#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:58:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180282 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/68/7116846.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_7116846
loop_
_publ_author_name
'Stephane A. Baudron'
'Herve Ruffin'
'Mir Wais Hosseini'
_publ_section_title
;
 On Zn(II) 2,2'-bisdipyrrin circular helicates
;
_journal_name_full               Chem.Commun.
_journal_page_first              5906
_journal_paper_doi               10.1039/C5cc00724K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C34 H24 N4 Ni O4'
_chemical_formula_sum            'C34 H24 N4 Ni O4'
_chemical_formula_weight         611.28
_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
_audit_update_record
;
2014-12-17 deposited with the CCDC.
2015-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.7240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   34.4732(8)
_cell_length_b                   9.8680(2)
_cell_length_c                   7.9143(2)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.41
_cell_volume                     2645.28(11)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28830
_diffrn_reflns_theta_full        29.59
_diffrn_reflns_theta_max         29.59
_diffrn_reflns_theta_min         1.20
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.9187
_exptl_absorpt_correction_T_min  0.9187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0310
_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)+(0.0500P)²+2.5665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                3289
_reflns_number_total             3688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00724k2.cif
_cod_data_source_block           compound2b
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               7116846
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
C1 C 0.46080(5) 0.05580(17) 0.1180(2) 0.0244(3) Uani 1 1 d .
H1 H 0.4846 0.0140 0.1107 0.029 Uiso 1 1 calc R
C2 C 0.42357(5) -0.00360(18) 0.0611(2) 0.0269(3) Uani 1 1 d .
H2 H 0.4185 -0.0887 0.0113 0.032 Uiso 1 1 calc R
C3 C 0.39620(4) 0.08982(17) 0.0941(2) 0.0239(3) Uani 1 1 d .
H3 H 0.3689 0.0790 0.0722 0.029 Uiso 1 1 calc R
C4 C 0.41745(4) 0.20624(16) 0.16812(19) 0.0207(3) Uani 1 1 d .
C5 C 0.40122(4) 0.33350(17) 0.19569(19) 0.0214(3) Uani 1 1 d .
C6 C 0.42418(4) 0.45096(17) 0.2239(2) 0.0246(3) Uani 1 1 d .
C7 C 0.41426(5) 0.59024(18) 0.2457(2) 0.0290(3) Uani 1 1 d .
H7 H 0.3893 0.6237 0.2513 0.035 Uiso 1 1 calc R
C8 C 0.44831(5) 0.66553(19) 0.2571(3) 0.0318(4) Uani 1 1 d .
H8 H 0.4508 0.7589 0.2705 0.038 Uiso 1 1 calc R
C9 C 0.47881(5) 0.57205(17) 0.2441(2) 0.0280(3) Uani 1 1 d .
C10 C 0.35769(4) 0.34316(16) 0.18478(18) 0.0207(3) Uani 1 1 d .
C11 C 0.33834(4) 0.25438(17) 0.27976(19) 0.0218(3) Uani 1 1 d .
H11 H 0.3528 0.1887 0.3486 0.026 Uiso 1 1 calc R
C12 C 0.29780(4) 0.26319(16) 0.27255(18) 0.0210(3) Uani 1 1 d .
H12 H 0.2853 0.2037 0.3363 0.025 Uiso 1 1 calc R
C13 C 0.27596(4) 0.36152(16) 0.16942(18) 0.0196(3) Uani 1 1 d .
C14 C 0.29478(4) 0.44877(17) 0.07240(19) 0.0235(3) Uani 1 1 d .
H14 H 0.2802 0.5136 0.0025 0.028 Uiso 1 1 calc R
C15 C 0.33528(4) 0.43958(17) 0.0793(2) 0.0239(3) Uani 1 1 d .
H15 H 0.3476 0.4979 0.0135 0.029 Uiso 1 1 calc R
C16 C 0.23263(4) 0.37729(16) 0.16051(18) 0.0209(3) Uani 1 1 d .
C17 C 0.17768(5) 0.31016(19) 0.2760(2) 0.0287(4) Uani 1 1 d .
H17A H 0.1713 0.4030 0.2944 0.043 Uiso 1 1 calc R
H17B H 0.1711 0.2552 0.3666 0.043 Uiso 1 1 calc R
H17C H 0.1629 0.2801 0.1675 0.043 Uiso 1 1 calc R
N1 N 0.45794(4) 0.17988(13) 0.18405(17) 0.0213(3) Uani 1 1 d .
N2 N 0.46413(4) 0.44504(14) 0.22544(19) 0.0259(3) Uani 1 1 d .
O1 O 0.21187(3) 0.45292(13) 0.06312(16) 0.0296(3) Uani 1 1 d .
O2 O 0.21932(3) 0.29848(12) 0.27511(15) 0.0262(2) Uani 1 1 d .
Ni1 Ni 0.5000 0.30375(3) 0.2500 0.02109(9) Uani 1 2 d S
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'
Ni Ni 0.3393 1.1124 '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 C1 C2 112.10(14) . .
N1 C1 H1 123.9 . .
C2 C1 H1 123.9 . .
C3 C2 C1 106.06(15) . .
C3 C2 H2 127.0 . .
C1 C2 H2 127.0 . .
C2 C3 C4 107.37(13) . .
C2 C3 H3 126.3 . .
C4 C3 H3 126.3 . .
N1 C4 C5 124.69(14) . .
N1 C4 C3 108.28(13) . .
C5 C4 C3 126.33(14) . .
C6 C5 C4 122.31(13) . .
C6 C5 C10 119.37(14) . .
C4 C5 C10 118.23(14) . .
N2 C6 C5 120.15(14) . .
N2 C6 C7 107.46(14) . .
C5 C6 C7 132.31(14) . .
C8 C7 C6 107.77(14) . .
C8 C7 H7 126.1 . .
C6 C7 H7 126.1 . .
C7 C8 C9 106.20(16) . .
C7 C8 H8 126.9 . .
C9 C8 H8 126.9 . .
N2 C9 C8 110.15(14) . .
N2 C9 C9 111.14(9) . 2_655
C8 C9 C9 138.56(11) . 2_655
C15 C10 C11 118.66(13) . .
C15 C10 C5 121.09(14) . .
C11 C10 C5 120.25(13) . .
C12 C11 C10 120.93(14) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C11 C12 C13 119.76(14) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
C14 C13 C12 119.79(13) . .
C14 C13 C16 118.38(13) . .
C12 C13 C16 121.83(13) . .
C15 C14 C13 120.39(14) . .
C15 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
C14 C15 C10 120.46(14) . .
C14 C15 H15 119.8 . .
C10 C15 H15 119.8 . .
O1 C16 O2 123.67(14) . .
O1 C16 C13 124.36(14) . .
O2 C16 C13 111.96(12) . .
O2 C17 H17A 109.5 . .
O2 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
O2 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C1 N1 C4 106.15(13) . .
C1 N1 Ni1 126.03(10) . .
C4 N1 Ni1 127.10(10) . .
C9 N2 C6 108.41(13) . .
C9 N2 Ni1 117.32(11) . .
C6 N2 Ni1 132.94(12) . .
C16 O2 C17 115.07(12) . .
N2 Ni1 N2 82.15(8) 2_655 .
N2 Ni1 N1 89.72(6) 2_655 2_655
N2 Ni1 N1 167.95(6) . 2_655
N2 Ni1 N1 167.95(6) 2_655 .
N2 Ni1 N1 89.72(6) . .
N1 Ni1 N1 99.61(8) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.342(2) .
C1 C2 1.406(2) .
C1 H1 0.9300 .
C2 C3 1.378(2) .
C2 H2 0.9300 .
C3 C4 1.428(2) .
C3 H3 0.9300 .
C4 N1 1.4022(18) .
C4 C5 1.408(2) .
C5 C6 1.398(2) .
C5 C10 1.490(2) .
C6 N2 1.3765(18) .
C6 C7 1.435(2) .
C7 C8 1.378(2) .
C7 H7 0.9300 .
C8 C9 1.417(2) .
C8 H8 0.9300 .
C9 N2 1.349(2) .
C9 C9 1.446(3) 2_655
C10 C15 1.400(2) .
C10 C11 1.402(2) .
C11 C12 1.391(2) .
C11 H11 0.9300 .
C12 C13 1.395(2) .
C12 H12 0.9300 .
C13 C14 1.392(2) .
C13 C16 1.4905(19) .
C14 C15 1.390(2) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 O1 1.2073(19) .
C16 O2 1.3389(19) .
C17 O2 1.4413(18) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
N1 Ni1 1.8940(13) .
N2 Ni1 1.8496(14) .
Ni1 N2 1.8496(14) 2_655
Ni1 N1 1.8940(13) 2_655
