#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:24:39 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179326 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/23/4322393.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_4322393
loop_
_publ_author_name
'James A. Johnson'
'Marilyn M. Olmstead'
'Alan L. Balch'
_publ_section_title
;
 Reactivity of the Verdoheme Analogues. Opening of the Planar Macrocycle
 by Amide and Thiolate Nucleophiles To Form Helical Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5379
_journal_page_last               5383
_journal_paper_doi               10.1021/ic9904283
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C37 H49 N5 O Zn'
_chemical_formula_weight         645.18
_chemical_name_common            Zn(OEBNMe₂)
_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                112.692(10)
_cell_angle_beta                 95.451(9)
_cell_angle_gamma                105.076(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8828(8)
_cell_length_b                   13.846(2)
_cell_length_c                   14.054(2)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      3.5
_cell_volume                     1671.5(4)
_computing_cell_refinement       'Siemens P3'
_computing_data_collection       'Siemens P3'
_computing_data_reduction        'Siemens XDISK'
_computing_molecular_graphics    'SHELXTL Plus 5.03, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97-2 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXL-97-2 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2θ-ω
_diffrn_radiation_monochromator  'nickel filter'
_diffrn_radiation_source         'Siemens 15kW rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.098
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4467
_diffrn_reflns_theta_full        56.45
_diffrn_reflns_theta_max         56.45
_diffrn_reflns_theta_min         3.49
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.294
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_correction_T_min  0.7818
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;XABS2: an empirical absorption correction program. Parkin, S.; Moezzi,
 B.; Hope, H. J. Appl. Cryst. 1995, 28, 53-56.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.552
_refine_diff_density_min         -1.221
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         4422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0763
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1057P)²+11.5152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2111
_refine_ls_wR_factor_ref         0.2296
_reflns_number_gt                3358
_reflns_number_total             4467
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9904283_2.cif
_cod_data_source_block           mn852
_cod_original_cell_volume        1671.4(4)
_cod_database_code               4322393
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
Zn Zn 0.30659(11) 0.70673(9) 0.64291(8) 0.0309(4) Uani 1 1 d . . .
O1 O 0.4701(5) 0.7253(4) 0.4464(4) 0.0224(11) Uani 1 1 d . . .
N1 N 0.2307(5) 0.5538(4) 0.5117(4) 0.0127(12) Uani 1 1 d . . .
N2 N 0.3427(6) 0.6282(5) 0.7312(4) 0.0176(13) Uani 1 1 d . . .
N3 N 0.2578(6) 0.8199(4) 0.7625(4) 0.0146(12) Uani 1 1 d . . .
N4 N 0.3610(5) 0.8130(4) 0.5761(4) 0.0159(12) Uani 1 1 d . . .
N5 N 0.0770(6) 0.5787(5) 0.3942(4) 0.0210(13) Uani 1 1 d . . .
C1 C 0.1648(7) 0.5258(5) 0.4147(5) 0.0154(15) Uani 1 1 d . . .
C2 C 0.1896(7) 0.4277(6) 0.3365(6) 0.0225(16) Uani 1 1 d . . .
C3 C 0.2781(7) 0.4006(5) 0.3957(5) 0.0153(15) Uani 1 1 d . . .
C4 C 0.3039(7) 0.4772(5) 0.5045(5) 0.0140(14) Uani 1 1 d . . .
C5 C 0.3700(7) 0.4686(5) 0.5894(5) 0.0148(15) Uani 1 1 d . . .
H5 H 0.4202 0.4163 0.5754 0.018 Uiso 1 1 calc R . .
C6 C 0.3701(7) 0.5312(6) 0.6969(5) 0.0179(15) Uani 1 1 d . . .
C7 C 0.3827(6) 0.4973(5) 0.7816(5) 0.0150(15) Uani 1 1 d . . .
C8 C 0.3539(6) 0.5757(5) 0.8663(5) 0.0142(14) Uani 1 1 d . . .
C9 C 0.3297(7) 0.6574(5) 0.8343(5) 0.0169(15) Uani 1 1 d . . .
C10 C 0.2913(6) 0.7498(5) 0.8943(5) 0.0150(15) Uani 1 1 d . . .
H10 H 0.2886 0.7622 0.9654 0.018 Uiso 1 1 calc R . .
C11 C 0.2569(7) 0.8248(5) 0.8622(5) 0.0173(15) Uani 1 1 d . . .
C12 C 0.2256(7) 0.9228(5) 0.9277(5) 0.0181(15) Uani 1 1 d . . .
C13 C 0.2091(7) 0.9767(5) 0.8646(5) 0.0171(15) Uani 1 1 d . . .
C14 C 0.2327(7) 0.9110(5) 0.7636(5) 0.0171(15) Uani 1 1 d . . .
C15 C 0.2366(6) 0.9389(5) 0.6745(5) 0.0133(14) Uani 1 1 d . . .
H15 H 0.1951 0.9936 0.6745 0.016 Uiso 1 1 calc R . .
C16 C 0.2946(6) 0.8937(5) 0.5908(5) 0.0148(15) Uani 1 1 d . . .
C17 C 0.3000(7) 0.9241(5) 0.5009(5) 0.0151(15) Uani 1 1 d . . .
C18 C 0.3678(7) 0.8645(5) 0.4363(5) 0.0153(15) Uani 1 1 d . . .
C19 C 0.4081(7) 0.7923(5) 0.4831(5) 0.0163(15) Uani 1 1 d . . .
C21 C 0.1200(8) 0.3580(6) 0.2216(6) 0.0295(18) Uani 1 1 d . . .
H21A H 0.0272 0.3697 0.2061 0.035 Uiso 1 1 calc R . .
H21B H 0.0999 0.2790 0.2062 0.035 Uiso 1 1 calc R . .
C22 C 0.2145(9) 0.3862(8) 0.1511(7) 0.042(2) Uani 1 1 d . . .
H22A H 0.1629 0.3435 0.0770 0.062 Uiso 1 1 calc R . .
H22B H 0.3025 0.3678 0.1614 0.062 Uiso 1 1 calc R . .
H22C H 0.2394 0.4654 0.1692 0.062 Uiso 1 1 calc R . .
C23 C 0.3249(8) 0.2995(6) 0.3573(6) 0.0223(16) Uani 1 1 d . . .
H23A H 0.4198 0.3164 0.4012 0.027 Uiso 1 1 calc R . .
H23B H 0.3354 0.2800 0.2835 0.027 Uiso 1 1 calc R . .
C24 C 0.2174(8) 0.2009(6) 0.3625(6) 0.0289(18) Uani 1 1 d . . .
H24A H 0.2467 0.1351 0.3308 0.043 Uiso 1 1 calc R . .
H24B H 0.1217 0.1875 0.3235 0.043 Uiso 1 1 calc R . .
H24C H 0.2148 0.2168 0.4364 0.043 Uiso 1 1 calc R . .
C25 C 0.4068(7) 0.3925(6) 0.7713(5) 0.0194(15) Uani 1 1 d . . .
H25A H 0.4498 0.4015 0.8420 0.023 Uiso 1 1 calc R . .
H25B H 0.4766 0.3781 0.7259 0.023 Uiso 1 1 calc R . .
C26 C 0.2693(8) 0.2921(6) 0.7242(6) 0.0315(19) Uani 1 1 d . . .
H26A H 0.2926 0.2259 0.7191 0.047 Uiso 1 1 calc R . .
H26B H 0.2269 0.2816 0.6535 0.047 Uiso 1 1 calc R . .
H26C H 0.2006 0.3046 0.7698 0.047 Uiso 1 1 calc R . .
C27 C 0.3373(7) 0.5728(6) 0.9707(5) 0.0178(15) Uani 1 1 d . . .
H27A H 0.3869 0.6475 1.0283 0.021 Uiso 1 1 calc R . .
H27B H 0.3843 0.5216 0.9813 0.021 Uiso 1 1 calc R . .
C28 C 0.1788(7) 0.5354(6) 0.9775(6) 0.0247(17) Uani 1 1 d . . .
H28A H 0.1738 0.5449 1.0497 0.037 Uiso 1 1 calc R . .
H28B H 0.1331 0.4573 0.9284 0.037 Uiso 1 1 calc R . .
H28C H 0.1288 0.5802 0.9587 0.037 Uiso 1 1 calc R . .
C29 C 0.2218(8) 0.9586(6) 1.0423(5) 0.0234(16) Uani 1 1 d . . .
H29A H 0.1771 0.8927 1.0543 0.028 Uiso 1 1 calc R . .
H29B H 0.1613 1.0071 1.0610 0.028 Uiso 1 1 calc R . .
C30 C 0.3727(8) 1.0211(7) 1.1150(6) 0.036(2) Uani 1 1 d . . .
H30A H 0.3654 1.0404 1.1887 0.055 Uiso 1 1 calc R . .
H30B H 0.4152 1.0887 1.1064 0.055 Uiso 1 1 calc R . .
H30C H 0.4334 0.9738 1.0961 0.055 Uiso 1 1 calc R . .
C31 C 0.1857(7) 1.0866(6) 0.8947(5) 0.0202(16) Uani 1 1 d . . .
H31A H 0.1381 1.1015 0.9553 0.024 Uiso 1 1 calc R . .
H31B H 0.1209 1.0835 0.8347 0.024 Uiso 1 1 calc R . .
C32 C 0.3258(8) 1.1809(6) 0.9246(6) 0.0296(18) Uani 1 1 d . . .
H32A H 0.3057 1.2510 0.9456 0.044 Uiso 1 1 calc R . .
H32B H 0.3710 1.1684 0.8637 0.044 Uiso 1 1 calc R . .
H32C H 0.3907 1.1838 0.9836 0.044 Uiso 1 1 calc R . .
C33 C 0.2368(7) 1.0049(5) 0.4847(6) 0.0188(15) Uani 1 1 d . . .
H33A H 0.3058 1.0523 0.4613 0.023 Uiso 1 1 calc R . .
H33B H 0.2208 1.0533 0.5529 0.023 Uiso 1 1 calc R . .
C34 C 0.0950(8) 0.9482(6) 0.4032(6) 0.0281(18) Uani 1 1 d . . .
H34A H 0.0532 1.0041 0.3999 0.042 Uiso 1 1 calc R . .
H34B H 0.0284 0.8973 0.4235 0.042 Uiso 1 1 calc R . .
H34C H 0.1120 0.9068 0.3337 0.042 Uiso 1 1 calc R . .
C35 C 0.4084(7) 0.8646(6) 0.3369(5) 0.0191(15) Uani 1 1 d . . .
H35A H 0.5074 0.8613 0.3384 0.023 Uiso 1 1 calc R . .
H35B H 0.4088 0.9353 0.3348 0.023 Uiso 1 1 calc R . .
C36 C 0.3098(8) 0.7699(6) 0.2368(5) 0.0280(18) Uani 1 1 d . . .
H36A H 0.3364 0.7802 0.1751 0.042 Uiso 1 1 calc R . .
H36B H 0.2102 0.7684 0.2374 0.042 Uiso 1 1 calc R . .
H36C H 0.3190 0.6998 0.2331 0.042 Uiso 1 1 calc R . .
C37 C 0.0250(7) 0.6499(6) 0.4757(6) 0.0217(16) Uani 1 1 d . . .
H37A H -0.0783 0.6332 0.4518 0.033 Uiso 1 1 calc R . .
H37B H 0.0753 0.7272 0.4915 0.033 Uiso 1 1 calc R . .
H37C H 0.0423 0.6380 0.5395 0.033 Uiso 1 1 calc R . .
C38 C 0.0255(8) 0.5677(6) 0.2881(6) 0.0242(17) Uani 1 1 d . . .
H38A H 0.0291 0.6405 0.2916 0.036 Uiso 1 1 calc R . .
H38B H -0.0737 0.5175 0.2602 0.036 Uiso 1 1 calc R . .
H38C H 0.0865 0.5379 0.2415 0.036 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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
N2 Zn N3 91.7(2) . . ?
N2 Zn N4 155.7(2) . . ?
N3 Zn N4 91.1(2) . . ?
N2 Zn N1 88.3(2) . . ?
N3 Zn N1 146.6(2) . . ?
N4 Zn N1 102.3(2) . . ?
C1 N1 C4 106.1(5) . . ?
C1 N1 Zn 130.7(4) . . ?
C4 N1 Zn 117.7(4) . . ?
C6 N2 C9 107.7(5) . . ?
C6 N2 Zn 125.9(4) . . ?
C9 N2 Zn 126.1(4) . . ?
C14 N3 C11 106.7(5) . . ?
C14 N3 Zn 126.3(4) . . ?
C11 N3 Zn 126.7(4) . . ?
C19 N4 C16 107.7(5) . . ?
C19 N4 Zn 126.6(4) . . ?
C16 N4 Zn 120.0(4) . . ?
C1 N5 C37 122.0(6) . . ?
C1 N5 C38 123.5(6) . . ?
C37 N5 C38 114.4(5) . . ?
N1 C1 N5 121.4(6) . . ?
N1 C1 C2 112.6(6) . . ?
N5 C1 C2 125.9(6) . . ?
C3 C2 C1 104.0(6) . . ?
C3 C2 C21 124.6(6) . . ?
C1 C2 C21 130.7(6) . . ?
C2 C3 C4 108.2(6) . . ?
C2 C3 C23 126.5(6) . . ?
C4 C3 C23 124.8(6) . . ?
C5 C4 N1 124.4(6) . . ?
C5 C4 C3 125.9(6) . . ?
N1 C4 C3 109.1(5) . . ?
C4 C5 C6 125.5(6) . . ?
N2 C6 C5 123.1(6) . . ?
N2 C6 C7 110.1(6) . . ?
C5 C6 C7 126.5(6) . . ?
C8 C7 C6 105.7(6) . . ?
C8 C7 C25 129.1(6) . . ?
C6 C7 C25 124.9(6) . . ?
C7 C8 C9 107.5(6) . . ?
C7 C8 C27 127.2(6) . . ?
C9 C8 C27 125.1(6) . . ?
N2 C9 C10 124.2(6) . . ?
N2 C9 C8 108.9(6) . . ?
C10 C9 C8 126.9(6) . . ?
C11 C10 C9 127.7(6) . . ?
N3 C11 C10 123.6(6) . . ?
N3 C11 C12 109.9(6) . . ?
C10 C11 C12 126.4(6) . . ?
C13 C12 C11 106.0(6) . . ?
C13 C12 C29 128.7(6) . . ?
C11 C12 C29 125.2(6) . . ?
C12 C13 C14 106.1(6) . . ?
C12 C13 C31 128.4(6) . . ?
C14 C13 C31 125.2(6) . . ?
N3 C14 C13 111.3(6) . . ?
N3 C14 C15 122.6(6) . . ?
C13 C14 C15 126.0(6) . . ?
C16 C15 C14 125.7(6) . . ?
C15 C16 N4 126.1(6) . . ?
C15 C16 C17 125.2(6) . . ?
N4 C16 C17 108.7(5) . . ?
C18 C17 C16 107.8(6) . . ?
C18 C17 C33 126.6(6) . . ?
C16 C17 C33 125.6(6) . . ?
C17 C18 C35 130.9(6) . . ?
C17 C18 C19 107.6(6) . . ?
C35 C18 C19 121.5(6) . . ?
O1 C19 N4 124.7(6) . . ?
O1 C19 C18 127.1(6) . . ?
N4 C19 C18 108.2(6) . . ?
C2 C21 C22 111.6(7) . . ?
C3 C23 C24 111.9(6) . . ?
C7 C25 C26 113.6(6) . . ?
C8 C27 C28 112.6(5) . . ?
C12 C29 C30 112.3(6) . . ?
C13 C31 C32 112.3(6) . . ?
C17 C33 C34 112.4(6) . . ?
C18 C35 C36 114.3(6) . . ?
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
Zn N2 2.002(5) . ?
Zn N3 2.006(5) . ?
Zn N4 2.022(5) . ?
Zn N1 2.084(5) . ?
O1 C19 1.220(8) . ?
N1 C1 1.314(8) . ?
N1 C4 1.410(8) . ?
N2 C6 1.351(9) . ?
N2 C9 1.375(8) . ?
N3 C14 1.342(8) . ?
N3 C11 1.378(9) . ?
N4 C19 1.380(9) . ?
N4 C16 1.396(8) . ?
N5 C1 1.348(9) . ?
N5 C37 1.432(9) . ?
N5 C38 1.466(9) . ?
C1 C2 1.478(10) . ?
C2 C3 1.368(9) . ?
C2 C21 1.501(10) . ?
C3 C4 1.435(9) . ?
C3 C23 1.505(10) . ?
C4 C5 1.367(9) . ?
C5 C6 1.422(10) . ?
C6 C7 1.444(9) . ?
C7 C8 1.380(9) . ?
C7 C25 1.486(9) . ?
C8 C9 1.431(9) . ?
C8 C27 1.506(9) . ?
C9 C10 1.405(9) . ?
C10 C11 1.384(9) . ?
C11 C12 1.446(10) . ?
C12 C13 1.384(10) . ?
C12 C29 1.499(10) . ?
C13 C14 1.439(9) . ?
C13 C31 1.501(9) . ?
C14 C15 1.447(9) . ?
C15 C16 1.361(9) . ?
C16 C17 1.479(9) . ?
C17 C18 1.334(9) . ?
C17 C33 1.492(9) . ?
C18 C35 1.489(9) . ?
C18 C19 1.502(9) . ?
C21 C22 1.514(12) . ?
C23 C24 1.528(10) . ?
C25 C26 1.535(10) . ?
C27 C28 1.541(10) . ?
C29 C30 1.541(11) . ?
C31 C32 1.524(10) . ?
C33 C34 1.524(10) . ?
C35 C36 1.517(10) . ?
