#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/64/4036495.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_4036495
loop_
_publ_author_name
'Kong, Lingkai'
'Shao, Yushang'
'Li, Yanli'
'Liu, Yuanyuan'
'Li, Yanzhong'
_publ_section_title
;
 LDA-Promoted Synthesis of 3-Amino Furans by Selective Lithiation of
 Enaminones.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12641
_journal_page_last               12645
_journal_paper_doi               10.1021/acs.joc.5b02211
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C23 H26 Br N O'
_chemical_formula_weight         412.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.583(2)
_cell_angle_beta                 107.719(2)
_cell_angle_gamma                91.208(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2984(10)
_cell_length_b                   10.7386(11)
_cell_length_c                   11.0409(11)
_cell_measurement_reflns_used    2498
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.135
_cell_measurement_theta_min      4.360
_cell_volume                     1011.74(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6177
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    2.043
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7534
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.3035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                3379
_reflns_number_total             3971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02211_si_002.cif
_cod_data_source_block           cd212637
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1011.74(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4036495
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.66619(3) -0.24638(3) 0.55915(3) 0.05834(12) Uani 1 1 d .
N1 N 0.59057(18) 0.20908(18) 0.94948(19) 0.0338(4) Uani 1 1 d .
O1 O 0.79929(15) 0.08451(15) 0.72158(16) 0.0374(3) Uani 1 1 d .
C1 C 0.7411(2) 0.0786(2) 0.8165(2) 0.0352(4) Uani 1 1 d .
C2 C 0.6645(2) 0.1828(2) 0.8530(2) 0.0334(4) Uani 1 1 d .
C3 C 0.6763(2) 0.2567(2) 0.7758(2) 0.0366(5) Uani 1 1 d .
H3 H 0.6346 0.3333 0.7780 0.044 Uiso 1 1 calc R
C4 C 0.7585(2) 0.1950(2) 0.6998(2) 0.0363(5) Uani 1 1 d .
C5 C 0.8178(2) 0.2287(2) 0.6112(2) 0.0369(5) Uani 1 1 d .
C6 C 0.7694(3) 0.3266(2) 0.5684(2) 0.0431(5) Uani 1 1 d .
H6 H 0.6954 0.3670 0.5914 0.052 Uiso 1 1 calc R
C7 C 0.8303(3) 0.3648(3) 0.4913(3) 0.0519(6) Uani 1 1 d .
H7 H 0.7980 0.4316 0.4642 0.062 Uiso 1 1 calc R
C8 C 0.9388(3) 0.3037(3) 0.4550(3) 0.0551(7) Uani 1 1 d .
H8 H 0.9796 0.3292 0.4032 0.066 Uiso 1 1 calc R
C9 C 0.9866(3) 0.2056(3) 0.4953(3) 0.0546(6) Uani 1 1 d .
H9 H 1.0596 0.1642 0.4703 0.065 Uiso 1 1 calc R
C10 C 0.9269(3) 0.1676(3) 0.5730(3) 0.0470(6) Uani 1 1 d .
H10 H 0.9600 0.1007 0.5998 0.056 Uiso 1 1 calc R
C11 C 0.7758(2) -0.0289(2) 0.8607(2) 0.0337(4) Uani 1 1 d .
C12 C 0.8321(2) 0.0115(2) 1.0082(2) 0.0380(5) Uani 1 1 d .
H12 H 0.8440 0.1071 1.0776 0.046 Uiso 1 1 calc R
C13 C 0.8710(2) -0.0856(2) 1.0548(3) 0.0414(5) Uani 1 1 d .
H13 H 0.9074 -0.0546 1.1544 0.050 Uiso 1 1 calc R
C14 C 0.8565(2) -0.2286(2) 0.9554(3) 0.0416(5) Uani 1 1 d .
C15 C 0.7986(2) -0.2710(2) 0.8086(3) 0.0427(5) Uani 1 1 d .
H15 H 0.7870 -0.3666 0.7396 0.051 Uiso 1 1 calc R
C16 C 0.7578(2) -0.1738(2) 0.7628(2) 0.0376(5) Uani 1 1 d .
C17 C 0.9005(3) -0.3355(3) 1.0047(3) 0.0589(7) Uani 1 1 d .
H17A H 0.8623 -0.4308 0.9238 0.088 Uiso 1 1 calc R
H17B H 0.8673 -0.3219 1.0814 0.088 Uiso 1 1 calc R
H17C H 1.0001 -0.3220 1.0401 0.088 Uiso 1 1 calc R
C18 C 0.6166(2) 0.3631(2) 1.0581(2) 0.0400(5) Uani 1 1 d .
H18 H 0.5862 0.4164 1.0059 0.048 Uiso 1 1 calc R
C19 C 0.7702(3) 0.4163(3) 1.1454(3) 0.0540(6) Uani 1 1 d .
H19A H 0.8020 0.3623 1.1940 0.081 Uiso 1 1 calc R
H19B H 0.7864 0.5157 1.2166 0.081 Uiso 1 1 calc R
H19C H 0.8196 0.4046 1.0810 0.081 Uiso 1 1 calc R
C20 C 0.5378(3) 0.3908(3) 1.1610(3) 0.0599(7) Uani 1 1 d .
H20A H 0.4399 0.3710 1.1077 0.090 Uiso 1 1 calc R
H20B H 0.5659 0.4892 1.2370 0.090 Uiso 1 1 calc R
H20C H 0.5577 0.3299 1.2035 0.090 Uiso 1 1 calc R
C21 C 0.4416(2) 0.1376(2) 0.8719(3) 0.0413(5) Uani 1 1 d .
H21 H 0.4005 0.1609 0.9473 0.050 Uiso 1 1 calc R
C22 C 0.3578(3) 0.1882(4) 0.7704(4) 0.0651(8) Uani 1 1 d .
H22A H 0.3666 0.2903 0.8236 0.098 Uiso 1 1 calc R
H22B H 0.2618 0.1435 0.7316 0.098 Uiso 1 1 calc R
H22C H 0.3917 0.1630 0.6917 0.098 Uiso 1 1 calc R
C23 C 0.4286(3) -0.0231(3) 0.7932(3) 0.0568(7) Uani 1 1 d .
H23A H 0.4562 -0.0520 0.7099 0.085 Uiso 1 1 calc R
H23B H 0.3339 -0.0680 0.7615 0.085 Uiso 1 1 calc R
H23C H 0.4874 -0.0516 0.8582 0.085 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'
Br Br -0.2901 2.4595 '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 N1 C18 111.86(16)
C2 N1 C21 112.95(16)
C18 N1 C21 115.15(16)
C4 O1 C1 107.10(15)
C2 C1 O1 109.68(18)
C2 C1 C11 133.51(19)
O1 C1 C11 116.77(17)
C1 C2 N1 125.21(19)
C1 C2 C3 105.84(18)
N1 C2 C3 128.95(18)
C4 C3 C2 107.43(19)
C4 C3 H3 126.3
C2 C3 H3 126.3
C3 C4 O1 109.93(18)
C3 C4 C5 133.4(2)
O1 C4 C5 116.54(18)
C6 C5 C10 118.6(2)
C6 C5 C4 120.3(2)
C10 C5 C4 121.0(2)
C5 C6 C7 120.6(2)
C5 C6 H6 119.7
C7 C6 H6 119.7
C8 C7 C6 120.0(2)
C8 C7 H7 120.0
C6 C7 H7 120.0
C9 C8 C7 120.0(2)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 120.3(2)
C8 C9 H9 119.8
C10 C9 H9 119.8
C9 C10 C5 120.5(2)
C9 C10 H10 119.8
C5 C10 H10 119.8
C16 C11 C12 116.07(19)
C16 C11 C1 123.8(2)
C12 C11 C1 120.16(19)
C13 C12 C11 122.1(2)
C13 C12 H12 118.9
C11 C12 H12 118.9
C12 C13 C14 120.9(2)
C12 C13 H13 119.6
C14 C13 H13 119.6
C15 C14 C13 117.8(2)
C15 C14 C17 120.7(2)
C13 C14 C17 121.5(2)
C16 C15 C14 121.0(2)
C16 C15 H15 119.5
C14 C15 H15 119.5
C15 C16 C11 122.1(2)
C15 C16 Br1 117.40(16)
C11 C16 Br1 120.45(17)
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N1 C18 C19 109.71(18)
N1 C18 C20 111.74(19)
C19 C18 C20 109.4(2)
N1 C18 H18 108.6
C19 C18 H18 108.6
C20 C18 H18 108.6
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
N1 C21 C23 110.36(18)
N1 C21 C22 114.6(2)
C23 C21 C22 111.3(2)
N1 C21 H21 106.7
C23 C21 H21 106.7
C22 C21 H21 106.7
C21 C22 H22A 109.5
C21 C22 H22B 109.5
H22A C22 H22B 109.5
C21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C21 C23 H23A 109.5
C21 C23 H23B 109.5
H23A C23 H23B 109.5
C21 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C16 1.899(2)
N1 C2 1.421(3)
N1 C18 1.482(3)
N1 C21 1.489(3)
O1 C4 1.366(3)
O1 C1 1.379(2)
C1 C2 1.360(3)
C1 C11 1.460(3)
C2 C3 1.434(3)
C3 C4 1.343(3)
C3 H3 0.9300
C4 C5 1.464(3)
C5 C6 1.384(3)
C5 C10 1.391(3)
C6 C7 1.386(3)
C6 H6 0.9300
C7 C8 1.378(4)
C7 H7 0.9300
C8 C9 1.369(4)
C8 H8 0.9300
C9 C10 1.383(3)
C9 H9 0.9300
C10 H10 0.9300
C11 C16 1.389(3)
C11 C12 1.392(3)
C12 C13 1.379(3)
C12 H12 0.9300
C13 C14 1.384(3)
C13 H13 0.9300
C14 C15 1.381(3)
C14 C17 1.507(3)
C15 C16 1.379(3)
C15 H15 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C19 1.510(3)
C18 C20 1.515(3)
C18 H18 0.9800
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 C23 1.511(3)
C21 C22 1.514(4)
C21 H21 0.9800
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
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
C4 O1 C1 C2 0.4(2)
C4 O1 C1 C11 -177.51(18)
O1 C1 C2 N1 -179.50(18)
C11 C1 C2 N1 -2.1(4)
O1 C1 C2 C3 0.1(2)
C11 C1 C2 C3 177.5(2)
C18 N1 C2 C1 132.7(2)
C21 N1 C2 C1 -95.4(2)
C18 N1 C2 C3 -46.8(3)
C21 N1 C2 C3 85.1(3)
C1 C2 C3 C4 -0.5(2)
N1 C2 C3 C4 179.1(2)
C2 C3 C4 O1 0.7(2)
C2 C3 C4 C5 -174.2(2)
C1 O1 C4 C3 -0.7(2)
C1 O1 C4 C5 175.15(18)
C3 C4 C5 C6 -13.5(4)
O1 C4 C5 C6 171.90(19)
C3 C4 C5 C10 164.1(3)
O1 C4 C5 C10 -10.5(3)
C10 C5 C6 C7 -1.2(3)
C4 C5 C6 C7 176.4(2)
C5 C6 C7 C8 0.9(4)
C6 C7 C8 C9 -0.1(4)
C7 C8 C9 C10 -0.3(4)
C8 C9 C10 C5 -0.1(4)
C6 C5 C10 C9 0.8(4)
C4 C5 C10 C9 -176.8(2)
C2 C1 C11 C16 128.8(3)
O1 C1 C11 C16 -53.9(3)
C2 C1 C11 C12 -52.2(3)
O1 C1 C11 C12 125.1(2)
C16 C11 C12 C13 1.5(3)
C1 C11 C12 C13 -177.6(2)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C15 -1.7(3)
C12 C13 C14 C17 179.1(2)
C13 C14 C15 C16 0.6(3)
C17 C14 C15 C16 179.8(2)
C14 C15 C16 C11 1.7(3)
C14 C15 C16 Br1 -175.17(17)
C12 C11 C16 C15 -2.6(3)
C1 C11 C16 C15 176.4(2)
C12 C11 C16 Br1 174.12(15)
C1 C11 C16 Br1 -6.8(3)
C2 N1 C18 C19 -58.4(2)
C21 N1 C18 C19 170.86(19)
C2 N1 C18 C20 -179.9(2)
C21 N1 C18 C20 49.4(3)
C2 N1 C21 C23 63.7(2)
C18 N1 C21 C23 -166.1(2)
C2 N1 C21 C22 -62.9(3)
C18 N1 C21 C22 67.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132554303
