#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:05:52 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179439 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/36/4333617.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_4333617
loop_
_publ_author_name
'Anna A. Sinelshchikova'
'Sergey E. Nefedov'
'Yulia Yu. Enakieva'
'Yulia G. Gorbunova'
'Aslan Yu. Tsivadze'
'Karl M. Kadish'
'Ping Chen'
'Alla Bessmertnykh-Lemeune'
'Christine Stern'
'Roger Guilard'
_publ_section_title
;
 Unusual Formation of a Stable 2D Copper Porphyrin Network
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              999
_journal_page_last               1008
_journal_paper_doi               10.1021/ic302257g
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C48 H54 Cu N4 O10 P2'
_chemical_formula_weight         972.43
_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                71.456(4)
_cell_angle_beta                 72.223(4)
_cell_angle_gamma                77.807(4)
_cell_formula_units_Z            1
_cell_length_a                   9.657(2)
_cell_length_b                   11.280(3)
_cell_length_c                   11.705(3)
_cell_measurement_reflns_used    2081
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.70
_cell_measurement_theta_min      2.23
_cell_volume                     1141.9(5)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0774
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10668
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  0.9413
_exptl_absorpt_correction_T_min  0.9192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       prizm
_exptl_crystal_F_000             509
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.423
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4914
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0795
_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)+(0.1000P)²+3.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2100
_reflns_number_gt                3357
_reflns_number_total             4914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302257g_si_004.cif
_cod_data_source_block           1
_cod_database_code               4333617
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
Cu1 Cu 0.0000 0.0000 0.0000 0.0232(2) Uani 1 2 d S
P1 P 0.42815(13) 0.24644(11) -0.33223(10) 0.0265(3) Uani 1 1 d .
O1 O 0.4778(4) 0.3417(3) -0.2989(3) 0.0367(9) Uani 1 1 d .
O2 O 0.3655(4) 0.2952(3) -0.4497(3) 0.0327(8) Uani 1 1 d .
O3 O 0.5592(4) 0.1419(3) -0.3693(3) 0.0358(8) Uani 1 1 d .
N1 N 0.1065(4) 0.1392(3) -0.0076(3) 0.0232(8) Uani 1 1 d .
N2 N 0.1237(4) -0.0014(4) -0.1724(3) 0.0243(8) Uani 1 1 d .
C1 C 0.2165(5) 0.1978(4) -0.1039(4) 0.0241(10) Uani 1 1 d .
C2 C 0.2552(5) 0.2972(5) -0.0713(4) 0.0298(11) Uani 1 1 d .
H2A H 0.3274 0.3512 -0.1213 0.036 Uiso 1 1 calc R
C3 C 0.2809(5) 0.1635(4) -0.2170(4) 0.0246(10) Uani 1 1 d .
C4 C 0.2363(5) 0.0701(4) -0.2467(4) 0.0262(10) Uani 1 1 d .
C5 C 0.3006(6) 0.0316(5) -0.3606(4) 0.0328(11) Uani 1 1 d .
H5A H 0.3790 0.0659 -0.4272 0.039 Uiso 1 1 calc R
C6 C 0.2294(6) -0.0612(5) -0.3552(4) 0.0337(12) Uani 1 1 d .
H6A H 0.2485 -0.1051 -0.4166 0.040 Uiso 1 1 calc R
C7 C 0.1182(5) -0.0813(4) -0.2381(4) 0.0275(10) Uani 1 1 d .
C8 C 0.0254(5) -0.1741(4) -0.1982(4) 0.0274(10) Uani 1 1 d .
C9 C -0.0771(5) -0.2006(4) -0.0838(4) 0.0260(10) Uani 1 1 d .
C10 C -0.1693(6) -0.2993(5) -0.0444(4) 0.0306(11) Uani 1 1 d .
H10A H -0.1698 -0.3550 -0.0904 0.037 Uiso 1 1 calc R
C11 C 0.0408(5) -0.2511(5) -0.2862(4) 0.0291(11) Uani 1 1 d .
C12 C -0.0256(7) -0.2069(6) -0.3837(5) 0.0466(15) Uani 1 1 d .
H12A H -0.0858 -0.1278 -0.3929 0.056 Uiso 1 1 calc R
C13 C -0.0062(8) -0.2757(7) -0.4687(6) 0.0558(17) Uani 1 1 d .
H13A H -0.0538 -0.2448 -0.5344 0.067 Uiso 1 1 calc R
C14 C 0.0831(7) -0.3890(6) -0.4559(5) 0.0469(15) Uani 1 1 d .
H14A H 0.0999 -0.4353 -0.5150 0.056 Uiso 1 1 calc R
C15 C 0.1481(7) -0.4358(6) -0.3587(6) 0.0487(15) Uani 1 1 d .
H15A H 0.2082 -0.5149 -0.3496 0.058 Uiso 1 1 calc R
C16 C 0.1259(6) -0.3670(5) -0.2735(5) 0.0404(13) Uani 1 1 d .
H16A H 0.1700 -0.4003 -0.2056 0.049 Uiso 1 1 calc R
C17 C 0.4494(10) 0.3732(8) -0.5657(5) 0.0726(17) Uani 1 1 d U
H17A H 0.4178 0.4635 -0.5694 0.087 Uiso 1 1 calc R
H17B H 0.5550 0.3548 -0.5683 0.087 Uiso 1 1 calc R
C18 C 0.4259(10) 0.3472(8) -0.6712(6) 0.0748(17) Uani 1 1 d U
H18A H 0.4897 0.3930 -0.7484 0.112 Uiso 1 1 calc R
H18B H 0.3232 0.3744 -0.6735 0.112 Uiso 1 1 calc R
H18C H 0.4489 0.2565 -0.6632 0.112 Uiso 1 1 calc R
C19 C 0.6731(7) 0.1005(8) -0.3036(7) 0.0689(16) Uani 1 1 d U
H19A H 0.6953 0.1733 -0.2853 0.083 Uiso 1 1 calc R
H19B H 0.7634 0.0663 -0.3570 0.083 Uiso 1 1 calc R
C20 C 0.6272(8) 0.0016(8) -0.1845(7) 0.0711(16) Uani 1 1 d U
H20A H 0.7033 -0.0208 -0.1392 0.107 Uiso 1 1 calc R
H20B H 0.6131 -0.0733 -0.2029 0.107 Uiso 1 1 calc R
H20C H 0.5351 0.0339 -0.1333 0.107 Uiso 1 1 calc R
O4 O 0.1918(5) -0.1938(5) 0.0956(5) 0.0722(9) Uani 1 1 d U
O5 O 0.3118(6) -0.4413(5) 0.0789(5) 0.0743(9) Uani 1 1 d U
C21 C 0.3391(9) -0.2191(8) 0.0285(8) 0.0751(10) Uani 1 1 d U
H21A H 0.3655 -0.1453 -0.0435 0.090 Uiso 1 1 calc R
H21B H 0.4047 -0.2322 0.0832 0.090 Uiso 1 1 calc R
C22 C 0.3610(9) -0.3265(8) -0.0148(8) 0.0754(10) Uani 1 1 d U
H22A H 0.4670 -0.3445 -0.0532 0.091 Uiso 1 1 calc R
H22B H 0.3095 -0.3062 -0.0812 0.091 Uiso 1 1 calc R
C23 C 0.1577(9) -0.4028(8) 0.1386(8) 0.0745(10) Uani 1 1 d U
H23A H 0.0996 -0.3802 0.0764 0.089 Uiso 1 1 calc R
H23B H 0.1185 -0.4755 0.2066 0.089 Uiso 1 1 calc R
C24 C 0.1392(9) -0.3023(8) 0.1870(7) 0.0735(10) Uani 1 1 d U
H24A H 0.1916 -0.3266 0.2533 0.088 Uiso 1 1 calc R
H24B H 0.0337 -0.2821 0.2254 0.088 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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 Cu1 N2 180.0 2 .
N2 Cu1 N1 91.46(14) 2 .
N2 Cu1 N1 88.54(14) . .
N2 Cu1 N1 88.53(14) 2 2
N2 Cu1 N1 91.46(14) . 2
N1 Cu1 N1 180.0 . 2
O1 P1 O2 115.7(2) . .
O1 P1 O3 111.9(2) . .
O2 P1 O3 102.34(19) . .
O1 P1 C3 117.0(2) . .
O2 P1 C3 101.4(2) . .
O3 P1 C3 107.0(2) . .
C17 O2 P1 119.6(4) . .
C19 O3 P1 119.6(4) . .
C9 N1 C1 105.5(4) 2 .
C9 N1 Cu1 125.4(3) 2 .
C1 N1 Cu1 129.0(3) . .
C7 N2 C4 105.7(4) . .
C7 N2 Cu1 125.6(3) . .
C4 N2 Cu1 128.5(3) . .
N1 C1 C3 124.5(4) . .
N1 C1 C2 110.0(4) . .
C3 C1 C2 125.5(4) . .
C10 C2 C1 107.3(4) 2 .
C4 C3 C1 123.6(4) . .
C4 C3 P1 117.2(3) . .
C1 C3 P1 119.1(3) . .
C3 C4 N2 125.7(4) . .
C3 C4 C5 125.1(4) . .
N2 C4 C5 109.2(4) . .
C6 C5 C4 107.8(4) . .
C5 C6 C7 106.8(4) . .
N2 C7 C8 126.4(4) . .
N2 C7 C6 110.4(4) . .
C8 C7 C6 123.2(4) . .
C9 C8 C7 124.8(4) . .
C9 C8 C11 118.5(4) . .
C7 C8 C11 116.7(4) . .
N1 C9 C8 126.3(4) 2 .
N1 C9 C10 110.4(4) 2 .
C8 C9 C10 123.3(4) . .
C2 C10 C9 106.8(4) 2 .
C16 C11 C12 118.3(5) . .
C16 C11 C8 120.3(5) . .
C12 C11 C8 121.4(5) . .
C11 C12 C13 121.4(6) . .
C14 C13 C12 118.9(6) . .
C15 C14 C13 120.6(5) . .
C14 C15 C16 119.8(6) . .
C11 C16 C15 120.9(6) . .
C18 C17 O2 109.7(6) . .
O3 C19 C20 111.0(6) . .
C21 O4 C24 112.1(6) . .
C22 O5 C23 104.5(6) . .
C22 C21 O4 111.9(7) . .
C21 C22 O5 116.1(7) . .
C24 C23 O5 113.6(7) . .
C23 C24 O4 112.6(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 2.010(3) 2
Cu1 N2 2.010(3) .
Cu1 N1 2.017(4) .
Cu1 N1 2.017(4) 2
P1 O1 1.461(4) .
P1 O2 1.564(4) .
P1 O3 1.593(4) .
P1 C3 1.818(5) .
O2 C17 1.464(7) .
O3 C19 1.446(8) .
N1 C9 1.382(6) 2
N1 C1 1.388(5) .
N2 C7 1.377(6) .
N2 C4 1.391(6) .
C1 C3 1.418(6) .
C1 C2 1.442(6) .
C2 C10 1.359(6) 2
C3 C4 1.390(7) .
C4 C5 1.449(6) .
C5 C6 1.344(7) .
C6 C7 1.445(6) .
C7 C8 1.396(7) .
C8 C9 1.387(6) .
C8 C11 1.504(6) .
C9 N1 1.382(6) 2
C9 C10 1.444(7) .
C10 C2 1.359(6) 2
C11 C16 1.380(7) .
C11 C12 1.382(8) .
C12 C13 1.394(8) .
C13 C14 1.375(9) .
C14 C15 1.372(9) .
C15 C16 1.390(8) .
C17 C18 1.446(10) .
C19 C20 1.491(10) .
O4 C21 1.418(8) .
O4 C24 1.414(9) .
O5 C22 1.464(9) .
O5 C23 1.476(9) .
C21 C22 1.409(11) .
C23 C24 1.377(11) .
