#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:19:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178778 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/32/4103244.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_4103244
loop_
_publ_author_name
'Jonathan L. Sessler'
'Jiajia Cai'
'Han-Yuan Gong'
'Xiaoping Yang'
'Jonathan F. Arambula'
'Benjamin P. Hay'
_publ_section_title
;
 A Pyrrolyl-Based Triazolophane: A Macrocyclic Receptor With CH and NH
 Donor Groups That Exhibits a Preference for Pyrophosphate Anions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14058
_journal_page_last               14060
_journal_paper_doi               10.1021/ja107098r
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C50 H52 N16, 4(C H4 O), O'
_chemical_formula_sum            'C54 H68 N16 O5'
_chemical_formula_weight         1021.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 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                 125.38(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.799(4)
_cell_length_b                   7.4924(15)
_cell_length_c                   23.685(5)
_cell_measurement_reflns_used    3378
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.4894
_cell_measurement_theta_min      2.0997
_cell_volume                     2720.0(14)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      223(1)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_reflns_av_R_equivalents  0.1952
_diffrn_reflns_av_sigmaI/netI    0.1734
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20062
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'DENZO and Scalepack (Otwinoski and Minor, 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1945
_refine_ls_R_factor_gt           0.0929
_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)+(0.0991P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2700
_reflns_number_gt                2102
_reflns_number_total             4785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja107098r_si_003.cif
_cod_data_source_block           Ligand
_cod_original_cell_volume        2719.9(9)
_cod_database_code               4103244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
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
N1 N 0.4458(2) 1.2440(5) 0.3101(2) 0.0580(12) Uani 1 1 d .
N2 N 0.4639(2) 1.4198(5) 0.3149(2) 0.0724(14) Uani 1 1 d .
N3 N 0.5463(2) 1.4383(5) 0.3686(2) 0.0713(14) Uani 1 1 d .
N4 N 0.7019(2) 1.0867(5) 0.4864(2) 0.0563(12) Uani 1 1 d .
H4A H 0.6790 0.9884 0.4644 0.068 Uiso 1 1 calc R
N5 N 0.8186(2) 0.6853(5) 0.6560(2) 0.0549(12) Uani 1 1 d .
H5A H 0.8724 0.6542 0.6772 0.066 Uiso 1 1 calc R
N6 N 0.8619(2) 0.3672(5) 0.7440(2) 0.0631(13) Uani 1 1 d .
N7 N 0.8586(2) 0.2174(5) 0.7716(2) 0.0609(12) Uani 1 1 d .
N8 N 0.7748(2) 0.1949(5) 0.7486(2) 0.0577(12) Uani 1 1 d .
C1 C 0.1892(3) 1.0622(6) 0.1761(3) 0.0590(15) Uani 1 1 d .
H1C H 0.1323 1.0202 0.1469 0.088 Uiso 1 1 calc R
C2 C 0.2125(3) 1.2226(6) 0.1616(3) 0.0563(14) Uani 1 1 d .
C3 C 0.2989(3) 1.2784(6) 0.2047(3) 0.0543(14) Uani 1 1 d .
H3A H 0.3162 1.3823 0.1943 0.065 Uiso 1 1 calc R
C4 C 0.3590(3) 1.1808(6) 0.2626(3) 0.0538(14) Uani 1 1 d .
C5 C 0.3362(3) 1.0239(6) 0.2787(3) 0.0561(14) Uani 1 1 d .
H5C H 0.3767 0.9594 0.3183 0.084 Uiso 1 1 calc R
C6 C 0.5158(3) 1.1532(6) 0.3608(3) 0.0601(15) Uani 1 1 d .
H6B H 0.5196 1.0306 0.3681 0.072 Uiso 1 1 calc R
C7 C 0.5801(3) 1.2752(6) 0.3992(3) 0.0568(15) Uani 1 1 d .
C8 C 0.6667(3) 1.2538(6) 0.4622(3) 0.0507(13) Uani 1 1 d .
C9 C 0.7230(3) 1.3738(6) 0.5130(3) 0.0609(15) Uani 1 1 d .
H9A H 0.7161 1.4971 0.5112 0.073 Uiso 1 1 calc R
C10 C 0.7922(3) 1.2763(6) 0.5679(3) 0.0567(15) Uani 1 1 d .
H10A H 0.8394 1.3238 0.6091 0.068 Uiso 1 1 calc R
C11 C 0.7787(3) 1.1004(6) 0.5507(3) 0.0524(13) Uani 1 1 d .
C12 C 0.8311(3) 0.9341(6) 0.5910(3) 0.0552(14) Uani 1 1 d .
C13 C 0.8470(3) 0.8178(6) 0.5452(3) 0.0658(16) Uani 1 1 d .
H13A H 0.7920 0.7799 0.5046 0.099 Uiso 1 1 calc R
H13B H 0.8810 0.7150 0.5709 0.099 Uiso 1 1 calc R
H13C H 0.8779 0.8863 0.5316 0.099 Uiso 1 1 calc R
C14 C 0.9194(3) 0.9947(7) 0.6559(3) 0.0746(18) Uani 1 1 d .
H14A H 0.9097 1.0669 0.6843 0.112 Uiso 1 1 calc R
H14B H 0.9503 1.0631 0.6422 0.112 Uiso 1 1 calc R
H14C H 0.9533 0.8919 0.6816 0.112 Uiso 1 1 calc R
C15 C 0.7808(3) 0.8267(6) 0.6112(3) 0.0530(14) Uani 1 1 d .
C16 C 0.6951(3) 0.8304(7) 0.5888(3) 0.0617(15) Uani 1 1 d .
H16A H 0.6534 0.9129 0.5581 0.074 Uiso 1 1 calc R
C17 C 0.6809(3) 0.6878(7) 0.6201(3) 0.0649(16) Uani 1 1 d .
H17A H 0.6286 0.6582 0.6135 0.078 Uiso 1 1 calc R
C18 C 0.7594(3) 0.6008(6) 0.6622(3) 0.0545(14) Uani 1 1 d .
C19 C 0.7793(3) 0.4393(6) 0.7028(3) 0.0538(14) Uani 1 1 d .
C20 C 0.7247(3) 0.3301(6) 0.7065(3) 0.0612(15) Uani 1 1 d .
H20A H 0.6651 0.3452 0.6846 0.073 Uiso 1 1 calc R
C21 C 0.7496(3) 0.0345(6) 0.7663(3) 0.0570(14) Uani 1 1 d .
C22 C 0.1426(3) 1.3289(7) 0.0970(3) 0.0615(15) Uani 1 1 d .
C23 C 0.0657(3) 1.3671(8) 0.1023(3) 0.0799(18) Uani 1 1 d .
H23A H 0.0214 1.4332 0.0623 0.120 Uiso 1 1 calc R
H23B H 0.0862 1.4355 0.1433 0.120 Uiso 1 1 calc R
H23C H 0.0417 1.2563 0.1044 0.120 Uiso 1 1 calc R
C24 C 0.1106(4) 1.2165(7) 0.0324(3) 0.0829(19) Uani 1 1 d .
H24A H 0.1584 1.1929 0.0293 0.124 Uiso 1 1 calc R
H24B H 0.0658 1.2804 -0.0081 0.124 Uiso 1 1 calc R
H24C H 0.0874 1.1056 0.0354 0.124 Uiso 1 1 calc R
C25 C 0.1768(3) 1.5088(7) 0.0920(3) 0.0824(19) Uani 1 1 d .
H25A H 0.2247 1.4898 0.0887 0.124 Uiso 1 1 calc R
H25B H 0.1960 1.5783 0.1325 0.124 Uiso 1 1 calc R
H25C H 0.1310 1.5712 0.0516 0.124 Uiso 1 1 calc R
C26 C 0.6268(4) 0.8155(8) 0.3354(4) 0.091(2) Uani 1 1 d .
H26A H 0.6015 0.9295 0.3150 0.136 Uiso 1 1 calc R
H26B H 0.5969 0.7239 0.3010 0.136 Uiso 1 1 calc R
H26C H 0.6874 0.8158 0.3529 0.136 Uiso 1 1 calc R
C27 C 0.5483(5) 0.2548(10) 0.5308(4) 0.128(3) Uani 1 1 d .
H27A H 0.5383 0.3776 0.5166 0.192 Uiso 1 1 calc R
H27B H 0.5154 0.1795 0.4907 0.192 Uiso 1 1 calc R
H27C H 0.6093 0.2281 0.5551 0.192 Uiso 1 1 calc R
O1 O 0.6189(2) 0.7825(5) 0.3901(2) 0.0778(12) Uani 1 1 d .
H1A H 0.5993 0.6819 0.3860 0.117 Uiso 1 1 calc R
O2 O 0.5217(3) 0.2241(7) 0.5748(3) 0.143(2) Uani 1 1 d .
H2C H 0.4730 0.2665 0.5573 0.214 Uiso 1 1 calc R
O1W O 1.0000 0.5361(6) 0.7500 0.0712(16) Uani 1 2 d S
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'
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
C6 N1 N2 110.6(4) . .
C6 N1 C4 128.3(4) . .
N2 N1 C4 120.6(4) . .
N3 N2 N1 106.2(3) . .
N2 N3 C7 109.9(4) . .
C11 N4 C8 109.8(4) . .
C11 N4 H4A 125.1 . .
C8 N4 H4A 125.1 . .
C18 N5 C15 110.6(4) . .
C18 N5 H5A 124.7 . .
C15 N5 H5A 124.7 . .
N7 N6 C19 109.1(4) . .
N6 N7 N8 106.6(3) . .
N7 N8 C20 111.0(4) . .
N7 N8 C21 119.4(4) . .
C20 N8 C21 129.4(4) . .
C21 C1 C2 119.9(4) 3_666 .
C21 C1 H1C 120.1 3_666 .
C2 C1 H1C 120.1 . .
C1 C2 C3 118.7(4) . .
C1 C2 C22 118.9(4) . .
C3 C2 C22 122.4(4) . .
C4 C3 C2 120.5(4) . .
C4 C3 H3A 119.8 . .
C2 C3 H3A 119.8 . .
C5 C4 C3 121.4(4) . .
C5 C4 N1 117.6(4) . .
C3 C4 N1 121.0(4) . .
C4 C5 C21 117.6(4) . 3_666
C4 C5 H5C 121.2 . .
C21 C5 H5C 121.2 3_666 .
N1 C6 C7 106.8(4) . .
N1 C6 H6B 126.6 . .
C7 C6 H6B 126.6 . .
C6 C7 N3 106.5(4) . .
C6 C7 C8 130.5(4) . .
N3 C7 C8 123.0(4) . .
N4 C8 C9 106.8(4) . .
N4 C8 C7 120.9(4) . .
C9 C8 C7 131.6(4) . .
C8 C9 C10 107.5(4) . .
C8 C9 H9A 126.3 . .
C10 C9 H9A 126.3 . .
C11 C10 C9 108.5(4) . .
C11 C10 H10A 125.8 . .
C9 C10 H10A 125.8 . .
C10 C11 N4 107.4(4) . .
C10 C11 C12 131.4(4) . .
N4 C11 C12 121.1(4) . .
C15 C12 C11 109.7(4) . .
C15 C12 C14 110.5(4) . .
C11 C12 C14 108.4(4) . .
C15 C12 C13 109.4(4) . .
C11 C12 C13 109.6(4) . .
C14 C12 C13 109.3(4) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N5 C15 C16 106.4(4) . .
N5 C15 C12 121.1(4) . .
C16 C15 C12 132.3(4) . .
C15 C16 C17 108.5(4) . .
C15 C16 H16A 125.8 . .
C17 C16 H16A 125.8 . .
C18 C17 C16 106.9(5) . .
C18 C17 H17A 126.5 . .
C16 C17 H17A 126.5 . .
N5 C18 C17 107.6(5) . .
N5 C18 C19 123.0(4) . .
C17 C18 C19 129.2(5) . .
C20 C19 N6 107.7(4) . .
C20 C19 C18 129.1(4) . .
N6 C19 C18 123.2(4) . .
N8 C20 C19 105.7(4) . .
N8 C20 H20A 127.1 . .
C19 C20 H20A 127.1 . .
C1 C21 C5 121.8(4) 3_666 3_666
C1 C21 N8 120.1(4) 3_666 .
C5 C21 N8 118.0(4) 3_666 .
C25 C22 C24 110.3(5) . .
C25 C22 C2 112.2(4) . .
C24 C22 C2 108.9(4) . .
C25 C22 C23 107.3(4) . .
C24 C22 C23 109.7(4) . .
C2 C22 C23 108.4(4) . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C22 C24 H24A 109.5 . .
C22 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C22 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C22 C25 H25A 109.5 . .
C22 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C22 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
O1 C26 H26A 109.5 . .
O1 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
O1 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
O2 C27 H27A 109.5 . .
O2 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
O2 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C26 O1 H1A 109.5 . .
C27 O2 H2C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.343(5) .
N1 N2 1.349(5) .
N1 C4 1.424(5) .
N2 N3 1.325(5) .
N3 C7 1.374(5) .
N4 C11 1.367(5) .
N4 C8 1.376(5) .
N4 H4A 0.8600 .
N5 C18 1.362(5) .
N5 C15 1.370(5) .
N5 H5A 0.8600 .
N6 N7 1.319(5) .
N6 C19 1.378(5) .
N7 N8 1.346(5) .
N8 C20 1.349(5) .
N8 C21 1.441(6) .
C1 C21 1.375(6) 3_666
C1 C2 1.388(6) .
C1 H1C 0.9300 .
C2 C3 1.390(6) .
C2 C22 1.541(6) .
C3 C4 1.378(6) .
C3 H3A 0.9300 .
C4 C5 1.378(6) .
C5 C21 1.392(6) 3_666
C5 H5C 0.9300 .
C6 C7 1.361(6) .
C6 H6B 0.9300 .
C7 C8 1.445(6) .
C8 C9 1.380(6) .
C9 C10 1.399(6) .
C9 H9A 0.9300 .
C10 C11 1.359(6) .
C10 H10A 0.9300 .
C11 C12 1.531(6) .
C12 C15 1.515(6) .
C12 C14 1.540(6) .
C12 C13 1.551(7) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 C16 1.374(6) .
C16 C17 1.411(7) .
C16 H16A 0.9300 .
C17 C18 1.375(6) .
C17 H17A 0.9300 .
C18 C19 1.454(7) .
C19 C20 1.354(6) .
C20 H20A 0.9300 .
C21 C1 1.375(6) 3_666
C21 C5 1.392(6) 3_666
C22 C25 1.527(7) .
C22 C24 1.533(7) .
C22 C23 1.548(7) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C26 O1 1.409(7) .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C27 O2 1.412(9) .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
O1 H1A 0.8200 .
O2 H2C 0.8200 .
