#------------------------------------------------------------------------------
#$Date: 2026-02-27 08:43:20 +0100 (Fri 27 de Feb de 2026) $
#$Revision: 304653 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151741.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_7151741
loop_
_publ_author_name
'Pan, Huan-Rui'
'Wang, Xiao-Rong'
'Yan, Cai-Xia'
'Sun, Zhong-Xin'
'Cheng, Ying'
_publ_section_title
;
 The multicomponent reaction of imidazo[1,5-a]pyridine carbenes with
 phthalaldehydes and dimethyl acetylenedicarboxylate: a facile
 construction of benzo[d]furo[3,2-b]azepines.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2166
_journal_page_last               2174
_journal_paper_doi               10.1039/c0ob00746c
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C24 H23 Br N2 O6'
_chemical_formula_sum            'C24 H23 Br N2 O6'
_chemical_formula_weight         515.35
_chemical_name_common
;
(5S,6S)-Dimethyl 8-bromo-6-hydroxyl-4-isopropyl-5-(2-pyridyl)-
5,6-dihydrobenzo(d)furo(3,2-b)azepine-2,3-dicarboxylate
;
_chemical_name_systematic
;
(5S,6S)-Dimethyl 8-bromo-6-hydroxyl-4-isopropyl-5-
(2-pyridyl)-5,6-dihydrobenzo[d]furo[3,2-b]azepine-2,3-dicarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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                65.855(3)
_cell_angle_beta                 88.718(4)
_cell_angle_gamma                84.251(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9953(17)
_cell_length_b                   12.083(3)
_cell_length_c                   13.275(3)
_cell_measurement_reflns_used    2300
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      3.01
_cell_volume                     1164.1(5)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5905
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    1.808
_exptl_absorpt_correction_T_max  0.7732
_exptl_absorpt_correction_T_min  0.4837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0352
_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)+(0.0343P)²+0.5980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                3252
_reflns_number_total             4184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00746c.txt
_cod_data_source_block           101125c_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1164.2(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151741
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.90982(5) 0.82873(3) 0.67517(2) 0.07314(14) Uani 1 1 d . . .
C1 C 0.8909(3) 0.7509(2) 0.5781(2) 0.0443(6) Uani 1 1 d . . .
C2 C 0.8055(3) 0.6486(2) 0.6101(2) 0.0470(6) Uani 1 1 d . . .
H2 H 0.7600 0.6156 0.6800 0.056 Uiso 1 1 calc R . .
C3 C 0.7888(3) 0.5963(2) 0.53678(19) 0.0432(6) Uani 1 1 d . . .
H3 H 0.7295 0.5282 0.5573 0.052 Uiso 1 1 calc R . .
C4 C 0.8598(3) 0.6438(2) 0.43121(18) 0.0345(5) Uani 1 1 d . . .
C5 C 0.9514(3) 0.7452(2) 0.40244(18) 0.0350(5) Uani 1 1 d . . .
C6 C 0.9633(3) 0.7986(2) 0.47671(19) 0.0411(6) Uani 1 1 d . . .
H6 H 1.0209 0.8673 0.4574 0.049 Uiso 1 1 calc R . .
C7 C 1.0437(3) 0.7956(2) 0.29421(19) 0.0397(5) Uani 1 1 d . . .
H7 H 1.1372 0.7349 0.2982 0.048 Uiso 1 1 calc R . .
C8 C 0.9354(3) 0.81979(19) 0.19016(18) 0.0341(5) Uani 1 1 d . . .
H8 H 0.9963 0.8750 0.1279 0.041 Uiso 1 1 calc R . .
C9 C 0.7677(3) 0.89116(19) 0.18943(18) 0.0364(5) Uani 1 1 d . . .
C10 C 0.6179(3) 0.8700(2) 0.1553(2) 0.0531(7) Uani 1 1 d . . .
H10 H 0.6134 0.8074 0.1320 0.064 Uiso 1 1 calc R . .
C11 C 0.4743(4) 0.9431(3) 0.1561(3) 0.0727(9) Uani 1 1 d . . .
H11 H 0.3714 0.9303 0.1336 0.087 Uiso 1 1 calc R . .
C12 C 0.4849(4) 1.0345(3) 0.1902(3) 0.0703(9) Uani 1 1 d . . .
H12 H 0.3891 1.0839 0.1924 0.084 Uiso 1 1 calc R . .
C13 C 0.6378(4) 1.0521(2) 0.2211(2) 0.0625(8) Uani 1 1 d . . .
H13 H 0.6445 1.1157 0.2427 0.075 Uiso 1 1 calc R . .
C14 C 1.0313(3) 0.7003(2) 0.0807(2) 0.0448(6) Uani 1 1 d . . .
H14 H 1.0105 0.6233 0.0774 0.054 Uiso 1 1 calc R . .
C15 C 1.2174(4) 0.6906(3) 0.1086(3) 0.0758(10) Uani 1 1 d . . .
H15A H 1.2433 0.7650 0.1118 0.114 Uiso 1 1 calc R . .
H15B H 1.2833 0.6768 0.0527 0.114 Uiso 1 1 calc R . .
H15C H 1.2430 0.6239 0.1788 0.114 Uiso 1 1 calc R . .
C16 C 0.9838(5) 0.8004(3) -0.0316(2) 0.0748(10) Uani 1 1 d . . .
H16A H 0.8650 0.8059 -0.0444 0.112 Uiso 1 1 calc R . .
H16B H 1.0432 0.7823 -0.0876 0.112 Uiso 1 1 calc R . .
H16C H 1.0132 0.8767 -0.0343 0.112 Uiso 1 1 calc R . .
C17 C 0.8550(3) 0.61384(19) 0.24587(17) 0.0319(5) Uani 1 1 d . . .
C18 C 0.7863(3) 0.51896(19) 0.22552(18) 0.0343(5) Uani 1 1 d . . .
C19 C 0.7708(3) 0.5090(2) 0.1176(2) 0.0412(6) Uani 1 1 d . . .
C20 C 0.6577(5) 0.6093(3) -0.0631(2) 0.0757(10) Uani 1 1 d . . .
H20A H 0.7638 0.6256 -0.0988 0.114 Uiso 1 1 calc R . .
H20B H 0.5731 0.6734 -0.1043 0.114 Uiso 1 1 calc R . .
H20C H 0.6271 0.5330 -0.0598 0.114 Uiso 1 1 calc R . .
C21 C 0.7304(3) 0.4410(2) 0.32340(19) 0.0375(5) Uani 1 1 d . . .
C22 C 0.6472(3) 0.3290(2) 0.3528(2) 0.0435(6) Uani 1 1 d . . .
C23 C 0.5716(5) 0.1517(3) 0.5014(3) 0.0820(11) Uani 1 1 d . . .
H23A H 0.4571 0.1639 0.4758 0.123 Uiso 1 1 calc R . .
H23B H 0.5754 0.1156 0.5807 0.123 Uiso 1 1 calc R . .
H23C H 0.6362 0.0987 0.4743 0.123 Uiso 1 1 calc R . .
C24 C 0.8331(3) 0.58615(19) 0.35665(18) 0.0336(5) Uani 1 1 d . . .
N1 N 0.7793(3) 0.98170(18) 0.22174(17) 0.0482(5) Uani 1 1 d . . .
N2 N 0.9199(2) 0.71477(16) 0.16575(15) 0.0347(4) Uani 1 1 d . . .
O1 O 1.1140(3) 0.9049(2) 0.27860(17) 0.0571(5) Uani 1 1 d . . .
H1 H 1.033(4) 0.951(3) 0.267(3) 0.081(14) Uiso 1 1 d . . .
O2 O 0.8389(3) 0.42972(18) 0.09556(16) 0.0704(6) Uani 1 1 d . . .
O3 O 0.6713(2) 0.60295(16) 0.04818(14) 0.0527(5) Uani 1 1 d . . .
O4 O 0.5932(3) 0.29864(17) 0.28551(16) 0.0637(5) Uani 1 1 d . . .
O5 O 0.6411(2) 0.26808(16) 0.46143(15) 0.0582(5) Uani 1 1 d . . .
O6 O 0.7553(2) 0.47987(13) 0.40388(12) 0.0390(4) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.4(2) . . ?
C6 C1 Br1 118.60(19) . . ?
C2 C1 Br1 120.04(18) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 C24 123.0(2) . . ?
C3 C4 C24 118.5(2) . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 C7 118.9(2) . . ?
C4 C5 C7 121.90(19) . . ?
C1 C6 C5 120.6(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C5 111.73(18) . . ?
O1 C7 C8 108.4(2) . . ?
C5 C7 C8 114.59(18) . . ?
O1 C7 H7 107.3 . . ?
C5 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
N2 C8 C9 113.15(18) . . ?
N2 C8 C7 115.76(18) . . ?
C9 C8 C7 111.51(18) . . ?
N2 C8 H8 105.1 . . ?
C9 C8 H8 105.1 . . ?
C7 C8 H8 105.1 . . ?
N1 C9 C10 122.2(2) . . ?
N1 C9 C8 113.5(2) . . ?
C10 C9 C8 124.3(2) . . ?
C9 C10 C11 118.8(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 119.3(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
N1 C13 C12 122.9(3) . . ?
N1 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
N2 C14 C16 110.3(2) . . ?
N2 C14 C15 113.2(2) . . ?
C16 C14 C15 112.2(3) . . ?
N2 C14 H14 106.9 . . ?
C16 C14 H14 106.9 . . ?
C15 C14 H14 106.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C24 C17 N2 128.84(19) . . ?
C24 C17 C18 106.03(18) . . ?
N2 C17 C18 125.04(19) . . ?
C21 C18 C17 106.67(19) . . ?
C21 C18 C19 125.5(2) . . ?
C17 C18 C19 127.72(19) . . ?
O2 C19 O3 124.4(2) . . ?
O2 C19 C18 125.4(2) . . ?
O3 C19 C18 110.18(19) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 O6 110.70(19) . . ?
C18 C21 C22 131.1(2) . . ?
O6 C21 C22 118.1(2) . . ?
O4 C22 O5 125.5(2) . . ?
O4 C22 C21 123.2(2) . . ?
O5 C22 C21 111.3(2) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C24 O6 109.05(18) . . ?
C17 C24 C4 136.4(2) . . ?
O6 C24 C4 114.36(18) . . ?
C9 N1 C13 117.8(2) . . ?
C17 N2 C8 118.44(17) . . ?
C17 N2 C14 120.06(17) . . ?
C8 N2 C14 117.00(17) . . ?
C7 O1 H1 101(3) . . ?
C19 O3 C20 115.4(2) . . ?
C22 O5 C23 116.9(2) . . ?
C21 O6 C24 107.54(16) . . ?
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
Br1 C1 1.897(2) . ?
C1 C6 1.370(3) . ?
C1 C2 1.378(4) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(3) . ?
C4 C24 1.453(3) . ?
C5 C6 1.391(3) . ?
C5 C7 1.518(3) . ?
C6 H6 0.9300 . ?
C7 O1 1.423(3) . ?
C7 C8 1.554(3) . ?
C7 H7 0.9800 . ?
C8 N2 1.449(3) . ?
C8 C9 1.518(3) . ?
C8 H8 0.9800 . ?
C9 N1 1.340(3) . ?
C9 C10 1.373(4) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(5) . ?
C12 H12 0.9300 . ?
C13 N1 1.344(4) . ?
C13 H13 0.9300 . ?
C14 N2 1.478(3) . ?
C14 C16 1.513(4) . ?
C14 C15 1.523(4) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C24 1.380(3) . ?
C17 N2 1.389(3) . ?
C17 C18 1.440(3) . ?
C18 C21 1.354(3) . ?
C18 C19 1.495(3) . ?
C19 O2 1.190(3) . ?
C19 O3 1.329(3) . ?
C20 O3 1.454(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O6 1.357(3) . ?
C21 C22 1.470(3) . ?
C22 O4 1.198(3) . ?
C22 O5 1.327(3) . ?
C23 O5 1.449(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O6 1.383(3) . ?
O1 H1 0.79(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190603
