#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:04:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180464 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/33/7213304.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_7213304
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            'C16 H16 N2 O3'
_chemical_formula_weight         284.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.1760(10)
_cell_length_b                   17.805(4)
_cell_length_c                   20.947(4)
_cell_measurement_reflns_used    16412
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      1.94
_cell_volume                     2676.4(9)
_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_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_av_sigmaI/netI    0.1167
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16412
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.935
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.815
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.815
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0576
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1595
_reflns_number_gt                1594
_reflns_number_total             3062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001830isup1.cif
_cod_data_source_block           s92
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7213304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
O1 O 0.7079(2) -0.06148(9) 0.89174(8) 0.0294(5) Uani 1 1 d .
O2 O 0.5439(2) 0.11100(10) 0.71227(9) 0.0310(5) Uani 1 1 d .
O3 O 0.6570(2) 0.01289(10) 0.65741(8) 0.0303(5) Uani 1 1 d .
N1 N 0.8375(3) -0.24328(12) 0.73077(10) 0.0238(5) Uani 1 1 d .
H1 H 0.8796 -0.2861 0.7431 0.029 Uiso 1 1 calc R
N2 N 0.7362(3) -0.12630(11) 0.73507(10) 0.0218(5) Uani 1 1 d .
C1 C 0.8179(3) -0.30694(14) 0.87865(12) 0.0239(6) Uani 1 1 d .
H1A H 0.7649 -0.3259 0.8415 0.029 Uiso 1 1 calc R
C2 C 0.8766(3) -0.35619(15) 0.92605(13) 0.0282(6) Uani 1 1 d .
H2 H 0.8631 -0.4077 0.9202 0.034 Uiso 1 1 calc R
C3 C 0.9549(3) -0.32919(15) 0.98181(13) 0.0284(6) Uani 1 1 d .
H3 H 0.9954 -0.3622 1.0133 0.034 Uiso 1 1 calc R
C4 C 0.9723(3) -0.25274(15) 0.99027(12) 0.0253(6) Uani 1 1 d .
H4 H 1.0246 -0.2343 1.0277 0.030 Uiso 1 1 calc R
C5 C 0.9130(3) -0.20321(15) 0.94371(12) 0.0233(6) Uani 1 1 d .
H5 H 0.9233 -0.1518 0.9506 0.028 Uiso 1 1 calc R
C6 C 0.8372(3) -0.22969(13) 0.88596(12) 0.0204(6) Uani 1 1 d .
C7 C 0.7863(3) -0.17621(13) 0.83581(12) 0.0198(6) Uani 1 1 d .
C8 C 0.7904(3) -0.18838(13) 0.77010(12) 0.0205(6) Uani 1 1 d .
C9 C 0.8096(3) -0.22268(14) 0.66359(12) 0.0243(6) Uani 1 1 d .
H9A H 0.7089 -0.2515 0.6448 0.029 Uiso 1 1 calc R
H9B H 0.9223 -0.2309 0.6390 0.029 Uiso 1 1 calc R
C10 C 0.7605(3) -0.13912(13) 0.66624(11) 0.0209(6) Uani 1 1 d .
H10A H 0.8604 -0.1085 0.6491 0.025 Uiso 1 1 calc R
H10B H 0.6465 -0.1286 0.6430 0.025 Uiso 1 1 calc R
C11 C 0.6990(3) -0.06748(13) 0.77600(11) 0.0185(6) Uani 1 1 d .
C12 C 0.7309(3) -0.09991(14) 0.84293(12) 0.0216(6) Uani 1 1 d .
C13 C 0.6435(3) 0.00391(14) 0.76862(12) 0.0227(6) Uani 1 1 d .
H13 H 0.6237 0.0297 0.8066 0.027 Uiso 1 1 calc R
C14 C 0.6089(3) 0.04789(15) 0.71115(12) 0.0231(6) Uani 1 1 d .
C15 C 0.6336(4) 0.05382(15) 0.59785(13) 0.0344(7) Uani 1 1 d .
H15A H 0.6934 0.1026 0.6005 0.041 Uiso 1 1 calc R
H15B H 0.5023 0.0613 0.5889 0.041 Uiso 1 1 calc R
C16 C 0.7220(4) 0.00747(16) 0.54650(13) 0.0357(7) Uani 1 1 d .
H16A H 0.8497 -0.0022 0.5574 0.054 Uiso 1 1 calc R
H16B H 0.7167 0.0342 0.5067 0.054 Uiso 1 1 calc R
H16C H 0.6564 -0.0393 0.5425 0.054 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
C14 O3 C15 117.42(19)
C8 N1 C9 112.2(2)
C11 N2 C8 109.4(2)
C11 N2 C10 138.6(2)
C8 N2 C10 111.27(19)
C2 C1 C6 121.0(2)
C3 C2 C1 120.5(3)
C4 C3 C2 119.3(2)
C3 C4 C5 120.8(2)
C4 C5 C6 120.8(2)
C1 C6 C5 117.7(2)
C1 C6 C7 122.6(2)
C5 C6 C7 119.7(2)
C8 C7 C12 105.0(2)
C8 C7 C6 127.0(2)
C12 C7 C6 128.0(2)
N1 C8 N2 109.4(2)
N1 C8 C7 137.4(2)
N2 C8 C7 113.2(2)
N1 C9 C10 103.86(19)
N2 C10 C9 102.35(19)
C13 C11 N2 134.9(2)
C13 C11 C12 120.4(2)
N2 C11 C12 104.7(2)
O1 C12 C7 130.5(2)
O1 C12 C11 121.7(2)
C7 C12 C11 107.8(2)
C11 C13 C14 130.9(2)
O2 C14 O3 123.2(2)
O2 C14 C13 123.1(2)
O3 C14 C13 113.7(2)
O3 C15 C16 106.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.241(3)
O2 C14 1.217(3)
O3 C14 1.332(3)
O3 C15 1.455(3)
N1 C8 1.322(3)
N1 C9 1.468(3)
N2 C11 1.379(3)
N2 C8 1.383(3)
N2 C10 1.470(3)
C1 C2 1.390(3)
C1 C6 1.391(3)
C2 C3 1.383(4)
C3 C4 1.378(4)
C4 C5 1.382(3)
C5 C6 1.407(3)
C6 C7 1.464(3)
C7 C8 1.394(3)
C7 C12 1.423(3)
C9 C10 1.530(3)
C11 C13 1.341(3)
C11 C12 1.534(3)
C13 C14 1.457(3)
C15 C16 1.497(4)
