#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:04:43 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180464 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/33/7213306.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213306
loop_
_publ_author_name
'Jones, Raymond C. F.'
'Dimopoulos, Paschalis'
'Coles, Simon C.'
'Light, Mark E.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Synthesis of imidazo[1,2-a]pyridines from unactivated
 2-alkyl-4,5-dihydroimidazoles through conjugate N-addition
;
_journal_issue                   15
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2331
_journal_paper_doi               10.1039/b001830i
_journal_year                    2000
_chemical_formula_sum            'C25 H28 N2 O4'
_chemical_formula_weight         420.49
_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                65.331(3)
_cell_angle_beta                 65.329(4)
_cell_angle_gamma                62.908(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0117(5)
_cell_length_b                   10.6661(8)
_cell_length_c                   12.2753(9)
_cell_measurement_reflns_used    na
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      na
_cell_measurement_theta_min      na
_cell_volume                     1119.42(13)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
 ?
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '9.091 pixels/mm'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_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  0.0767
_diffrn_reflns_av_sigmaI/netI    0.1198
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8067
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         3.26
_diffrn_standards_decay_%        na
_diffrn_standards_interval_count na
_diffrn_standards_interval_time  na
_diffrn_standards_number         'not measured'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9916
_exptl_absorpt_correction_type   'Empirical, SORTAV'
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.013(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   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                1568
_reflns_number_total             3169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001830isup1.cif
_cod_data_source_block           s92-3
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7213306
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
O1 O 0.8439(2) 0.3568(3) 0.3073(2) 0.0636(8) Uani 1 1 d .
N1 N 1.1696(3) 0.5842(3) 0.0080(3) 0.0496(8) Uani 1 1 d .
O4 O 1.2665(2) 0.2695(3) -0.0316(3) 0.0671(8) Uani 1 1 d .
O3 O 1.3308(3) 0.2511(3) 0.1277(2) 0.0631(8) Uani 1 1 d .
N2 N 1.2853(3) 0.7457(3) -0.1162(3) 0.0559(9) Uani 1 1 d .
O2 O 1.0484(3) 0.2000(3) 0.2217(3) 0.0797(9) Uani 1 1 d .
C6 C 1.7401(3) 0.6370(4) -0.4716(4) 0.0498(10) Uani 1 1 d .
C18 C 1.1398(3) 0.4564(4) 0.0738(3) 0.0466(10) Uani 1 1 d .
C17 C 1.0645(3) 0.7231(4) 0.0330(4) 0.0555(10) Uani 1 1 d .
H17A H 1.0439 0.7207 0.1186 0.067 Uiso 1 1 calc R
H17B H 0.9768 0.7459 0.0165 0.067 Uiso 1 1 calc R
C14 C 1.4270(3) 0.4951(4) -0.1227(3) 0.0500(10) Uani 1 1 d .
H14A H 1.4060 0.4489 -0.1629 0.060 Uiso 1 1 calc R
H14B H 1.4586 0.4207 -0.0513 0.060 Uiso 1 1 calc R
C13 C 1.5457(3) 0.5547(4) -0.2140(3) 0.0499(10) Uani 1 1 d .
H13A H 1.5698 0.5955 -0.1715 0.060 Uiso 1 1 calc R
H13B H 1.5107 0.6342 -0.2818 0.060 Uiso 1 1 calc R
C7 C 1.7697(3) 0.4837(4) -0.3887(3) 0.0473(10) Uani 1 1 d .
C19 C 1.0135(3) 0.4550(4) 0.1592(3) 0.0526(10) Uani 1 1 d .
H19 H 0.9467 0.5433 0.1745 0.063 Uiso 1 1 calc R
C12 C 1.6803(3) 0.4421(4) -0.2692(4) 0.0477(10) Uani 1 1 d .
C15 C 1.2945(3) 0.6130(4) -0.0785(3) 0.0479(10) Uani 1 1 d .
C1 C 1.7144(3) 0.7540(5) -0.4329(4) 0.0599(11) Uani 1 1 d .
H1 H 1.7137 0.7381 -0.3522 0.072 Uiso 1 1 calc R
C16 C 1.1400(3) 0.8331(4) -0.0593(4) 0.0622(11) Uani 1 1 d .
H16A H 1.0912 0.8999 -0.1228 0.075 Uiso 1 1 calc R
H16B H 1.1423 0.8899 -0.0161 0.075 Uiso 1 1 calc R
C11 C 1.7167(3) 0.2950(4) -0.2018(4) 0.0626(11) Uani 1 1 d .
H11 H 1.6584 0.2664 -0.1222 0.075 Uiso 1 1 calc R
C10 C 1.8375(4) 0.1897(4) -0.2498(4) 0.0698(12) Uani 1 1 d .
H10 H 1.8593 0.0916 -0.2033 0.084 Uiso 1 1 calc R
C8 C 1.8912(3) 0.3759(5) -0.4351(4) 0.0606(11) Uani 1 1 d .
H8 H 1.9508 0.4026 -0.5144 0.073 Uiso 1 1 calc R
C20 C 0.9763(4) 0.3224(5) 0.2287(4) 0.0566(11) Uani 1 1 d .
C21 C 0.7903(4) 0.2374(4) 0.3870(4) 0.0661(12) Uani 1 1 d .
H21A H 0.8547 0.1622 0.4359 0.079 Uiso 1 1 calc R
H21B H 0.7803 0.1937 0.3374 0.079 Uiso 1 1 calc R
C5 C 1.7422(3) 0.6664(5) -0.5940(4) 0.0612(11) Uani 1 1 d .
H5 H 1.7598 0.5900 -0.6227 0.073 Uiso 1 1 calc R
C2 C 1.6897(4) 0.8944(5) -0.5139(5) 0.0719(13) Uani 1 1 d .
H2 H 1.6717 0.9721 -0.4865 0.086 Uiso 1 1 calc R
C3 C 1.6915(4) 0.9207(5) -0.6335(5) 0.0748(14) Uani 1 1 d .
H3 H 1.6743 1.0156 -0.6870 0.090 Uiso 1 1 calc R
C22 C 0.6484(4) 0.3022(4) 0.4711(4) 0.0733(13) Uani 1 1 d .
H22A H 0.6613 0.3339 0.5269 0.110 Uiso 1 1 calc R
H22B H 0.6031 0.2295 0.5187 0.110 Uiso 1 1 calc R
H22C H 0.5900 0.3846 0.4216 0.110 Uiso 1 1 calc R
C9 C 1.9248(4) 0.2312(5) -0.3664(5) 0.0710(13) Uani 1 1 d .
H9 H 2.0068 0.1614 -0.3989 0.085 Uiso 1 1 calc R
C4 C 1.7187(4) 0.8069(6) -0.6733(4) 0.0733(13) Uani 1 1 d .
H4 H 1.7215 0.8239 -0.7549 0.088 Uiso 1 1 calc R
C23 C 1.2511(4) 0.3153(4) 0.0494(4) 0.0507(10) Uani 1 1 d .
C24 C 1.4474(4) 0.1111(5) 0.1190(5) 0.0912(15) Uani 1 1 d .
H24A H 1.4824 0.1055 0.0338 0.109 Uiso 1 1 calc R
H24B H 1.5250 0.1062 0.1407 0.109 Uiso 1 1 calc R
C25 C 1.4004(5) -0.0105(5) 0.2012(5) 0.1131(18) Uani 1 1 d .
H25A H 1.3620 -0.0029 0.2851 0.170 Uiso 1 1 calc R
H25B H 1.4793 -0.1005 0.1976 0.170 Uiso 1 1 calc R
H25C H 1.3283 -0.0097 0.1761 0.170 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
C20 O1 C21 117.0(3)
C18 N1 C15 132.4(3)
C18 N1 C17 119.8(2)
C15 N1 C17 107.5(3)
C23 O3 C24 119.3(3)
C15 N2 C16 108.8(3)
C1 C6 C5 117.5(4)
C1 C6 C7 122.3(4)
C5 C6 C7 120.1(4)
C19 C18 N1 121.8(3)
C19 C18 C23 119.5(3)
N1 C18 C23 118.7(3)
N1 C17 C16 102.2(2)
C15 C14 C13 112.1(3)
C14 C13 C12 114.7(3)
C8 C7 C12 118.8(3)
C8 C7 C6 117.6(3)
C12 C7 C6 123.6(3)
C18 C19 C20 123.5(3)
C11 C12 C7 118.5(3)
C11 C12 C13 120.3(3)
C7 C12 C13 121.2(3)
N2 C15 N1 114.9(3)
N2 C15 C14 122.5(3)
N1 C15 C14 122.6(3)
C2 C1 C6 120.4(4)
N2 C16 C17 106.2(3)
C10 C11 C12 121.8(4)
C9 C10 C11 119.4(4)
C9 C8 C7 121.5(4)
O2 C20 O1 123.2(3)
O2 C20 C19 127.5(3)
O1 C20 C19 109.3(3)
O1 C21 C22 106.4(3)
C4 C5 C6 121.1(4)
C3 C2 C1 121.0(4)
C4 C3 C2 119.3(4)
C10 C9 C8 120.0(4)
C3 C4 C5 120.7(5)
O4 C23 O3 125.5(4)
O4 C23 C18 124.0(4)
O3 C23 C18 110.5(4)
C25 C24 O3 110.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C20 1.351(4)
O1 C21 1.446(4)
N1 C18 1.373(4)
N1 C15 1.417(4)
N1 C17 1.466(4)
O4 C23 1.202(4)
O3 C23 1.331(4)
O3 C24 1.470(4)
N2 C15 1.261(4)
N2 C16 1.473(4)
O2 C20 1.199(4)
C6 C1 1.387(5)
C6 C5 1.394(5)
C6 C7 1.489(5)
C18 C19 1.350(4)
C18 C23 1.499(5)
C17 C16 1.531(4)
C14 C15 1.497(4)
C14 C13 1.519(4)
C13 C12 1.522(4)
C7 C8 1.395(5)
C7 C12 1.403(4)
C19 C20 1.457(5)
C12 C11 1.388(5)
C1 C2 1.385(5)
C11 C10 1.384(5)
C10 C9 1.371(5)
C8 C9 1.372(5)
C21 C22 1.500(5)
C5 C4 1.378(5)
C2 C3 1.369(6)
C3 C4 1.358(6)
C24 C25 1.432(5)
