#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:11:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178839 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/93/4109395.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_4109395
loop_
_publ_author_name
'Jarrod F. Eubank'
'Victor Ch. Kravtsov'
'Mohamed Eddaoudi'
_publ_section_title
;
 Synthesis of Organic Photodimeric Cage Molecules Based on Cycloaddition
 via Metal-Ligand Directed Assembly
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5820
_journal_page_last               5821
_journal_paper_doi               10.1021/ja070924n
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C17 H14 Cu N2 O7'
_chemical_formula_weight         421.84
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                63.080(7)
_cell_angle_beta                 83.713(8)
_cell_angle_gamma                76.770(7)
_cell_formula_units_Z            2
_cell_length_a                   8.738(3)
_cell_length_b                   10.188(4)
_cell_length_c                   10.760(4)
_cell_measurement_temperature    571(2)
_cell_volume                     831.4(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.1196
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4890
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3359
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0597
_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)+(0.0180P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                2229
_reflns_number_total             3359
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja070924nsi20070208_031609.cif
_cod_data_source_block           me137_v1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        831.5(5)
_cod_database_code               4109395
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.60872(7) 0.15668(6) 0.18812(6) 0.03338(18) Uani 1 1 d .
N1 N 0.3849(4) 0.1858(4) 0.2503(4) 0.0355(10) Uani 1 1 d .
C1 C 0.2800(6) 0.3104(5) 0.1783(6) 0.0439(14) Uani 1 1 d .
H1 H 0.3136 0.3857 0.0983 0.053 Uiso 1 1 calc R
C2 C 0.1257(6) 0.3321(6) 0.2168(6) 0.0558(16) Uani 1 1 d .
H2 H 0.0562 0.4202 0.1633 0.067 Uiso 1 1 calc R
C3 C 0.0733(6) 0.2218(6) 0.3363(6) 0.0550(16) Uani 1 1 d .
H3 H -0.0317 0.2337 0.3636 0.066 Uiso 1 1 calc R
C4 C 0.1805(6) 0.0947(6) 0.4131(5) 0.0445(14) Uani 1 1 d .
H4 H 0.1502 0.0186 0.4944 0.053 Uiso 1 1 calc R
C5 C 0.3325(6) 0.0827(5) 0.3673(5) 0.0386(12) Uani 1 1 d .
H5 H 0.4048 -0.0029 0.4211 0.046 Uiso 1 1 calc R
N2 N 0.8345(5) 0.1349(4) 0.1253(4) 0.0371(10) Uani 1 1 d .
C6 C 0.9447(6) 0.0140(5) 0.1970(5) 0.0429(13) Uani 1 1 d .
H6 H 0.9153 -0.0621 0.2787 0.052 Uiso 1 1 calc R
C7 C 1.0982(6) -0.0019(6) 0.1552(6) 0.0481(15) Uani 1 1 d .
H7 H 1.1704 -0.0880 0.2080 0.058 Uiso 1 1 calc R
C8 C 1.1466(6) 0.1085(6) 0.0355(6) 0.0503(15) Uani 1 1 d .
H8 H 1.2512 0.0999 0.0067 0.060 Uiso 1 1 calc R
C9 C 1.0349(7) 0.2316(6) -0.0399(6) 0.0522(15) Uani 1 1 d .
H9 H 1.0621 0.3084 -0.1222 0.063 Uiso 1 1 calc R
C10 C 0.8809(6) 0.2406(5) 0.0080(5) 0.0431(13) Uani 1 1 d .
H10 H 0.8062 0.3247 -0.0444 0.052 Uiso 1 1 calc R
O1 O 0.6647(4) 0.2295(3) 0.3287(3) 0.0376(9) Uani 1 1 d .
O2 O 0.5846(4) 0.4513(3) 0.1500(4) 0.0489(10) Uani 1 1 d .
O3 O 0.6428(4) 0.9258(3) 0.3112(3) 0.0368(9) Uani 1 1 d .
O4 O 0.5177(4) 0.8915(3) 0.1625(4) 0.0504(11) Uani 1 1 d .
O5 O 0.6249(3) 0.5972(3) 0.2888(3) 0.0317(8) Uani 1 1 d .
O6 O 0.8284(6) 0.3896(4) 0.6687(4) 0.099(2) Uani 1 1 d .
C11 C 0.6334(5) 0.3704(5) 0.2707(5) 0.0321(11) Uani 1 1 d .
C12 C 0.6641(5) 0.4443(4) 0.3575(5) 0.0308(11) Uani 1 1 d .
C13 C 0.7265(6) 0.3732(5) 0.4837(5) 0.0396(13) Uani 1 1 d .
H13 H 0.7467 0.2687 0.5279 0.047 Uiso 1 1 calc R
C14 C 0.7645(7) 0.4526(5) 0.5555(6) 0.0525(17) Uani 1 1 d .
C15 C 0.7182(6) 0.6141(5) 0.4768(5) 0.0424(14) Uani 1 1 d .
H15 H 0.7354 0.6746 0.5155 0.051 Uiso 1 1 calc R
C16 C 0.6523(5) 0.6797(5) 0.3519(5) 0.0299(11) Uani 1 1 d .
C17 C 0.5977(5) 0.8466(5) 0.2656(5) 0.0325(11) Uani 1 1 d .
O1W O 0.5408(5) 0.2491(3) -0.0144(4) 0.0453(10) Uani 1 1 d D
H1W H 0.530(6) 0.186(4) -0.040(5) 0.068 Uiso 1 1 d D
H2W H 0.502(6) 0.337(3) -0.063(5) 0.068 Uiso 1 1 d 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'
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
N1 Cu1 N2 177.81(15) . .
N1 Cu1 O1W 90.92(16) . .
N2 Cu1 O1W 89.26(16) . .
N1 Cu1 O3 91.62(14) . 1_545
N2 Cu1 O3 90.16(14) . 1_545
O1W Cu1 O3 120.72(12) . 1_545
N1 Cu1 O1 88.40(14) . .
N2 Cu1 O1 90.00(14) . .
O1W Cu1 O1 138.00(12) . .
O3 Cu1 O1 101.27(11) 1_545 .
C1 N1 C5 116.5(5) . .
C1 N1 Cu1 121.7(4) . .
C5 N1 Cu1 121.9(3) . .
N1 C1 C2 122.9(5) . .
C1 C2 C3 119.5(5) . .
C4 C3 C2 118.2(5) . .
C5 C4 C3 118.3(5) . .
N1 C5 C4 124.5(5) . .
C10 N2 C6 116.8(5) . .
C10 N2 Cu1 120.9(3) . .
C6 N2 Cu1 122.3(4) . .
N2 C6 C7 122.8(5) . .
C6 C7 C8 120.4(5) . .
C9 C8 C7 117.5(5) . .
C8 C9 C10 119.3(5) . .
N2 C10 C9 123.3(5) . .
C11 O1 Cu1 107.5(3) . .
C17 O3 Cu1 118.6(3) . 1_565
C12 O5 C16 118.8(3) . .
O2 C11 O1 125.9(4) . .
O2 C11 C12 118.8(4) . .
O1 C11 C12 115.3(4) . .
C13 C12 O5 122.2(4) . .
C13 C12 C11 125.7(4) . .
O5 C12 C11 112.1(4) . .
C12 C13 C14 122.4(4) . .
O6 C14 C15 124.3(4) . .
O6 C14 C13 123.5(4) . .
C15 C14 C13 112.2(4) . .
C16 C15 C14 123.0(4) . .
C15 C16 O5 121.4(4) . .
C15 C16 C17 125.9(4) . .
O5 C16 C17 112.7(4) . .
O4 C17 O3 126.9(4) . .
O4 C17 C16 119.3(4) . .
O3 C17 C16 113.7(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.997(4) .
Cu1 N2 2.011(4) .
Cu1 O1W 2.039(4) .
Cu1 O3 2.078(3) 1_545
Cu1 O1 2.103(3) .
N1 C1 1.336(5) .
N1 C5 1.340(6) .
C1 C2 1.365(7) .
C2 C3 1.387(7) .
C3 C4 1.372(6) .
C4 C5 1.364(7) .
N2 C10 1.333(6) .
N2 C6 1.341(5) .
C6 C7 1.364(7) .
C7 C8 1.375(7) .
C8 C9 1.370(6) .
C9 C10 1.385(7) .
O1 C11 1.253(5) .
O2 C11 1.240(5) .
O3 C17 1.263(5) .
O3 Cu1 2.078(3) 1_565
O4 C17 1.222(5) .
O5 C12 1.364(4) .
O5 C16 1.368(5) .
O6 C14 1.219(5) .
C11 C12 1.515(6) .
C12 C13 1.326(6) .
C13 C14 1.451(6) .
C14 C15 1.448(6) .
C15 C16 1.329(6) .
C16 C17 1.508(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H2W O2 0.820(19) 1.91(2) 2.726(4) 170(5) 2_665
O1W H1W O4 0.836(19) 1.93(3) 2.726(5) 158(5) 2_665
