#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:14:35 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179473 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/70/4337061.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_4337061
loop_
_publ_author_name
'Antoine Béziau'
'Stéphane A. Baudron'
'Audrey Fluck'
'Mir Wais Hosseini'
_publ_contact_author
; Prof Mir Wais Hosseini
  Laboratoire de Tectonique Moléculaire, 
  UMR CNRS 7140, Université de Strasbourg,
  CS 90032
  F-67081 Strasbourg Cedex, France 
;
_publ_contact_author_email       hosseini@unistra.fr
_publ_contact_author_fax         '33 3 68 85 13 23'
_publ_contact_author_phone       '33 3 68 85 13 25'
_publ_section_title
;
 From Sequential to One-Pot Synthesis of Dipyrrin Based Grid-Type Mixed
 Metal-Organic Frameworks
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              14439
_journal_page_last               14448
_journal_paper_doi               10.1021/ic402892f
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C28 H20 Cu N6'
_chemical_formula_sum            'C28 H20 Cu N6'
_chemical_formula_weight         504.04
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 110.6360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6990(4)
_cell_length_b                   8.9494(3)
_cell_length_c                   19.4160(7)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.24
_cell_volume                     2227.63(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35497
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_T_max  0.9056
_exptl_absorpt_correction_T_min  0.9056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       prism
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.9881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                5439
_reflns_number_total             6517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic402892f_si_002_03.cif
_cod_data_source_block           compound4
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4337061
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.19059(13) 1.18919(19) 0.32315(9) 0.0217(3) Uani 1 1 d .
H1 H 0.2590 1.1583 0.3330 0.026 Uiso 1 1 calc R
C2 C 0.14176(14) 1.3057(2) 0.27407(9) 0.0253(3) Uani 1 1 d .
H2 H 0.1710 1.3631 0.2464 0.030 Uiso 1 1 calc R
C3 C 0.04214(13) 1.31735(19) 0.27545(9) 0.0232(3) Uani 1 1 d .
H3 H -0.0088 1.3853 0.2492 0.028 Uiso 1 1 calc R
C4 C 0.03197(12) 1.20529(18) 0.32480(8) 0.0193(3) Uani 1 1 d .
C5 C -0.05814(12) 1.16772(18) 0.33912(8) 0.0184(3) Uani 1 1 d .
C6 C -0.07028(12) 1.04464(18) 0.37955(8) 0.0188(3) Uani 1 1 d .
C7 C -0.16371(13) 0.9963(2) 0.38942(9) 0.0226(3) Uani 1 1 d .
H7 H -0.2282 1.0437 0.3720 0.027 Uiso 1 1 calc R
C8 C -0.14011(14) 0.8666(2) 0.42945(9) 0.0250(3) Uani 1 1 d .
H8 H -0.1856 0.8083 0.4440 0.030 Uiso 1 1 calc R
C9 C -0.03327(13) 0.83896(19) 0.44419(9) 0.0226(3) Uani 1 1 d .
H9 H 0.0031 0.7582 0.4715 0.027 Uiso 1 1 calc R
C10 C -0.15131(12) 1.26505(19) 0.30405(9) 0.0204(3) Uani 1 1 d .
C11 C -0.17506(16) 1.3842(2) 0.34079(10) 0.0354(5) Uani 1 1 d .
H11 H -0.1346 1.4040 0.3896 0.043 Uiso 1 1 calc R
C12 C -0.26038(17) 1.4740(2) 0.30365(12) 0.0381(5) Uani 1 1 d .
H12 H -0.2750 1.5542 0.3289 0.046 Uiso 1 1 calc R
C13 C -0.29811(14) 1.3366(2) 0.19957(10) 0.0305(4) Uani 1 1 d .
H13 H -0.3398 1.3191 0.1508 0.037 Uiso 1 1 calc R
C14 C -0.21481(13) 1.2411(2) 0.23179(10) 0.0265(4) Uani 1 1 d .
H14 H -0.2018 1.1620 0.2052 0.032 Uiso 1 1 calc R
C15 C 0.34010(13) 1.16175(19) 0.49178(9) 0.0220(3) Uani 1 1 d .
H15 H 0.3084 1.2423 0.4620 0.026 Uiso 1 1 calc R
C16 C 0.43545(13) 1.1710(2) 0.55163(9) 0.0247(3) Uani 1 1 d .
H16 H 0.4762 1.2559 0.5679 0.030 Uiso 1 1 calc R
C17 C 0.45617(13) 1.03011(19) 0.58101(9) 0.0219(3) Uani 1 1 d .
H17 H 0.5141 1.0007 0.6209 0.026 Uiso 1 1 calc R
C18 C 0.37164(12) 0.93740(18) 0.53849(8) 0.0174(3) Uani 1 1 d .
C19 C 0.36139(12) 0.78431(18) 0.54783(8) 0.0175(3) Uani 1 1 d .
C20 C 0.27856(12) 0.69462(17) 0.50381(8) 0.0183(3) Uani 1 1 d .
C21 C 0.26826(14) 0.53683(18) 0.50706(9) 0.0230(3) Uani 1 1 d .
H21 H 0.3143 0.4721 0.5404 0.028 Uiso 1 1 calc R
C22 C 0.17678(14) 0.4981(2) 0.45125(10) 0.0254(3) Uani 1 1 d .
H22 H 0.1496 0.4024 0.4393 0.030 Uiso 1 1 calc R
C23 C 0.13301(13) 0.63240(19) 0.41613(9) 0.0236(3) Uani 1 1 d .
H23 H 0.0706 0.6385 0.3764 0.028 Uiso 1 1 calc R
C24 C 0.44675(12) 0.71012(18) 0.60843(9) 0.0203(3) Uani 1 1 d .
C25 C 0.46387(15) 0.7395(2) 0.68214(9) 0.0299(4) Uani 1 1 d .
H25 H 0.4219 0.8066 0.6955 0.036 Uiso 1 1 calc R
C26 C 0.54571(17) 0.6656(3) 0.73546(11) 0.0399(5) Uani 1 1 d .
H26 H 0.5561 0.6849 0.7846 0.048 Uiso 1 1 calc R
C27 C 0.59406(16) 0.5459(2) 0.64973(13) 0.0377(5) Uani 1 1 d .
H27 H 0.6391 0.4816 0.6380 0.045 Uiso 1 1 calc R
C28 C 0.51461(14) 0.6115(2) 0.59263(10) 0.0278(4) Uani 1 1 d .
H28 H 0.5065 0.5899 0.5441 0.033 Uiso 1 1 calc R
N1 N 0.12595(10) 1.12842(15) 0.35381(7) 0.0189(3) Uani 1 1 d .
N2 N 0.00945(11) 0.94303(15) 0.41409(7) 0.0187(3) Uani 1 1 d .
N3 N -0.32222(12) 1.45218(18) 0.23417(9) 0.0303(3) Uani 1 1 d .
N4 N 0.30083(10) 1.02313(15) 0.48296(7) 0.0179(3) Uani 1 1 d .
N5 N 0.19268(11) 0.75064(15) 0.44720(7) 0.0199(3) Uani 1 1 d .
N6 N 0.61005(14) 0.5693(2) 0.72069(11) 0.0423(5) Uani 1 1 d .
Cu1 Cu 0.157142(14) 0.96189(2) 0.424115(10) 0.01774(6) 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'
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
N1 C1 C2 111.62(15)
N1 C1 H1 124.2
C2 C1 H1 124.2
C3 C2 C1 106.23(15)
C3 C2 H2 126.9
C1 C2 H2 126.9
C2 C3 C4 106.95(15)
C2 C3 H3 126.5
C4 C3 H3 126.5
N1 C4 C5 123.79(14)
N1 C4 C3 108.90(14)
C5 C4 C3 127.16(15)
C6 C5 C4 126.14(15)
C6 C5 C10 117.62(14)
C4 C5 C10 116.15(14)
C5 C6 N2 123.73(15)
C5 C6 C7 127.25(15)
N2 C6 C7 108.94(14)
C8 C7 C6 106.84(15)
C8 C7 H7 126.6
C6 C7 H7 126.6
C7 C8 C9 106.49(15)
C7 C8 H8 126.8
C9 C8 H8 126.8
N2 C9 C8 111.80(15)
N2 C9 H9 124.1
C8 C9 H9 124.1
C14 C10 C11 117.67(16)
C14 C10 C5 120.15(15)
C11 C10 C5 122.13(15)
C10 C11 C12 119.01(18)
C10 C11 H11 120.5
C12 C11 H11 120.5
N3 C12 C11 123.96(19)
N3 C12 H12 118.0
C11 C12 H12 118.0
N3 C13 C14 124.08(17)
N3 C13 H13 118.0
C14 C13 H13 118.0
C10 C14 C13 119.08(17)
C10 C14 H14 120.5
C13 C14 H14 120.5
N4 C15 C16 111.89(15)
N4 C15 H15 124.1
C16 C15 H15 124.1
C17 C16 C15 106.52(15)
C17 C16 H16 126.7
C15 C16 H16 126.7
C16 C17 C18 106.68(14)
C16 C17 H17 126.7
C18 C17 H17 126.7
C19 C18 N4 124.38(14)
C19 C18 C17 126.43(14)
N4 C18 C17 109.15(14)
C18 C19 C20 125.30(14)
C18 C19 C24 116.93(14)
C20 C19 C24 117.76(14)
N5 C20 C19 123.46(14)
N5 C20 C21 108.88(14)
C19 C20 C21 127.65(15)
C22 C21 C20 106.93(15)
C22 C21 H21 126.5
C20 C21 H21 126.5
C21 C22 C23 106.22(15)
C21 C22 H22 126.9
C23 C22 H22 126.9
N5 C23 C22 111.55(15)
N5 C23 H23 124.2
C22 C23 H23 124.2
C25 C24 C28 117.56(16)
C25 C24 C19 121.92(16)
C28 C24 C19 120.49(15)
C24 C25 C26 118.29(19)
C24 C25 H25 120.9
C26 C25 H25 120.9
N6 C26 C25 124.42(19)
N6 C26 H26 117.8
C25 C26 H26 117.8
N6 C27 C28 124.0(2)
N6 C27 H27 118.0
C28 C27 H27 118.0
C27 C28 C24 119.40(18)
C27 C28 H28 120.3
C24 C28 H28 120.3
C1 N1 C4 106.29(13)
C1 N1 Cu1 126.81(11)
C4 N1 Cu1 126.88(11)
C9 N2 C6 105.91(14)
C9 N2 Cu1 127.45(11)
C6 N2 Cu1 126.39(11)
C12 N3 C13 116.20(16)
C15 N4 C18 105.75(13)
C15 N4 Cu1 127.24(11)
C18 N4 Cu1 124.99(11)
C23 N5 C20 106.41(13)
C23 N5 Cu1 126.37(11)
C20 N5 Cu1 126.89(11)
C27 N6 C26 116.30(17)
N1 Cu1 N5 149.86(6)
N1 Cu1 N2 91.84(5)
N5 Cu1 N2 95.94(6)
N1 Cu1 N4 96.89(6)
N5 Cu1 N4 91.07(6)
N2 Cu1 N4 149.41(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.344(2)
C1 C2 1.412(2)
C1 H1 0.9300
C2 C3 1.378(2)
C2 H2 0.9300
C3 C4 1.427(2)
C3 H3 0.9300
C4 N1 1.392(2)
C4 C5 1.399(2)
C5 C6 1.396(2)
C5 C10 1.496(2)
C6 N2 1.398(2)
C6 C7 1.427(2)
C7 C8 1.371(3)
C7 H7 0.9300
C8 C9 1.411(2)
C8 H8 0.9300
C9 N2 1.339(2)
C9 H9 0.9300
C10 C14 1.382(2)
C10 C11 1.384(2)
C11 C12 1.392(3)
C11 H11 0.9300
C12 N3 1.330(3)
C12 H12 0.9300
C13 N3 1.337(3)
C13 C14 1.386(2)
C13 H13 0.9300
C14 H14 0.9300
C15 N4 1.339(2)
C15 C16 1.412(2)
C15 H15 0.9300
C16 C17 1.371(2)
C16 H16 0.9300
C17 C18 1.427(2)
C17 H17 0.9300
C18 C19 1.396(2)
C18 N4 1.3982(19)
C19 C20 1.407(2)
C19 C24 1.491(2)
C20 N5 1.3899(19)
C20 C21 1.423(2)
C21 C22 1.381(2)
C21 H21 0.9300
C22 C23 1.408(2)
C22 H22 0.9300
C23 N5 1.343(2)
C23 H23 0.9300
C24 C25 1.391(2)
C24 C28 1.392(2)
C25 C26 1.395(3)
C25 H25 0.9300
C26 N6 1.334(3)
C26 H26 0.9300
C27 N6 1.333(3)
C27 C28 1.381(3)
C27 H27 0.9300
C28 H28 0.9300
N1 Cu1 1.9636(13)
N2 Cu1 1.9703(14)
N4 Cu1 1.9736(13)
N5 Cu1 1.9642(14)
