#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/58/7155834.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_7155834
loop_
_publ_author_name
'Zhang, Yu'
'Sun, Jing'
'Shen, Guo-Liang'
'Yan, Chao Guo'
_publ_section_title
;
 Selective synthesis of tetrahydroimidazo[1,2-a]pyridine and pyrrolidine
 derivatives via One-pot two-step reaction
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01860F
_journal_year                    2017
_chemical_formula_moiety         'C20 H20 Cl N3 O6, C H2 Cl2'
_chemical_formula_sum            'C21 H22 Cl3 N3 O6'
_chemical_formula_weight         518.77
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-17 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.755(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7002(19)
_cell_length_b                   10.3645(14)
_cell_length_c                   20.605(3)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.47
_cell_volume                     2475.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23342
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.056(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0865
_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)+(0.1349P)²+2.2158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2264
_refine_ls_wR_factor_ref         0.2564
_reflns_number_gt                3969
_reflns_number_total             5587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01860f2.cif
_cod_data_source_block           3i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7155834
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.9431(3) 0.7971(3) 0.12189(16) 0.0454(8) Uani 1 1 d .
H1 H 0.9975 0.8629 0.1257 0.054 Uiso 1 1 calc R
C2 C 0.9682(3) 0.6831(3) 0.15503(17) 0.0510(8) Uani 1 1 d .
H2 H 1.0388 0.6720 0.1811 0.061 Uiso 1 1 calc R
C3 C 0.8877(3) 0.5859(3) 0.14906(16) 0.0480(8) Uani 1 1 d .
C4 C 0.7829(3) 0.6014(3) 0.11064(19) 0.0528(9) Uani 1 1 d .
H4 H 0.7292 0.5348 0.1069 0.063 Uiso 1 1 calc R
C5 C 0.7579(3) 0.7153(3) 0.07782(18) 0.0485(8) Uani 1 1 d .
H5 H 0.6869 0.7256 0.0520 0.058 Uiso 1 1 calc R
C6 C 0.8378(2) 0.8157(3) 0.08279(14) 0.0364(7) Uani 1 1 d .
C7 C 0.8144(2) 0.9442(3) 0.04914(13) 0.0318(6) Uani 1 1 d .
H7 H 0.8893 0.9821 0.0438 0.038 Uiso 1 1 calc R
C8 C 0.7494(2) 1.0442(3) 0.08715(13) 0.0334(6) Uani 1 1 d .
C9 C 0.6434(3) 0.9870(3) 0.10705(15) 0.0411(7) Uani 1 1 d .
C10 C 0.8233(3) 1.0894(3) 0.14647(14) 0.0380(7) Uani 1 1 d .
C11 C 0.7409(2) 0.9452(3) -0.01852(13) 0.0338(6) Uani 1 1 d .
H11 H 0.6766 0.8842 -0.0195 0.041 Uiso 1 1 calc R
C12 C 0.8148(2) 0.9125(3) -0.07152(14) 0.0364(7) Uani 1 1 d .
C13 C 0.8173(4) 0.8173(5) -0.17529(19) 0.0636(11) Uani 1 1 d .
H13A H 0.8872 0.7698 -0.1601 0.076 Uiso 1 1 calc R
H13B H 0.8385 0.8961 -0.1961 0.076 Uiso 1 1 calc R
C14 C 0.7417(5) 0.7393(6) -0.2223(2) 0.0985(19) Uani 1 1 d .
H14A H 0.7151 0.6656 -0.2003 0.148 Uiso 1 1 calc R
H14B H 0.7837 0.7109 -0.2566 0.148 Uiso 1 1 calc R
H14C H 0.6767 0.7901 -0.2407 0.148 Uiso 1 1 calc R
C15 C 0.7166(2) 1.1508(3) 0.03306(13) 0.0335(6) Uani 1 1 d .
C16 C 0.6043(2) 1.2186(3) 0.04473(16) 0.0397(7) Uani 1 1 d .
C17 C 0.5208(4) 1.3599(5) 0.1137(3) 0.0841(15) Uani 1 1 d .
H17A H 0.4937 1.4217 0.0804 0.126 Uiso 1 1 calc R
H17B H 0.5398 1.4033 0.1549 0.126 Uiso 1 1 calc R
H17C H 0.4616 1.2972 0.1172 0.126 Uiso 1 1 calc R
C18 C 0.8160(2) 1.2475(3) 0.03288(16) 0.0403(7) Uani 1 1 d .
H18A H 0.8368 1.2814 0.0768 0.048 Uiso 1 1 calc R
H18B H 0.8828 1.2032 0.0205 0.048 Uiso 1 1 calc R
C19 C 0.7845(3) 1.3572(3) -0.01345(16) 0.0432(7) Uani 1 1 d .
C20 C 0.8586(5) 1.5335(5) -0.0655(3) 0.0881(16) Uani 1 1 d .
H20A H 0.8171 1.5098 -0.1072 0.132 Uiso 1 1 calc R
H20B H 0.9315 1.5705 -0.0718 0.132 Uiso 1 1 calc R
H20C H 0.8145 1.5956 -0.0448 0.132 Uiso 1 1 calc R
C21 C 0.6078(6) 0.2428(7) 0.3163(3) 0.1034(19) Uani 1 1 d .
H21A H 0.5379 0.2940 0.3136 0.124 Uiso 1 1 calc R
H21B H 0.6287 0.2170 0.3615 0.124 Uiso 1 1 calc R
Cl1 Cl 0.91907(11) 0.44107(9) 0.19005(5) 0.0695(4) Uani 1 1 d .
Cl2 Cl 0.5810(2) 0.1070(2) 0.26845(12) 0.1467(9) Uani 1 1 d .
Cl3 Cl 0.7149(2) 0.3346(3) 0.29294(14) 0.1776(12) Uani 1 1 d .
N1 N 0.5611(3) 0.9454(4) 0.12119(17) 0.0649(9) Uani 1 1 d .
N2 N 0.8815(3) 1.1216(3) 0.19197(15) 0.0586(8) Uani 1 1 d .
N3 N 0.6974(2) 1.0777(3) -0.02774(12) 0.0413(6) Uani 1 1 d .
H3 H 0.6647 1.1083 -0.0644 0.050 Uiso 1 1 calc R
O1 O 0.9141(2) 0.9409(3) -0.06966(13) 0.0689(9) Uani 1 1 d .
O2 O 0.75627(19) 0.8482(2) -0.12007(11) 0.0494(6) Uani 1 1 d .
O3 O 0.51237(19) 1.1978(3) 0.01358(13) 0.0593(7) Uani 1 1 d .
O4 O 0.62267(19) 1.2957(2) 0.09628(12) 0.0508(6) Uani 1 1 d .
O5 O 0.6888(2) 1.3872(3) -0.03561(14) 0.0651(8) Uani 1 1 d .
O6 O 0.8775(2) 1.4203(3) -0.02451(15) 0.0664(8) 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.3(3)
C2 C1 H1 119.3
C6 C1 H1 119.3
C3 C2 C1 119.1(3)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 120.9(3)
C2 C3 Cl1 119.5(3)
C4 C3 Cl1 119.6(3)
C5 C4 C3 119.9(3)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.6(3)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 118.2(3)
C1 C6 C7 118.7(3)
C5 C6 C7 123.2(3)
C6 C7 C11 117.8(2)
C6 C7 C8 115.3(2)
C11 C7 C8 101.5(2)
C6 C7 H7 107.2
C11 C7 H7 107.2
C8 C7 H7 107.2
C10 C8 C9 108.4(2)
C10 C8 C7 110.9(2)
C9 C8 C7 110.9(2)
C10 C8 C15 115.0(2)
C9 C8 C15 110.0(2)
C7 C8 C15 101.5(2)
N1 C9 C8 178.3(4)
N2 C10 C8 178.4(4)
N3 C11 C12 109.7(2)
N3 C11 C7 105.4(2)
C12 C11 C7 110.3(2)
N3 C11 H11 110.4
C12 C11 H11 110.4
C7 C11 H11 110.4
O1 C12 O2 123.7(3)
O1 C12 C11 124.6(3)
O2 C12 C11 111.8(2)
O2 C13 C14 108.8(3)
O2 C13 H13A 109.9
C14 C13 H13A 109.9
O2 C13 H13B 109.9
C14 C13 H13B 109.9
H13A C13 H13B 108.3
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N3 C15 C18 111.5(2)
N3 C15 C16 109.7(2)
C18 C15 C16 111.4(2)
N3 C15 C8 103.8(2)
C18 C15 C8 110.3(2)
C16 C15 C8 109.9(2)
O3 C16 O4 125.2(3)
O3 C16 C15 124.0(3)
O4 C16 C15 110.6(2)
O4 C17 H17A 109.5
O4 C17 H17B 109.5
H17A C17 H17B 109.5
O4 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C19 C18 C15 112.1(2)
C19 C18 H18A 109.2
C15 C18 H18A 109.2
C19 C18 H18B 109.2
C15 C18 H18B 109.2
H18A C18 H18B 107.9
O5 C19 O6 124.1(3)
O5 C19 C18 125.4(3)
O6 C19 C18 110.5(3)
O6 C20 H20A 109.5
O6 C20 H20B 109.5
H20A C20 H20B 109.5
O6 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
Cl3 C21 Cl2 112.4(3)
Cl3 C21 H21A 109.1
Cl2 C21 H21A 109.1
Cl3 C21 H21B 109.1
Cl2 C21 H21B 109.1
H21A C21 H21B 107.9
C15 N3 C11 111.4(2)
C15 N3 H3 124.3
C11 N3 H3 124.3
C12 O2 C13 116.5(3)
C16 O4 C17 115.2(3)
C19 O6 C20 116.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.377(5)
C1 C6 1.391(4)
C1 H1 0.9300
C2 C3 1.373(5)
C2 H2 0.9300
C3 C4 1.376(5)
C3 Cl1 1.737(3)
C4 C5 1.373(5)
C4 H4 0.9300
C5 C6 1.394(4)
C5 H5 0.9300
C6 C7 1.510(4)
C7 C11 1.536(4)
C7 C8 1.557(4)
C7 H7 0.9800
C8 C10 1.475(4)
C8 C9 1.481(4)
C8 C15 1.579(4)
C9 N1 1.129(4)
C10 N2 1.132(4)
C11 N3 1.468(4)
C11 C12 1.520(4)
C11 H11 0.9800
C12 O1 1.195(4)
C12 O2 1.314(4)
C13 O2 1.458(4)
C13 C14 1.463(6)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 N3 1.455(4)
C15 C18 1.536(4)
C15 C16 1.537(4)
C16 O3 1.196(4)
C16 O4 1.324(4)
C17 O4 1.451(5)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C19 1.498(4)
C18 H18A 0.9700
C18 H18B 0.9700
C19 O5 1.193(4)
C19 O6 1.315(4)
C20 O6 1.446(5)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 Cl3 1.694(7)
C21 Cl2 1.722(7)
C21 H21A 0.9700
C21 H21B 0.9700
N3 H3 0.8600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193159
