#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:26:17 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179019 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/17/4121778.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_4121778
loop_
_publ_author_name
'Takasaki, Yuichi'
'Takamizawa, Satoshi'
_publ_section_title
;
 Gas permeation in a molecular crystal and space expansion.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6806
_journal_page_last               6809
_journal_paper_doi               10.1021/ja501045u
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C33 H22 Cu2 F4 N2 O8'
_chemical_formula_weight         777.61
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.328(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.7516(17)
_cell_length_b                   9.7376(11)
_cell_length_c                   11.7980(12)
_cell_measurement_reflns_used    1411
_cell_measurement_temperature    90
_cell_measurement_theta_max      22.63
_cell_measurement_theta_min      2.51
_cell_volume                     1694.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5471
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    1.329
_exptl_absorpt_correction_T_max  0.8897
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS; sheldrick, 1996
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.060
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0958P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                1535
_reflns_number_total             1833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja501045u_si_002.cif
_cod_data_source_block           d0226t2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4121778.cif.
;
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               4121778
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4445(3) 0.0000 0.2594(5) 0.0296(11) Uani 1 2 d SU . .
C2 C 0.4106(4) 0.0000 0.1180(5) 0.0401(14) Uani 1 2 d SU . .
C3 C 0.3954(4) 0.1223(5) 0.0513(5) 0.0654(16) Uani 1 1 d U . .
H3 H 0.4049 0.2070 0.0959 0.079 Uiso 1 1 calc R . .
C4 C 0.3667(6) 0.1225(8) -0.0789(6) 0.099(3) Uani 1 1 d U . .
H4 H 0.3542 0.2064 -0.1253 0.119 Uiso 1 1 calc R . .
C5 C 0.3564(8) 0.0000 -0.1399(8) 0.102(3) Uani 1 2 d SU . .
C6 C 0.3350(4) 0.0000 0.4465(5) 0.0269(11) Uani 1 2 d S . .
C7 C 0.2346(4) 0.0000 0.3910(5) 0.0265(11) Uani 1 2 d S . .
C8 C 0.1862(3) 0.1235(4) 0.3604(4) 0.0303(8) Uani 1 1 d . . .
H8 H 0.2183 0.2081 0.3850 0.036 Uiso 1 1 calc R . .
C9 C 0.0927(3) 0.1247(4) 0.2950(4) 0.0363(10) Uani 1 1 d . . .
H9 H 0.0600 0.2087 0.2737 0.044 Uiso 1 1 calc R . .
C10 C 0.0478(4) 0.0000 0.2613(5) 0.0365(13) Uani 1 2 d S . .
C11 C 0.4267(2) 0.4283(4) 0.4213(3) 0.0281(8) Uani 1 1 d . . .
H11 H 0.3733 0.3803 0.3639 0.034 Uiso 0.75 1 calc PR A 1
C12 C 0.3358(9) 0.3788(13) 0.3091(14) 0.028(3) Uani 0.25 1 d PU B 2
H12A H 0.3457 0.2938 0.2731 0.041 Uiso 0.25 1 calc PR B 2
H12B H 0.3117 0.4495 0.2420 0.041 Uiso 0.25 1 calc PR B 2
H12C H 0.2923 0.3618 0.3411 0.041 Uiso 0.25 1 calc PR B 2
Cu1 Cu 0.5000 0.13443(5) 0.5000 0.0243(3) Uani 1 2 d S . .
F1 F 0.3267(6) 0.0000 -0.2700(5) 0.162(3) Uani 1 2 d SU . .
F2 F -0.0438(2) 0.0000 0.1919(3) 0.0478(9) Uani 1 2 d S . .
N1 N 0.5000 0.3584(4) 0.5000 0.0274(9) Uani 1 2 d S . .
O1 O 0.45740(18) 0.1150(3) 0.3142(2) 0.0319(6) Uani 1 1 d . B .
O2 O 0.37403(18) 0.1148(2) 0.4657(3) 0.0307(6) Uani 1 1 d . B .
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'
F F 0.0171 0.0103 '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 C1 O1 125.5(5) . 6
O1 C1 C2 117.3(2) . .
O1 C1 C2 117.3(2) 6 .
C3 C2 C3 118.9(6) 6 .
C3 C2 C1 120.5(3) 6 .
C3 C2 C1 120.5(3) . .
C4 C3 C2 120.6(6) . .
C5 C4 C3 118.6(6) . .
C4 C5 C4 122.4(8) . 6
C4 C5 F1 118.7(4) . .
C4 C5 F1 118.7(4) 6 .
O2 C6 O2 125.1(5) . 6
O2 C6 C7 117.4(3) . .
O2 C6 C7 117.4(3) 6 .
C8 C7 C8 118.6(5) 6 .
C8 C7 C6 120.6(2) 6 .
C8 C7 C6 120.6(2) . .
C9 C8 C7 121.1(4) . .
C8 C9 C10 118.1(4) . .
F2 C10 C9 118.6(3) . .
F2 C10 C9 118.6(3) . 6
C9 C10 C9 122.8(5) . 6
N1 C11 C11 121.0(2) . 6_565
N1 C11 C12 130.5(6) . .
C11 C11 C12 108.2(5) 6_565 .
O2 Cu1 O2 168.82(14) 2_656 .
O2 Cu1 O1 90.36(12) 2_656 .
O2 Cu1 O1 88.57(12) . .
O2 Cu1 O1 88.57(12) 2_656 2_656
O2 Cu1 O1 90.36(12) . 2_656
O1 Cu1 O1 168.98(15) . 2_656
O2 Cu1 N1 95.59(7) 2_656 .
O2 Cu1 N1 95.59(7) . .
O1 Cu1 N1 95.51(7) . .
O1 Cu1 N1 95.51(7) 2_656 .
O2 Cu1 Cu1 84.41(7) 2_656 5_656
O2 Cu1 Cu1 84.41(7) . 5_656
O1 Cu1 Cu1 84.49(7) . 5_656
O1 Cu1 Cu1 84.49(7) 2_656 5_656
N1 Cu1 Cu1 180.000(1) . 5_656
C11 N1 C11 118.1(4) 2_656 .
C11 N1 Cu1 121.0(2) 2_656 .
C11 N1 Cu1 121.0(2) . .
C1 O1 Cu1 122.8(3) . .
C6 O2 Cu1 122.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.260(3) .
C1 O1 1.260(3) 6
C1 C2 1.485(7) .
C2 C3 1.383(5) 6
C2 C3 1.383(5) .
C3 C4 1.374(8) .
C4 C5 1.361(8) .
C5 C4 1.361(8) 6
C5 F1 1.371(9) .
C6 O2 1.260(3) .
C6 O2 1.260(3) 6
C6 C7 1.488(7) .
C7 C8 1.399(4) 6
C7 C8 1.399(4) .
C8 C9 1.380(5) .
C9 C10 1.383(5) .
C10 F2 1.354(6) .
C10 C9 1.383(5) 6
C11 N1 1.323(4) .
C11 C11 1.396(7) 6_565
C11 C12 1.547(13) .
Cu1 O2 1.960(3) 2_656
Cu1 O2 1.960(3) .
Cu1 O1 1.966(3) .
Cu1 O1 1.966(3) 2_656
Cu1 N1 2.181(4) .
Cu1 Cu1 2.6181(11) 5_656
N1 C11 1.323(4) 2_656
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
O1 C1 C2 C3 179.6(5) . 6
O1 C1 C2 C3 -0.9(8) 6 6
O1 C1 C2 C3 0.9(8) . .
O1 C1 C2 C3 -179.6(5) 6 .
C3 C2 C3 C4 -0.7(11) 6 .
C1 C2 C3 C4 178.0(6) . .
C2 C3 C4 C5 -2.1(13) . .
C3 C4 C5 C4 5.2(19) . 6
C3 C4 C5 F1 179.2(8) . .
O2 C6 C7 C8 176.4(4) . 6
O2 C6 C7 C8 -0.9(6) 6 6
O2 C6 C7 C8 0.9(6) . .
O2 C6 C7 C8 -176.4(4) 6 .
C8 C7 C8 C9 -3.5(7) 6 .
C6 C7 C8 C9 172.2(4) . .
C7 C8 C9 C10 0.5(6) . .
C8 C9 C10 F2 -177.0(4) . .
C8 C9 C10 C9 2.7(8) . 6
C11 C11 N1 C11 0.000(1) 6_565 2_656
C12 C11 N1 C11 172.0(9) . 2_656
C11 C11 N1 Cu1 180.0 6_565 .
C12 C11 N1 Cu1 -8.0(9) . .
O2 Cu1 N1 C11 -35.58(19) 2_656 2_656
O2 Cu1 N1 C11 144.42(19) . 2_656
O1 Cu1 N1 C11 -126.49(19) . 2_656
O1 Cu1 N1 C11 53.51(19) 2_656 2_656
Cu1 Cu1 N1 C11 -86(100) 5_656 2_656
O2 Cu1 N1 C11 144.42(19) 2_656 .
O2 Cu1 N1 C11 -35.58(19) . .
O1 Cu1 N1 C11 53.51(19) . .
O1 Cu1 N1 C11 -126.49(19) 2_656 .
Cu1 Cu1 N1 C11 94(100) 5_656 .
O1 C1 O1 Cu1 -0.6(7) 6 .
C2 C1 O1 Cu1 178.9(3) . .
O2 Cu1 O1 C1 84.6(4) 2_656 .
O2 Cu1 O1 C1 -84.3(4) . .
O1 Cu1 O1 C1 0.3(3) 2_656 .
N1 Cu1 O1 C1 -179.7(3) . .
Cu1 Cu1 O1 C1 0.3(3) 5_656 .
O2 C6 O2 Cu1 11.4(7) 6 .
C7 C6 O2 Cu1 -165.6(3) . .
O2 Cu1 O2 C6 -5.3(3) 2_656 .
O1 Cu1 O2 C6 79.3(3) . .
O1 Cu1 O2 C6 -89.7(3) 2_656 .
N1 Cu1 O2 C6 174.7(3) . .
Cu1 Cu1 O2 C6 -5.3(3) 5_656 .
