#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:36:45 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178877 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/06/4110649.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_4110649
loop_
_publ_author_name
'Z. Jane Li'
'Yuriy Abramov'
'Jon Bordner'
'Jason Leonard'
'Ales Medek'
'Andrew V. Trask'
_publ_section_title
;
 Solid-State Acid-Base Interactions in Complexes of Heterocyclic Bases
 with Dicarboxylic Acids: Crystallography, Hydrogen Bond Analysis, and 15N
 NMR Spectroscopy
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8199
_journal_page_last               8210
_journal_paper_doi               10.1021/ja0541332
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C33 H36 N5 O9'
_chemical_formula_weight         646.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 103.6520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.1414(11)
_cell_length_b                   5.1132(2)
_cell_length_c                   44.2072(17)
_cell_measurement_temperature    298(2)
_cell_volume                     6401.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            6386
_diffrn_reflns_theta_full        45.20
_diffrn_reflns_theta_max         45.20
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             2728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         2597
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0918P)²+1.3198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                1797
_reflns_number_total             2597
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0541332si20050622_023342.cif
_cod_data_source_block           f385
_cod_database_code               4110649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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 0.40810(10) 2.2430(6) 0.02676(7) 0.0655(11) Uani 1 1 d .
C2 C 0.44771(13) 2.1205(8) 0.04108(9) 0.0666(14) Uani 1 1 d .
C3 C 0.44589(13) 1.9040(8) 0.05934(9) 0.0697(14) Uani 1 1 d .
H3A H 0.4737 1.8193 0.0690 0.080 Uiso 1 1 calc R
C4 C 0.40360(13) 1.8114(8) 0.06351(8) 0.0606(13) Uani 1 1 d .
H4A H 0.4023 1.6638 0.0756 0.080 Uiso 1 1 calc R
C5 C 0.36304(12) 1.9438(7) 0.04925(8) 0.0505(12) Uani 1 1 d .
C6 C 0.36685(13) 2.1552(7) 0.03093(8) 0.0577(13) Uani 1 1 d .
H6A H 0.3394 2.2418 0.0209 0.080 Uiso 1 1 calc R
O7 O 0.31787(8) 1.8742(5) 0.05024(5) 0.0660(9) Uani 1 1 d .
C8 C 0.30989(12) 1.7124(7) 0.07429(8) 0.0483(11) Uani 1 1 d .
C9 C 0.27461(11) 1.5290(7) 0.06621(8) 0.0432(11) Uani 1 1 d .
C10 C 0.26557(11) 1.3727(7) 0.08956(8) 0.0433(11) Uani 1 1 d .
H10A H 0.2418 1.2474 0.0846 0.080 Uiso 1 1 calc R
C11 C 0.29075(11) 1.3971(6) 0.12006(8) 0.0402(11) Uani 1 1 d .
C12 C 0.32478(12) 1.5893(7) 0.12760(8) 0.0488(12) Uani 1 1 d .
H12A H 0.3413 1.6112 0.1482 0.080 Uiso 1 1 calc R
C13 C 0.33434(12) 1.7486(7) 0.10478(8) 0.0547(12) Uani 1 1 d .
H13A H 0.3570 1.8794 0.1098 0.080 Uiso 1 1 calc R
N14 N 0.27928(9) 1.2310(6) 0.14324(6) 0.0475(9) Uani 1 1 d .
H14A H 0.2497(11) 1.184(7) 0.1394(8) 0.080 Uiso 1 1 d .
C15 C 0.30998(12) 1.1084(7) 0.16653(8) 0.0421(11) Uani 1 1 d .
N16 N 0.35586(9) 1.1556(5) 0.16995(6) 0.0466(9) Uani 1 1 d .
C17 C 0.38529(13) 1.0120(7) 0.19156(8) 0.0552(13) Uani 1 1 d .
H17A H 0.4173 1.0448 0.1937 0.080 Uiso 1 1 calc R
N18 N 0.37539(10) 0.8328(6) 0.21005(7) 0.0570(10) Uani 1 1 d .
C19 C 0.32811(13) 0.7863(7) 0.20736(8) 0.0492(12) Uani 1 1 d .
C20 C 0.29315(12) 0.9235(7) 0.18599(8) 0.0426(11) Uani 1 1 d .
C21 C 0.24538(12) 0.8601(7) 0.18364(8) 0.0550(12) Uani 1 1 d .
H21A H 0.2223 0.9537 0.1697 0.080 Uiso 1 1 calc R
C22 C 0.23190(12) 0.6703(8) 0.20065(9) 0.0735(14) Uani 1 1 d D
C23 C 0.26703(16) 0.5381(8) 0.22209(10) 0.0869(15) Uani 1 1 d .
H23A H 0.2583 0.4087 0.2344 0.080 Uiso 1 1 calc R
C24 C 0.31402(15) 0.5928(8) 0.22558(9) 0.0706(14) Uani 1 1 d .
H24A H 0.3366 0.5010 0.2401 0.080 Uiso 1 1 calc R
C25 C 0.18034(14) 0.6093(8) 0.19411(12) 0.1501(18) Uani 1 1 d D
H25A H 0.1630 0.7636 0.1913 0.080 Uiso 1 1 calc R
C26 C 0.15583(15) 0.4366(11) 0.19150(15) 0.162(3) Uani 1 1 d D
H26A H 0.1731 0.2829 0.1963 0.080 Uiso 1 1 calc R
C27 C 0.10573(12) 0.3789(9) 0.18295(11) 0.0985(19) Uani 1 1 d D
H27A H 0.1014 0.2356 0.1682 0.080 Uiso 1 1 calc R
H27B H 0.0973 0.3127 0.2015 0.080 Uiso 1 1 calc R
N28 N 0.07168(10) 0.5737(6) 0.17004(7) 0.0663(11) Uani 1 1 d .
H28A H 0.0630(11) 0.691(7) 0.1850(8) 0.080 Uiso 1 1 d .
C29 C 0.04964(12) 0.5847(8) 0.14050(10) 0.0633(14) Uani 1 1 d .
C30 C 0.01131(13) 0.7824(9) 0.13193(10) 0.0772(15) Uani 1 1 d .
H30A H 0.0212 0.9208 0.1199 0.080 Uiso 1 1 calc R
H30B H -0.0166 0.7007 0.1190 0.080 Uiso 1 1 calc R
O31 O 0.00036(11) 0.8877(7) 0.15805(7) 0.1229(13) Uani 1 1 d .
C32 C -0.03747(16) 1.0534(10) 0.15306(11) 0.116(2) Uani 1 1 d .
H32A H -0.0420 1.1147 0.1727 0.080 Uiso 1 1 calc R
H32B H -0.0653 0.9623 0.1422 0.080 Uiso 1 1 calc R
H32C H -0.0318 1.1996 0.1408 0.080 Uiso 1 1 calc R
O33 O 0.05820(9) 0.4426(6) 0.11982(7) 0.0856(10) Uani 1 1 d .
C34 C 0.24620(13) 1.5033(8) 0.03314(8) 0.0641(13) Uani 1 1 d .
H34A H 0.2575 1.6267 0.0202 0.080 Uiso 1 1 calc R
H34B H 0.2135 1.5377 0.0323 0.080 Uiso 1 1 calc R
H34C H 0.2495 1.3292 0.0258 0.080 Uiso 1 1 calc R
C35 C 0.49312(13) 2.2300(10) 0.03614(11) 0.1027(19) Uani 1 1 d .
H35A H 0.4865 2.3779 0.0224 0.080 Uiso 1 1 calc R
H35B H 0.5092 2.0984 0.0271 0.080 Uiso 1 1 calc R
H35C H 0.5127 2.2839 0.0558 0.080 Uiso 1 1 calc R
C1X C 0.13138(13) -0.1095(8) 0.03823(9) 0.0583(13) Uani 1 1 d .
O2X O 0.09540(10) -0.1342(6) 0.01470(6) 0.0833(10) Uani 1 1 d .
H2X H 0.0941(12) -0.014(7) 0.0002(8) 0.080 Uiso 1 1 d .
O3X O 0.16037(9) 0.0610(6) 0.04022(7) 0.0839(10) Uani 1 1 d .
C4X C 0.13307(13) -0.3129(8) 0.06309(9) 0.0636(13) Uani 1 1 d .
H4XA H 0.1457 -0.4744 0.0569 0.080 Uiso 1 1 calc R
H4XB H 0.1013 -0.3475 0.0652 0.080 Uiso 1 1 calc R
C5X C 0.16341(12) -0.2253(8) 0.09425(9) 0.0641(13) Uani 1 1 d .
H5XA H 0.1642 -0.3653 0.1092 0.080 Uiso 1 1 calc R
H5XB H 0.1954 -0.1999 0.0920 0.080 Uiso 1 1 calc R
C6X C 0.14797(12) 0.0192(8) 0.10744(9) 0.0521(12) Uani 1 1 d .
O7X O 0.17392(8) 0.1640(5) 0.12467(6) 0.0681(9) Uani 1 1 d .
O8X O 0.10178(8) 0.0566(5) 0.09884(6) 0.0725(10) Uani 1 1 d .
H8X H 0.0921(12) 0.192(7) 0.1058(8) 0.080 Uiso 1 1 d .
C1Y C 0.05301(13) 0.8575(8) 0.24449(9) 0.0623(14) Uani 1 1 d .
O2Y O 0.05518(8) 0.9989(5) 0.26968(6) 0.0646(9) Uani 1 1 d .
H2YA H 0.0831(11) 1.110(7) 0.2749(8) 0.080 Uiso 1 1 d .
O3Y O 0.07861(11) 0.8911(7) 0.22698(7) 0.1061(12) Uani 1 1 d .
C4Y C 0.01683(12) 0.6463(8) 0.23953(9) 0.0624(14) Uani 1 1 d .
H4YA H 0.0382(11) 0.481(7) 0.2423(8) 0.080 Uiso 1 1 d .
H4YB H 0.0011(11) 0.644(7) 0.2193(8) 0.080 Uiso 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 0.0181 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'
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_3
C2 N1 C6 118.9(3) .
N1 C2 C3 120.4(4) .
N1 C2 C35 116.7(4) .
C3 C2 C35 122.9(4) .
C4 C3 C2 121.0(4) .
C3 C4 C5 118.0(4) .
C6 C5 O7 115.8(3) .
C6 C5 C4 118.5(4) .
O7 C5 C4 125.6(3) .
N1 C6 C5 123.2(3) .
C5 O7 C8 120.4(3) .
C9 C8 C13 121.8(3) .
C9 C8 O7 116.8(3) .
C13 C8 O7 121.3(3) .
C8 C9 C10 117.6(3) .
C8 C9 C34 121.2(3) .
C10 C9 C34 121.2(3) .
C9 C10 C11 121.8(3) .
C10 C11 C12 119.1(3) .
C10 C11 N14 119.1(3) .
C12 C11 N14 121.7(3) .
C13 C12 C11 120.2(3) .
C12 C13 C8 119.3(3) .
C15 N14 C11 126.7(3) .
N16 C15 N14 118.0(3) .
N16 C15 C20 121.7(3) .
N14 C15 C20 120.2(3) .
C15 N16 C17 115.9(3) .
N18 C17 N16 129.2(3) .
C17 N18 C19 115.6(3) .
N18 C19 C24 119.8(3) .
N18 C19 C20 121.7(3) .
C24 C19 C20 118.5(4) .
C19 C20 C21 118.8(3) .
C19 C20 C15 115.8(3) .
C21 C20 C15 125.2(3) .
C22 C21 C20 122.7(3) .
C21 C22 C23 117.8(4) .
C21 C22 C25 117.2(4) .
C23 C22 C25 125.0(4) .
C24 C23 C22 122.1(4) .
C23 C24 C19 120.1(4) .
C26 C25 C22 140.3(5) .
C25 C26 C27 139.7(6) .
N28 C27 C26 121.7(4) .
C29 N28 C27 124.0(4) .
O33 C29 N28 124.9(4) .
O33 C29 C30 118.7(4) .
N28 C29 C30 116.4(4) .
O31 C30 C29 111.1(3) .
C32 O31 C30 116.4(3) .
O3X C1X O2X 123.4(4) .
O3X C1X C4X 123.1(3) .
O2X C1X C4X 113.5(3) .
C1X C4X C5X 111.7(3) .
C6X C5X C4X 115.9(3) .
O7X C6X O8X 122.8(4) .
O7X C6X C5X 124.3(3) .
O8X C6X C5X 112.9(3) .
O3Y C1Y O2Y 123.4(4) .
O3Y C1Y C4Y 122.2(4) .
O2Y C1Y C4Y 114.4(4) .
C1Y C4Y C4Y 116.9(3) 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.334(4) .
N1 C6 1.336(4) .
C2 C3 1.378(6) .
C2 C35 1.500(5) .
C3 C4 1.373(5) .
C4 C5 1.379(5) .
C5 C6 1.371(5) .
C5 O7 1.374(4) .
O7 C8 1.409(4) .
C8 C9 1.375(5) .
C8 C13 1.381(5) .
C9 C10 1.379(5) .
C9 C34 1.506(4) .
C10 C11 1.380(4) .
C11 C12 1.380(5) .
C11 N14 1.430(4) .
C12 C13 1.375(5) .
N14 C15 1.349(4) .
C15 N16 1.332(4) .
C15 C20 1.440(5) .
N16 C17 1.342(4) .
C17 N18 1.304(5) .
N18 C19 1.375(4) .
C19 C24 1.397(5) .
C19 C20 1.403(4) .
C20 C21 1.409(5) .
C21 C22 1.342(5) .
C22 C23 1.395(5) .
C22 C25 1.494(5) .
C23 C24 1.370(6) .
C25 C26 1.124(5) .
C26 C27 1.449(5) .
C27 N28 1.427(5) .
N28 C29 1.313(5) .
C29 O33 1.239(5) .
C29 C30 1.488(5) .
C30 O31 1.378(5) .
O31 C32 1.366(5) .
C1X O3X 1.203(4) .
C1X O2X 1.297(4) .
C1X C4X 1.505(5) .
C4X C5X 1.519(5) .
C5X C6X 1.493(5) .
C6X O7X 1.195(4) .
C6X O8X 1.323(4) .
C1Y O3Y 1.207(5) .
C1Y O2Y 1.317(4) .
C1Y C4Y 1.489(5) .
C4Y C4Y 1.499(8) 2
