#------------------------------------------------------------------------------
#$Date: 2017-09-26 02:00:15 +0300 (Tue, 26 Sep 2017) $
#$Revision: 201276 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/64/4126478.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_4126478
loop_
_publ_author_name
'Fujiwara, Yu-Ichi'
'Kadota, Kentaro'
'Nagarkar, Sanjog S.'
'Tobori, Prof Norio'
'Kitagawa, Susumu'
'Horike, Satoshi'
_publ_section_title
;
 Synthesis of Oligodiacetylene Derivatives from Flexible Porous
 Coordination Frameworks.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b07699
_journal_year                    2017
_chemical_formula_moiety         'C22 H12 Cu N2 O4'
_chemical_formula_sum            'C22 H12 Cu N2 O4'
_chemical_formula_weight         431.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_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-2017/1
_cell_angle_alpha                87.602(17)
_cell_angle_beta                 88.566(16)
_cell_angle_gamma                77.818(9)
_cell_formula_units_Z            2
_cell_length_a                   9.215(4)
_cell_length_b                   10.116(4)
_cell_length_c                   13.616(6)
_cell_measurement_reflns_used    3584
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4507
_cell_measurement_theta_min      3.0504
_cell_volume                     1239.4(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14947
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.050
_diffrn_source                   'Rotating Anode'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  0.8397
_exptl_absorpt_correction_T_min  0.8397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.362
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0894P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4617
_reflns_number_total             5634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            CuCID-24.cif
_cod_data_source_block           ydkr_a
_cod_original_cell_volume        1239.5(10)
_cod_database_code               4126478
_shelx_shelxl_version_number     2017/1
_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.
;
_platon_squeeze_void_probe_radius 1.20
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.65716(3) 1.11823(3) 0.03301(2) 0.01822(13) Uani 1 1 d . .
O1 O 0.7529(2) 0.92750(18) 0.05744(14) 0.0220(4) Uani 1 1 d . .
O2 O 0.6488(2) 0.32107(17) 0.03643(13) 0.0199(4) Uani 1 1 d . .
O3 O 0.5533(2) 0.83446(19) 0.05013(15) 0.0267(4) Uani 1 1 d . .
O4 O 0.8521(2) 0.20976(19) 0.11124(16) 0.0316(5) Uani 1 1 d . .
N1 N -0.2418(2) 1.1150(2) 0.89819(16) 0.0177(4) Uani 1 1 d . .
N2 N 0.5369(3) 1.1264(2) 0.16086(16) 0.0215(5) Uani 1 1 d . .
C1 C 0.6889(3) 0.8274(2) 0.05999(18) 0.0179(5) Uani 1 1 d . .
C2 C -0.1222(3) 1.0199(3) 0.87538(19) 0.0204(5) Uani 1 1 d . .
H1 H -0.087726 0.950733 0.921529 0.025 Uiso 1 1 calc R U
C3 C -0.2914(3) 1.2149(3) 0.8308(2) 0.0240(6) Uani 1 1 d . .
H2 H -0.374775 1.280704 0.846068 0.029 Uiso 1 1 calc R U
C4 C 0.7873(3) 0.6910(3) 0.0808(2) 0.0219(5) Uani 1 1 d . .
C5 C 0.7720(3) 0.3174(3) 0.0798(2) 0.0204(5) Uani 1 1 d . .
C6 C -0.0478(3) 1.0208(3) 0.7854(2) 0.0235(6) Uani 1 1 d . .
H3 H 0.033797 0.952269 0.771596 0.028 Uiso 1 1 calc R U
C7 C 0.4161(3) 1.2270(3) 0.1711(2) 0.0256(6) Uani 1 1 d . .
H4 H 0.397292 1.295168 0.122268 0.031 Uiso 1 1 calc R U
C8 C 0.7315(3) 0.5737(3) 0.07182(19) 0.0200(5) Uani 1 1 d . .
H5 H 0.634221 0.580070 0.052270 0.024 Uiso 1 1 calc R U
C9 C -0.0964(3) 1.1251(3) 0.7159(2) 0.0225(5) Uani 1 1 d . .
C10 C 0.8225(3) 0.4471(3) 0.0923(2) 0.0226(6) Uani 1 1 d . .
C11 C -0.2228(3) 1.2229(3) 0.7397(2) 0.0270(6) Uani 1 1 d . .
H6 H -0.260367 1.292750 0.694727 0.032 Uiso 1 1 calc R U
C12 C 0.5632(4) 1.0287(3) 0.2320(2) 0.0340(7) Uani 1 1 d . .
H7 H 0.646537 0.959146 0.226206 0.041 Uiso 1 1 calc R U
C13 C -0.0143(3) 1.1312(3) 0.6262(2) 0.0299(6) Uani 1 1 d . .
C14 C 0.3191(3) 1.2340(3) 0.2507(2) 0.0307(7) Uani 1 1 d . .
H8 H 0.238347 1.306242 0.255733 0.037 Uiso 1 1 calc R U
C15 C 0.1595(4) 1.1317(3) 0.4745(2) 0.0347(7) Uani 1 1 d . .
C16 C 0.0662(4) 1.1316(3) 0.5546(2) 0.0343(7) Uani 1 1 d . .
C17 C 0.9329(3) 0.6814(3) 0.1100(2) 0.0282(6) Uani 1 1 d . .
H9 H 0.969979 0.759422 0.115201 0.034 Uiso 1 1 calc R U
C18 C 0.3442(3) 1.1311(3) 0.3228(2) 0.0318(7) Uani 1 1 d . .
C19 C 1.0236(3) 0.5547(3) 0.1317(3) 0.0342(7) Uani 1 1 d . .
H10 H 1.120681 0.548226 0.151641 0.041 Uiso 1 1 calc R U
C20 C 0.4706(4) 1.0278(3) 0.3137(2) 0.0423(8) Uani 1 1 d . .
H11 H 0.492456 0.959141 0.362037 0.051 Uiso 1 1 calc R U
C21 C 0.9682(3) 0.4396(3) 0.1232(2) 0.0296(7) Uani 1 1 d . .
H12 H 1.028284 0.355458 0.138219 0.035 Uiso 1 1 calc R U
C22 C 0.2439(4) 1.1330(3) 0.4055(2) 0.0372(7) 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'
O O 0.0106 0.0060 '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'
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 N2 92.90(8) . .
O1 Cu1 N1 89.95(8) . 1_654
N2 Cu1 N1 174.39(8) . 1_654
O1 Cu1 O2 153.18(8) . 1_565
N2 Cu1 O2 90.00(8) . 1_565
N1 Cu1 O2 89.63(8) 1_654 1_565
O1 Cu1 O3 118.38(8) . 2_675
N2 Cu1 O3 89.36(9) . 2_675
N1 Cu1 O3 85.04(8) 1_654 2_675
O2 Cu1 O3 88.29(7) 1_565 2_675
C1 O1 Cu1 126.17(17) . .
C5 O2 Cu1 98.90(15) . 1_545
C1 O3 Cu1 153.90(18) . 2_675
C2 N1 C3 118.4(2) . .
C2 N1 Cu1 122.04(17) . 1_456
C3 N1 Cu1 119.45(17) . 1_456
C12 N2 C7 117.9(2) . .
C12 N2 Cu1 122.92(19) . .
C7 N2 Cu1 118.89(18) . .
O3 C1 O1 125.6(2) . .
O3 C1 C4 118.5(2) . .
O1 C1 C4 115.8(2) . .
N1 C2 C6 122.5(2) . .
N1 C2 H1 118.8 . .
C6 C2 H1 118.7 . .
N1 C3 C11 122.4(2) . .
N1 C3 H2 118.8 . .
C11 C3 H2 118.8 . .
C17 C4 C8 120.1(2) . .
C17 C4 C1 120.1(2) . .
C8 C4 C1 119.8(2) . .
O4 C5 O2 122.5(2) . .
O4 C5 C10 118.5(2) . .
O2 C5 C10 119.0(2) . .
C9 C6 C2 119.6(2) . .
C9 C6 H3 120.2 . .
C2 C6 H3 120.2 . .
N2 C7 C14 123.3(3) . .
N2 C7 H4 118.4 . .
C14 C7 H4 118.4 . .
C10 C8 C4 119.7(2) . .
C10 C8 H5 120.1 . .
C4 C8 H5 120.1 . .
C6 C9 C11 117.6(2) . .
C6 C9 C13 119.6(2) . .
C11 C9 C13 122.8(2) . .
C8 C10 C21 119.3(2) . .
C8 C10 C5 122.4(2) . .
C21 C10 C5 118.2(2) . .
C3 C11 C9 119.5(2) . .
C3 C11 H6 120.3 . .
C9 C11 H6 120.3 . .
N2 C12 C20 122.4(3) . .
N2 C12 H7 118.8 . .
C20 C12 H7 118.8 . .
C16 C13 C9 174.4(3) . .
C7 C14 C18 118.8(3) . .
C7 C14 H8 120.6 . .
C18 C14 H8 120.6 . .
C22 C15 C16 178.4(4) . .
C13 C16 C15 179.0(3) . .
C4 C17 C19 120.2(3) . .
C4 C17 H9 119.9 . .
C19 C17 H9 119.9 . .
C14 C18 C20 118.2(3) . .
C14 C18 C22 120.5(3) . .
C20 C18 C22 121.3(3) . .
C21 C19 C17 119.6(3) . .
C21 C19 H10 120.2 . .
C17 C19 H10 120.2 . .
C12 C20 C18 119.4(3) . .
C12 C20 H11 120.3 . .
C18 C20 H11 120.3 . .
C19 C21 C10 121.1(3) . .
C19 C21 H12 119.5 . .
C10 C21 H12 119.5 . .
C15 C22 C18 178.6(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9631(19) .
Cu1 N2 2.035(2) .
Cu1 N1 2.036(2) 1_654
Cu1 O2 2.0394(19) 1_565
Cu1 O3 2.223(2) 2_675
O1 C1 1.273(3) .
O2 C5 1.285(3) .
O3 C1 1.247(3) .
O4 C5 1.245(3) .
N1 C2 1.340(3) .
N1 C3 1.349(3) .
N2 C12 1.343(4) .
N2 C7 1.349(3) .
C1 C4 1.503(3) .
C2 C6 1.389(4) .
C2 H1 0.9300 .
C3 C11 1.385(4) .
C3 H2 0.9300 .
C4 C17 1.391(4) .
C4 C8 1.400(4) .
C5 C10 1.500(4) .
C6 C9 1.396(4) .
C6 H3 0.9300 .
C7 C14 1.382(4) .
C7 H4 0.9300 .
C8 C10 1.396(4) .
C8 H5 0.9300 .
C9 C11 1.401(4) .
C9 C13 1.426(4) .
C10 C21 1.403(4) .
C11 H6 0.9300 .
C12 C20 1.386(4) .
C12 H7 0.9300 .
C13 C16 1.210(4) .
C14 C18 1.388(4) .
C14 H8 0.9300 .
C15 C22 1.206(4) .
C15 C16 1.372(4) .
C17 C19 1.399(4) .
C17 H9 0.9300 .
C18 C20 1.398(4) .
C18 C22 1.436(4) .
C19 C21 1.376(4) .
C19 H10 0.9300 .
C20 H11 0.9300 .
C21 H12 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
Cu1 O3 C1 O1 64.0(5) 2_675
Cu1 O3 C1 C4 -118.6(4) 2_675
Cu1 O1 C1 O3 -2.2(4) .
Cu1 O1 C1 C4 -179.63(16) .
C3 N1 C2 C6 0.2(4) .
Cu1 N1 C2 C6 -176.6(2) 1_456
C2 N1 C3 C11 -0.5(4) .
Cu1 N1 C3 C11 176.4(2) 1_456
O3 C1 C4 C17 -168.2(3) .
O1 C1 C4 C17 9.4(4) .
O3 C1 C4 C8 11.1(4) .
O1 C1 C4 C8 -171.3(2) .
Cu1 O2 C5 O4 -4.3(3) 1_545
Cu1 O2 C5 C10 175.1(2) 1_545
N1 C2 C6 C9 1.1(4) .
C12 N2 C7 C14 -0.1(4) .
Cu1 N2 C7 C14 173.4(2) .
C17 C4 C8 C10 0.0(4) .
C1 C4 C8 C10 -179.2(2) .
C2 C6 C9 C11 -2.0(4) .
C2 C6 C9 C13 175.8(3) .
C4 C8 C10 C21 1.0(4) .
C4 C8 C10 C5 -177.2(2) .
O4 C5 C10 C8 -171.0(3) .
O2 C5 C10 C8 9.5(4) .
O4 C5 C10 C21 10.8(4) .
O2 C5 C10 C21 -168.6(3) .
N1 C3 C11 C9 -0.5(4) .
C6 C9 C11 C3 1.8(4) .
C13 C9 C11 C3 -176.0(3) .
C7 N2 C12 C20 0.6(5) .
Cu1 N2 C12 C20 -172.6(3) .
N2 C7 C14 C18 -1.5(5) .
C8 C4 C17 C19 -0.8(4) .
C1 C4 C17 C19 178.5(3) .
C7 C14 C18 C20 2.7(5) .
C7 C14 C18 C22 -178.6(3) .
C4 C17 C19 C21 0.4(5) .
N2 C12 C20 C18 0.6(6) .
C14 C18 C20 C12 -2.3(5) .
C22 C18 C20 C12 179.0(3) .
C17 C19 C21 C10 0.6(5) .
C8 C10 C21 C19 -1.3(5) .
C5 C10 C21 C19 176.9(3) .
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 -0.120 0.500 0.500 415 103 ' '
