#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:23:31 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262707 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157841.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_7157841
loop_
_publ_author_name
'P, Rajesh'
'Almansour, Abdulrahman I.'
'Arumugam, Natarajan'
'Yaragorla, Srinivasarao'
_publ_section_title
;
 Calcium-catalyzed formal [3 + 2] annulation of
 C,N-diacyliminium ions with nucleophilic phenols: a
 diversity oriented synthesis of 3-aminofurans.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1060
_journal_page_last               1065
_journal_paper_doi               10.1039/d0ob02276d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C24 H20 Cl N O2'
_chemical_formula_weight         389.86
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
;
2020-10-02 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.400(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2034(4)
_cell_length_b                   8.3948(3)
_cell_length_c                   19.2731(6)
_cell_measurement_reflns_used    8017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7620
_cell_measurement_theta_min      2.1080
_cell_volume                     1973.85(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω 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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18149
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81297
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0058(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0436
_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)+(0.0596P)²+0.1519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                2399
_reflns_number_total             3475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob02276d2.cif
_cod_data_source_block           ysr03
_cod_depositor_comments          'Adding full bibliography for 7157841.cif.'
_cod_original_cell_volume        1973.84(11)
_cod_database_code               7157841
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.02534(5) 0.68434(9) 0.10808(4) 0.1006(3) Uani 1 1 d . . .
O1 O 0.47803(10) 0.28103(15) 0.03366(6) 0.0544(4) Uani 1 1 d . . .
N1 N 0.59435(11) 0.53511(17) 0.16801(7) 0.0450(4) Uani 1 1 d . . .
C11 C 0.36246(15) 0.4698(2) 0.08970(9) 0.0464(5) Uani 1 1 d . . .
C15 C 0.58343(16) 0.2243(2) 0.03763(10) 0.0528(5) Uani 1 1 d . . .
C13 C 0.56900(14) 0.4148(2) 0.11781(9) 0.0444(4) Uani 1 1 d . . .
C12 C 0.47044(15) 0.3980(2) 0.08387(9) 0.0470(5) Uani 1 1 d . . .
C8 C 0.15499(16) 0.6001(3) 0.10114(12) 0.0630(6) Uani 1 1 d . . .
C6 C 0.34000(16) 0.5798(2) 0.14113(10) 0.0565(5) Uani 1 1 d . . .
H6 H 0.3954 0.6103 0.1723 0.068 Uiso 1 1 calc R . .
C14 C 0.64327(15) 0.3001(2) 0.08921(9) 0.0482(5) Uani 1 1 d . . .
C19 C 0.75464(16) 0.2536(2) 0.10128(10) 0.0542(5) Uani 1 1 d . . .
C7 C 0.23695(17) 0.6446(2) 0.14677(11) 0.0631(6) Uani 1 1 d . . .
H7 H 0.2231 0.7184 0.1815 0.076 Uiso 1 1 calc R . .
C10 C 0.27760(15) 0.4274(3) 0.04369(10) 0.0608(6) Uani 1 1 d . . .
H10 H 0.2907 0.3542 0.0086 0.073 Uiso 1 1 calc R . .
C24 C 0.60528(15) 0.4941(3) 0.23584(10) 0.0547(5) Uani 1 1 d . . .
C18 C 0.79691(18) 0.1339(3) 0.05681(11) 0.0626(6) Uani 1 1 d . . .
O2 O 0.59084(13) 0.35556(19) 0.25410(7) 0.0752(5) Uani 1 1 d . . .
C9 C 0.17479(17) 0.4921(3) 0.04933(12) 0.0714(6) Uani 1 1 d . . .
H9 H 0.1189 0.4630 0.0182 0.086 Uiso 1 1 calc R . .
C5 C 0.60912(16) 0.6991(2) 0.14275(10) 0.0526(5) Uani 1 1 d . . .
H5A H 0.5635 0.7699 0.1694 0.063 Uiso 1 1 calc R . .
H5B H 0.5838 0.7045 0.0947 0.063 Uiso 1 1 calc R . .
C16 C 0.62441(19) 0.1090(3) -0.00728(11) 0.0661(6) Uani 1 1 d . . .
H16 H 0.5810 0.0636 -0.0423 0.079 Uiso 1 1 calc R . .
C1 C 0.63809(18) 0.6237(3) 0.28663(10) 0.0685(6) Uani 1 1 d . . .
H1A H 0.6354 0.5807 0.3333 0.082 Uiso 1 1 calc R . .
H1B H 0.5846 0.7089 0.2831 0.082 Uiso 1 1 calc R . .
C20 C 0.82343(17) 0.3147(3) 0.15414(12) 0.0703(6) Uani 1 1 d . . .
H20 H 0.7969 0.3923 0.1838 0.084 Uiso 1 1 calc R . .
C4 C 0.72611(19) 0.7582(3) 0.14750(12) 0.0727(7) Uani 1 1 d . . .
H4A H 0.7747 0.6725 0.1343 0.087 Uiso 1 1 calc R . .
H4B H 0.7348 0.8444 0.1146 0.087 Uiso 1 1 calc R . .
C17 C 0.7305(2) 0.0673(3) 0.00296(12) 0.0727(7) Uani 1 1 d . . .
H17 H 0.7609 -0.0078 -0.0264 0.087 Uiso 1 1 calc R . .
C23 C 0.9054(2) 0.0822(3) 0.06849(15) 0.0848(8) Uani 1 1 d . . .
H23 H 0.9336 0.0032 0.0402 0.102 Uiso 1 1 calc R . .
C21 C 0.9291(2) 0.2619(3) 0.16292(16) 0.0915(8) Uani 1 1 d . . .
H21 H 0.9738 0.3052 0.1979 0.110 Uiso 1 1 calc R . .
C2 C 0.75268(19) 0.6945(3) 0.27600(13) 0.0819(8) Uani 1 1 d . . .
H2A H 0.7776 0.7434 0.3192 0.098 Uiso 1 1 calc R . .
H2B H 0.8027 0.6081 0.2661 0.098 Uiso 1 1 calc R . .
C3 C 0.7600(2) 0.8164(3) 0.21896(14) 0.0888(8) Uani 1 1 d . . .
H3A H 0.8350 0.8542 0.2175 0.107 Uiso 1 1 calc R . .
H3B H 0.7142 0.9065 0.2306 0.107 Uiso 1 1 calc R . .
C22 C 0.9700(2) 0.1442(4) 0.11990(18) 0.0990(9) Uani 1 1 d . . .
H22 H 1.0415 0.1080 0.1264 0.119 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'
Cl Cl 0.1484 0.1585 '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
C15 O1 C12 106.63(14) . . ?
C24 N1 C13 119.27(15) . . ?
C24 N1 C5 123.10(16) . . ?
C13 N1 C5 117.62(14) . . ?
C6 C11 C10 117.91(17) . . ?
C6 C11 C12 121.72(16) . . ?
C10 C11 C12 120.37(17) . . ?
O1 C15 C14 111.12(17) . . ?
O1 C15 C16 123.68(18) . . ?
C14 C15 C16 125.2(2) . . ?
C12 C13 N1 124.95(16) . . ?
C12 C13 C14 107.66(16) . . ?
N1 C13 C14 127.17(16) . . ?
C13 C12 O1 109.62(15) . . ?
C13 C12 C11 135.27(17) . . ?
O1 C12 C11 115.08(15) . . ?
C7 C8 C9 120.56(19) . . ?
C7 C8 Cl1 119.43(18) . . ?
C9 C8 Cl1 120.00(17) . . ?
C7 C6 C11 121.09(18) . . ?
C15 C14 C19 118.54(18) . . ?
C15 C14 C13 104.94(17) . . ?
C19 C14 C13 136.52(18) . . ?
C20 C19 C18 118.42(19) . . ?
C20 C19 C14 124.70(19) . . ?
C18 C19 C14 116.87(19) . . ?
C8 C7 C6 119.8(2) . . ?
C9 C10 C11 121.0(2) . . ?
O2 C24 N1 120.33(18) . . ?
O2 C24 C1 122.22(18) . . ?
N1 C24 C1 117.43(18) . . ?
C23 C18 C17 121.0(2) . . ?
C23 C18 C19 118.3(2) . . ?
C17 C18 C19 120.7(2) . . ?
C10 C9 C8 119.70(19) . . ?
N1 C5 C4 114.18(17) . . ?
C17 C16 C15 116.4(2) . . ?
C24 C1 C2 114.80(17) . . ?
C21 C20 C19 121.1(2) . . ?
C3 C4 C5 113.48(19) . . ?
C16 C17 C18 122.3(2) . . ?
C22 C23 C18 121.8(2) . . ?
C20 C21 C22 120.4(3) . . ?
C3 C2 C1 115.47(19) . . ?
C2 C3 C4 115.2(2) . . ?
C23 C22 C21 119.9(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
Cl1 C8 1.741(2) . ?
O1 C15 1.372(2) . ?
O1 C12 1.384(2) . ?
N1 C24 1.355(2) . ?
N1 C13 1.427(2) . ?
N1 C5 1.473(2) . ?
C11 C6 1.387(3) . ?
C11 C10 1.393(2) . ?
C11 C12 1.456(2) . ?
C15 C14 1.375(3) . ?
C15 C16 1.399(3) . ?
C13 C12 1.362(2) . ?
C13 C14 1.441(2) . ?
C8 C7 1.368(3) . ?
C8 C9 1.374(3) . ?
C6 C7 1.377(3) . ?
C14 C19 1.428(3) . ?
C19 C20 1.401(3) . ?
C19 C18 1.425(3) . ?
C10 C9 1.374(3) . ?
C24 O2 1.229(2) . ?
C24 C1 1.511(3) . ?
C18 C23 1.406(3) . ?
C18 C17 1.416(3) . ?
C5 C4 1.512(3) . ?
C16 C17 1.351(3) . ?
C1 C2 1.538(3) . ?
C20 C21 1.370(3) . ?
C4 C3 1.510(3) . ?
C23 C22 1.355(3) . ?
C21 C22 1.391(4) . ?
C2 C3 1.506(3) . ?
