#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:38:45 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180149 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/46/7104687.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_7104687
loop_
_publ_author_name
'Bäuerlein, Patrick S'
'Gonzalez, Ismael Arenas'
'Weemers, Jarno J M'
'Lutz, Martin'
'Spek, Anthony L'
'Vogt, Dieter'
'Müller, Christian'
_publ_section_title
;
 Phosphabarrelene-modified Rh-catalysts: a new and selective route
 towards hydroxy-functionalized bicyclic imidazoles via tandem
 reactions.
;
_journal_issue                   33
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4944
_journal_page_last               4946
_journal_paper_doi               10.1039/b911612e
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C8 H12 N2 O'
_chemical_formula_sum            'C8 H12 N2 O'
_chemical_formula_weight         152.20
_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                 129.266(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.4857(5)
_cell_length_b                   8.0251(6)
_cell_length_c                   19.0553(8)
_cell_measurement_reflns_used    4320
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.76
_cell_volume                     1596.62(16)
_computing_cell_refinement       Peakref
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Eval14, Sadabs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10235
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1487
_refine_ls_number_restraints     103
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0584
_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)+(0.0541P)²+2.1161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1481
_reflns_number_gt                1122
_reflns_number_total             1487
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b911612e.txt
_cod_data_source_block           s4292a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7104687
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O -0.00860(18) 0.2495(3) 0.15150(13) 0.0325(6) Uani 0.756(4) 1 d PDU A 1
H1A H -0.0659 0.2248 0.1591 0.049 Uiso 0.756(4) 1 d P A 1
O1B O -0.0017(6) -0.0072(9) 0.1557(5) 0.048(2) Uani 0.244(4) 1 d PDU A 2
H2B H -0.0688 0.0357 0.1546 0.072 Uiso 0.244(4) 1 d P A 2
N1 N 0.31432(16) 0.1188(2) 0.30201(12) 0.0264(5) Uani 1 1 d DU A .
C2 C 0.3947(2) 0.1213(3) 0.39478(14) 0.0300(5) Uani 1 1 d U . .
H2 H 0.4856 0.1191 0.4347 0.036 Uiso 1 1 calc R . .
C3 C 0.3190(2) 0.1274(3) 0.41834(15) 0.0322(6) Uani 1 1 d U . .
H3 H 0.3487 0.1309 0.4787 0.039 Uiso 1 1 calc R . .
N4 N 0.19220(18) 0.1277(3) 0.34146(13) 0.0365(5) Uani 1 1 d U . .
C5 C 0.1925(2) 0.1232(3) 0.27237(15) 0.0293(5) Uani 1 1 d DU A .
C6 C 0.0781(2) 0.1235(3) 0.17337(15) 0.0355(6) Uani 1 1 d DU . .
H6A H 0.0344 0.0127 0.1557 0.043 Uiso 0.756(4) 1 calc PR A 1
H6B H 0.0330 0.2334 0.1518 0.043 Uiso 0.244(4) 1 calc PR A 2
C7A C 0.1189(3) 0.1626(5) 0.1152(2) 0.0306(8) Uani 0.756(4) 1 d PDU A 1
H7A H 0.0476 0.1357 0.0509 0.037 Uiso 0.756(4) 1 calc PR A 1
H7B H 0.1381 0.2829 0.1193 0.037 Uiso 0.756(4) 1 calc PR A 1
C8A C 0.2365(3) 0.0615(5) 0.1478(2) 0.0319(8) Uani 0.756(4) 1 d PDU A 1
H8A H 0.2183 -0.0586 0.1494 0.038 Uiso 0.756(4) 1 calc PR A 1
C7B C 0.1212(8) 0.0631(13) 0.1200(5) 0.026(2) Uani 0.244(4) 1 d PDU A 2
H7C H 0.1483 -0.0550 0.1341 0.031 Uiso 0.244(4) 1 calc PR A 2
H7D H 0.0508 0.0740 0.0540 0.031 Uiso 0.244(4) 1 calc PR A 2
C8B C 0.2334(7) 0.1747(12) 0.1501(5) 0.028(2) Uani 0.244(4) 1 d PDU A 2
H8B H 0.2139 0.2934 0.1531 0.034 Uiso 0.244(4) 1 calc PR A 2
C9 C 0.3499(2) 0.1148(3) 0.24368(15) 0.0315(6) Uani 1 1 d DU . .
H9A H 0.4217 0.0358 0.2690 0.038 Uiso 0.756(4) 1 calc PR A 1
H9B H 0.3792 0.2268 0.2420 0.038 Uiso 0.756(4) 1 calc PR A 1
H9C H 0.3733 0.0001 0.2400 0.038 Uiso 0.244(4) 1 calc PR A 2
H9D H 0.4241 0.1888 0.2682 0.038 Uiso 0.244(4) 1 calc PR A 2
C10A C 0.2698(5) 0.0796(6) 0.0852(3) 0.0425(12) Uani 0.756(4) 1 d PDU A 1
H10A H 0.1952 0.0499 0.0233 0.064 Uiso 0.756(4) 1 calc PR A 1
H10B H 0.3413 0.0054 0.1057 0.064 Uiso 0.756(4) 1 calc PR A 1
H10C H 0.2944 0.1952 0.0865 0.064 Uiso 0.756(4) 1 calc PR A 1
C10B C 0.2626(16) 0.157(2) 0.0850(10) 0.057(5) Uani 0.244(4) 1 d PDU A 2
H10D H 0.3488 0.2001 0.1140 0.085 Uiso 0.244(4) 1 calc PR A 2
H10E H 0.1998 0.2212 0.0297 0.085 Uiso 0.244(4) 1 calc PR A 2
H10F H 0.2581 0.0396 0.0695 0.085 Uiso 0.244(4) 1 calc PR A 2
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
_geom_angle_publ_flag
C6 O1A H1A 116.0 . . ?
C6 O1B H2B 108.2 . . ?
C5 N1 C2 107.29(18) . . ?
C5 N1 C9 125.20(18) . . ?
C2 N1 C9 127.50(18) . . ?
C3 C2 N1 106.40(19) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C2 C3 N4 109.67(19) . . ?
C2 C3 H3 125.2 . . ?
N4 C3 H3 125.2 . . ?
C5 N4 C3 105.98(18) . . ?
N4 C5 N1 110.65(19) . . ?
N4 C5 C6 127.12(19) . . ?
N1 C5 C6 122.24(19) . . ?
O1B C6 C5 109.1(4) . . ?
O1A C6 C5 112.2(2) . . ?
O1B C6 C7B 99.3(4) . . ?
C5 C6 C7B 108.2(4) . . ?
O1A C6 C7A 104.4(2) . . ?
C5 C6 C7A 110.6(2) . . ?
O1A C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C7A C6 H6A 109.9 . . ?
O1B C6 H6B 113.1 . . ?
C5 C6 H6B 113.1 . . ?
C7B C6 H6B 113.1 . . ?
C8A C7A C6 110.5(3) . . ?
C8A C7A H7A 109.6 . . ?
C6 C7A H7A 109.6 . . ?
C8A C7A H7B 109.6 . . ?
C6 C7A H7B 109.6 . . ?
H7A C7A H7B 108.1 . . ?
C7A C8A C9 109.7(3) . . ?
C7A C8A C10A 112.1(3) . . ?
C9 C8A C10A 110.0(3) . . ?
C7A C8A H8A 108.3 . . ?
C9 C8A H8A 108.3 . . ?
C10A C8A H8A 108.3 . . ?
C8B C7B C6 105.6(6) . . ?
C8B C7B H7C 110.6 . . ?
C6 C7B H7C 110.6 . . ?
C8B C7B H7D 110.6 . . ?
C6 C7B H7D 110.6 . . ?
H7C C7B H7D 108.8 . . ?
C7B C8B C10B 110.3(8) . . ?
C7B C8B C9 107.3(6) . . ?
C10B C8B C9 108.5(8) . . ?
C7B C8B H8B 110.3 . . ?
C10B C8B H8B 110.3 . . ?
C9 C8B H8B 110.3 . . ?
N1 C9 C8A 110.69(19) . . ?
N1 C9 C8B 106.9(3) . . ?
N1 C9 H9A 109.5 . . ?
C8A C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C8A C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C9 H9C 110.3 . . ?
C8B C9 H9C 110.3 . . ?
N1 C9 H9D 110.3 . . ?
H9C C9 H9D 108.6 . . ?
C8B C10B H10D 109.5 . . ?
C8B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C8B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
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
O1A C6 1.395(3) . ?
O1A H1A 0.8940 . ?
O1B C6 1.383(6) . ?
O1B H2B 0.9565 . ?
N1 C5 1.358(3) . ?
N1 C2 1.369(3) . ?
N1 C9 1.464(3) . ?
C2 C3 1.351(3) . ?
C2 H2 0.9500 . ?
C3 N4 1.378(3) . ?
C3 H3 0.9500 . ?
N4 C5 1.320(3) . ?
C5 C6 1.502(3) . ?
C6 C7B 1.535(7) . ?
C6 C7A 1.550(4) . ?
C6 H6A 1.0000 . ?
C6 H6B 1.0000 . ?
C7A C8A 1.520(4) . ?
C7A H7A 0.9900 . ?
C7A H7B 0.9900 . ?
C8A C9 1.524(4) . ?
C8A C10A 1.525(4) . ?
C8A H8A 1.0000 . ?
C7B C8B 1.524(8) . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C8B C10B 1.526(8) . ?
C8B C9 1.528(7) . ?
C8B H8B 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 H9C 0.9900 . ?
C9 H9D 0.9900 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 -0.1(3) . . . . ?
C9 N1 C2 C3 179.0(2) . . . . ?
N1 C2 C3 N4 0.4(3) . . . . ?
C2 C3 N4 C5 -0.5(3) . . . . ?
C3 N4 C5 N1 0.4(3) . . . . ?
C3 N4 C5 C6 -179.2(2) . . . . ?
C2 N1 C5 N4 -0.2(3) . . . . ?
C9 N1 C5 N4 -179.4(2) . . . . ?
C2 N1 C5 C6 179.5(2) . . . . ?
C9 N1 C5 C6 0.3(4) . . . . ?
N4 C5 C6 O1B -55.5(4) . . . . ?
N1 C5 C6 O1B 124.9(4) . . . . ?
N4 C5 C6 O1A 49.4(3) . . . . ?
N1 C5 C6 O1A -130.2(2) . . . . ?
N4 C5 C6 C7B -162.6(4) . . . . ?
N1 C5 C6 C7B 17.8(5) . . . . ?
N4 C5 C6 C7A 165.5(3) . . . . ?
N1 C5 C6 C7A -14.1(3) . . . . ?
O1B C6 C7A C8A -86.4(5) . . . . ?
O1A C6 C7A C8A 166.4(3) . . . . ?
C5 C6 C7A C8A 45.5(4) . . . . ?
C7B C6 C7A C8A -45.5(6) . . . . ?
C6 C7A C8A C9 -64.7(4) . . . . ?
C6 C7A C8A C10A 172.8(3) . . . . ?
O1B C6 C7B C8B -167.5(7) . . . . ?
O1A C6 C7B C8B 87.2(7) . . . . ?
C5 C6 C7B C8B -53.7(7) . . . . ?
C7A C6 C7B C8B 46.1(5) . . . . ?
C6 C7B C8B C10B -165.5(8) . . . . ?
C6 C7B C8B C9 76.6(8) . . . . ?
C5 N1 C9 C8A -17.9(3) . . . . ?
C2 N1 C9 C8A 163.1(2) . . . . ?
C5 N1 C9 C8B 18.7(5) . . . . ?
C2 N1 C9 C8B -160.3(4) . . . . ?
C7A C8A C9 N1 48.9(3) . . . . ?
C10A C8A C9 N1 172.7(3) . . . . ?
C7A C8A C9 C8B -41.1(5) . . . . ?
C10A C8A C9 C8B 82.7(6) . . . . ?
C7B C8B C9 N1 -55.9(7) . . . . ?
C10B C8B C9 N1 -175.0(8) . . . . ?
C7B C8B C9 C8A 46.3(5) . . . . ?
C10B C8B C9 C8A -72.8(9) . . . . ?
