#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:27:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180340 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/09/7200934.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_7200934
loop_
_publ_author_name
'Baudron, Stéphane A.'
'Salazar-Mendoza, Domingo'
'Hosseini, Mir Wais'
_publ_section_title
;
 Combination of primary amide and dipyrrin for the elaboration of
 extended architectures built upon both coordination and hydrogen
 bonding
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1245
_journal_paper_doi               10.1039/b901167f
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C32 H24 Cu N6 O2, 2(C4 H8 O)'
_chemical_formula_sum            'C40 H40 Cu N6 O4'
_chemical_formula_weight         732.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 105.4940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.9322(12)
_cell_length_b                   15.8716(8)
_cell_length_c                   10.2807(5)
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.39
_cell_volume                     3605.9(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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10737
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.8967
_exptl_absorpt_correction_T_min  0.7981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       rod
_exptl_crystal_F_000             1532
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.214
_refine_diff_density_min         -1.079
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0521
_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)+(0.0827P)²+8.7717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                3423
_reflns_number_total             4095
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b901167f.txt
_cod_data_source_block           compound4THF
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C2/c '
_cod_database_code               7200934
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.06073(13) 0.73801(17) 0.1854(3) 0.0232(6) Uani 1 1 d . . .
H1 H 0.0243 0.7099 0.1509 0.028 Uiso 1 1 calc R . .
C2 C 0.11711(13) 0.70862(18) 0.1747(3) 0.0246(6) Uani 1 1 d . . .
H2 H 0.1244 0.6592 0.1331 0.030 Uiso 1 1 calc R . .
C3 C 0.15935(12) 0.76750(18) 0.2379(3) 0.0228(6) Uani 1 1 d . . .
H3 H 0.2008 0.7652 0.2473 0.027 Uiso 1 1 calc R . .
C4 C 0.12781(11) 0.83220(17) 0.2859(3) 0.0192(5) Uani 1 1 d . . .
C5 C 0.15177(12) 0.90837(18) 0.3472(3) 0.0200(5) Uani 1 1 d . . .
C6 C 0.11840(12) 0.97406(17) 0.3817(3) 0.0216(6) Uani 1 1 d . . .
C7 C 0.14044(13) 1.04902(18) 0.4549(3) 0.0262(6) Uani 1 1 d . . .
H7 H 0.1808 1.0649 0.4872 0.031 Uiso 1 1 calc R . .
C8 C 0.09115(14) 1.09338(19) 0.4690(3) 0.0281(6) Uani 1 1 d . . .
H8 H 0.0914 1.1445 0.5132 0.034 Uiso 1 1 calc R . .
C9 C 0.03987(13) 1.04552(18) 0.4026(3) 0.0251(6) Uani 1 1 d . . .
H9 H 0.0001 1.0616 0.3955 0.030 Uiso 1 1 calc R . .
C10 C 0.21827(12) 0.92262(18) 0.3757(3) 0.0210(5) Uani 1 1 d . . .
C11 C 0.23945(13) 0.98313(19) 0.3005(3) 0.0268(6) Uani 1 1 d . . .
H11 H 0.2122 1.0124 0.2322 0.032 Uiso 1 1 calc R . .
C12 C 0.30070(13) 0.99948(19) 0.3272(3) 0.0257(6) Uani 1 1 d . . .
H12 H 0.3145 1.0384 0.2747 0.031 Uiso 1 1 calc R . .
C13 C 0.34174(12) 0.95844(18) 0.4318(3) 0.0209(5) Uani 1 1 d . . .
C14 C 0.32077(12) 0.89813(18) 0.5069(3) 0.0240(6) Uani 1 1 d . . .
H14 H 0.3480 0.8699 0.5766 0.029 Uiso 1 1 calc R . .
C15 C 0.25950(13) 0.88002(19) 0.4781(3) 0.0245(6) Uani 1 1 d . . .
H15 H 0.2459 0.8391 0.5278 0.029 Uiso 1 1 calc R . .
C16 C 0.40772(12) 0.97869(18) 0.4589(3) 0.0220(6) Uani 1 1 d . . .
N1 N 0.06612(10) 0.81162(14) 0.2518(2) 0.0196(5) Uani 1 1 d . . .
N2 N 0.05556(10) 0.97428(15) 0.3513(2) 0.0219(5) Uani 1 1 d . . .
N3 N 0.44148(11) 0.97134(19) 0.5852(3) 0.0324(6) Uani 1 1 d . . .
H3A H 0.4795 0.9828 0.6047 0.039 Uiso 1 1 calc R . .
H3B H 0.4253 0.9551 0.6474 0.039 Uiso 1 1 calc R . .
O1 O 0.42877(9) 1.00185(14) 0.3654(2) 0.0263(5) Uani 1 1 d . . .
Cu1 Cu 0.0000 0.89034(3) 0.2500 0.01997(17) Uani 1 2 d S . .
C17 C 0.1733(3) 0.2736(4) 0.3222(7) 0.0885(8) Uani 1 1 d . . .
H17A H 0.1982 0.3231 0.3225 0.106 Uiso 1 1 calc R . .
H17B H 0.1864 0.2472 0.4103 0.106 Uiso 1 1 calc R . .
C18 C 0.1087(3) 0.2986(4) 0.2943(7) 0.0885(8) Uani 1 1 d . . .
H18A H 0.1043 0.3593 0.2849 0.106 Uiso 1 1 calc R . .
H18B H 0.0916 0.2801 0.3662 0.106 Uiso 1 1 calc R . .
C19 C 0.0783(3) 0.2548(4) 0.1631(7) 0.0885(8) Uani 1 1 d . . .
H19A H 0.0404 0.2292 0.1671 0.106 Uiso 1 1 calc R . .
H19B H 0.0706 0.2938 0.0878 0.106 Uiso 1 1 calc R . .
C20 C 0.1235(3) 0.1894(4) 0.1514(7) 0.0885(8) Uani 1 1 d . . .
H20A H 0.1143 0.1362 0.1878 0.106 Uiso 1 1 calc R . .
H20B H 0.1228 0.1811 0.0575 0.106 Uiso 1 1 calc R . .
O2 O 0.1799(2) 0.2182(3) 0.2242(4) 0.0885(8) 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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 '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
_geom_angle_publ_flag
N1 C1 C2 111.5(2) . . ?
N1 C1 H1 124.2 . . ?
C2 C1 H1 124.2 . . ?
C3 C2 C1 106.5(2) . . ?
C3 C2 H2 126.8 . . ?
C1 C2 H2 126.8 . . ?
C2 C3 C4 107.2(2) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C5 124.1(2) . . ?
N1 C4 C3 108.6(2) . . ?
C5 C4 C3 127.2(2) . . ?
C6 C5 C4 125.6(2) . . ?
C6 C5 C10 116.0(2) . . ?
C4 C5 C10 118.4(2) . . ?
N2 C6 C5 123.5(2) . . ?
N2 C6 C7 108.4(2) . . ?
C5 C6 C7 128.1(3) . . ?
C8 C7 C6 107.3(3) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 106.0(3) . . ?
C7 C8 H8 127.0 . . ?
C9 C8 H8 127.0 . . ?
N2 C9 C8 111.6(3) . . ?
N2 C9 H9 124.2 . . ?
C8 C9 H9 124.2 . . ?
C15 C10 C11 119.1(2) . . ?
C15 C10 C5 121.9(2) . . ?
C11 C10 C5 118.9(3) . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 C16 119.1(2) . . ?
C14 C13 C16 121.7(3) . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
O1 C16 N3 122.5(3) . . ?
O1 C16 C13 120.1(3) . . ?
N3 C16 C13 117.3(2) . . ?
C1 N1 C4 106.3(2) . . ?
C1 N1 Cu1 125.73(19) . . ?
C4 N1 Cu1 125.44(18) . . ?
C9 N2 C6 106.6(2) . . ?
C9 N2 Cu1 125.8(2) . . ?
C6 N2 Cu1 127.62(19) . . ?
C16 N3 H3A 120.0 . . ?
C16 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N2 Cu1 N2 93.42(14) . 2 ?
N2 Cu1 N1 146.79(10) . 2 ?
N2 Cu1 N1 92.13(9) 2 2 ?
N2 Cu1 N1 92.13(9) . . ?
N2 Cu1 N1 146.79(10) 2 . ?
N1 Cu1 N1 100.85(13) 2 . ?
O2 C17 C18 109.2(6) . . ?
O2 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O2 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 C19 104.4(5) . . ?
C17 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C20 C19 C18 103.1(6) . . ?
C20 C19 H19A 111.1 . . ?
C18 C19 H19A 111.1 . . ?
C20 C19 H19B 111.1 . . ?
C18 C19 H19B 111.1 . . ?
H19A C19 H19B 109.1 . . ?
O2 C20 C19 107.2(6) . . ?
O2 C20 H20A 110.3 . . ?
C19 C20 H20A 110.3 . . ?
O2 C20 H20B 110.3 . . ?
C19 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
C17 O2 C20 109.6(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.342(4) . ?
C1 C2 1.406(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.418(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.402(3) . ?
C4 C5 1.406(4) . ?
C5 C6 1.394(4) . ?
C5 C10 1.491(4) . ?
C6 N2 1.390(3) . ?
C6 C7 1.427(4) . ?
C7 C8 1.372(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.413(4) . ?
C8 H8 0.9300 . ?
C9 N2 1.337(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.388(4) . ?
C10 C11 1.399(4) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(4) . ?
C13 C16 1.499(4) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O1 1.241(3) . ?
C16 N3 1.327(4) . ?
N1 Cu1 1.961(2) . ?
N2 Cu1 1.943(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
Cu1 N2 1.943(2) 2 ?
Cu1 N1 1.961(2) 2 ?
C17 O2 1.377(7) . ?
C17 C18 1.485(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.512(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.495(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O2 1.388(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
