#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:39:33 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258088 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/00/7240049.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_7240049
loop_
_publ_author_name
'Changunda, Charles R. K.'
'Venkatesh, B. C.'
'Mokone, William K.'
'Rousseau, Amanda L.'
'Brady, Dean'
'Fernandes, Manuel A.'
'Bode, Moira L.'
_publ_section_title
;
 Efficient one-pot synthesis of functionalised imidazo[1,2-a]pyridines and
 unexpected synthesis of novel tetracyclic derivatives by nucleophilic
 aromatic substitution
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              8104
_journal_page_last               8114
_journal_paper_doi               10.1039/C9RA10447J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C20 H16 N4 O'
_chemical_formula_sum            'C20 H16 N4 O'
_chemical_formula_weight         328.37
_chemical_melting_point          404.0(10)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-20 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.116(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0432(7)
_cell_length_b                   7.3016(4)
_cell_length_c                   18.3346(12)
_cell_measurement_reflns_used    816
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.55
_cell_measurement_theta_min      2.23
_cell_volume                     1603.07(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 Ver. 2013.10-0 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1479
_diffrn_reflns_av_unetI/netI     0.2114
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         1.933
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.716
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.716
_refine_ls_R_factor_all          0.1629
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0135P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1032
_reflns_number_total             2831
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra10447j2.cif
_cod_data_source_block           cmpd_17C
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '403-405' was changed to
'404.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7240048--7240049.cif.
;
_cod_database_code               7240049
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C17(H17), C19(H19)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.4787(3) 0.8520(4) 0.41290(16) 0.0292(8) Uani 1 1 d . . . . .
C2 C 0.3985(3) 0.9114(4) 0.35751(15) 0.0328(9) Uani 1 1 d . . . . .
H2 H 0.420216 0.963562 0.313727 0.039 Uiso 1 1 calc R . . . .
C3 C 0.2881(3) 0.8931(4) 0.36736(17) 0.0374(9) Uani 1 1 d . . . . .
H3 H 0.232614 0.934529 0.330335 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2560(2) 0.8140(4) 0.43133(16) 0.0334(9) Uani 1 1 d . . . . .
H4 H 0.178854 0.801693 0.437119 0.040 Uiso 1 1 calc R . . . .
C5 C 0.3333(3) 0.7549(4) 0.48504(16) 0.0290(8) Uani 1 1 d . . . . .
C6 C 0.3568(2) 0.6984(4) 0.61793(15) 0.0328(9) Uani 1 1 d . . . . .
H6 H 0.358768 0.833965 0.625785 0.039 Uiso 1 1 calc R . . . .
C7 C 0.2736(2) 0.6148(4) 0.66518(14) 0.0370(9) Uani 1 1 d . . . . .
H7A H 0.206960 0.694671 0.663268 0.044 Uiso 1 1 calc R . . . .
H7B H 0.249308 0.494279 0.644458 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3206(2) 0.5892(4) 0.74470(15) 0.0405(10) Uani 1 1 d . . . . .
H8A H 0.341310 0.709689 0.766914 0.049 Uiso 1 1 calc R . . . .
H8B H 0.263266 0.533354 0.772604 0.049 Uiso 1 1 calc R . . . .
C9 C 0.4221(2) 0.4671(4) 0.74866(16) 0.0453(10) Uani 1 1 d . . . . .
H9A H 0.401385 0.347109 0.726042 0.054 Uiso 1 1 calc R . . . .
H9B H 0.450780 0.446005 0.800605 0.054 Uiso 1 1 calc R . . . .
C10 C 0.5127(2) 0.5559(4) 0.70857(15) 0.0376(9) Uani 1 1 d . . . . .
H10A H 0.544671 0.660139 0.738307 0.045 Uiso 1 1 calc R . . . .
H10B H 0.573234 0.465637 0.705088 0.045 Uiso 1 1 calc R . . . .
C11 C 0.4737(2) 0.6250(4) 0.63184(16) 0.0270(8) Uani 1 1 d . . . . .
C12 C 0.5413(2) 0.7181(4) 0.52059(16) 0.0249(8) Uani 1 1 d . . . . .
C13 C 0.6288(3) 0.7698(4) 0.48062(16) 0.0262(8) Uani 1 1 d . . . . .
C14 C 0.7489(3) 0.7501(4) 0.49993(15) 0.0265(8) Uani 1 1 d . . . . .
C15 C 0.8205(2) 0.8163(4) 0.45113(16) 0.0331(9) Uani 1 1 d . . . . .
H15 H 0.789587 0.873748 0.407088 0.040 Uiso 1 1 calc R . . . .
C16 C 0.9355(2) 0.8008(4) 0.46503(16) 0.0376(9) Uani 1 1 d . . . . .
H16 H 0.982380 0.847604 0.430893 0.045 Uiso 1 1 calc R . . . .
C17 C 0.9818(2) 0.7168(4) 0.52894(15) 0.0367(9) Uani 1 1 d . . . . .
H17 H 1.060470 0.705605 0.539233 0.044 Uiso 1 1 calc R . . . .
C18 C 0.9113(3) 0.6496(4) 0.57749(15) 0.0291(8) Uani 1 1 d . . . . .
C19 C 0.7962(2) 0.6657(4) 0.56392(16) 0.0297(8) Uani 1 1 d . . . . .
H19 H 0.749658 0.619152 0.598285 0.036 Uiso 1 1 calc R . . . .
C20 C 0.9581(3) 0.5540(5) 0.64250(19) 0.0390(10) Uani 1 1 d . . . . .
N1 N 0.5900(2) 0.8513(3) 0.41535(12) 0.0291(7) Uani 1 1 d . . . . .
N2 N 0.4447(2) 0.7733(3) 0.47676(13) 0.0261(7) Uani 1 1 d . . . . .
N3 N 0.55106(19) 0.6381(3) 0.58857(13) 0.0285(7) Uani 1 1 d . . . . .
N4 N 0.9962(2) 0.4755(4) 0.69366(15) 0.0543(9) Uani 1 1 d . . . . .
O1 O 0.30450(15) 0.6604(3) 0.54335(10) 0.0330(6) 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 N2 119.6(3) . . ?
N1 C1 C2 129.8(3) . . ?
N1 C1 N2 110.6(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 N2 119.6(3) . . ?
O1 C5 C4 121.7(3) . . ?
O1 C5 N2 118.3(3) . . ?
C7 C6 H6 108.8 . . ?
C11 C6 H6 108.8 . . ?
C11 C6 C7 115.0(3) . . ?
O1 C6 H6 108.8 . . ?
O1 C6 C7 102.2(2) . . ?
O1 C6 C11 113.1(3) . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.3(2) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 109.6(3) . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C8 C9 C10 110.1(3) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 114.9(3) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C6 C11 C10 117.8(3) . . ?
N3 C11 C6 126.4(3) . . ?
N3 C11 C10 114.9(3) . . ?
C13 C12 N2 104.4(2) . . ?
N3 C12 C13 126.5(3) . . ?
N3 C12 N2 129.1(3) . . ?
C12 C13 C14 129.0(3) . . ?
N1 C13 C12 111.6(3) . . ?
N1 C13 C14 119.3(3) . . ?
C15 C14 C13 118.4(3) . . ?
C19 C14 C13 123.6(3) . . ?
C19 C14 C15 118.0(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C19 121.6(3) . . ?
C17 C18 C20 119.3(3) . . ?
C19 C18 C20 119.0(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
N4 C20 C18 178.8(4) . . ?
C1 N1 C13 106.1(3) . . ?
C5 N2 C1 120.5(3) . . ?
C5 N2 C12 132.1(3) . . ?
C12 N2 C1 107.3(2) . . ?
C11 N3 C12 126.4(3) . . ?
C5 O1 C6 121.3(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
C1 C2 1.394(3) . ?
C1 N1 1.337(3) . ?
C1 N2 1.404(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.352(3) . ?
C5 N2 1.373(3) . ?
C5 O1 1.348(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.521(3) . ?
C6 C11 1.502(4) . ?
C6 O1 1.470(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.518(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.509(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.521(3) . ?
C11 N3 1.290(3) . ?
C12 C13 1.398(4) . ?
C12 N2 1.401(3) . ?
C12 N3 1.370(3) . ?
C13 C14 1.460(4) . ?
C13 N1 1.373(3) . ?
C14 C15 1.393(4) . ?
C14 C19 1.392(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(4) . ?
C18 C19 1.386(4) . ?
C18 C20 1.443(4) . ?
C19 H19 0.9500 . ?
C20 N4 1.152(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C1 N1 C13 -176.9(3) . . . . ?
C2 C1 N2 C5 -0.1(4) . . . . ?
C2 C1 N2 C12 176.9(3) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 N2 0.2(4) . . . . ?
C3 C4 C5 O1 -172.6(3) . . . . ?
C4 C5 N2 C1 -0.4(4) . . . . ?
C4 C5 N2 C12 -176.6(3) . . . . ?
C4 C5 O1 C6 -137.7(3) . . . . ?
C6 C7 C8 C9 -58.8(3) . . . . ?
C6 C11 N3 C12 -1.6(5) . . . . ?
C7 C6 C11 C10 -29.2(4) . . . . ?
C7 C6 C11 N3 161.7(3) . . . . ?
C7 C6 O1 C5 160.7(3) . . . . ?
C7 C8 C9 C10 61.8(3) . . . . ?
C8 C9 C10 C11 -49.4(4) . . . . ?
C9 C10 C11 C6 33.5(4) . . . . ?
C9 C10 C11 N3 -156.1(3) . . . . ?
C10 C11 N3 C12 -171.0(3) . . . . ?
C11 C6 C7 C8 41.8(4) . . . . ?
C11 C6 O1 C5 -75.1(4) . . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?
C12 C13 C14 C19 2.5(5) . . . . ?
C12 C13 N1 C1 -0.2(3) . . . . ?
C13 C12 N2 C1 0.9(3) . . . . ?
C13 C12 N2 C5 177.4(3) . . . . ?
C13 C12 N3 C11 164.5(3) . . . . ?
C13 C14 C15 C16 -179.2(3) . . . . ?
C13 C14 C19 C18 178.8(3) . . . . ?
C14 C13 N1 C1 -179.4(2) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C14 C19 C18 0.0(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C16 C17 C18 C20 177.0(3) . . . . ?
C17 C18 C19 C14 0.4(5) . . . . ?
C19 C14 C15 C16 -0.3(5) . . . . ?
C20 C18 C19 C14 -177.1(3) . . . . ?
N1 C1 C2 C3 178.3(3) . . . . ?
N1 C1 N2 C5 -178.1(3) . . . . ?
N1 C1 N2 C12 -1.0(3) . . . . ?
N1 C13 C14 C15 0.4(4) . . . . ?
N1 C13 C14 C19 -178.4(3) . . . . ?
N2 C1 C2 C3 0.7(4) . . . . ?
N2 C1 N1 C13 0.8(3) . . . . ?
N2 C5 O1 C6 49.4(4) . . . . ?
N2 C12 C13 C14 178.7(3) . . . . ?
N2 C12 C13 N1 -0.4(3) . . . . ?
N2 C12 N3 C11 -12.7(5) . . . . ?
N3 C12 C13 C14 0.9(5) . . . . ?
N3 C12 C13 N1 -178.2(3) . . . . ?
N3 C12 N2 C1 178.5(3) . . . . ?
N3 C12 N2 C5 -4.9(5) . . . . ?
O1 C5 N2 C1 172.7(3) . . . . ?
O1 C5 N2 C12 -3.5(5) . . . . ?
O1 C6 C7 C8 164.7(2) . . . . ?
O1 C6 C11 C10 -146.0(3) . . . . ?
O1 C6 C11 N3 44.9(4) . . . . ?
