#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/45/1504526.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_1504526
loop_
_publ_author_name
'Matano, Yoshihiro'
'Nakashima, Makoto'
'Nakabuchi, Takashi'
'Imahori, Hiroshi'
'Fujishige, Shinya'
'Nakano, Haruyuki'
_publ_section_title
;
 Monophosphaporphyrins: oxidative pi-extension at the peripherally fused
 carbocycle of the phosphaporphyrin ring.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              553
_journal_page_last               556
_journal_paper_doi               10.1021/ol7029118
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C41 H28 N3 O P, C H2 Cl2'
_chemical_formula_sum            'C42 H30 Cl2 N3 O P'
_chemical_formula_weight         694.56
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 106.679(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6044(16)
_cell_length_b                   15.398(3)
_cell_length_c                   13.408(3)
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.06
_cell_volume                     1701.7(6)
_computing_cell_refinement       HKL2000
_computing_data_collection       CrystalClear
_computing_data_reduction        HKL2000
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0948
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11692
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_correction_T_min  0.8854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1730
_refine_ls_R_factor_gt           0.0728
_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)+(0.0437P)²+1.7560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1730
_reflns_number_gt                1549
_reflns_number_total             3283
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7029118-file002.cif
_cod_data_source_block           1
_cod_original_cell_volume        1701.7(5)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               1504526
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
P1 P 0.04498(19) 0.2500 0.59975(13) 0.0493(5) Uani 1 2 d S . .
O1 O -0.0466(4) 0.2500 0.4863(3) 0.0493(11) Uani 1 2 d S . .
C1 C 0.2583(7) 0.2500 0.6108(5) 0.0481(16) Uani 1 2 d S . .
C2 C 0.3011(7) 0.2500 0.5195(5) 0.0527(17) Uani 1 2 d S . .
H3 H 0.2193 0.2500 0.4545 0.063 Uiso 1 2 calc SR . .
C3 C 0.4645(8) 0.2500 0.5223(5) 0.0628(19) Uani 1 2 d S . .
H4 H 0.4944 0.2500 0.4594 0.075 Uiso 1 2 calc SR . .
C4 C 0.5835(7) 0.2500 0.6180(6) 0.0584(19) Uani 1 2 d S . .
H5 H 0.6948 0.2500 0.6202 0.070 Uiso 1 2 calc SR . .
C5 C 0.5421(8) 0.2500 0.7073(6) 0.067(2) Uani 1 2 d S . .
H6 H 0.6245 0.2500 0.7720 0.081 Uiso 1 2 calc SR . .
C6 C 0.3787(8) 0.2500 0.7061(5) 0.0572(18) Uani 1 2 d S . .
H7 H 0.3502 0.2500 0.7695 0.069 Uiso 1 2 calc SR . .
C7 C 0.0085(5) 0.1636(3) 0.6822(3) 0.0519(12) Uani 1 1 d . . .
C8 C 0.0605(5) 0.2019(3) 0.7827(3) 0.0536(12) Uani 1 1 d . . .
C9 C 0.0960(5) 0.1753(4) 0.8867(4) 0.0651(14) Uani 1 1 d . . .
H1 H 0.1040 0.1171 0.9111 0.078 Uiso 1 1 calc R . .
C10 C 0.1174(8) 0.2500 0.9477(5) 0.071(2) Uani 1 2 d S . .
H2 H 0.1433 0.2500 1.0215 0.085 Uiso 1 2 calc SR . .
C11 C -0.0584(5) 0.0836(3) 0.6520(3) 0.0565(13) Uani 1 1 d . . .
H8 H -0.0343 0.0406 0.7051 0.068 Uiso 1 1 calc R . .
C12 C -0.1566(5) 0.0554(3) 0.5554(3) 0.0524(12) Uani 1 1 d . . .
C13 C -0.2294(5) -0.0276(3) 0.5309(4) 0.0605(13) Uani 1 1 d . . .
H9 H -0.2122 -0.0761 0.5765 0.073 Uiso 1 1 calc R . .
C14 C -0.3287(6) -0.0263(3) 0.4307(4) 0.0607(13) Uani 1 1 d . . .
H10 H -0.3900 -0.0739 0.3948 0.073 Uiso 1 1 calc R . .
C15 C -0.3243(5) 0.0584(3) 0.3897(4) 0.0513(12) Uani 1 1 d . . .
N1 N -0.2181(4) 0.1049(2) 0.4681(3) 0.0517(10) Uani 1 1 d . . .
H17 H -0.1929 0.1598 0.4628 0.062 Uiso 1 1 calc R . .
C16 C -0.4127(5) 0.0910(3) 0.2927(3) 0.0506(12) Uani 1 1 d . . .
C17 C -0.5017(6) 0.0258(3) 0.2145(3) 0.0558(12) Uani 1 1 d . . .
C18 C -0.4194(6) -0.0364(4) 0.1757(4) 0.0705(15) Uani 1 1 d . . .
H11 H -0.3044 -0.0393 0.2010 0.085 Uiso 1 1 calc R . .
C19 C -0.5015(8) -0.0944(4) 0.1008(4) 0.0877(18) Uani 1 1 d . . .
H12 H -0.4426 -0.1366 0.0748 0.105 Uiso 1 1 calc R . .
C20 C -0.6662(9) -0.0916(4) 0.0637(5) 0.094(2) Uani 1 1 d . . .
H13 H -0.7222 -0.1318 0.0121 0.113 Uiso 1 1 calc R . .
C21 C -0.7505(8) -0.0307(5) 0.1010(5) 0.099(2) Uani 1 1 d . . .
H14 H -0.8655 -0.0291 0.0761 0.119 Uiso 1 1 calc R . .
C22 C -0.6683(6) 0.0290(4) 0.1755(4) 0.0861(18) Uani 1 1 d . . .
H15 H -0.7275 0.0724 0.1996 0.103 Uiso 1 1 calc R . .
C23 C -0.4272(5) 0.1789(3) 0.2614(3) 0.0504(12) Uani 1 1 d . . .
C24 C -0.5055(5) 0.2062(3) 0.1564(3) 0.0559(13) Uani 1 1 d . . .
H16 H -0.5489 0.1695 0.0981 0.067 Uiso 1 1 calc R . .
N2 N -0.3767(6) 0.2500 0.3247(4) 0.0501(13) Uani 1 2 d S . .
C25 C -0.0669(9) 0.2500 0.2357(6) 0.094(3) Uani 1 2 d S . .
H18 H -0.1651 0.2761 0.1875 0.113 Uiso 0.50 1 calc PR A -1
H19 H -0.0749 0.2553 0.3077 0.113 Uiso 0.50 1 calc PR A -1
Cl1 Cl -0.0495(5) 0.1364(3) 0.2031(3) 0.1247(14) Uani 0.50 1 d P B -1
Cl2 Cl 0.1002(6) 0.3007(4) 0.2249(3) 0.211(4) Uani 0.50 1 d P B -1
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 P1 C1 108.1(3) . .
O1 P1 C7 119.09(17) . 4_565
C1 P1 C7 107.5(2) . 4_565
O1 P1 C7 119.09(18) . .
C1 P1 C7 107.51(19) . .
C7 P1 C7 94.3(3) 4_565 .
C2 C1 C6 119.8(6) . .
C2 C1 P1 117.0(5) . .
C6 C1 P1 123.2(5) . .
C1 C2 C3 120.0(6) . .
C1 C2 H3 120.0 . .
C3 C2 H3 120.0 . .
C4 C3 C2 119.5(6) . .
C4 C3 H4 120.2 . .
C2 C3 H4 120.2 . .
C5 C4 C3 120.5(6) . .
C5 C4 H5 119.7 . .
C3 C4 H5 119.7 . .
C4 C5 C6 120.8(7) . .
C4 C5 H6 119.6 . .
C6 C5 H6 119.6 . .
C1 C6 C5 119.3(6) . .
C1 C6 H7 120.4 . .
C5 C6 H7 120.4 . .
C11 C7 C8 130.1(4) . .
C11 C7 P1 127.6(3) . .
C8 C7 P1 102.2(3) . .
C9 C8 C7 137.9(5) . .
C9 C8 C8 107.0(3) . 4_565
C7 C8 C8 114.5(3) . 4_565
C10 C9 C8 107.3(5) . .
C10 C9 H1 126.4 . .
C8 C9 H1 126.4 . .
C9 C10 C9 111.4(6) . 4_565
C9 C10 H2 124.3 . .
C9 C10 H2 124.3 4_565 .
C7 C11 C12 130.1(4) . .
C7 C11 H8 115.0 . .
C12 C11 H8 115.0 . .
N1 C12 C11 127.0(4) . .
N1 C12 C13 105.5(4) . .
C11 C12 C13 127.1(4) . .
C14 C13 C12 108.9(4) . .
C14 C13 H9 125.6 . .
C12 C13 H9 125.6 . .
C13 C14 C15 108.4(4) . .
C13 C14 H10 125.8 . .
C15 C14 H10 125.8 . .
N1 C15 C16 126.0(4) . .
N1 C15 C14 105.5(4) . .
C16 C15 C14 128.5(4) . .
C12 N1 C15 111.8(4) . .
C12 N1 H17 124.1 . .
C15 N1 H17 124.1 . .
C15 C16 C23 126.7(4) . .
C15 C16 C17 116.4(4) . .
C23 C16 C17 116.9(4) . .
C18 C17 C22 118.2(5) . .
C18 C17 C16 121.1(4) . .
C22 C17 C16 120.6(5) . .
C19 C18 C17 120.9(5) . .
C19 C18 H11 119.6 . .
C17 C18 H11 119.6 . .
C20 C19 C18 120.6(6) . .
C20 C19 H12 119.7 . .
C18 C19 H12 119.7 . .
C19 C20 C21 119.6(6) . .
C19 C20 H13 120.2 . .
C21 C20 H13 120.2 . .
C20 C21 C22 120.2(6) . .
C20 C21 H14 119.9 . .
C22 C21 H14 119.9 . .
C17 C22 C21 120.4(6) . .
C17 C22 H15 119.8 . .
C21 C22 H15 119.8 . .
N2 C23 C16 126.5(4) . .
N2 C23 C24 110.3(4) . .
C16 C23 C24 123.2(4) . .
C24 C24 C23 107.0(3) 4_565 .
C24 C24 H16 126.5 4_565 .
C23 C24 H16 126.5 . .
C23 N2 C23 105.4(5) . 4_565
Cl2 C25 Cl2 55.4(5) 4_565 .
Cl2 C25 Cl1 53.2(3) 4_565 .
Cl2 C25 Cl1 107.1(5) . .
Cl2 C25 Cl1 107.1(5) 4_565 4_565
Cl2 C25 Cl1 53.2(3) . 4_565
Cl1 C25 Cl1 148.0(5) . 4_565
Cl2 C25 H18 136.4 4_565 .
Cl2 C25 H18 110.3 . .
Cl1 C25 H18 110.3 . .
Cl1 C25 H18 64.3 4_565 .
Cl2 C25 H19 115.0 4_565 .
Cl2 C25 H19 110.3 . .
Cl1 C25 H19 110.3 . .
Cl1 C25 H19 100.9 4_565 .
H18 C25 H19 108.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.499(4) .
P1 C1 1.798(6) .
P1 C7 1.814(5) 4_565
P1 C7 1.814(5) .
C1 C2 1.376(8) .
C1 C6 1.395(8) .
C2 C3 1.396(8) .
C2 H3 0.9500 .
C3 C4 1.394(9) .
C3 H4 0.9500 .
C4 C5 1.342(9) .
C4 H5 0.9500 .
C5 C6 1.402(8) .
C5 H6 0.9500 .
C6 H7 0.9500 .
C7 C11 1.372(6) .
C7 C8 1.420(6) .
C8 C9 1.401(6) .
C8 C8 1.480(9) 4_565
C9 C10 1.393(6) .
C9 H1 0.9500 .
C10 C9 1.393(6) 4_565
C10 H2 0.9500 .
C11 C12 1.397(6) .
C11 H8 0.9500 .
C12 N1 1.370(5) .
C12 C13 1.419(6) .
C13 C14 1.370(6) .
C13 H9 0.9500 .
C14 C15 1.420(6) .
C14 H10 0.9500 .
C15 N1 1.379(5) .
C15 C16 1.398(6) .
N1 H17 0.8800 .
C16 C23 1.412(6) .
C16 C17 1.494(6) .
C17 C18 1.378(6) .
C17 C22 1.379(6) .
C18 C19 1.377(7) .
C18 H11 0.9500 .
C19 C20 1.362(8) .
C19 H12 0.9500 .
C20 C21 1.366(8) .
C20 H13 0.9500 .
C21 C22 1.392(7) .
C21 H14 0.9500 .
C22 H15 0.9500 .
C23 N2 1.377(5) .
C23 C24 1.438(6) .
C24 C24 1.349(8) 4_565
C24 H16 0.9500 .
N2 C23 1.377(5) 4_565
C25 Cl2 1.678(7) 4_565
C25 Cl2 1.678(7) .
C25 Cl1 1.820(5) .
C25 Cl1 1.820(5) 4_565
C25 H18 0.9900 .
C25 H19 0.9900 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 P1 C1 C2 0.000(2) . .
C7 P1 C1 C2 -129.74(17) 4_565 .
C7 P1 C1 C2 129.74(17) . .
O1 P1 C1 C6 180.000(2) . .
C7 P1 C1 C6 50.26(17) 4_565 .
C7 P1 C1 C6 -50.26(17) . .
C6 C1 C2 C3 0.000(3) . .
P1 C1 C2 C3 180.000(2) . .
C1 C2 C3 C4 0.000(2) . .
C2 C3 C4 C5 0.000(3) . .
C3 C4 C5 C6 0.000(3) . .
C2 C1 C6 C5 0.000(3) . .
P1 C1 C6 C5 180.000(3) . .
C4 C5 C6 C1 0.000(3) . .
O1 P1 C7 C11 20.0(5) . .
C1 P1 C7 C11 -103.2(4) . .
C7 P1 C7 C11 146.9(3) 4_565 .
O1 P1 C7 C8 -157.8(3) . .
C1 P1 C7 C8 79.0(3) . .
C7 P1 C7 C8 -30.9(4) 4_565 .
C11 C7 C8 C9 15.1(9) . .
P1 C7 C8 C9 -167.1(5) . .
C11 C7 C8 C8 -155.2(4) . 4_565
P1 C7 C8 C8 22.6(3) . 4_565
C7 C8 C9 C10 -171.0(5) . .
C8 C8 C9 C10 -0.2(4) 4_565 .
C8 C9 C10 C9 0.4(8) . 4_565
C8 C7 C11 C12 156.3(5) . .
P1 C7 C11 C12 -20.9(7) . .
C7 C11 C12 N1 -4.6(8) . .
C7 C11 C12 C13 -176.2(5) . .
N1 C12 C13 C14 1.1(5) . .
C11 C12 C13 C14 174.1(5) . .
C12 C13 C14 C15 -1.3(6) . .
C13 C14 C15 N1 1.0(5) . .
C13 C14 C15 C16 -176.3(4) . .
C11 C12 N1 C15 -173.5(4) . .
C13 C12 N1 C15 -0.5(5) . .
C16 C15 N1 C12 177.1(4) . .
C14 C15 N1 C12 -0.3(5) . .
N1 C15 C16 C23 -8.9(7) . .
C14 C15 C16 C23 167.8(4) . .
N1 C15 C16 C17 171.5(4) . .
C14 C15 C16 C17 -11.8(7) . .
C15 C16 C17 C18 -64.6(6) . .
C23 C16 C17 C18 115.7(5) . .
C15 C16 C17 C22 118.6(5) . .
C23 C16 C17 C22 -61.1(6) . .
C22 C17 C18 C19 -0.7(8) . .
C16 C17 C18 C19 -177.6(5) . .
C17 C18 C19 C20 -0.2(9) . .
C18 C19 C20 C21 0.1(10) . .
C19 C20 C21 C22 1.0(10) . .
C18 C17 C22 C21 1.8(8) . .
C16 C17 C22 C21 178.6(5) . .
C20 C21 C22 C17 -1.9(10) . .
C15 C16 C23 N2 -10.1(8) . .
C17 C16 C23 N2 169.6(4) . .
C15 C16 C23 C24 172.7(4) . .
C17 C16 C23 C24 -7.7(6) . .
N2 C23 C24 C24 -1.2(4) . 4_565
C16 C23 C24 C24 176.4(3) . 4_565
C16 C23 N2 C23 -175.6(3) . 4_565
C24 C23 N2 C23 2.0(6) . 4_565
