#------------------------------------------------------------------------------
#$Date: 2019-09-20 06:25:54 +0300 (Fri, 20 Sep 2019) $
#$Revision: 218569 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233988.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_7233988
loop_
_publ_author_name
'Sivappa, Rasapalli'
'Sammeta, Vamshikrishna Reddy'
'Huang, Yanchang'
'Golen, James A.'
'Savinov, Sergey N.'
_publ_section_title
;
 Facile synthesis of 3-substituted imidazo[1,2-a]pyridines through
 formimidamide chemistry
;
_journal_issue                   51
_journal_name_full               'RSC Advances'
_journal_page_first              29659
_journal_paper_doi               10.1039/C9RA05841A
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C15 H20 Br N3 O'
_chemical_formula_weight         338.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2019-06-10 deposited with the CCDC.    2019-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.622(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.110(3)
_cell_length_b                   10.9556(18)
_cell_length_c                   17.217(3)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      24.74
_cell_measurement_theta_min      3.03
_cell_volume                     3217.6(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39434
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.462
_diffrn_reflns_theta_min         3.030
_exptl_absorpt_coefficient_mu    2.555
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0387
_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)+(0.0595P)²+2.6844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2305
_reflns_number_total             2977
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra05841a2.cif
_cod_data_source_block           UMD1780g_a
_cod_original_cell_volume        3217.5(10)
_cod_database_code               7233988
_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_min   0.535
_shelx_estimated_absorpt_t_max   0.629
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Br1 Br 0.40771(2) 0.30770(3) 0.55108(2) 0.05904(16) Uani 1 1 d . .
O1 O 0.22685(17) 0.4170(2) 0.4780(2) 0.0865(9) Uani 1 1 d D .
H1WB H 0.2719(17) 0.379(5) 0.486(4) 0.130 Uiso 1 1 d D U
H1WA H 0.193(3) 0.357(3) 0.461(3) 0.130 Uiso 1 1 d D U
N1 N 0.32470(14) 0.68487(19) 0.77341(15) 0.0431(6) Uani 1 1 d . .
N2 N 0.24133(14) 0.7135(2) 0.64124(15) 0.0424(5) Uani 1 1 d . .
N3 N 0.14860(14) 0.7314(2) 0.51269(16) 0.0501(6) Uani 1 1 d . .
C1 C 0.32805(19) 0.9760(3) 0.73165(19) 0.0509(7) Uani 1 1 d . .
H1A H 0.2902 0.9539 0.6820 0.061 Uiso 1 1 calc R U
C2 C 0.3741(2) 1.0773(3) 0.7349(2) 0.0585(8) Uani 1 1 d . .
H2A H 0.3675 1.1225 0.6873 0.070 Uiso 1 1 calc R U
C3 C 0.42968(19) 1.1119(3) 0.8077(2) 0.0571(8) Uani 1 1 d . .
H3A H 0.4606 1.1803 0.8094 0.069 Uiso 1 1 calc R U
C4 C 0.43966(19) 1.0456(3) 0.8782(2) 0.0543(8) Uani 1 1 d . .
H4A H 0.4773 1.0690 0.9276 0.065 Uiso 1 1 calc R U
C5 C 0.39351(17) 0.9436(3) 0.87545(19) 0.0489(7) Uani 1 1 d . .
H5A H 0.4000 0.8993 0.9234 0.059 Uiso 1 1 calc R U
C6 C 0.33769(16) 0.9069(2) 0.80197(18) 0.0427(6) Uani 1 1 d . .
C7 C 0.28933(18) 0.7942(2) 0.7992(2) 0.0485(7) Uani 1 1 d . .
H7A H 0.2855 0.7798 0.8533 0.058 Uiso 1 1 calc R U
H7B H 0.2368 0.8068 0.7608 0.058 Uiso 1 1 calc R U
C8 C 0.38425(19) 0.6273(3) 0.8320(2) 0.0534(8) Uani 1 1 d . .
H8A H 0.4007 0.6571 0.8857 0.064 Uiso 1 1 calc R U
C9 C 0.4203(2) 0.5282(3) 0.8146(2) 0.0581(8) Uani 1 1 d . .
H9A H 0.4610 0.4900 0.8554 0.070 Uiso 1 1 calc R U
C10 C 0.39504(19) 0.4852(3) 0.7345(2) 0.0532(8) Uani 1 1 d . .
H10A H 0.4189 0.4171 0.7211 0.064 Uiso 1 1 calc R U
C11 C 0.33547(17) 0.5418(3) 0.67523(19) 0.0479(7) Uani 1 1 d . .
H11A H 0.3189 0.5112 0.6217 0.057 Uiso 1 1 calc R U
C12 C 0.29834(16) 0.6462(3) 0.69334(18) 0.0423(6) Uani 1 1 d . .
C13 C 0.20380(16) 0.6699(3) 0.56770(19) 0.0448(7) Uani 1 1 d . .
H13A H 0.2168 0.5926 0.5541 0.054 Uiso 1 1 calc R U
C14 C 0.1242(2) 0.8510(3) 0.5307(3) 0.0784(11) Uani 1 1 d . .
H14A H 0.1359 0.9107 0.4957 0.118 Uiso 1 1 calc R U
H14B H 0.1518 0.8711 0.5874 0.118 Uiso 1 1 calc R U
H14C H 0.0689 0.8505 0.5211 0.118 Uiso 1 1 calc R U
C15 C 0.1032(2) 0.6772(3) 0.4339(2) 0.0689(10) Uani 1 1 d . .
H15A H 0.1027 0.7315 0.3900 0.103 Uiso 1 1 calc R U
H15B H 0.0504 0.6633 0.4326 0.103 Uiso 1 1 calc R U
H15C H 0.1265 0.6009 0.4272 0.103 Uiso 1 1 calc R U
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'
Br Br -0.2901 2.4595 '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
H1WB O1 H1WA 101(5)
C8 N1 C12 121.7(2)
C8 N1 C7 117.6(3)
C12 N1 C7 120.6(2)
C13 N2 C12 118.7(2)
C13 N3 C14 121.6(3)
C13 N3 C15 121.2(3)
C14 N3 C15 116.8(3)
C2 C1 C6 120.5(3)
C2 C1 H1A 119.8
C6 C1 H1A 119.8
C3 C2 C1 120.5(3)
C3 C2 H2A 119.7
C1 C2 H2A 119.7
C2 C3 C4 120.0(3)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
C3 C4 C5 119.8(3)
C3 C4 H4A 120.1
C5 C4 H4A 120.1
C4 C5 C6 120.7(3)
C4 C5 H5A 119.7
C6 C5 H5A 119.7
C5 C6 C1 118.5(3)
C5 C6 C7 120.3(3)
C1 C6 C7 121.2(3)
N1 C7 C6 111.3(2)
N1 C7 H7A 109.4
C6 C7 H7A 109.4
N1 C7 H7B 109.4
C6 C7 H7B 109.4
H7A C7 H7B 108.0
C9 C8 N1 122.0(3)
C9 C8 H8A 119.0
N1 C8 H8A 119.0
C8 C9 C10 118.2(3)
C8 C9 H9A 120.9
C10 C9 H9A 120.9
C11 C10 C9 120.5(3)
C11 C10 H10A 119.8
C9 C10 H10A 119.8
C10 C11 C12 121.3(3)
C10 C11 H11A 119.4
C12 C11 H11A 119.4
N2 C12 N1 115.8(2)
N2 C12 C11 127.9(3)
N1 C12 C11 116.3(3)
N3 C13 N2 122.2(3)
N3 C13 H13A 118.9
N2 C13 H13A 118.9
N3 C14 H14A 109.5
N3 C14 H14B 109.5
H14A C14 H14B 109.5
N3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N3 C15 H15A 109.5
N3 C15 H15B 109.5
H15A C15 H15B 109.5
N3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1WB 0.883(10)
O1 H1WA 0.876(10)
N1 C8 1.359(4)
N1 C12 1.366(4)
N1 C7 1.494(3)
N2 C13 1.310(4)
N2 C12 1.339(4)
N3 C13 1.310(4)
N3 C14 1.449(5)
N3 C15 1.456(4)
C1 C2 1.377(4)
C1 C6 1.388(4)
C1 H1A 0.9300
C2 C3 1.372(5)
C2 H2A 0.9300
C3 C4 1.372(5)
C3 H3A 0.9300
C4 C5 1.387(4)
C4 H4A 0.9300
C5 C6 1.387(4)
C5 H5A 0.9300
C6 C7 1.506(4)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.352(5)
C8 H8A 0.9300
C9 C10 1.381(5)
C9 H9A 0.9300
C10 C11 1.360(4)
C10 H10A 0.9300
C11 C12 1.414(4)
C11 H11A 0.9300
C13 H13A 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A Br1 0.93 2.83 3.720(3) 159.7 6_566
C9 H9A Br1 0.93 3.11 4.006(3) 162.8 2_656
C13 H13A O1 0.93 2.37 3.266(4) 162.2 .
C15 H15C O1 0.96 2.66 3.546(5) 154.2 .
O1 H1WB Br1 0.883(10) 2.46(2) 3.313(3) 162(5) .
O1 H1WA Br1 0.876(10) 2.527(18) 3.381(3) 165(5) 7_556
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
C6 C1 C2 C3 -0.6(5)
C1 C2 C3 C4 -0.1(5)
C2 C3 C4 C5 0.1(5)
C3 C4 C5 C6 0.6(5)
C4 C5 C6 C1 -1.3(4)
C4 C5 C6 C7 178.4(3)
C2 C1 C6 C5 1.2(4)
C2 C1 C6 C7 -178.4(3)
C8 N1 C7 C6 81.7(3)
C12 N1 C7 C6 -97.4(3)
C5 C6 C7 N1 -94.7(3)
C1 C6 C7 N1 84.9(3)
C12 N1 C8 C9 -0.5(5)
C7 N1 C8 C9 -179.6(3)
N1 C8 C9 C10 -0.1(5)
C8 C9 C10 C11 0.1(5)
C9 C10 C11 C12 0.6(5)
C13 N2 C12 N1 -167.8(2)
C13 N2 C12 C11 13.6(4)
C8 N1 C12 N2 -177.7(3)
C7 N1 C12 N2 1.4(4)
C8 N1 C12 C11 1.1(4)
C7 N1 C12 C11 -179.8(2)
C10 C11 C12 N2 177.4(3)
C10 C11 C12 N1 -1.2(4)
C14 N3 C13 N2 -1.6(4)
C15 N3 C13 N2 -174.8(3)
C12 N2 C13 N3 -178.4(3)
