'Inorganic chemistry'
_journal_page_first              4794
_journal_page_last               4796
_journal_paper_doi               10.1021/ic500436g
_journal_volume                  53
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 Cu2 N6 O6, C9 H12 O'
_chemical_formula_sum            'C28 H36 Cu2 N6 O7'
_chemical_formula_weight         695.71
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.492(2)
_cell_length_b                   14.377(2)
_cell_length_c                   16.191(3)
_cell_measurement_reflns_used    9429
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      2.0700
_cell_volume                     3140.6(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25158
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.070
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 2108 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.021(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         7004
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0579P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                6001
_reflns_number_total             7004
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic500436g_si_001.cif
_cod_data_source_block           L-3-1-PPP
_cod_depositor_comments
'Adding full bibliography for 4338272--4338281.cif.'
_cod_original_cell_volume        3140.5(9)
_cod_database_code               4338276
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.872
_shelx_estimated_absorpt_t_max   0.933
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu -0.70060(4) -0.20674(4) 0.33602(3) 0.02811(14) Uani 1 1 d . .
Cu2 Cu -0.42989(4) -0.45121(4) 0.41501(3) 0.02860(14) Uani 1 1 d . .
N1 N -0.6218(3) -0.2392(3) 0.4289(2) 0.0324(9) Uani 1 1 d . .
N2 N -0.4837(3) -0.3965(3) 0.3176(2) 0.0319(9) Uani 1 1 d . .
N3 N -0.7990(3) -0.2023(3) 0.2477(2) 0.0319(8) Uani 1 1 d . .
N4 N -0.7808(3) -0.1631(3) 0.1744(2) 0.0353(9) Uani 1 1 d . .
H4A H -0.7259 -0.1349 0.1615 0.042 Uiso 1 1 calc R U
N5 N -0.3998(3) -0.5094(3) 0.5848(3) 0.0355(9) Uani 1 1 d . .
H5A H -0.3764 -0.4542 0.5950 0.043 Uiso 1 1 calc R U
N6 N -0.4319(3) -0.5373(3) 0.5106(2) 0.0325(8) Uani 1 1 d . .
C1 C -0.7453(4) -0.1482(3) 0.4984(3) 0.0298(10) Uani 1 1 d . .
C2 C -0.5670(5) -0.1186(4) 0.5239(4) 0.0531(15) Uani 1 1 d . .
H2A H -0.5021 -0.1472 0.5293 0.080 Uiso 1 1 calc R U
H2B H -0.5833 -0.0861 0.5746 0.080 Uiso 1 1 calc R U
H2C H -0.5662 -0.0749 0.4783 0.080 Uiso 1 1 calc R U
C3 C -0.6443(4) -0.1937(4) 0.5075(3) 0.0358(11) Uani 1 1 d . .
H3A H -0.6451 -0.2397 0.5530 0.043 Uiso 1 1 calc R U
C4 C -0.5592(3) -0.3069(3) 0.4186(3) 0.0281(9) Uani 1 1 d . .
C5 C -0.5525(3) -0.3350(3) 0.3290(3) 0.0293(9) Uani 1 1 d . .
C6 C -0.4598(4) -0.4379(4) 0.2384(3) 0.0434(14) Uani 1 1 d . .
H6A H -0.5217 -0.4549 0.2092 0.052 Uiso 1 1 calc R U
C7 C -0.3983(7) -0.3719(5) 0.1843(4) 0.089(3) Uani 1 1 d . .
H7A H -0.4367 -0.3165 0.1723 0.133 Uiso 1 1 calc R U
H7B H -0.3811 -0.4029 0.1331 0.133 Uiso 1 1 calc R U
H7C H -0.3382 -0.3546 0.2134 0.133 Uiso 1 1 calc R U
C8 C -0.3994(4) -0.5251(3) 0.2560(3) 0.0323(10) Uani 1 1 d . .
C9 C -0.8516(6) -0.1343(5) 0.0360(4) 0.068(2) Uani 1 1 d . .
H9A H -0.7898 -0.1005 0.0302 0.101 Uiso 1 1 calc R U
H9B H -0.9067 -0.0924 0.0260 0.101 Uiso 1 1 calc R U
H9C H -0.8535 -0.1848 -0.0036 0.101 Uiso 1 1 calc R U
C10 C -0.8592(4) -0.1733(3) 0.1226(3) 0.0403(12) Uani 1 1 d . .
C11 C -0.9299(4) -0.2240(3) 0.1639(3) 0.0326(10) Uani 1 1 d . .
C12 C -0.8893(4) -0.2406(3) 0.2424(3) 0.0345(11) Uani 1 1 d . .
C13 C -0.9312(5) -0.2898(5) 0.3140(3) 0.069(2) Uani 1 1 d . .
H13A H -0.8844 -0.2879 0.3594 0.104 Uiso 1 1 calc R U
H13B H -0.9444 -0.3540 0.2992 0.104 Uiso 1 1 calc R U
H13C H -0.9926 -0.2600 0.3305 0.104 Uiso 1 1 calc R U
C14 C -0.4662(4) -0.7497(3) 0.6357(4) 0.0416(13) Uani 1 1 d . .
H14A H -0.4486 -0.7962 0.5963 0.050 Uiso 1 1 d R U
H14B H -0.4284 -0.7924 0.6676 0.050 Uiso 1 1 d R U
C15 C -0.5053(5) -0.6782(4) 0.4498(4) 0.0538(15) Uani 1 1 d . .
H15A H -0.5046 -0.6401 0.4004 0.081 Uiso 1 1 calc R U
H15B H -0.5730 -0.6955 0.4629 0.081 Uiso 1 1 calc R U
H15C H -0.4663 -0.7339 0.4406 0.081 Uiso 1 1 calc R U
C16 C -0.4624(3) -0.6247(3) 0.5198(3) 0.0327(10) Uani 1 1 d . .
C17 C -0.4491(3) -0.6531(3) 0.6023(3) 0.0339(11) Uani 1 1 d . .
C18 C -0.4083(4) -0.5772(4) 0.6418(3) 0.0359(11) Uani 1 1 d . .
C19 C -0.3765(6) -0.5587(5) 0.7286(4) 0.0635(19) Uani 1 1 d . .
H19A H -0.3873 -0.6139 0.7619 0.095 Uiso 1 1 calc R U
H19B H -0.4148 -0.5075 0.7510 0.095 Uiso 1 1 calc R U
H19C H -0.3066 -0.5428 0.7294 0.095 Uiso 1 1 calc R U
C20 C -0.8214(5) -0.5159(5) 0.1601(6) 0.185(6) Uani 1 1 d G U
H20A H -0.8728 -0.4728 0.1519 0.222 Uiso 1 1 calc R U
C21 C -0.8344(6) -0.5897(6) 0.2145(6) 0.199(5) Uani 1 1 d G U
H21A H -0.8946 -0.5965 0.2431 0.239 Uiso 1 1 calc R U
C22 C -0.7583(7) -0.6534(5) 0.2268(5) 0.198(6) Uani 1 1 d G U
H22A H -0.7671 -0.7033 0.2636 0.237 Uiso 1 1 calc R U
C23 C -0.6692(6) -0.6433(5) 0.1846(5) 0.155(6) Uani 1 1 d G .
H23A H -0.6177 -0.6864 0.1928 0.186 Uiso 1 1 calc R U
C24 C -0.6562(5) -0.5695(6) 0.1302(5) 0.143(5) Uani 1 1 d G .
H24A H -0.5959 -0.5627 0.1016 0.171 Uiso 1 1 calc R U
C25 C -0.7323(6) -0.5058(5) 0.1179(5) 0.116(4) Uani 1 1 d G .
O1 O -0.7817(3) -0.1100(3) 0.5588(2) 0.0418(9) Uani 1 1 d . .
O2 O -0.7846(2) -0.1490(2) 0.4252(2) 0.0338(7) Uani 1 1 d . .
O3 O -0.6114(3) -0.2983(3) 0.2763(2) 0.0401(8) Uani 1 1 d . .
O4 O -0.5070(3) -0.3489(2) 0.4717(2) 0.0353(8) Uani 1 1 d . .
O5 O -0.3782(2) -0.5426(2) 0.3310(2) 0.0337(7) Uani 1 1 d . .
O6 O -0.3728(3) -0.5728(2) 0.1967(2) 0.0459(10) Uani 1 1 d . .
O7 O -0.6527(7) -0.3575(5) 0.0907(6) 0.169(3) Uani 1 1 d . U
H7F H -0.6524 -0.3503 0.1428 0.203 Uiso 1 1 d R U
C27 C -0.7144(11) -0.4329(9) -0.0232(8) 0.151(4) Uani 1 1 d . U
H27A H -0.7387 -0.3773 -0.0517 0.181 Uiso 1 1 calc R U
H27B H -0.6441 -0.4401 -0.0370 0.181 Uiso 1 1 calc R U
C26 C -0.7232(12) -0.4182(8) 0.0659(8) 0.151(4) Uani 1 1 d . U
H26A H -0.7869 -0.3850 0.0734 0.182 Uiso 1 1 calc R U
C28 C -0.7642(14) -0.5076(11) -0.0521(8) 0.208(8) Uani 1 1 d . .
H28A H -0.7516 -0.5145 -0.1107 0.313 Uiso 1 1 calc R U
H28B H -0.8347 -0.4989 -0.0430 0.313 Uiso 1 1 calc R U
H28C H -0.7422 -0.5630 -0.0232 0.313 Uiso 1 1 calc R U
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'
Cu Cu 0.3201 1.2651 '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_3
N1 Cu1 N3 165.55(17) .
N1 Cu1 O2 81.32(14) .
N3 Cu1 O2 97.37(16) .
N1 Cu1 O3 83.43(14) .
N3 Cu1 O3 94.36(16) .
O2 Cu1 O3 160.48(13) .
N1 Cu1 O6 98.74(17) 4_455
N3 Cu1 O6 95.70(15) 4_455
O2 Cu1 O6 93.71(14) 4_455
O3 Cu1 O6 100.60(15) 4_455
N2 Cu2 N6 154.00(18) .
N2 Cu2 O5 80.93(14) .
N6 Cu2 O5 97.17(15) .
N2 Cu2 O4 83.05(14) .
N6 Cu2 O4 95.33(15) .
O5 Cu2 O4 163.42(13) .
N2 Cu2 O1 109.68(16) 3_546
N6 Cu2 O1 96.32(15) 3_546
O5 Cu2 O1 94.35(14) 3_546
O4 Cu2 O1 95.07(14) 3_546
C4 N1 C3 125.6(4) .
C4 N1 Cu1 116.5(3) .
C3 N1 Cu1 117.5(3) .
C5 N2 C6 124.4(4) .
C5 N2 Cu2 115.9(3) .
C6 N2 Cu2 118.5(3) .
N4 N3 C12 106.5(4) .
N4 N3 Cu1 122.6(3) .
C12 N3 Cu1 130.7(3) .
N3 N4 C10 111.1(4) .
N6 N5 C18 111.7(4) .
C16 N6 N5 106.4(4) .
C16 N6 Cu2 133.0(3) .
N5 N6 Cu2 120.6(3) .
O1 C1 O2 124.7(4) .
O1 C1 C3 118.3(4) .
O2 C1 C3 116.9(4) .
N1 C3 C1 107.1(4) .
N1 C3 C2 109.0(4) .
C1 C3 C2 109.0(4) .
O4 C4 N1 129.2(4) .
O4 C4 C5 119.5(4) .
N1 C4 C5 111.3(4) .
O3 C5 N2 129.2(4) .
O3 C5 C4 119.5(4) .
N2 C5 C4 111.3(4) .
N2 C6 C8 107.0(4) .
N2 C6 C7 111.8(5) .
C8 C6 C7 109.0(5) .
O6 C8 O5 124.5(4) .
O6 C8 C6 117.9(4) .
O5 C8 C6 117.5(4) .
N4 C10 C11 107.3(4) .
N4 C10 C9 118.7(5) .
C11 C10 C9 134.0(5) .
C10 C11 C12 105.0(4) .
C10 C11 C14 128.7(5) 2_344
C12 C11 C14 126.1(5) 2_344
N3 C12 C11 110.1(4) .
N3 C12 C13 119.8(5) .
C11 C12 C13 130.1(5) .
C17 C14 C11 118.5(4) 2_345
N6 C16 C17 109.9(4) .
N6 C16 C15 121.6(5) .
C17 C16 C15 128.5(4) .
C18 C17 C16 105.1(4) .
C18 C17 C14 128.5(5) .
C16 C17 C14 126.0(5) .
N5 C18 C17 106.8(4) .
N5 C18 C19 119.4(5) .
C17 C18 C19 133.8(5) .
C21 C20 C25 120.0 .
C22 C21 C20 120.0 .
C21 C22 C23 120.0 .
C22 C23 C24 120.0 .
C25 C24 C23 120.0 .
C24 C25 C20 120.0 .
C24 C25 C26 124.5(8) .
C20 C25 C26 115.3(8) .
C1 O1 Cu2 133.6(3) 3_446
C1 O2 Cu1 115.3(3) .
C5 O3 Cu1 108.6(3) .
C4 O4 Cu2 109.0(3) .
C8 O5 Cu2 115.9(3) .
C8 O6 Cu1 142.7(3) 4_445
C28 C27 C26 114.6(13) .
O7 C26 C27 109.2(12) .
O7 C26 C25 115.2(11) .
C27 C26 C25 115.7(10) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.900(4) .
Cu1 N3 1.952(4) .
Cu1 O2 2.014(3) .
Cu1 O3 2.029(3) .
Cu1 O6 2.230(3) 4_455
Cu2 N2 1.906(4) .
Cu2 N6 1.982(4) .
Cu2 O5 2.016(3) .
Cu2 O4 2.022(3) .
Cu2 O1 2.226(3) 3_546
N1 C4 1.300(5) .
N1 C3 1.463(6) .
N2 C5 1.294(6) .
N2 C6 1.450(6) .
N3 N4 1.337(5) .
N3 C12 1.339(6) .
N4 C10 1.359(6) .
N5 N6 1.339(6) .
N5 C18 1.348(6) .
N6 C16 1.330(6) .
C1 O1 1.224(6) .
C1 O2 1.298(6) .
C1 C3 1.519(6) .
C2 C3 1.524(8) .
C4 O4 1.265(5) .
C4 C5 1.508(6) .
C5 O3 1.280(6) .
C6 C8 1.522(6) .
C6 C7 1.535(9) .
C8 O6 1.233(6) .
C8 O5 1.272(6) .
C9 C10 1.513(7) .
C10 C11 1.375(7) .
C11 C12 1.405(7) .
C11 C14 1.521(6) 2_344
C12 C13 1.471(7) .
C14 C17 1.508(6) .
C14 C11 1.521(6) 2_345
C15 C16 1.487(7) .
C16 C17 1.408(7) .
C17 C18 1.379(7) .
C18 C19 1.494(8) .
C20 C21 1.3900 .
C20 C25 1.3900 .
C21 C22 1.3900 .
C22 C23 1.3900 .
C23 C24 1.3900 .
C24 C25 1.3900 .
C25 C26 1.521(11) .
O1 Cu2 2.226(3) 3_446
O6 Cu1 2.230(3) 4_445
O7 C26 1.352(13) .
C27 C28 1.350(16) .
C27 C26 1.463(17) .
