#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:25:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180298 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/12/7151250.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_7151250
loop_
_publ_author_name
'Lory, Pedro M. J.'
'Jones, Raymond C. F.'
'Iley, James N.'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Intramolecular 1,3-dipolar cycloadditions of dihydroimidazolium
 ylides: synthesis of pyrrolo[1,2,3-de]quinoxalines and
 imidazo[1,2-a]indoles.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3155
_journal_page_last               3165
_journal_paper_doi               10.1039/b605458g
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C20 H24 N2 O2'
_chemical_formula_weight         324.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.91(3)
_cell_angle_beta                 87.82(3)
_cell_angle_gamma                88.80(3)
_cell_formula_units_Z            2
_cell_length_a                   5.3447(11)
_cell_length_b                   10.854(2)
_cell_length_c                   14.722(3)
_cell_measurement_reflns_used    7239
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     844.8(3)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'CAMERON (Watkin, Pearce 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald Sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1814
_diffrn_reflns_av_sigmaI/netI    0.1771
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12313
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0161P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                1806
_reflns_number_total             3729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b605458g.txt
_cod_data_source_block           03HUR485
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151250
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C -1.1992(4) 1.2141(2) 0.35155(17) 0.0321(6) Uani 1 1 d . . .
H1 H -1.3223 1.1779 0.3191 0.039 Uiso 1 1 calc R . .
C2 C -1.2284(4) 1.3363(2) 0.36735(17) 0.0334(6) Uani 1 1 d . . .
H2 H -1.3706 1.3836 0.3453 0.040 Uiso 1 1 calc R . .
C3 C -1.0532(4) 1.3898(2) 0.41468(17) 0.0334(6) Uani 1 1 d . . .
H3 H -1.0724 1.4742 0.4245 0.040 Uiso 1 1 calc R . .
C4 C -0.8484(4) 1.3199(2) 0.44800(17) 0.0344(6) Uani 1 1 d . . .
H4 H -0.7287 1.3555 0.4823 0.041 Uiso 1 1 calc R . .
C5 C -0.8184(4) 1.1984(2) 0.43128(17) 0.0319(6) Uani 1 1 d . . .
H5 H -0.6760 1.1515 0.4536 0.038 Uiso 1 1 calc R . .
C6 C -0.9917(4) 1.1437(2) 0.38267(16) 0.0272(6) Uani 1 1 d . . .
C7 C -0.9505(4) 1.0137(2) 0.36123(17) 0.0321(6) Uani 1 1 d . . .
H7A H -0.9205 0.9574 0.4189 0.038 Uiso 1 1 calc R . .
H7B H -1.1038 0.9861 0.3348 0.038 Uiso 1 1 calc R . .
C8 C -0.7872(4) 1.08013(19) 0.20739(15) 0.0276(6) Uani 1 1 d . . .
H8A H -0.8422 1.1647 0.2182 0.033 Uiso 1 1 calc R . .
H8B H -0.9249 1.0427 0.1780 0.033 Uiso 1 1 calc R . .
C9 C -0.5592(4) 1.08946(18) 0.14389(16) 0.0277(6) Uani 1 1 d . . .
H9A H -0.6043 1.1310 0.0823 0.033 Uiso 1 1 calc R . .
H9B H -0.4308 1.1398 0.1677 0.033 Uiso 1 1 calc R . .
C10 C -0.5080(4) 0.86677(19) 0.20607(15) 0.0246(6) Uani 1 1 d . . .
C11 C -0.7037(4) 0.87329(19) 0.27897(16) 0.0258(6) Uani 1 1 d . . .
H11 H -0.8649 0.8453 0.2570 0.031 Uiso 1 1 calc R . .
C12 C -0.6256(4) 0.7805(2) 0.36118(16) 0.0316(6) Uani 1 1 d . . .
H12A H -0.4750 0.8106 0.3878 0.038 Uiso 1 1 calc R . .
H12B H -0.7620 0.7727 0.4090 0.038 Uiso 1 1 calc R . .
C13 C -0.5692(4) 0.6539(2) 0.33046(17) 0.0303(6) Uani 1 1 d . . .
H13A H -0.7195 0.6265 0.3020 0.036 Uiso 1 1 calc R . .
H13B H -0.5354 0.5927 0.3852 0.036 Uiso 1 1 calc R . .
C14 C -0.3465(4) 0.6536(2) 0.26212(16) 0.0293(6) Uani 1 1 d . . .
H14A H -0.1885 0.6483 0.2955 0.035 Uiso 1 1 calc R . .
H14B H -0.3542 0.5797 0.2298 0.035 Uiso 1 1 calc R . .
C15 C -0.3494(4) 0.76988(19) 0.19331(15) 0.0243(5) Uani 1 1 d . . .
C16 C -0.2000(4) 0.80953(19) 0.11258(16) 0.0242(6) Uani 1 1 d . . .
C17 C -0.2721(4) 0.93069(19) 0.08155(16) 0.0269(6) Uani 1 1 d . . .
H17 H -0.2016 0.9817 0.0295 0.032 Uiso 1 1 calc R . .
C18 C -0.0040(4) 0.7439(2) 0.06744(17) 0.0287(6) Uani 1 1 d . . .
C19 C 0.2445(4) 0.55762(19) 0.07632(18) 0.0350(7) Uani 1 1 d . . .
H19A H 0.4056 0.5995 0.0805 0.042 Uiso 1 1 calc R . .
H19B H 0.2182 0.5503 0.0111 0.042 Uiso 1 1 calc R . .
C20 C 0.2471(4) 0.4307(2) 0.13313(19) 0.0435(7) Uani 1 1 d . . .
H20A H 0.2672 0.4395 0.1978 0.065 Uiso 1 1 calc R . .
H20B H 0.3867 0.3808 0.1119 0.065 Uiso 1 1 calc R . .
H20C H 0.0889 0.3892 0.1267 0.065 Uiso 1 1 calc R . .
N1 N -0.7369(3) 1.00382(15) 0.29635(12) 0.0244(5) Uani 1 1 d . . .
N2 N -0.4589(3) 0.96426(16) 0.13732(13) 0.0254(5) Uani 1 1 d . . .
O1 O 0.1147(3) 0.78315(14) -0.00230(12) 0.0399(5) Uani 1 1 d . . .
O2 O 0.0404(3) 0.62800(13) 0.11306(11) 0.0332(4) Uani 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 0.0033 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
C2 C1 C6 120.6(2) . . ?
C3 C2 C1 120.5(2) . . ?
C2 C3 C4 119.6(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 121.3(2) . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 120.67(19) . . ?
C1 C6 C7 121.1(2) . . ?
N1 C7 C6 112.45(17) . . ?
N1 C8 C9 111.70(15) . . ?
N2 C9 C8 109.26(16) . . ?
C15 C10 N2 108.56(19) . . ?
C15 C10 C11 128.51(19) . . ?
N2 C10 C11 122.94(18) . . ?
C10 C11 N1 109.44(17) . . ?
C10 C11 C12 106.57(17) . . ?
N1 C11 C12 115.5(2) . . ?
C13 C12 C11 109.6(2) . . ?
C12 C13 C14 113.96(18) . . ?
C15 C14 C13 110.44(17) . . ?
C10 C15 C16 106.65(18) . . ?
C10 C15 C14 120.6(2) . . ?
C16 C15 C14 132.7(2) . . ?
C17 C16 C15 107.0(2) . . ?
C17 C16 C18 123.0(2) . . ?
C15 C16 C18 130.07(19) . . ?
N2 C17 C16 108.58(19) . . ?
O1 C18 O2 121.3(2) . . ?
O1 C18 C16 126.6(2) . . ?
O2 C18 C16 112.03(19) . . ?
O2 C19 C20 106.82(18) . . ?
C7 N1 C8 109.77(15) . . ?
C7 N1 C11 109.88(16) . . ?
C8 N1 C11 107.28(18) . . ?
C17 N2 C10 109.21(16) . . ?
C17 N2 C9 128.21(18) . . ?
C10 N2 C9 120.88(19) . . ?
C18 O2 C19 116.20(17) . . ?
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
C1 C2 1.384(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.499(3) . ?
C7 N1 1.473(3) . ?
C8 N1 1.478(2) . ?
C8 C9 1.504(3) . ?
C9 N2 1.465(3) . ?
C10 C15 1.366(3) . ?
C10 N2 1.379(2) . ?
C10 C11 1.478(3) . ?
C11 N1 1.481(3) . ?
C11 C12 1.527(3) . ?
C12 C13 1.527(3) . ?
C13 C14 1.529(3) . ?
C14 C15 1.504(3) . ?
C15 C16 1.426(3) . ?
C16 C17 1.382(3) . ?
C16 C18 1.447(3) . ?
C17 N2 1.345(3) . ?
C18 O1 1.215(3) . ?
C18 O2 1.361(2) . ?
C19 O2 1.450(3) . ?
C19 C20 1.508(3) . ?
