#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:33:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178816 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/70/4107039.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_4107039
loop_
_publ_author_name
'Jarrod F. Eubank'
'Lukasz Wojtas'
'Matthew R. Hight'
'Till Bousquet'
'Victor Ch. Kravtsov'
'Mohamed Eddaoudi'
_publ_section_title
;
 The Next Chapter in MOF Pillaring Strategies: Trigonal Heterofunctional
 Ligands To Access Targeted High-Connected Three Dimensional Nets,
 Isoreticular Platforms
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17532
_journal_page_last               17535
_journal_paper_doi               10.1021/ja203898s
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C14 H9 Cu N O5'
_chemical_formula_weight         334.76
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           148
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   19.132(4)
_cell_length_b                   19.132(4)
_cell_length_c                   37.505(15)
_cell_measurement_temperature    293(2)
_cell_volume                     11889(6)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD'
_diffrn_measurement_method       '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  0.1720
_diffrn_reflns_av_sigmaI/netI    0.1925
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            16421
_diffrn_reflns_theta_full        23.30
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.9437
_exptl_absorpt_correction_T_min  0.8847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    0.842
_exptl_crystal_description       block
_exptl_crystal_F_000             3042
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_platon_squeeze_details
;
;
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0314P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                1770
_reflns_number_total             3804
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203898s_si_003.cif
_cod_data_source_block           2
_cod_original_cell_volume        11888(6)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4107039
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
Cu1 Cu 0.52110(5) 0.47890(5) 1.030609(19) 0.0352(3) Uani 1 1 d . . .
O1 O 0.6275(2) 0.5146(3) 1.01047(12) 0.0472(13) Uani 1 1 d . . .
O2 O 0.5920(3) 0.5532(3) 0.95991(11) 0.0536(14) Uani 1 1 d . . .
O3 O 0.8876(2) 0.5149(3) 1.01005(12) 0.0468(13) Uani 1 1 d . . .
O4 O 0.9613(3) 0.5537(3) 0.96019(11) 0.0527(14) Uani 1 1 d . . .
C1 C 0.6401(5) 0.5439(4) 0.9793(2) 0.046(2) Uani 1 1 d . . .
C2 C 0.7204(2) 0.5672(3) 0.96267(12) 0.047(2) Uani 1 1 d G . .
C3 C 0.7399(3) 0.6060(3) 0.92981(13) 0.062(2) Uani 1 1 d G . .
H3 H 0.7042 0.6189 0.9188 0.074 Uiso 1 1 calc R . .
C4 C 0.8127(3) 0.6256(3) 0.91348(10) 0.068(2) Uani 1 1 d G A .
C5 C 0.8659(2) 0.6064(3) 0.93001(13) 0.059(2) Uani 1 1 d G . .
H5 H 0.9146 0.6195 0.9191 0.071 Uiso 1 1 calc R . .
C6 C 0.8464(3) 0.5676(3) 0.96287(13) 0.0436(19) Uani 1 1 d G . .
C7 C 0.7736(3) 0.5480(2) 0.97920(9) 0.0393(18) Uani 1 1 d G . .
H7 H 0.7606 0.5220 1.0012 0.047 Uiso 1 1 calc R . .
C8 C 0.9032(4) 0.5444(4) 0.9787(2) 0.046(2) Uani 1 1 d . . .
O5 O 0.8303(4) 0.6625(4) 0.88121(13) 0.103(2) Uani 1 1 d . . .
C9A C 0.7811(9) 0.6809(10) 0.8632(3) 0.076(5) Uani 0.50 1 d PDU A 1
H9A1 H 0.7787 0.7251 0.8746 0.092 Uiso 0.50 1 calc PR A 1
H9A2 H 0.7270 0.6346 0.8620 0.092 Uiso 0.50 1 calc PR A 1
C10A C 0.8173(9) 0.7050(10) 0.8264(2) 0.063(7) Uani 0.50 1 d PGD A 1
C11A C 0.7791(8) 0.7320(9) 0.8034(3) 0.098(7) Uani 0.50 1 d PG A 1
H11A H 0.7384 0.7408 0.8118 0.117 Uiso 0.50 1 calc PR A 1
C12A C 0.8018(9) 0.7457(10) 0.7678(3) 0.066(7) Uani 0.50 1 d PG A 1
H12A H 0.7748 0.7628 0.7527 0.079 Uiso 0.50 1 calc PR A 1
N1A N 0.8609(9) 0.7355(11) 0.7543(3) 0.044(2) Uani 0.50 1 d PGU A 1
C13A C 0.9002(7) 0.7120(9) 0.7768(3) 0.075(7) Uani 0.50 1 d PG A 1
H13A H 0.9429 0.7067 0.7682 0.090 Uiso 0.50 1 calc PR A 1
C14A C 0.8789(9) 0.6959(10) 0.8120(3) 0.055(6) Uani 0.50 1 d PGU A 1
H14A H 0.9065 0.6784 0.8266 0.067 Uiso 0.50 1 calc PR A 1
C9B C 0.8993(11) 0.6827(11) 0.8639(4) 0.089(6) Uani 0.50 1 d PDU A 2
H9B1 H 0.9081 0.6371 0.8630 0.107 Uiso 0.50 1 calc PR A 2
H9B2 H 0.9446 0.7269 0.8760 0.107 Uiso 0.50 1 calc PR A 2
C10B C 0.8910(9) 0.7079(10) 0.8263(2) 0.073(7) Uani 0.50 1 d PGD A 2
C11B C 0.9552(7) 0.7321(8) 0.8030(3) 0.090(6) Uani 0.50 1 d PG A 2
H11B H 1.0038 0.7377 0.8110 0.108 Uiso 0.50 1 calc PR A 2
C12B C 0.9466(8) 0.7479(10) 0.7676(3) 0.079(8) Uani 0.50 1 d PG A 2
H12B H 0.9907 0.7651 0.7525 0.095 Uiso 0.50 1 calc PR A 2
N1B N 0.8777(10) 0.7394(11) 0.7544(3) 0.044(2) Uani 0.50 1 d PGU A 2
C13B C 0.8143(8) 0.7131(9) 0.7767(3) 0.068(7) Uani 0.50 1 d PG A 2
H13B H 0.7652 0.7046 0.7678 0.082 Uiso 0.50 1 calc PR A 2
C14B C 0.8201(7) 0.6984(10) 0.8120(3) 0.057(6) Uani 0.50 1 d PGU A 2
H14B H 0.7753 0.6817 0.8268 0.069 Uiso 0.50 1 calc PR A 2
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_1
_geom_angle_site_symmetry_3
O1 Cu1 O3 88.56(18) . 2_655
O1 Cu1 O2 167.22(17) . 10_667
O3 Cu1 O2 89.16(19) 2_655 10_667
O1 Cu1 O4 88.96(19) . 11_567
O3 Cu1 O4 166.44(17) 2_655 11_567
O2 Cu1 O4 90.31(19) 10_667 11_567
O1 Cu1 N1A 102(3) . 6_565
O3 Cu1 N1A 108(3) 2_655 6_565
O2 Cu1 N1A 90(3) 10_667 6_565
O4 Cu1 N1A 86(3) 11_567 6_565
O1 Cu1 N1B 107(3) . 6_565
O3 Cu1 N1B 101(2) 2_655 6_565
O2 Cu1 N1B 86(3) 10_667 6_565
O4 Cu1 N1B 92(2) 11_567 6_565
N1A Cu1 N1B 8(4) 6_565 6_565
O1 Cu1 Cu1 88.94(14) . 10_667
O3 Cu1 Cu1 88.43(14) 2_655 10_667
O2 Cu1 Cu1 78.42(13) 10_667 10_667
O4 Cu1 Cu1 78.20(13) 11_567 10_667
N1A Cu1 Cu1 160(3) 6_565 10_667
N1B Cu1 Cu1 162(3) 6_565 10_667
C1 O1 Cu1 116.6(4) . .
C1 O2 Cu1 128.6(5) . 10_667
C8 O3 Cu1 118.1(4) . 3_665
C8 O4 Cu1 130.1(5) . 12_657
O2 C1 O1 127.4(7) . .
O2 C1 C2 115.6(7) . .
O1 C1 C2 117.0(6) . .
C3 C2 C7 120.0 . .
C3 C2 C1 119.2(5) . .
C7 C2 C1 120.8(5) . .
C2 C3 C4 120.0 . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
O5 C4 C5 120.7(5) . .
O5 C4 C3 119.3(5) . .
C5 C4 C3 120.0 . .
C4 C5 C6 120.0 . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C7 C6 C5 120.0 . .
C7 C6 C8 121.7(5) . .
C5 C6 C8 118.2(5) . .
C6 C7 C2 120.0 . .
C6 C7 H7 120.0 . .
C2 C7 H7 120.0 . .
O4 C8 O3 125.0(7) . .
O4 C8 C6 117.8(7) . .
O3 C8 C6 117.1(6) . .
C9A O5 C4 124.2(7) . .
C9A O5 C9B 113.5(9) . .
C4 O5 C9B 122.4(8) . .
O5 C9A C10A 105.5(11) . .
O5 C9A H9A1 110.6 . .
C10A C9A H9A1 110.6 . .
O5 C9A H9A2 110.6 . .
C10A C9A H9A2 110.6 . .
H9A1 C9A H9A2 108.8 . .
C14A C10A C11A 116.6 . .
C14A C10A C9A 127.2(11) . .
C11A C10A C9A 115.9(11) . .
C10A C11A C12A 119.7 . .
C10A C11A H11A 120.2 . .
C12A C11A H11A 120.2 . .
N1A C12A C11A 122.9 . .
N1A C12A H12A 118.5 . .
C11A C12A H12A 118.5 . .
C12A N1A C13A 117.5 . .
C12A N1A Cu1 116.8(7) . 8_654
C13A N1A Cu1 120.8(8) . 8_654
N1A C13A C14A 121.8 . .
N1A C13A H13A 119.1 . .
C14A C13A H13A 119.1 . .
C13A C14A C10A 121.4 . .
C13A C14A H14A 119.3 . .
C10A C14A H14A 119.3 . .
O5 C9B C10B 107.3(12) . .
O5 C9B H9B1 110.3 . .
C10B C9B H9B1 110.3 . .
O5 C9B H9B2 110.3 . .
C10B C9B H9B2 110.3 . .
H9B1 C9B H9B2 108.5 . .
C11B C10B C14B 116.6 . .
C11B C10B C9B 118.4(11) . .
C14B C10B C9B 124.5(11) . .
C10B C11B C12B 119.7 . .
C10B C11B H11B 120.2 . .
C12B C11B H11B 120.2 . .
N1B C12B C11B 122.9 . .
N1B C12B H12B 118.5 . .
C11B C12B H12B 118.5 . .
C12B N1B C13B 117.5 . .
C12B N1B Cu1 116.6(8) . 8_654
C13B N1B Cu1 118.6(8) . 8_654
N1B C13B C14B 121.8 . .
N1B C13B H13B 119.1 . .
C14B C13B H13B 119.1 . .
C13B C14B C10B 121.4 . .
C13B C14B H14B 119.3 . .
C10B C14B H14B 119.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.947(4) .
Cu1 O3 1.949(4) 2_655
Cu1 O2 1.963(5) 10_667
Cu1 O4 1.966(5) 11_567
Cu1 N1A 2.19(7) 6_565
Cu1 N1B 2.21(9) 6_565
Cu1 Cu1 2.6882(17) 10_667
O1 C1 1.267(7) .
O2 C1 1.254(7) .
O2 Cu1 1.963(5) 10_667
O3 C8 1.272(7) .
O3 Cu1 1.949(4) 3_665
O4 C8 1.246(7) .
O4 Cu1 1.966(5) 12_657
C1 C2 1.503(8) .
C2 C3 1.3900 .
C2 C7 1.3900 .
C3 C4 1.3900 .
C3 H3 0.9300 .
C4 O5 1.356(6) .
C4 C5 1.3900 .
C5 C6 1.3900 .
C5 H5 0.9300 .
C6 C7 1.3900 .
C6 C8 1.489(8) .
C7 H7 0.9300 .
O5 C9A 1.340(14) .
O5 C9B 1.342(16) .
C9A C10A 1.511(13) .
C9A H9A1 0.9700 .
C9A H9A2 0.9700 .
C10A C14A 1.3842 .
C10A C11A 1.3844 .
C11A C12A 1.3883 .
C11A H11A 0.9300 .
C12A N1A 1.3408 .
C12A H12A 0.9300 .
N1A C13A 1.3473 .
N1A Cu1 2.186(11) 8_654
C13A C14A 1.3715 .
C13A H13A 0.9300 .
C14A H14A 0.9300 .
C9B C10B 1.523(14) .
C9B H9B1 0.9700 .
C9B H9B2 0.9700 .
C10B C11B 1.3842 .
C10B C14B 1.3843 .
C11B C12B 1.3882 .
C11B H11B 0.9300 .
C12B N1B 1.3408 .
C12B H12B 0.9300 .
N1B C13B 1.3473 .
N1B Cu1 2.206(12) 8_654
C13B C14B 1.3715 .
C13B H13B 0.9300 .
C14B H14B 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O3 Cu1 O1 C1 89.8(5) 2_655 .
O2 Cu1 O1 C1 10.0(12) 10_667 .
O4 Cu1 O1 C1 -76.9(5) 11_567 .
N1A Cu1 O1 C1 -162(3) 6_565 .
N1B Cu1 O1 C1 -169(2) 6_565 .
Cu1 Cu1 O1 C1 1.4(5) 10_667 .
Cu1 O2 C1 O1 -3.6(11) 10_667 .
Cu1 O2 C1 C2 173.6(4) 10_667 .
Cu1 O1 C1 O2 0.7(9) . .
Cu1 O1 C1 C2 -176.6(4) . .
O2 C1 C2 C3 8.0(7) . .
O1 C1 C2 C3 -174.5(4) . .
O2 C1 C2 C7 -169.9(5) . .
O1 C1 C2 C7 7.7(7) . .
C7 C2 C3 C4 0.0 . .
C1 C2 C3 C4 -177.9(5) . .
C2 C3 C4 O5 179.2(5) . .
C2 C3 C4 C5 0.0 . .
O5 C4 C5 C6 -179.1(5) . .
C3 C4 C5 C6 0.0 . .
C4 C5 C6 C7 0.0 . .
C4 C5 C6 C8 176.9(5) . .
C5 C6 C7 C2 0.0 . .
C8 C6 C7 C2 -176.8(5) . .
C3 C2 C7 C6 0.0 . .
C1 C2 C7 C6 177.8(5) . .
Cu1 O4 C8 O3 5.2(11) 12_657 .
Cu1 O4 C8 C6 -173.3(4) 12_657 .
Cu1 O3 C8 O4 -1.6(9) 3_665 .
Cu1 O3 C8 C6 177.0(4) 3_665 .
C7 C6 C8 O4 169.9(5) . .
C5 C6 C8 O4 -6.9(7) . .
C7 C6 C8 O3 -8.7(8) . .
C5 C6 C8 O3 174.4(5) . .
C5 C4 O5 C9A 178.1(10) . .
C3 C4 O5 C9A -1.1(12) . .
C5 C4 O5 C9B -0.5(12) . .
C3 C4 O5 C9B -179.6(10) . .
C4 O5 C9A C10A -168.9(9) . .
C9B O5 C9A C10A 9.8(17) . .
O5 C9A C10A C14A 10.8(18) . .
O5 C9A C10A C11A -175.9(10) . .
C14A C10A C11A C12A 2.1 . .
C9A C10A C11A C12A -171.9(16) . .
C10A C11A C12A N1A -1.3 . .
C11A C12A N1A C13A -1.1 . .
C11A C12A N1A Cu1 154.4(12) . 8_654
C12A N1A C13A C14A 2.6 . .
Cu1 N1A C13A C14A -151.8(12) 8_654 .
N1A C13A C14A C10A -1.8 . .
C11A C10A C14A C13A -0.6 . .
C9A C10A C14A C13A 172.6(18) . .
C9A O5 C9B C10B -9.1(18) . .
C4 O5 C9B C10B 169.6(9) . .
O5 C9B C10B C11B 179.7(11) . .
O5 C9B C10B C14B -9.3(19) . .
C14B C10B C11B C12B 2.1 . .
C9B C10B C11B C12B 173.8(16) . .
C10B C11B C12B N1B -1.3 . .
C11B C12B N1B C13B -1.1 . .
C11B C12B N1B Cu1 -151.1(12) . 8_654
C12B N1B C13B C14B 2.6 . .
Cu1 N1B C13B C14B 152.0(11) 8_654 .
N1B C13B C14B C10B -1.8 . .
C11B C10B C14B C13B -0.6 . .
C9B C10B C14B C13B -171.8(17) . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.073 -0.060 -0.001 6547 2203 ' '
