#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151248.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_7151248
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            'C25 H26 N2 O2'
_chemical_formula_weight         386.48
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 112.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.559(2)
_cell_length_b                   9.6567(19)
_cell_length_c                   11.052(2)
_cell_measurement_reflns_used    12125
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.0
_cell_volume                     1041.4(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12212
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9807
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_coef       0.031(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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.0171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                3968
_reflns_number_total             4640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b605458g.txt
_cod_data_source_block           s92_1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        1041.5(4)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7151248
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
N1 N 0.72182(11) 0.25769(13) 0.61448(11) 0.0230(2) Uani 1 1 d . . .
N2 N 0.64861(11) 0.12170(12) 0.79966(11) 0.0258(3) Uani 1 1 d . . .
O1 O 1.05872(12) 0.58390(13) 0.70151(12) 0.0489(3) Uani 1 1 d . . .
O2 O 0.87378(11) 0.61408(12) 0.51625(11) 0.0436(3) Uani 1 1 d . . .
C1 C 1.01379(14) 0.37654(15) 0.90065(14) 0.0285(3) Uani 1 1 d . . .
H1A H 0.9959 0.4676 0.9321 0.034 Uiso 1 1 calc R . .
H1B H 1.1063 0.3793 0.8977 0.034 Uiso 1 1 calc R . .
C2 C 1.00875(15) 0.26281(17) 0.99559(15) 0.0307(3) Uani 1 1 d . . .
H2A H 1.0598 0.1809 0.9849 0.037 Uiso 1 1 calc R . .
H2B H 1.0547 0.2966 1.0866 0.037 Uiso 1 1 calc R . .
C3 C 0.86202(14) 0.21982(15) 0.97300(13) 0.0263(3) Uani 1 1 d . . .
H3A H 0.8630 0.1546 1.0425 0.032 Uiso 1 1 calc R . .
H3B H 0.8084 0.3024 0.9773 0.032 Uiso 1 1 calc R . .
C4 C 0.79499(13) 0.15079(14) 0.83944(13) 0.0251(3) Uani 1 1 d . . .
H4 H 0.8443 0.0625 0.8391 0.030 Uiso 1 1 calc R . .
C5 C 0.81309(13) 0.24842(14) 0.74260(13) 0.0225(3) Uani 1 1 d . . .
C6 C 0.90905(13) 0.34975(14) 0.76598(13) 0.0230(3) Uani 1 1 d . . .
C7 C 0.87436(14) 0.42576(14) 0.64708(14) 0.0235(3) Uani 1 1 d . . .
C8 C 0.94687(16) 0.54611(16) 0.62728(14) 0.0299(3) Uani 1 1 d . . .
C9 C 0.9403(2) 0.7330(2) 0.4872(2) 0.0605(6) Uani 1 1 d . . .
H9A H 0.9700 0.7963 0.5622 0.091 Uiso 1 1 calc R . .
H9B H 0.8758 0.7808 0.4100 0.091 Uiso 1 1 calc R . .
H9C H 1.0201 0.7025 0.4696 0.091 Uiso 1 1 calc R . .
C10 C 0.75768(14) 0.36670(14) 0.55650(13) 0.0241(3) Uani 1 1 d . . .
H10 H 0.7106 0.3969 0.4689 0.029 Uiso 1 1 calc R . .
C11 C 0.58937(13) 0.18625(16) 0.56737(13) 0.0255(3) Uani 1 1 d . . .
H11 H 0.5174 0.2540 0.5664 0.031 Uiso 1 1 calc R . .
C12 C 0.59606(15) 0.07123(15) 0.66456(13) 0.0284(3) Uani 1 1 d . . .
H12A H 0.5032 0.0322 0.6427 0.034 Uiso 1 1 calc R . .
H12B H 0.6561 -0.0040 0.6565 0.034 Uiso 1 1 calc R . .
C13 C 0.54948(14) 0.12746(15) 0.43125(13) 0.0257(3) Uani 1 1 d . . .
C14 C 0.64540(15) 0.06617(16) 0.39000(15) 0.0312(3) Uani 1 1 d . . .
H14 H 0.7398 0.0675 0.4456 0.037 Uiso 1 1 calc R . .
C15 C 0.60404(17) 0.00309(18) 0.26812(15) 0.0367(4) Uani 1 1 d . . .
H15 H 0.6702 -0.0374 0.2400 0.044 Uiso 1 1 calc R . .
C16 C 0.46695(17) -0.00081(18) 0.18780(15) 0.0370(4) Uani 1 1 d . . .
H16 H 0.4385 -0.0455 0.1051 0.044 Uiso 1 1 calc R . .
C17 C 0.37171(16) 0.05990(17) 0.22746(15) 0.0362(4) Uani 1 1 d . . .
H17 H 0.2774 0.0576 0.1717 0.043 Uiso 1 1 calc R . .
C18 C 0.41225(14) 0.12454(16) 0.34834(14) 0.0309(3) Uani 1 1 d . . .
H18 H 0.3457 0.1671 0.3746 0.037 Uiso 1 1 calc R . .
C19 C 0.62212(15) 0.01967(17) 0.88579(14) 0.0316(3) Uani 1 1 d . . .
H19A H 0.6700 0.0484 0.9781 0.038 Uiso 1 1 calc R . .
H19B H 0.6593 -0.0714 0.8745 0.038 Uiso 1 1 calc R . .
C20 C 0.47122(15) 0.00583(16) 0.85602(13) 0.0282(3) Uani 1 1 d . . .
C21 C 0.39532(16) 0.12084(17) 0.86013(15) 0.0371(4) Uani 1 1 d . . .
H21 H 0.4383 0.2089 0.8805 0.044 Uiso 1 1 calc R . .
C22 C 0.25612(18) 0.1085(2) 0.83465(18) 0.0457(4) Uani 1 1 d . . .
H22 H 0.2046 0.1880 0.8382 0.055 Uiso 1 1 calc R . .
C23 C 0.19316(18) -0.0185(2) 0.80440(17) 0.0462(5) Uani 1 1 d . . .
H23 H 0.0981 -0.0268 0.7869 0.055 Uiso 1 1 calc R . .
C24 C 0.26741(17) -0.13350(19) 0.79941(16) 0.0411(4) Uani 1 1 d . . .
H24 H 0.2238 -0.2212 0.7783 0.049 Uiso 1 1 calc R . .
C25 C 0.40617(16) -0.12151(16) 0.82519(14) 0.0322(4) Uani 1 1 d . . .
H25 H 0.4572 -0.2014 0.8217 0.039 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'
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
C10 N1 C5 108.86(12) . . ?
C10 N1 C11 126.67(11) . . ?
C5 N1 C11 122.17(12) . . ?
C12 N2 C4 108.39(11) . . ?
C12 N2 C19 110.23(11) . . ?
C4 N2 C19 112.01(11) . . ?
C8 O2 C9 115.63(13) . . ?
C6 C1 C2 110.51(12) . . ?
C3 C2 C1 112.36(12) . . ?
C4 C3 C2 110.07(12) . . ?
N2 C4 C5 108.41(11) . . ?
N2 C4 C3 114.89(11) . . ?
C5 C4 C3 106.18(11) . . ?
C6 C5 N1 109.03(12) . . ?
C6 C5 C4 127.48(12) . . ?
N1 C5 C4 123.16(12) . . ?
C5 C6 C7 106.55(12) . . ?
C5 C6 C1 121.73(12) . . ?
C7 C6 C1 131.20(12) . . ?
C10 C7 C6 107.44(12) . . ?
C10 C7 C8 126.66(13) . . ?
C6 C7 C8 125.86(13) . . ?
O1 C8 O2 122.90(14) . . ?
O1 C8 C7 125.00(14) . . ?
O2 C8 C7 112.08(13) . . ?
N1 C10 C7 108.09(12) . . ?
N1 C11 C13 113.34(11) . . ?
N1 C11 C12 108.12(11) . . ?
C13 C11 C12 110.34(12) . . ?
N2 C12 C11 111.89(12) . . ?
C18 C13 C14 118.82(13) . . ?
C18 C13 C11 119.28(12) . . ?
C14 C13 C11 121.71(13) . . ?
C15 C14 C13 120.40(14) . . ?
C16 C15 C14 120.01(15) . . ?
C17 C16 C15 119.97(15) . . ?
C16 C17 C18 120.41(14) . . ?
C17 C18 C13 120.38(14) . . ?
N2 C19 C20 111.46(12) . . ?
C21 C20 C25 118.84(14) . . ?
C21 C20 C19 120.06(13) . . ?
C25 C20 C19 121.09(14) . . ?
C20 C21 C22 120.40(16) . . ?
C23 C22 C21 120.04(18) . . ?
C24 C23 C22 120.09(15) . . ?
C23 C24 C25 119.95(16) . . ?
C20 C25 C24 120.67(16) . . ?
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
N1 C10 1.3593(18) . ?
N1 C5 1.3780(18) . ?
N1 C11 1.4651(17) . ?
N2 C12 1.4635(18) . ?
N2 C4 1.4635(17) . ?
N2 C19 1.4693(18) . ?
O1 C8 1.2086(19) . ?
O2 C8 1.3449(19) . ?
O2 C9 1.445(2) . ?
C1 C6 1.499(2) . ?
C1 C2 1.534(2) . ?
C2 C3 1.530(2) . ?
C3 C4 1.5251(19) . ?
C4 C5 1.4924(19) . ?
C5 C6 1.3605(19) . ?
C6 C7 1.425(2) . ?
C7 C10 1.379(2) . ?
C7 C8 1.454(2) . ?
C11 C13 1.5096(19) . ?
C11 C12 1.528(2) . ?
C13 C18 1.3876(19) . ?
C13 C14 1.392(2) . ?
C14 C15 1.388(2) . ?
C15 C16 1.379(2) . ?
C16 C17 1.373(2) . ?
C17 C18 1.386(2) . ?
C19 C20 1.505(2) . ?
C20 C21 1.380(2) . ?
C20 C25 1.386(2) . ?
C21 C22 1.392(2) . ?
C22 C23 1.375(3) . ?
C23 C24 1.372(3) . ?
C24 C25 1.386(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188813
