#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:02:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180285 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117123.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_7117123
loop_
_publ_author_name
'Santosh C. Gadekar'
'Baddigam Kiran Reddy'
'Venkataramanarao G. Anand'
_publ_section_title
;
 Metal assisted cyclodimerization of doubly N-confused dipyrrins into
 planar aza-heptalenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              8342
_journal_paper_doi               10.1039/C5cc01367D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C30 H8 F10 N4'
_chemical_formula_sum            'C30 H8 F10 N4'
_chemical_formula_weight         614.40
_chemical_name_systematic        2N-Nornorrole
_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
_audit_update_record
;
2014-09-16 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                87.325(8)
_cell_angle_beta                 86.010(8)
_cell_angle_gamma                71.490(8)
_cell_formula_units_Z            1
_cell_length_a                   5.996(2)
_cell_length_b                   7.348(3)
_cell_length_c                   13.198(5)
_cell_measurement_temperature    100
_cell_volume                     549.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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      100
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8664
_diffrn_reflns_theta_full        27.67
_diffrn_reflns_theta_max         27.67
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0385
_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)+(0.0578P)²+0.2771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                1930
_reflns_number_total             2526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01367d2.cif
_cod_data_source_block           614p
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117123
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.25793(19) 0.68202(16) -0.10205(7) 0.0215(3) Uani 1 1 d . . .
F2 F 0.19120(19) 0.46387(15) 0.23431(7) 0.0188(3) Uani 1 1 d . . .
F3 F 0.26334(19) 1.07945(15) 0.16515(8) 0.0198(3) Uani 1 1 d . . .
F4 F 0.28335(19) 1.01918(15) -0.03651(7) 0.0193(3) Uani 1 1 d . . .
F5 F 0.21811(19) 0.40341(15) 0.03387(8) 0.0198(3) Uani 1 1 d . . .
N1 N 0.3037(3) 0.8710(2) 0.54465(11) 0.0133(3) Uani 1 1 d . . .
N2 N 0.6716(3) 0.6599(2) 0.49466(11) 0.0157(3) Uani 1 1 d . . .
C1 C 0.2469(3) 0.7122(3) -0.00232(13) 0.0158(4) Uani 1 1 d . . .
C2 C 0.2605(3) 0.8827(3) 0.03122(13) 0.0150(4) Uani 1 1 d . . .
C3 C 0.2490(3) 0.9124(2) 0.13426(13) 0.0143(4) Uani 1 1 d . . .
C4 C 0.2231(3) 0.7749(3) 0.20623(12) 0.0136(4) Uani 1 1 d . . .
C5 C 0.2117(3) 0.8140(2) 0.31708(12) 0.0127(3) Uani 1 1 d . . .
C6 C -0.0046(3) 0.9404(2) 0.35692(13) 0.0138(4) Uani 1 1 d . . .
C7 C 0.0674(3) 0.9853(2) 0.54324(12) 0.0125(3) Uani 1 1 d . . .
C8 C 0.2118(3) 0.6040(3) 0.16963(13) 0.0146(4) Uani 1 1 d . . .
C9 C 0.2243(3) 0.5713(2) 0.06679(13) 0.0153(4) Uani 1 1 d . . .
C10 C -0.2086(3) 1.0127(3) 0.29989(13) 0.0156(4) Uani 1 1 d . . .
H10 H -0.2187 0.9871 0.2323 0.019 Uiso 1 1 calc R . .
C11 C 0.3857(3) 0.8749(3) 0.63974(13) 0.0159(4) Uani 1 1 d . . .
H11 H 0.5376 0.8107 0.6590 0.019 Uiso 1 1 calc R . .
C12 C 0.4118(3) 0.7288(3) 0.36718(13) 0.0143(4) Uani 1 1 d . . .
C13 C 0.4570(3) 0.7560(2) 0.47119(13) 0.0134(4) Uani 1 1 d . . .
C14 C 0.7790(3) 0.5619(3) 0.40633(13) 0.0157(4) Uani 1 1 d . . .
H14 H 0.9337 0.4806 0.4016 0.019 Uiso 1 1 calc R . .
C15 C 0.6332(3) 0.5985(3) 0.32875(13) 0.0160(4) Uani 1 1 d . . .
H15 H 0.6686 0.5495 0.2638 0.019 Uiso 1 1 calc R . .
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'
F F 0.0171 0.0103 '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
C11 N1 C13 118.22(15) . .
C11 N1 C7 109.69(14) . .
C13 N1 C7 132.05(15) . .
C13 N2 C14 104.99(15) . .
F1 C1 C2 120.01(16) . .
F1 C1 C9 119.91(16) . .
C2 C1 C9 120.08(16) . .
F4 C2 C1 119.79(15) . .
F4 C2 C3 120.66(16) . .
C1 C2 C3 119.55(16) . .
F3 C3 C2 118.50(15) . .
F3 C3 C4 119.46(15) . .
C2 C3 C4 122.04(16) . .
C8 C4 C3 116.82(15) . .
C8 C4 C5 123.21(15) . .
C3 C4 C5 119.97(15) . .
C12 C5 C6 127.63(16) . .
C12 C5 C4 116.56(15) . .
C6 C5 C4 115.78(15) . .
C5 C6 C10 123.38(16) . .
C5 C6 C7 129.56(16) . 2_576
C10 C6 C7 107.03(15) . 2_576
N1 C7 C7 123.89(19) . 2_576
N1 C7 C6 105.75(14) . 2_576
C7 C7 C6 130.4(2) 2_576 2_576
F2 C8 C9 117.86(16) . .
F2 C8 C4 120.18(15) . .
C9 C8 C4 121.96(16) . .
F5 C9 C1 119.89(15) . .
F5 C9 C8 120.55(16) . .
C1 C9 C8 119.55(16) . .
C11 C10 C6 108.69(15) 2_576 .
C11 C10 H10 125.7 2_576 .
C6 C10 H10 125.7 . .
C10 C11 N1 108.84(16) 2_576 .
C10 C11 H11 125.6 2_576 .
N1 C11 H11 125.6 . .
C5 C12 C15 128.74(16) . .
C5 C12 C13 128.10(16) . .
C15 C12 C13 103.09(15) . .
N2 C13 N1 118.79(16) . .
N2 C13 C12 112.96(15) . .
N1 C13 C12 128.25(16) . .
C15 C14 N2 112.79(16) . .
C15 C14 H14 123.6 . .
N2 C14 H14 123.6 . .
C14 C15 C12 106.17(16) . .
C14 C15 H15 126.9 . .
C12 C15 H15 126.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.339(2) .
F2 C8 1.337(2) .
F3 C3 1.341(2) .
F4 C2 1.345(2) .
F5 C9 1.339(2) .
N1 C11 1.384(2) .
N1 C13 1.399(2) .
N1 C7 1.400(2) .
N2 C13 1.307(2) .
N2 C14 1.404(2) .
C1 C2 1.376(3) .
C1 C9 1.380(3) .
C2 C3 1.381(2) .
C3 C4 1.392(2) .
C4 C8 1.389(3) .
C4 C5 1.497(2) .
C5 C12 1.365(3) .
C5 C6 1.417(2) .
C6 C10 1.422(2) .
C6 C7 1.430(2) 2_576
C7 C7 1.413(3) 2_576
C7 C6 1.430(2) 2_576
C8 C9 1.382(2) .
C10 C11 1.353(2) 2_576
C10 H10 0.9300 .
C11 C10 1.353(2) 2_576
C11 H11 0.9300 .
C12 C15 1.442(2) .
C12 C13 1.452(2) .
C14 C15 1.355(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
