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#$Date: 2016-03-26 15:38:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180309 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/23/7152387.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_7152387
loop_
_publ_author_name
'Murai, Toshiaki'
'Nagaya, Eri'
'Shibahara, Fumitoshi'
'Maruyama, Toshifumi'
_publ_section_title
;
 Imidazo[1,5-a]pyridine-1-ylalkylalcohols: synthesis via intramolecular
 cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers and
 molecular structures.
;
_journal_issue                   25
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4943
_journal_page_last               4953
_journal_paper_doi               10.1039/c2ob25438g
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C41 H32 N4'
_chemical_formula_sum            'C41 H32 N4'
_chemical_formula_weight         580.71
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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                 133.986(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.232(18)
_cell_length_b                   10.636(7)
_cell_length_c                   17.824(14)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     3032(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_sigmaI/netI    0.0873
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12275
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1551
_refine_ls_R_factor_gt           0.1049
_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)+(0.0400P)²+19.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.2078
_reflns_number_gt                2512
_reflns_number_total             3463
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25438g.txt
_cod_data_source_block           en013-3
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               7152387
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
C21 C 0.5000 0.0558(4) 0.7500 0.0240(11) Uani 1 2 d S
N1 N 0.37910(18) 0.0921(3) 0.7341(2) 0.0264(7) Uani 1 1 d .
N2 N 0.32444(18) 0.2705(3) 0.6444(2) 0.0240(7) Uani 1 1 d .
C1 C 0.5445(2) -0.0273(3) 0.8486(3) 0.0254(8) Uani 1 1 d .
C2 C 0.5904(2) -0.1311(3) 0.8641(3) 0.0312(9) Uani 1 1 d .
H2A H 0.5893 -0.1548 0.8118 0.037 Uiso 1 1 calc R
C3 C 0.6376(2) -0.1996(4) 0.9560(3) 0.0370(10) Uani 1 1 d .
H3A H 0.6686 -0.2703 0.9659 0.044 Uiso 1 1 calc R
C4 C 0.6402(3) -0.1669(4) 1.0327(3) 0.0396(10) Uani 1 1 d .
H4A H 0.6725 -0.2148 1.0951 0.048 Uiso 1 1 calc R
C5 C 0.5950(2) -0.0629(4) 1.0183(3) 0.0351(9) Uani 1 1 d .
H5A H 0.5965 -0.0395 1.0709 0.042 Uiso 1 1 calc R
C6 C 0.5481(2) 0.0064(4) 0.9273(3) 0.0283(8) Uani 1 1 d .
H6A H 0.5180 0.0778 0.9183 0.034 Uiso 1 1 calc R
C7 C 0.4293(2) 0.1354(3) 0.7207(3) 0.0239(8) Uani 1 1 d .
C8 C 0.3169(2) 0.1746(3) 0.6892(3) 0.0241(8) Uani 1 1 d .
C9 C 0.3965(2) 0.2461(3) 0.6635(3) 0.0237(8) Uani 1 1 d .
C10 C 0.2718(2) 0.3708(3) 0.5820(3) 0.0261(8) Uani 1 1 d .
H10A H 0.2221 0.3839 0.5672 0.031 Uiso 1 1 calc R
C11 C 0.2919(2) 0.4487(4) 0.5431(3) 0.0340(9) Uani 1 1 d .
H11A H 0.2563 0.5175 0.5008 0.041 Uiso 1 1 calc R
C12 C 0.3653(2) 0.4300(4) 0.5639(3) 0.0330(9) Uani 1 1 d .
H12A H 0.3793 0.4877 0.5373 0.040 Uiso 1 1 calc R
C13 C 0.4158(2) 0.3303(3) 0.6214(3) 0.0282(8) Uani 1 1 d .
H13A H 0.4642 0.3170 0.6334 0.034 Uiso 1 1 calc R
C14 C 0.2487(2) 0.1572(4) 0.6834(3) 0.0275(8) Uani 1 1 d .
C15 C 0.2262(2) 0.0354(4) 0.6840(3) 0.0339(9) Uani 1 1 d .
H15A H 0.2558 -0.0340 0.6892 0.041 Uiso 1 1 calc R
C16 C 0.1614(3) 0.0142(4) 0.6773(4) 0.0414(11) Uani 1 1 d .
H16A H 0.1464 -0.0698 0.6764 0.050 Uiso 1 1 calc R
C17 C 0.1176(3) 0.1129(4) 0.6717(4) 0.0448(12) Uani 1 1 d .
C18 C 0.1390(3) 0.2333(4) 0.6711(4) 0.0407(11) Uani 1 1 d .
H18A H 0.1096 0.3019 0.6671 0.049 Uiso 1 1 calc R
C19 C 0.2038(2) 0.2564(4) 0.6764(3) 0.0326(9) Uani 1 1 d .
H19A H 0.2174 0.3405 0.6751 0.039 Uiso 1 1 calc R
C20 C 0.0468(3) 0.0868(5) 0.6642(6) 0.077(2) Uani 1 1 d .
H20A H 0.0099 0.1603 0.6347 0.116 Uiso 1 1 calc R
H20B H 0.0696 0.0695 0.7339 0.116 Uiso 1 1 calc R
H20C H 0.0149 0.0138 0.6191 0.116 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 0.0033 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'
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
C7 C21 C7 112.4(4) . 2_656
C7 C21 C1 113.39(19) . .
C7 C21 C1 103.46(18) 2_656 .
C7 C21 C1 103.46(18) . 2_656
C7 C21 C1 113.38(19) 2_656 2_656
C1 C21 C1 111.0(4) . 2_656
C8 N1 C7 107.7(3) . .
C8 N2 C10 131.2(3) . .
C8 N2 C9 107.4(3) . .
C10 N2 C9 121.2(3) . .
C6 C1 C2 118.7(3) . .
C6 C1 C21 122.5(3) . .
C2 C1 C21 118.3(3) . .
C3 C2 C1 119.9(4) . .
C3 C2 H2A 120.0 . .
C1 C2 H2A 120.0 . .
C4 C3 C2 121.1(4) . .
C4 C3 H3A 119.5 . .
C2 C3 H3A 119.5 . .
C3 C4 C5 119.4(4) . .
C3 C4 H4A 120.3 . .
C5 C4 H4A 120.3 . .
C6 C5 C4 120.0(4) . .
C6 C5 H5A 120.0 . .
C4 C5 H5A 120.0 . .
C5 C6 C1 120.9(4) . .
C5 C6 H6A 119.6 . .
C1 C6 H6A 119.6 . .
N1 C7 C9 109.6(3) . .
N1 C7 C21 121.6(3) . .
C9 C7 C21 128.0(3) . .
N1 C8 N2 110.0(3) . .
N1 C8 C14 123.5(3) . .
N2 C8 C14 126.3(3) . .
C7 C9 N2 105.3(3) . .
C7 C9 C13 136.7(3) . .
N2 C9 C13 118.0(3) . .
C11 C10 N2 119.3(3) . .
C11 C10 H10A 120.4 . .
N2 C10 H10A 120.4 . .
C10 C11 C12 121.1(4) . .
C10 C11 H11A 119.5 . .
C12 C11 H11A 119.5 . .
C13 C12 C11 120.5(4) . .
C13 C12 H12A 119.8 . .
C11 C12 H12A 119.8 . .
C12 C13 C9 119.9(4) . .
C12 C13 H13A 120.0 . .
C9 C13 H13A 120.0 . .
C15 C14 C19 117.7(3) . .
C15 C14 C8 118.6(3) . .
C19 C14 C8 123.6(3) . .
C16 C15 C14 120.8(4) . .
C16 C15 H15A 119.6 . .
C14 C15 H15A 119.6 . .
C15 C16 C17 121.4(4) . .
C15 C16 H16A 119.3 . .
C17 C16 H16A 119.3 . .
C18 C17 C16 118.5(4) . .
C18 C17 C20 121.2(4) . .
C16 C17 C20 120.2(4) . .
C17 C18 C19 120.8(4) . .
C17 C18 H18A 119.6 . .
C19 C18 H18A 119.6 . .
C14 C19 C18 120.8(4) . .
C14 C19 H19A 119.6 . .
C18 C19 H19A 119.6 . .
C17 C20 H20A 109.5 . .
C17 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C17 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C21 C7 1.522(4) .
C21 C7 1.522(4) 2_656
C21 C1 1.560(5) .
C21 C1 1.560(5) 2_656
N1 C8 1.335(4) .
N1 C7 1.373(5) .
N2 C8 1.375(5) .
N2 C10 1.391(4) .
N2 C9 1.410(5) .
C1 C6 1.393(5) .
C1 C2 1.395(5) .
C2 C3 1.388(6) .
C2 H2A 0.9500 .
C3 C4 1.373(6) .
C3 H3A 0.9500 .
C4 C5 1.392(6) .
C4 H4A 0.9500 .
C5 C6 1.382(5) .
C5 H5A 0.9500 .
C6 H6A 0.9500 .
C7 C9 1.388(5) .
C8 C14 1.459(5) .
C9 C13 1.414(5) .
C10 C11 1.341(5) .
C10 H10A 0.9500 .
C11 C12 1.414(6) .
C11 H11A 0.9500 .
C12 C13 1.355(5) .
C12 H12A 0.9500 .
C13 H13A 0.9500 .
C14 C15 1.392(5) .
C14 C19 1.397(5) .
C15 C16 1.379(6) .
C15 H15A 0.9500 .
C16 C17 1.388(6) .
C16 H16A 0.9500 .
C17 C18 1.368(6) .
C17 C20 1.510(6) .
C18 C19 1.399(5) .
C18 H18A 0.9500 .
C19 H19A 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C7 C21 C1 C6 -27.8(5) .
C7 C21 C1 C6 94.3(3) 2_656
C1 C21 C1 C6 -143.8(4) 2_656
C7 C21 C1 C2 159.9(3) .
C7 C21 C1 C2 -78.1(4) 2_656
C1 C21 C1 C2 43.9(3) 2_656
C6 C1 C2 C3 0.9(5) .
C21 C1 C2 C3 173.5(3) .
C1 C2 C3 C4 -0.1(6) .
C2 C3 C4 C5 -0.3(6) .
C3 C4 C5 C6 0.0(6) .
C4 C5 C6 C1 0.8(6) .
C2 C1 C6 C5 -1.2(5) .
C21 C1 C6 C5 -173.5(3) .
C8 N1 C7 C9 -1.6(4) .
C8 N1 C7 C21 -171.9(3) .
C7 C21 C7 N1 -152.2(4) 2_656
C1 C21 C7 N1 -35.3(4) .
C1 C21 C7 N1 85.1(4) 2_656
C7 C21 C7 C9 39.4(3) 2_656
C1 C21 C7 C9 156.3(3) .
C1 C21 C7 C9 -83.3(4) 2_656
C7 N1 C8 N2 1.2(4) .
C7 N1 C8 C14 177.1(3) .
C10 N2 C8 N1 173.7(3) .
C9 N2 C8 N1 -0.4(4) .
C10 N2 C8 C14 -2.0(6) .
C9 N2 C8 C14 -176.1(3) .
N1 C7 C9 N2 1.3(4) .
C21 C7 C9 N2 170.9(3) .
N1 C7 C9 C13 -176.6(4) .
C21 C7 C9 C13 -7.0(7) .
C8 N2 C9 C7 -0.6(4) .
C10 N2 C9 C7 -175.4(3) .
C8 N2 C9 C13 177.8(3) .
C10 N2 C9 C13 2.9(5) .
C8 N2 C10 C11 -176.3(4) .
C9 N2 C10 C11 -2.8(5) .
N2 C10 C11 C12 0.4(6) .
C10 C11 C12 C13 1.9(6) .
C11 C12 C13 C9 -1.8(6) .
C7 C9 C13 C12 177.1(4) .
N2 C9 C13 C12 -0.6(5) .
N1 C8 C14 C15 -27.0(6) .
N2 C8 C14 C15 148.1(4) .
N1 C8 C14 C19 153.6(4) .
N2 C8 C14 C19 -31.3(6) .
C19 C14 C15 C16 0.4(6) .
C8 C14 C15 C16 -179.1(4) .
C14 C15 C16 C17 -1.3(7) .
C15 C16 C17 C18 1.2(7) .
C15 C16 C17 C20 179.9(5) .
C16 C17 C18 C19 -0.2(7) .
C20 C17 C18 C19 -179.0(5) .
C15 C14 C19 C18 0.6(6) .
C8 C14 C19 C18 -180.0(4) .
C17 C18 C19 C14 -0.7(7) .
