#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103187.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_7103187
loop_
_publ_author_name
'Shimakoshi, Hisashi'
'Baba, Tatsushi'
'Iseki, Yusuke'
'Aritome, Isao'
'Endo, Ayataka'
'Adachi, Chihaya'
'Hisaeda, Yoshio'
_publ_section_title
;
 Photophysical and photosensitizing properties of brominated
 porphycenes.
;
_journal_issue                   25
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2882
_journal_page_last               2884
_journal_paper_doi               10.1039/b802730g
_journal_year                    2008
_chemical_formula_sum            'C32 H35 Br3 N4'
_chemical_formula_weight         715.37
_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                96.076(2)
_cell_angle_beta                 91.373(2)
_cell_angle_gamma                94.714(2)
_cell_formula_units_Z            1
_cell_length_a                   5.3757(5)
_cell_length_b                   10.3624(9)
_cell_length_c                   13.4652(12)
_cell_measurement_reflns_used    3053
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.625
_cell_volume                     742.94(12)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'π 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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6513
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  1110
_diffrn_standards_number         76
_exptl_absorpt_coefficient_mu    4.101
_exptl_absorpt_correction_T_max  0.6845
_exptl_absorpt_correction_T_min  0.2777
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS; Sheldrick 1996'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.574
_refine_diff_density_min         -1.553
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.1091
_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)+(0.0404P)²+7.6683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2413
_refine_ls_wR_factor_ref         0.2459
_reflns_number_gt                2515
_reflns_number_total             2837
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b802730g.txt
_cod_data_source_block           Tribromoporphycene
_cod_database_code               7103187
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
Br1 Br -0.1627(4) 0.0182(2) 0.58912(14) 0.0957(7) Uani 0.75 1 d P . .
Br2 Br 0.2688(3) 0.22626(17) 0.65207(10) 0.0702(5) Uani 0.75 1 d P . .
C1 C -0.4072(15) -0.1200(7) 0.8326(7) 0.046(2) Uani 1 1 d . . .
C2 C -0.4144(16) -0.1021(7) 0.7309(7) 0.047(2) Uani 1 1 d . . .
C3 C -0.2153(17) -0.0194(8) 0.7150(7) 0.048(2) Uani 1 1 d . . .
H3 H -0.1722 0.0096 0.6525 0.058 Uiso 0.25 1 calc PR . .
C4 C -0.0807(15) 0.0172(8) 0.8074(7) 0.0426(19) Uani 1 1 d . . .
C5 C 0.1380(15) 0.1004(7) 0.8359(6) 0.0402(18) Uani 1 1 d . . .
C6 C 0.2966(15) 0.1844(8) 0.7826(7) 0.0447(19) Uani 1 1 d . . .
H6 H 0.2725 0.1988 0.7147 0.054 Uiso 0.25 1 calc PR . .
C7 C 0.4875(15) 0.2403(7) 0.8447(7) 0.044(2) Uani 1 1 d . . .
C8 C 0.4411(14) 0.1939(7) 0.9378(7) 0.043(2) Uani 1 1 d . . .
C9 C 0.5984(15) 0.2278(7) 1.0241(7) 0.048(2) Uani 1 1 d . . .
H9 H 0.7435 0.2827 1.0135 0.057 Uiso 1 1 calc R . .
C10 C 0.5802(15) 0.1963(8) 1.1189(7) 0.048(2) Uani 1 1 d . . .
H10 H 0.7154 0.2348 1.1616 0.058 Uiso 1 1 calc R . .
C11 C -0.6061(18) -0.1684(9) 0.6528(8) 0.059(3) Uani 1 1 d . . .
H11A H -0.7722 -0.1740 0.6831 0.070 Uiso 1 1 calc R . .
H11B H -0.6154 -0.1138 0.5970 0.070 Uiso 1 1 calc R . .
C12 C -0.5484(16) -0.3015(8) 0.6122(7) 0.047(2) Uani 1 1 d . . .
H12A H -0.5359 -0.3562 0.6679 0.057 Uiso 1 1 calc R . .
H12B H -0.3849 -0.2962 0.5800 0.057 Uiso 1 1 calc R . .
C13 C -0.7486(18) -0.3653(10) 0.5362(7) 0.061(3) Uani 1 1 d . . .
H13A H -0.9109 -0.3702 0.5678 0.091 Uiso 1 1 calc R . .
H13B H -0.7070 -0.4533 0.5123 0.091 Uiso 1 1 calc R . .
H13C H -0.7564 -0.3133 0.4797 0.091 Uiso 1 1 calc R . .
C14 C 0.7016(16) 0.3327(8) 0.8208(8) 0.051(2) Uani 1 1 d . . .
H14A H 0.7331 0.3174 0.7485 0.062 Uiso 1 1 calc R . .
H14B H 0.8533 0.3139 0.8579 0.062 Uiso 1 1 calc R . .
C15 C 0.6573(15) 0.4740(8) 0.8465(8) 0.049(2) Uani 1 1 d . . .
H15A H 0.6236 0.4899 0.9185 0.059 Uiso 1 1 calc R . .
H15B H 0.5084 0.4942 0.8082 0.059 Uiso 1 1 calc R . .
C16 C 0.8821(17) 0.5636(10) 0.8225(9) 0.062(3) Uani 1 1 d . . .
H16A H 1.0330 0.5375 0.8545 0.093 Uiso 1 1 calc R . .
H16B H 0.8569 0.6537 0.8477 0.093 Uiso 1 1 calc R . .
H16C H 0.9010 0.5573 0.7500 0.093 Uiso 1 1 calc R . .
N1 N -0.2003(12) -0.0469(6) 0.8777(5) 0.0396(15) Uani 1 1 d . . .
H1 H -0.1540 -0.0426 0.9411 0.047 Uiso 0.50 1 calc PR . .
N2 N 0.2294(12) 0.1092(6) 0.9312(5) 0.0389(15) Uani 1 1 d . . .
H2 H 0.1651 0.0683 0.9798 0.047 Uiso 0.50 1 calc PR . .
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'
Br Br -0.2901 2.4595 '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 C10 125.4(9) . 2_557 ?
N1 C1 C2 108.4(8) . . ?
C10 C1 C2 126.2(8) 2_557 . ?
C3 C2 C1 107.2(7) . . ?
C3 C2 C11 126.8(9) . . ?
C1 C2 C11 125.9(9) . . ?
C2 C3 C4 108.7(9) . . ?
C2 C3 Br1 118.3(7) . . ?
C4 C3 Br1 133.0(7) . . ?
N1 C4 C5 119.1(8) . . ?
N1 C4 C3 107.2(7) . . ?
C5 C4 C3 133.7(9) . . ?
N2 C5 C4 119.4(8) . . ?
N2 C5 C6 107.8(7) . . ?
C4 C5 C6 132.7(8) . . ?
C7 C6 C5 109.1(8) . . ?
C7 C6 Br2 120.5(7) . . ?
C5 C6 Br2 130.4(6) . . ?
C6 C7 C8 105.3(7) . . ?
C6 C7 C14 127.9(9) . . ?
C8 C7 C14 126.8(8) . . ?
N2 C8 C7 110.4(7) . . ?
N2 C8 C9 125.7(9) . . ?
C7 C8 C9 123.9(8) . . ?
C10 C9 C8 131.9(8) . . ?
C9 C10 C1 134.1(8) . 2_557 ?
C12 C11 C2 113.5(7) . . ?
C11 C12 C13 111.6(8) . . ?
C7 C14 C15 113.4(7) . . ?
C14 C15 C16 111.3(7) . . ?
C4 N1 C1 108.4(7) . . ?
C5 N2 C8 107.3(7) . . ?
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
Br1 C3 1.802(10) . ?
Br2 C6 1.860(9) . ?
C1 N1 1.382(10) . ?
C1 C10 1.391(13) 2_557 ?
C1 C2 1.401(13) . ?
C2 C3 1.351(13) . ?
C2 C11 1.523(11) . ?
C3 C4 1.424(11) . ?
C4 N1 1.357(11) . ?
C4 C5 1.419(11) . ?
C5 N2 1.354(11) . ?
C5 C6 1.428(12) . ?
C6 C7 1.359(12) . ?
C7 C8 1.410(13) . ?
C7 C14 1.499(11) . ?
C8 N2 1.374(10) . ?
C8 C9 1.416(12) . ?
C9 C10 1.354(13) . ?
C10 C1 1.391(13) 2_557 ?
C11 C12 1.489(12) . ?
C12 C13 1.526(11) . ?
C14 C15 1.509(11) . ?
C15 C16 1.525(12) . ?
