#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/53/1515318.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_1515318
loop_
_publ_author_name
'Jesorka, Aldo'
'Holzwarth, Alfred R.'
'Eichhöfer, Andreas'
'Reddy, Chilla Malla'
'Kinoshita, Yusuke'
'Tamiaki, Hitoshi'
'Katterle, Martin'
'Naubron, Jean-Valère'
'Balaban, Teodor Silviu'
_publ_section_title
;
 Water coordinated zinc dioxo-chlorin and porphyrin self-assemblies as
 chlorosomal mimics: variability of supramolecular interactions.
;
_journal_issue                   6
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              1069
_journal_page_last               1080
_journal_paper_doi               10.1039/c2pp25016k
_journal_volume                  11
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_sum            'C35 H34 Cl2 N4 O4 Zn'
_chemical_formula_weight         710.93
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 114.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5690(19)
_cell_length_b                   17.605(4)
_cell_length_c                   10.472(2)
_cell_measurement_reflns_used    22160
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.14
_cell_volume                     1599.2(7)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12376
_diffrn_reflns_theta_full        26.72
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         6125
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.1942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                5992
_reflns_number_total             6125
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2pp25016k.txt
_cod_data_source_block           2
_cod_original_cell_volume        1599.4(6)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1515318
loop_
_symmetry_equiv_pos_as_xyz
'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
Zn1 Zn 0.59752(2) 0.045068(14) 0.67621(2) 0.02779(7) Uani 1 1 d . . .
Cl1 Cl 0.57827(9) -0.10462(6) 0.86510(10) 0.0645(2) Uani 1 1 d . A .
Cl2 Cl 0.7600(8) -0.0325(4) 1.1473(8) 0.0736(11) Uani 0.50 1 d P A 1
Cl2A Cl 0.7140(9) -0.0370(5) 1.1322(9) 0.115(3) Uani 0.50 1 d P A 2
N1 N 0.3933(2) 0.08300(11) 0.66123(18) 0.0280(3) Uani 1 1 d . . .
N2 N 0.7143(2) 0.10601(11) 0.85835(19) 0.0301(4) Uani 1 1 d . . .
N3 N 0.8002(2) -0.00298(10) 0.71217(19) 0.0289(4) Uani 1 1 d . . .
N4 N 0.4834(2) -0.03893(10) 0.51309(18) 0.0276(3) Uani 1 1 d . . .
C1 C 0.2519(2) 0.06387(12) 0.5595(2) 0.0301(5) Uani 1 1 d . . .
C2 C 0.1335(2) 0.10891(13) 0.5756(2) 0.0319(4) Uani 1 1 d . . .
C3 C 0.2072(3) 0.15410(13) 0.6916(2) 0.0317(4) Uani 1 1 d . B .
C4 C 0.3716(2) 0.13759(12) 0.7452(2) 0.0285(4) Uani 1 1 d . . .
C5 C 0.4890(3) 0.17005(13) 0.8621(2) 0.0308(4) Uani 1 1 d . . .
H5A H 0.456(3) 0.2054(16) 0.911(3) 0.025(6) Uiso 1 1 d . . .
C6 C 0.6481(3) 0.15602(13) 0.9153(2) 0.0311(4) Uani 1 1 d . . .
C7 C 0.7637(3) 0.19224(17) 1.0379(3) 0.0400(5) Uani 1 1 d . . .
C8 C 0.9016(3) 0.16203(15) 1.0557(3) 0.0403(5) Uani 1 1 d . . .
C9 C 0.8708(3) 0.10947(13) 0.9403(2) 0.0321(4) Uani 1 1 d . . .
C10 C 0.9806(2) 0.06746(13) 0.9153(2) 0.0322(5) Uani 1 1 d . . .
H10A H 1.095(3) 0.0741(15) 0.977(3) 0.031(7) Uiso 1 1 d . . .
C11 C 0.9496(2) 0.01491(13) 0.8069(2) 0.0294(4) Uani 1 1 d . . .
C12 C 1.0602(2) -0.02978(13) 0.7784(2) 0.0305(4) Uani 1 1 d . . .
C13 C 0.9709(3) -0.07572(13) 0.6650(2) 0.0314(4) Uani 1 1 d . . .
C14 C 0.8145(2) -0.05756(12) 0.6291(2) 0.0298(4) Uani 1 1 d . . .
C15 C 0.7085(3) -0.10126(13) 0.5174(2) 0.0308(4) Uani 1 1 d . . .
C16 C 0.5514(3) -0.09379(13) 0.4652(2) 0.0297(4) Uani 1 1 d . . .
C17 C 0.4325(3) -0.14327(13) 0.3545(2) 0.0313(4) Uani 1 1 d . . .
H17A H 0.444(3) -0.1436(18) 0.261(3) 0.036(7) Uiso 1 1 d . . .
C18 C 0.2782(3) -0.10428(13) 0.3307(2) 0.0315(4) Uani 1 1 d . . .
H18A H 0.217(4) -0.1416(19) 0.347(3) 0.041(7) Uiso 1 1 d . . .
C19 C 0.3291(2) -0.04149(12) 0.4401(2) 0.0288(4) Uani 1 1 d . . .
C20 C 0.2234(3) 0.00657(13) 0.4587(2) 0.0317(4) Uani 1 1 d . . .
H20A H 0.121(4) -0.0026(18) 0.393(3) 0.036(7) Uiso 1 1 d . . .
C21 C -0.0351(3) 0.10336(17) 0.4775(3) 0.0401(5) Uani 1 1 d . . .
H21C H -0.083(4) 0.1474(18) 0.455(3) 0.036(7) Uiso 1 1 d . . .
H21B H -0.093(3) 0.0769(17) 0.527(3) 0.037(7) Uiso 1 1 d . . .
H21A H -0.046(4) 0.081(2) 0.396(4) 0.049(9) Uiso 1 1 d . . .
C22 C 0.1403(3) 0.20958(15) 0.7572(3) 0.0387(5) Uani 1 1 d . . .
C23 C -0.0316(3) 0.21650(16) 0.7041(3) 0.0412(5) Uani 1 1 d . B .
H23C H -0.073(4) 0.2406(19) 0.610(3) 0.042(8) Uiso 1 1 d . . .
H23B H -0.061(4) 0.243(2) 0.774(3) 0.048(8) Uiso 1 1 d . . .
H23A H -0.086(4) 0.163(2) 0.687(3) 0.045(8) Uiso 1 1 d . . .
C24 C 0.7325(3) 0.25145(19) 1.1257(3) 0.0516(7) Uani 1 1 d . . .
H24A H 0.6216 0.2617 1.0867 0.077 Uiso 1 1 calc R . .
H24B H 0.7876 0.2983 1.1250 0.077 Uiso 1 1 calc R . .
H24C H 0.7681 0.2330 1.2226 0.077 Uiso 1 1 calc R . .
C25 C 1.0579(3) 0.18162(19) 1.1711(3) 0.0500(6) Uani 1 1 d . . .
H25B H 1.105(3) 0.1785(16) 1.274(3) 0.033(7) Uiso 1 1 d . . .
H25A H 1.143(6) 0.138(3) 1.198(5) 0.079(13) Uiso 1 1 d . . .
C26 C 1.1210(4) 0.2552(2) 1.1402(4) 0.0663(9) Uani 1 1 d . . .
H26A H 1.133(6) 0.243(3) 1.037(5) 0.096(15) Uiso 1 1 d . . .
H26B H 1.021(6) 0.302(3) 1.133(5) 0.083(13) Uiso 1 1 d . . .
H26C H 1.244(6) 0.269(3) 1.235(5) 0.100(16) Uiso 1 1 d . . .
C27 C 1.2313(3) -0.02621(16) 0.8537(3) 0.0368(5) Uani 1 1 d . . .
H27C H 1.265(5) -0.061(2) 0.932(4) 0.068(11) Uiso 1 1 d . . .
H27B H 1.281(4) -0.031(2) 0.797(4) 0.061(10) Uiso 1 1 d . . .
H27A H 1.261(5) 0.023(3) 0.892(4) 0.078(13) Uiso 1 1 d . . .
C28 C 0.9744(3) -0.13425(14) 0.5673(2) 0.0346(5) Uani 1 1 d . . .
C29 C 0.8046(3) -0.15543(15) 0.4733(3) 0.0377(5) Uani 1 1 d . . .
H29B H 0.787(5) -0.214(3) 0.484(4) 0.072(11) Uiso 1 1 d . . .
H29A H 0.786(4) -0.148(2) 0.371(3) 0.048(8) Uiso 1 1 d . . .
C30 C 0.5606(3) 0.27295(13) 0.6030(2) 0.0333(4) Uani 1 1 d . . .
H30B H 0.464(3) 0.2495(17) 0.598(3) 0.036(7) Uiso 1 1 d . . .
H30A H 0.644(4) 0.2447(17) 0.671(3) 0.033(6) Uiso 1 1 d . . .
C31 C 0.5651(3) 0.26193(13) 0.4607(2) 0.0335(4) Uani 1 1 d . . .
H31B H 0.480(3) 0.2843(16) 0.385(3) 0.023(6) Uiso 1 1 d . . .
H31A H 0.676(4) 0.2860(19) 0.468(3) 0.044(8) Uiso 1 1 d . . .
C32 C 0.5622(3) 0.17944(14) 0.4214(3) 0.0337(5) Uani 1 1 d . . .
C33 C 0.5152(5) 0.09328(19) 0.2369(4) 0.0665(9) Uani 1 1 d . . .
H33A H 0.4776 0.0926 0.1341 0.100 Uiso 1 1 calc R . .
H33B H 0.4480 0.0617 0.2643 0.100 Uiso 1 1 calc R . .
H33C H 0.6205 0.0732 0.2802 0.100 Uiso 1 1 calc R . .
C34 C 0.1890(4) -0.07461(19) 0.1810(3) 0.0485(6) Uani 1 1 d . . .
H34C H 0.095(4) -0.048(3) 0.160(4) 0.058(11) Uiso 1 1 d . . .
H34B H 0.256(4) -0.040(2) 0.158(3) 0.044(8) Uiso 1 1 d . . .
H34A H 0.157(5) -0.119(3) 0.113(4) 0.068(11) Uiso 1 1 d . . .
C35 C 0.7570(4) -0.08773(18) 1.0066(3) 0.0492(6) Uani 1 1 d . . .
O1 O 0.2152(13) 0.2563(5) 0.8371(11) 0.0405(15) Uani 0.50 1 d P B 1
O1A O 0.2272(17) 0.2398(8) 0.8724(14) 0.101(5) Uani 0.50 1 d P B 2
O2 O 1.0852(2) -0.16402(11) 0.5583(2) 0.0451(4) Uani 1 1 d . . .
O3 O 0.5991(2) 0.12668(10) 0.50313(19) 0.0393(4) Uani 1 1 d . . .
O4 O 0.5143(3) 0.17032(11) 0.28386(19) 0.0510(5) Uani 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
N3 Zn1 N1 171.76(7) . .
N3 Zn1 N2 86.67(8) . .
N1 Zn1 N2 91.66(8) . .
N3 Zn1 N4 89.20(7) . .
N1 Zn1 N4 90.87(7) . .
N2 Zn1 N4 168.24(7) . .
N3 Zn1 O3 94.78(7) . .
N1 Zn1 O3 93.45(7) . .
N2 Zn1 O3 102.78(7) . .
N4 Zn1 O3 88.52(7) . .
C1 N1 C4 107.68(18) . .
C1 N1 Zn1 126.21(14) . .
C4 N1 Zn1 125.93(14) . .
C6 N2 C9 106.45(18) . .
C6 N2 Zn1 124.90(16) . .
C9 N2 Zn1 128.50(15) . .
C14 N3 C11 105.63(18) . .
C14 N3 Zn1 122.48(15) . .
C11 N3 Zn1 131.48(15) . .
C19 N4 C16 110.16(18) . .
C19 N4 Zn1 122.40(14) . .
C16 N4 Zn1 127.41(15) . .
N1 C1 C20 125.37(19) . .
N1 C1 C2 109.91(18) . .
C20 C1 C2 124.64(19) . .
C3 C2 C1 106.54(19) . .
C3 C2 C21 130.1(2) . .
C1 C2 C21 123.4(2) . .
C2 C3 C4 107.04(19) . .
C2 C3 C22 129.0(2) . .
C4 C3 C22 123.9(2) . .
N1 C4 C5 124.56(19) . .
N1 C4 C3 108.81(19) . .
C5 C4 C3 126.6(2) . .
C4 C5 C6 128.0(2) . .
N2 C6 C5 124.6(2) . .
N2 C6 C7 110.6(2) . .
C5 C6 C7 124.8(2) . .
C8 C7 C6 106.5(2) . .
C8 C7 C24 128.3(2) . .
C6 C7 C24 125.2(2) . .
C7 C8 C9 106.9(2) . .
C7 C8 C25 126.5(2) . .
C9 C8 C25 126.6(2) . .
N2 C9 C10 124.5(2) . .
N2 C9 C8 109.4(2) . .
C10 C9 C8 126.1(2) . .
C11 C10 C9 125.8(2) . .
N3 C11 C10 122.14(19) . .
N3 C11 C12 110.56(19) . .
C10 C11 C12 127.3(2) . .
C13 C12 C11 104.67(19) . .
C13 C12 C27 128.2(2) . .
C11 C12 C27 127.2(2) . .
C12 C13 C14 107.1(2) . .
C12 C13 C28 145.0(2) . .
C14 C13 C28 107.8(2) . .
N3 C14 C15 134.0(2) . .
N3 C14 C13 112.0(2) . .
C15 C14 C13 113.99(19) . .
C16 C15 C14 124.2(2) . .
C16 C15 C29 129.7(2) . .
C14 C15 C29 106.11(19) . .
C15 C16 N4 122.1(2) . .
C15 C16 C17 126.4(2) . .
N4 C16 C17 111.49(19) . .
C16 C17 C30 113.92(19) . 2_646
C16 C17 C18 103.06(17) . .
C30 C17 C18 113.21(18) 2_646 .
C19 C18 C34 112.9(2) . .
C19 C18 C17 102.76(17) . .
C34 C18 C17 113.5(2) . .
N4 C19 C20 125.9(2) . .
N4 C19 C18 112.24(19) . .
C20 C19 C18 121.85(19) . .
C19 C20 C1 128.4(2) . .
O1 C22 O1A 20.7(8) . .
O1 C22 C3 122.4(6) . .
O1A C22 C3 118.8(7) . .
O1 C22 C23 116.7(6) . .
O1A C22 C23 119.9(7) . .
C3 C22 C23 120.0(2) . .
C8 C25 C26 111.8(3) . .
O2 C28 C13 129.3(2) . .
O2 C28 C29 124.0(2) . .
C13 C28 C29 106.69(19) . .
C15 C29 C28 105.18(19) . .
C31 C30 C17 113.01(18) . 2_656
C32 C31 C30 112.67(19) . .
O3 C32 O4 122.7(2) . .
O3 C32 C31 125.5(2) . .
O4 C32 C31 111.8(2) . .
Cl1 C35 Cl2 117.9(3) . .
Cl1 C35 Cl2A 105.2(3) . .
Cl2 C35 Cl2A 13.3(4) . .
C32 O3 Zn1 158.81(17) . .
C32 O4 C33 115.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N3 2.0006(18) .
Zn1 N1 2.0077(18) .
Zn1 N2 2.0589(19) .
Zn1 N4 2.1733(18) .
Zn1 O3 2.3181(17) .
Cl1 C35 1.752(3) .
Cl2 C35 1.755(9) .
Cl2A C35 1.776(9) .
N1 C1 1.365(3) .
N1 C4 1.376(3) .
N2 C6 1.360(3) .
N2 C9 1.377(3) .
N3 C14 1.342(3) .
N3 C11 1.389(3) .
N4 C19 1.347(3) .
N4 C16 1.373(3) .
C1 C20 1.401(3) .
C1 C2 1.450(3) .
C2 C3 1.372(3) .
C2 C21 1.506(3) .
C3 C4 1.459(3) .
C3 C22 1.486(3) .
C4 C5 1.388(3) .
C5 C6 1.405(3) .
C6 C7 1.442(3) .
C7 C8 1.361(4) .
C7 C24 1.500(4) .
C8 C9 1.450(3) .
C8 C25 1.513(4) .
C9 C10 1.397(3) .
C10 C11 1.396(3) .
C11 C12 1.447(3) .
C12 C13 1.392(3) .
C12 C27 1.489(3) .
C13 C14 1.417(3) .
C13 C28 1.462(3) .
C14 C15 1.410(3) .
C15 C16 1.372(3) .
C15 C29 1.525(3) .
C16 C17 1.511(3) .
C17 C30 1.534(3) 2_646
C17 C18 1.550(3) .
C18 C19 1.517(3) .
C18 C34 1.526(3) .
C19 C20 1.394(3) .
C22 O1 1.177(11) .
C22 O1A 1.258(15) .
C22 C23 1.502(3) .
C25 C26 1.521(5) .
C28 O2 1.222(3) .
C28 C29 1.548(4) .
C30 C31 1.522(3) .
C30 C17 1.534(3) 2_656
C31 C32 1.507(3) .
C32 O3 1.211(3) .
C32 O4 1.324(3) .
C33 O4 1.444(4) .
