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#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150550.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_7150550
loop_
_publ_author_name
'King, Frank D.'
'Aliev, Abil E.'
'Caddick, Stephen'
'Tocher, Derek A.'
'Courtier-Murias, Denis'
_publ_section_title
;
 A facile synthesis of pyrrolo-(di)-benzazocinones via an
 intramolecular N-acyliminium ion cyclisation
;
_journal_issue                   1
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              167
_journal_page_last               177
_journal_paper_doi               10.1039/b815195d
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C16 H21 N O3'
_chemical_formula_weight         275.34
_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                65.628(2)
_cell_angle_beta                 77.548(2)
_cell_angle_gamma                75.070(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3607(11)
_cell_length_b                   9.2365(13)
_cell_length_c                   10.0371(14)
_cell_measurement_temperature    150(2)
_cell_volume                     676.91(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5715
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_correction_T_min  0.9551
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0494
_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)+(0.1037P)²+0.2467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                2808
_reflns_number_total             3056
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b815195d.txt
_cod_data_source_block           str0633
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150550
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
N1 N 0.06445(13) 0.25902(13) 0.35025(12) 0.0189(2) Uani 1 1 d . . .
O1 O 0.19896(13) 0.35794(13) 0.45718(11) 0.0284(3) Uani 1 1 d . . .
O2 O 0.42796(12) 0.33551(12) -0.17836(10) 0.0243(2) Uani 1 1 d . . .
O3 O 0.06475(12) -0.11469(11) 0.23109(10) 0.0226(2) Uani 1 1 d . . .
C1 C 0.20353(16) 0.27174(16) 0.38950(14) 0.0201(3) Uani 1 1 d . . .
C2 C 0.36867(16) 0.19562(16) 0.32734(15) 0.0221(3) Uani 1 1 d . . .
H2A H 0.3579 0.0970 0.3164 0.027 Uiso 1 1 calc R . .
H2B H 0.4544 0.1656 0.3933 0.027 Uiso 1 1 calc R . .
C3 C 0.41731(16) 0.32391(16) 0.17577(15) 0.0230(3) Uani 1 1 d . . .
H3A H 0.4379 0.4170 0.1903 0.028 Uiso 1 1 calc R . .
H3B H 0.5225 0.2769 0.1286 0.028 Uiso 1 1 calc R . .
C4 C 0.28198(16) 0.38498(15) 0.07194(14) 0.0203(3) Uani 1 1 d . . .
H4A H 0.1772 0.4355 0.1167 0.024 Uiso 1 1 calc R . .
H4B H 0.3184 0.4680 -0.0229 0.024 Uiso 1 1 calc R . .
C5 C 0.25143(15) 0.24554(14) 0.04496(13) 0.0171(3) Uani 1 1 d . . .
C6 C 0.33678(16) 0.21969(15) -0.08320(14) 0.0195(3) Uani 1 1 d . . .
C7 C 0.32964(17) 0.08491(17) -0.10781(15) 0.0224(3) Uani 1 1 d . . .
H7A H 0.3858 0.0704 -0.1957 0.027 Uiso 1 1 calc R . .
C8 C 0.23970(16) -0.02919(16) -0.00312(15) 0.0218(3) Uani 1 1 d . . .
H8A H 0.2367 -0.1232 -0.0185 0.026 Uiso 1 1 calc R . .
C9 C 0.15479(15) -0.00666(15) 0.12291(14) 0.0185(3) Uani 1 1 d . . .
C10 C 0.15699(15) 0.13270(14) 0.14836(13) 0.0167(3) Uani 1 1 d . . .
C11 C 0.04689(15) 0.14447(14) 0.28745(13) 0.0169(3) Uani 1 1 d . . .
H11A H 0.0618 0.0337 0.3667 0.020 Uiso 1 1 calc R . .
C12 C -0.13861(16) 0.19580(17) 0.26338(15) 0.0228(3) Uani 1 1 d . . .
H12A H -0.1534 0.2798 0.1638 0.027 Uiso 1 1 calc R . .
H12B H -0.1844 0.1019 0.2751 0.027 Uiso 1 1 calc R . .
C13 C -0.22361(16) 0.26247(16) 0.38203(14) 0.0222(3) Uani 1 1 d . . .
H13A H -0.3312 0.3358 0.3554 0.027 Uiso 1 1 calc R . .
H13B H -0.2432 0.1741 0.4786 0.027 Uiso 1 1 calc R . .
C14 C -0.09830(17) 0.35362(18) 0.38480(17) 0.0263(3) Uani 1 1 d . . .
H14A H -0.1145 0.4654 0.3100 0.032 Uiso 1 1 calc R . .
H14B H -0.1080 0.3580 0.4832 0.032 Uiso 1 1 calc R . .
C15 C 0.50756(18) 0.31861(18) -0.31345(14) 0.0264(3) Uani 1 1 d . . .
H15A H 0.5679 0.4075 -0.3716 0.040 Uiso 1 1 calc R . .
H15B H 0.4232 0.3216 -0.3693 0.040 Uiso 1 1 calc R . .
H15C H 0.5862 0.2151 -0.2921 0.040 Uiso 1 1 calc R . .
C16 C 0.06780(19) -0.26165(16) 0.21404(16) 0.0257(3) Uani 1 1 d . . .
H16A H -0.0016 -0.3276 0.2975 0.039 Uiso 1 1 calc R . .
H16B H 0.1828 -0.3219 0.2109 0.039 Uiso 1 1 calc R . .
H16C H 0.0243 -0.2362 0.1221 0.039 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'
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
C1 N1 C14 119.89(11) . . ?
C1 N1 C11 128.04(11) . . ?
C14 N1 C11 111.72(10) . . ?
C6 O2 C15 116.93(11) . . ?
C9 O3 C16 117.38(10) . . ?
O1 C1 N1 122.06(12) . . ?
O1 C1 C2 120.40(12) . . ?
N1 C1 C2 116.93(11) . . ?
C1 C2 C3 106.32(10) . . ?
C4 C3 C2 112.85(10) . . ?
C5 C4 C3 110.00(10) . . ?
C10 C5 C6 119.14(11) . . ?
C10 C5 C4 122.79(11) . . ?
C6 C5 C4 117.72(11) . . ?
C7 C6 O2 123.38(12) . . ?
C7 C6 C5 121.20(12) . . ?
O2 C6 C5 115.42(11) . . ?
C6 C7 C8 119.56(12) . . ?
C9 C8 C7 120.40(12) . . ?
O3 C9 C8 123.47(11) . . ?
O3 C9 C10 115.63(11) . . ?
C8 C9 C10 120.89(12) . . ?
C5 C10 C9 118.76(11) . . ?
C5 C10 C11 127.10(11) . . ?
C9 C10 C11 114.10(10) . . ?
N1 C11 C10 121.06(10) . . ?
N1 C11 C12 102.19(10) . . ?
C10 C11 C12 110.65(10) . . ?
C13 C12 C11 104.40(10) . . ?
C14 C13 C12 102.65(10) . . ?
N1 C14 C13 103.98(10) . . ?
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
N1 C1 1.3517(16) . ?
N1 C14 1.4729(16) . ?
N1 C11 1.4862(15) . ?
O1 C1 1.2314(16) . ?
O2 C6 1.3786(15) . ?
O2 C15 1.4275(16) . ?
O3 C9 1.3718(15) . ?
O3 C16 1.4299(15) . ?
C1 C2 1.5100(18) . ?
C2 C3 1.5419(19) . ?
C3 C4 1.5424(18) . ?
C4 C5 1.5115(16) . ?
C5 C10 1.4017(17) . ?
C5 C6 1.4109(17) . ?
C6 C7 1.3830(19) . ?
C7 C8 1.3907(19) . ?
C8 C9 1.3789(19) . ?
C9 C10 1.4171(17) . ?
C10 C11 1.5257(16) . ?
C11 C12 1.5417(17) . ?
C12 C13 1.5223(18) . ?
C13 C14 1.5145(18) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C1 O1 1.74(19) . . . . ?
C11 N1 C1 O1 -170.88(12) . . . . ?
C14 N1 C1 C2 -169.33(12) . . . . ?
C11 N1 C1 C2 18.04(18) . . . . ?
O1 C1 C2 C3 -84.87(14) . . . . ?
N1 C1 C2 C3 86.36(14) . . . . ?
C1 C2 C3 C4 -55.80(14) . . . . ?
C2 C3 C4 C5 -60.16(14) . . . . ?
C3 C4 C5 C10 77.37(14) . . . . ?
C3 C4 C5 C6 -95.78(13) . . . . ?
C15 O2 C6 C7 4.81(18) . . . . ?
C15 O2 C6 C5 -176.25(11) . . . . ?
C10 C5 C6 C7 -0.43(19) . . . . ?
C4 C5 C6 C7 172.98(12) . . . . ?
C10 C5 C6 O2 -179.39(10) . . . . ?
C4 C5 C6 O2 -5.98(16) . . . . ?
O2 C6 C7 C8 177.51(11) . . . . ?
C5 C6 C7 C8 -1.4(2) . . . . ?
C6 C7 C8 C9 1.5(2) . . . . ?
C16 O3 C9 C8 3.40(18) . . . . ?
C16 O3 C9 C10 -176.23(10) . . . . ?
C7 C8 C9 O3 -179.50(11) . . . . ?
C7 C8 C9 C10 0.11(19) . . . . ?
C6 C5 C10 C9 2.03(18) . . . . ?
C4 C5 C10 C9 -171.03(11) . . . . ?
C6 C5 C10 C11 -175.46(11) . . . . ?
C4 C5 C10 C11 11.48(19) . . . . ?
O3 C9 C10 C5 177.74(10) . . . . ?
C8 C9 C10 C5 -1.90(18) . . . . ?
O3 C9 C10 C11 -4.45(15) . . . . ?
C8 C9 C10 C11 175.90(11) . . . . ?
C1 N1 C11 C10 -54.83(17) . . . . ?
C14 N1 C11 C10 132.05(12) . . . . ?
C1 N1 C11 C12 -178.29(12) . . . . ?
C14 N1 C11 C12 8.60(13) . . . . ?
C5 C10 C11 N1 -17.16(18) . . . . ?
C9 C10 C11 N1 165.26(10) . . . . ?
C5 C10 C11 C12 102.21(14) . . . . ?
C9 C10 C11 C12 -75.37(13) . . . . ?
N1 C11 C12 C13 -29.31(12) . . . . ?
C10 C11 C12 C13 -159.52(10) . . . . ?
C11 C12 C13 C14 39.18(13) . . . . ?
C1 N1 C14 C13 -158.26(11) . . . . ?
C11 N1 C14 C13 15.49(14) . . . . ?
C12 C13 C14 N1 -33.23(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190117
