#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:23:24 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243503 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556146.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_1556146
loop_
_publ_author_name
'Rigol, Stephan'
'Beyer, Lothar'
'Hennig, Lothar'
'Sieler, Joachim'
'Giannis, Athanassios'
_publ_section_title
;
 Hünlich base: (re)discovery, synthesis, and structure elucidation after
 a century.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1418
_journal_page_last               1420
_journal_paper_doi               10.1021/ol400357t
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C17 H20 N4, 3(H2 O1)'
_chemical_formula_sum            'C17 H26 N4 O3'
_chemical_formula_weight         334.42
_space_group_IT_number           37
_space_group_name_Hall           'C 2 -2c'
_space_group_name_H-M_alt        'C c c 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C c c 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.754(3)
_cell_length_b                   22.060(4)
_cell_length_c                   5.1460(10)
_cell_measurement_reflns_used    584
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1674.9(6)
_computing_cell_refinement       'IPDS1 software /Fa.STOE)'
_computing_data_collection       'IPDS1 software /Fa.STOE)'
_computing_data_reduction        'IPDS1 software /Fa.STOE)'
_computing_molecular_graphics    'Ortep3 for Windows  (L.J. Farrujia)'
_computing_publication_material  'WINGX (L.J.Farrugia)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  PDS1(Fa.STOE)
_diffrn_measurement_method       Omega-sans
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3871
_diffrn_reflns_theta_full        28.04
_diffrn_reflns_theta_max         28.04
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1869
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0483
_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)+(0.0534P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                1124
_reflns_number_total             1869
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400357t_si_002.cif
_cod_data_source_block           ip1_1540
_cod_original_sg_symbol_H-M      Ccc2
_cod_database_code               1556146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x, y, z+1/2'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
'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
C1 C 0.7500 0.2500 0.2993(6) 0.0387(10) Uani 1 2 d S
H1A H 0.7875 0.2243 0.4114 0.046 Uiso 0.50 1 calc PR
H1B H 0.7125 0.2757 0.4114 0.046 Uiso 0.50 1 calc PR
C2 C 0.83349(19) 0.19186(13) -0.1007(4) 0.0305(6) Uani 1 1 d .
C3 C 0.8805(2) 0.15514(14) -0.2750(4) 0.0316(6) Uani 1 1 d .
H3 H 0.9413 0.1648 -0.3111 0.038 Uiso 1 1 calc R
C4 C 0.84275(19) 0.10513(13) -0.3986(4) 0.0329(6) Uani 1 1 d .
C5 C 0.7517(2) 0.09129(12) -0.3410(4) 0.0322(6) Uani 1 1 d .
C6 C 0.70379(19) 0.12634(13) -0.1627(5) 0.0323(6) Uani 1 1 d .
H6 H 0.6436 0.1162 -0.1219 0.039 Uiso 1 1 calc R
C7 C 0.74412(18) 0.17632(13) -0.0443(4) 0.0289(6) Uani 1 1 d .
C8 C 0.62384(18) 0.25208(14) 0.0129(5) 0.0361(7) Uani 1 1 d .
H8A H 0.5782 0.2641 0.1412 0.043 Uiso 1 1 calc R
H8B H 0.5928 0.2297 -0.1257 0.043 Uiso 1 1 calc R
C9 C 0.8950(2) 0.06800(14) -0.5925(5) 0.0425(8) Uani 1 1 d .
H9A H 0.8570 0.0354 -0.6567 0.064 Uiso 0.50 1 calc PR
H9B H 0.9483 0.0511 -0.5095 0.064 Uiso 0.50 1 calc PR
H9C H 0.9134 0.0936 -0.7364 0.064 Uiso 0.50 1 calc PR
H9D H 0.9555 0.0846 -0.6117 0.064 Uiso 0.50 1 calc PR
H9E H 0.8642 0.0690 -0.7589 0.064 Uiso 0.50 1 calc PR
H9F H 0.8991 0.0265 -0.5320 0.064 Uiso 0.50 1 calc PR
N1 N 0.69098(15) 0.21147(11) 0.1393(4) 0.0334(6) Uani 1 1 d .
N2 N 0.7112(2) 0.03956(13) -0.4479(5) 0.0423(6) Uani 1 1 d .
H2N H 0.730(2) 0.0289(16) -0.599(7) 0.056(10) Uiso 1 1 d .
H1N H 0.655(2) 0.0385(15) -0.448(5) 0.036(8) Uiso 1 1 d .
O1 O 0.54199(15) 0.14086(12) 0.3403(4) 0.0543(6) Uani 1 1 d D
H1O H 0.526(2) 0.1378(18) 0.492(3) 0.082 Uiso 1 1 d D
H2O H 0.5965(10) 0.149(2) 0.332(6) 0.082 Uiso 1 1 d D
O2 O 0.5047(5) 0.0218(2) 0.1936(10) 0.0731(16) Uani 0.50 1 d PD
H3O H 0.518(7) 0.012(3) 0.344(7) 0.110 Uiso 0.50 1 d PD
H4O H 0.497(9) 0.0588(10) 0.189(13) 0.110 Uiso 0.50 1 d PD
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
N1 C1 N1 111.8(3) . 6_655
N1 C1 H1A 109.3 . .
N1 C1 H1A 109.3 6_655 .
N1 C1 H1B 109.3 . .
N1 C1 H1B 109.3 6_655 .
H1A C1 H1B 107.9 . .
C7 C2 C3 117.5(2) . .
C7 C2 C8 121.1(2) . 6_655
C3 C2 C8 121.3(2) . 6_655
C4 C3 C2 123.8(3) . .
C4 C3 H3 118.1 . .
C2 C3 H3 118.1 . .
C3 C4 C5 117.3(2) . .
C3 C4 C9 122.0(2) . .
C5 C4 C9 120.7(3) . .
C6 C5 N2 119.6(3) . .
C6 C5 C4 120.2(2) . .
N2 C5 C4 120.1(3) . .
C5 C6 C7 120.7(2) . .
C5 C6 H6 119.6 . .
C7 C6 H6 119.6 . .
C2 C7 C6 120.5(2) . .
C2 C7 N1 121.0(2) . .
C6 C7 N1 118.5(2) . .
N1 C8 C2 112.7(2) . 6_655
N1 C8 H8A 109.0 . .
C2 C8 H8A 109.0 6_655 .
N1 C8 H8B 109.0 . .
C2 C8 H8B 109.0 6_655 .
H8A C8 H8B 107.8 . .
C4 C9 H9A 109.5 . .
C4 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C4 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C4 C9 H9D 109.5 . .
H9A C9 H9D 141.1 . .
H9B C9 H9D 56.3 . .
H9C C9 H9D 56.3 . .
C4 C9 H9E 109.5 . .
H9A C9 H9E 56.3 . .
H9B C9 H9E 141.1 . .
H9C C9 H9E 56.3 . .
H9D C9 H9E 109.5 . .
C4 C9 H9F 109.5 . .
H9A C9 H9F 56.3 . .
H9B C9 H9F 56.3 . .
H9C C9 H9F 141.1 . .
H9D C9 H9F 109.5 . .
H9E C9 H9F 109.5 . .
C7 N1 C1 110.71(19) . .
C7 N1 C8 113.38(18) . .
C1 N1 C8 107.0(2) . .
C5 N2 H2N 116(2) . .
C5 N2 H1N 117(2) . .
H2N N2 H1N 109(3) . .
H1O O1 H2O 110.7(17) . .
O2 O2 H3O 76(5) 2_655 .
O2 O2 H4O 164(10) 2_655 .
H3O O2 H4O 109.1(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.469(3) .
C1 N1 1.469(3) 6_655
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C2 C7 1.393(4) .
C2 C3 1.394(4) .
C2 C8 1.506(4) 6_655
C3 C4 1.390(4) .
C3 H3 0.9400 .
C4 C5 1.409(4) .
C4 C9 1.504(4) .
C5 C6 1.393(4) .
C5 N2 1.401(4) .
C6 C7 1.393(4) .
C6 H6 0.9400 .
C7 N1 1.452(3) .
C8 N1 1.486(4) .
C8 C2 1.506(4) 6_655
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 H9C 0.9700 .
C9 H9D 0.9700 .
C9 H9E 0.9700 .
C9 H9F 0.9700 .
N2 H2N 0.86(4) .
N2 H1N 0.83(3) .
O1 H1O 0.817(10) .
O1 H2O 0.826(10) .
O2 O2 0.971(10) 2_655
O2 H3O 0.829(10) .
O2 H4O 0.825(10) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N2 0.86(4) 2.36(3) 3.109(3) 145(3) 4_554
N2 H1N O2 0.83(3) 2.49(4) 3.290(9) 162(3) 3_654
O1 H1O O1 0.817(10) 2.056(13) 2.856(2) 166(4) 3_655
O1 H2O N1 0.826(10) 2.19(3) 2.886(3) 141(4) .
