#------------------------------------------------------------------------------
#$Date: 2020-05-28 02:27:46 +0300 (Thu, 28 May 2020) $
#$Revision: 252410 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038426.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_4038426
loop_
_publ_author_name
'Patel, Om P. S.'
'Jaspal, Sonam'
'Shinde, Vikki N.'
'Nandwana, Nitesh Kumar'
'Rangan, Krishnan'
'Kumar, Anil'
_publ_section_title
;
 PIDA-Mediated 1,2-ipso-Migration in Mannich Bases of
 Imidazo[1,2-a]pyridines: Preparation of N-Acetoxymethyl/
 Alkoxymethyl-N-arylimidazo[1,2-a]pyridine-3-amines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00674
_journal_year                    2020
_chemical_formula_moiety         'C20 H18 N4 O'
_chemical_formula_sum            'C20 H18 N4 O'
_chemical_formula_weight         330.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                69.082(6)
_cell_angle_beta                 84.898(6)
_cell_angle_gamma                88.480(5)
_cell_formula_units_Z            2
_cell_length_a                   8.7653(6)
_cell_length_b                   9.1903(6)
_cell_length_c                   11.0216(7)
_cell_measurement_reflns_used    5984
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      31.0030
_cell_measurement_theta_min      3.2990
_cell_volume                     826.04(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -78.00  15.00   0.50   15.00    --   -3.60 -37.00 -60.00  186
  2  ω      7.00  36.00   0.50   15.00    --    3.60  37.00  30.00   58
  3  ω    -14.00  91.00   0.50   15.00    --    3.60  19.00 -60.00  210
  4  ω     23.00  64.00   0.50   15.00    --    3.60  57.00 120.00   82
  5  ω    -15.00  87.00   0.50   15.00    --    3.60  37.00-180.00  204
  6  ω    -29.00  77.00   0.50   15.00    --    3.60  82.00-120.00  212
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288533000
_diffrn_orient_matrix_UB_12      -0.0675087000
_diffrn_orient_matrix_UB_13      0.0515986000
_diffrn_orient_matrix_UB_21      0.0112140000
_diffrn_orient_matrix_UB_22      -0.0437306000
_diffrn_orient_matrix_UB_23      -0.0416180000
_diffrn_orient_matrix_UB_31      0.0751161000
_diffrn_orient_matrix_UB_32      -0.0189017000
_diffrn_orient_matrix_UB_33      0.0196692000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14537
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.248
_diffrn_reflns_theta_min         3.190
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       Block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0779
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1196P)²+1.4260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2427
_refine_ls_wR_factor_ref         0.2546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3661
_reflns_number_total             4603
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00674_si_003.cif
_cod_data_source_block           exp_427-osp-2-211
_cod_database_code               4038426
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C11(H11), C13(H13), C5(H5), C16(H16), C9(H9), C17(H17),
 C10(H10), C12(H12), C4(H4), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.651
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5508(2) 0.6385(2) 0.10773(18) 0.0244(4) Uani 1 1 d . . . . .
N3 N 0.6437(2) 0.4166(2) 0.26524(19) 0.0174(4) Uani 1 1 d . . . . .
N2 N 0.3916(2) 0.2047(2) 0.5540(2) 0.0190(4) Uani 1 1 d . . . . .
N1 N 0.3824(2) 0.3166(2) 0.33637(19) 0.0170(4) Uani 1 1 d . . . . .
N4 N 0.8002(2) 0.3996(2) 0.08788(19) 0.0199(4) Uani 1 1 d . . . . .
C14 C 0.7144(3) 0.3243(3) 0.1990(2) 0.0159(4) Uani 1 1 d . . . . .
C15 C 0.6957(3) 0.1612(3) 0.2504(2) 0.0184(5) Uani 1 1 d . . . . .
H15 H 0.635251 0.113055 0.327613 0.022 Uiso 1 1 calc R . . . .
C7 C 0.5296(3) 0.2768(3) 0.4981(2) 0.0168(4) Uani 1 1 d . . . . .
C1 C 0.3039(3) 0.2301(3) 0.4550(2) 0.0179(5) Uani 1 1 d . . . . .
C18 C 0.8697(3) 0.3119(3) 0.0247(2) 0.0229(5) Uani 1 1 d . . . . .
H18 H 0.929718 0.362431 -0.052312 0.027 Uiso 1 1 calc R . . . .
C11 C 0.9098(3) 0.2380(3) 0.7239(2) 0.0219(5) Uani 1 1 d . . . . .
H11 H 0.993408 0.228618 0.772513 0.026 Uiso 1 1 calc R . . . .
C8 C 0.6606(3) 0.2660(3) 0.5757(2) 0.0169(5) Uani 1 1 d . . . . .
C6 C 0.5273(3) 0.3479(3) 0.3644(2) 0.0169(4) Uani 1 1 d . . . . .
C13 C 0.6926(3) 0.1227(3) 0.6721(2) 0.0212(5) Uani 1 1 d . . . . .
H13 H 0.630182 0.036659 0.687224 0.025 Uiso 1 1 calc R . . . .
C5 C 0.3192(3) 0.3552(3) 0.2187(2) 0.0211(5) Uani 1 1 d . . . . .
H5 H 0.374842 0.411908 0.140914 0.025 Uiso 1 1 calc R . . . .
C16 C 0.7692(3) 0.0745(3) 0.1834(2) 0.0207(5) Uani 1 1 d . . . . .
H16 H 0.760047 -0.033448 0.215236 0.025 Uiso 1 1 calc R . . . .
C9 C 0.7539(3) 0.3944(3) 0.5551(2) 0.0195(5) Uani 1 1 d . . . . .
H9 H 0.733813 0.489474 0.491148 0.023 Uiso 1 1 calc R . . . .
C17 C 0.8579(3) 0.1515(3) 0.0666(2) 0.0236(5) Uani 1 1 d . . . . .
H17 H 0.907500 0.096313 0.018619 0.028 Uiso 1 1 calc R . . . .
C19 C 0.6536(3) 0.5843(3) 0.2067(2) 0.0184(5) Uani 1 1 d . . . . .
H19A H 0.627973 0.630167 0.272661 0.022 Uiso 1 1 calc R . . . .
H19B H 0.757421 0.615348 0.169555 0.022 Uiso 1 1 calc R . . . .
C10 C 0.8774(3) 0.3811(3) 0.6301(2) 0.0222(5) Uani 1 1 d . . . . .
H10 H 0.937905 0.467713 0.617420 0.027 Uiso 1 1 calc R . . . .
C12 C 0.8174(3) 0.1093(3) 0.7447(2) 0.0238(5) Uani 1 1 d . . . . .
H12 H 0.839072 0.013942 0.807529 0.029 Uiso 1 1 calc R . . . .
C4 C 0.1735(3) 0.3081(3) 0.2196(3) 0.0243(5) Uani 1 1 d . . . . .
H4 H 0.128982 0.332056 0.141345 0.029 Uiso 1 1 calc R . . . .
C2 C 0.1516(3) 0.1835(3) 0.4555(3) 0.0231(5) Uani 1 1 d . . . . .
H2 H 0.095663 0.127417 0.533303 0.028 Uiso 1 1 calc R . . . .
C3 C 0.0879(3) 0.2224(3) 0.3389(3) 0.0247(5) Uani 1 1 d . . . . .
H3 H -0.012313 0.192570 0.337739 0.030 Uiso 1 1 calc R . . . .
C20 C 0.5575(4) 0.8034(3) 0.0479(3) 0.0305(6) Uani 1 1 d . . . . .
H20A H 0.492887 0.836405 -0.022931 0.046 Uiso 1 1 calc GR . . . .
H20B H 0.661079 0.835517 0.015232 0.046 Uiso 1 1 calc GR . . . .
H20C H 0.522889 0.849742 0.110838 0.046 Uiso 1 1 calc GR . . . .
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
C19 O1 C20 111.1(2) . . ?
C14 N3 C6 117.83(19) . . ?
C14 N3 C19 119.78(19) . . ?
C6 N3 C19 119.4(2) . . ?
C1 N2 C7 105.52(19) . . ?
C1 N1 C6 106.62(19) . . ?
C5 N1 C1 122.8(2) . . ?
C5 N1 C6 130.5(2) . . ?
C14 N4 C18 116.9(2) . . ?
N3 C14 C15 120.3(2) . . ?
N4 C14 N3 116.5(2) . . ?
N4 C14 C15 123.2(2) . . ?
C16 C15 C14 118.4(2) . . ?
N2 C7 C8 121.7(2) . . ?
N2 C7 C6 111.1(2) . . ?
C6 C7 C8 127.1(2) . . ?
N2 C1 N1 111.2(2) . . ?
N2 C1 C2 130.1(2) . . ?
N1 C1 C2 118.7(2) . . ?
N4 C18 C17 124.3(2) . . ?
C12 C11 C10 120.0(2) . . ?
C13 C8 C7 119.2(2) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 C13 119.4(2) . . ?
N1 C6 N3 121.8(2) . . ?
C7 C6 N3 131.9(2) . . ?
C7 C6 N1 105.5(2) . . ?
C12 C13 C8 120.1(2) . . ?
C4 C5 N1 118.2(2) . . ?
C15 C16 C17 119.0(2) . . ?
C8 C9 C10 120.3(2) . . ?
C18 C17 C16 118.1(2) . . ?
O1 C19 N3 109.54(19) . . ?
C11 C10 C9 120.0(2) . . ?
C13 C12 C11 120.2(2) . . ?
C5 C4 C3 120.9(2) . . ?
C3 C2 C1 118.7(2) . . ?
C2 C3 C4 120.7(2) . . ?
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
O1 C19 1.419(3) . ?
O1 C20 1.421(3) . ?
N3 C14 1.404(3) . ?
N3 C6 1.406(3) . ?
N3 C19 1.444(3) . ?
N2 C7 1.378(3) . ?
N2 C1 1.339(3) . ?
N1 C1 1.394(3) . ?
N1 C6 1.394(3) . ?
N1 C5 1.380(3) . ?
N4 C14 1.343(3) . ?
N4 C18 1.344(3) . ?
C14 C15 1.409(3) . ?
C15 C16 1.379(3) . ?
C7 C8 1.472(3) . ?
C7 C6 1.384(3) . ?
C1 C2 1.412(3) . ?
C18 C17 1.382(4) . ?
C11 C10 1.393(4) . ?
C11 C12 1.390(4) . ?
C8 C13 1.406(3) . ?
C8 C9 1.393(3) . ?
C13 C12 1.389(3) . ?
C5 C4 1.357(4) . ?
C16 C17 1.401(3) . ?
C9 C10 1.396(3) . ?
C4 C3 1.424(4) . ?
C2 C3 1.371(4) . ?
