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#$Date: 2016-03-26 02:47:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180155 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/51/7105149.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_7105149
loop_
_publ_author_name
'Wu, Liang'
'Aliev, Abil E'
'Caddick, Stephen'
'Fitzmaurice, Richard J'
'Tocher, Derek A'
'King, Frank D'
_publ_section_title
;
 A facile synthesis of dibenzopyrroloazepinones as tetracyclic
 allocolchicinoids--an unusual 1,2-phenyl shift.
;
_journal_issue                   2
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              318
_journal_page_last               320
_journal_paper_doi               10.1039/b919114c
_journal_volume                  46
_journal_year                    2009
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.680(2)
_cell_length_b                   7.2722(8)
_cell_length_c                   19.090(2)
_cell_measurement_temperature    150(2)
_cell_volume                     2593.3(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20861
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.051
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.5933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                2278
_reflns_number_total             3153
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b919114c.txt
_cod_data_source_block           str0764
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7105149
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O1 O 0.14053(7) 0.06116(18) 1.01416(6) 0.0317(3) Uani 1 1 d . . .
N1 N 0.06261(7) 0.11413(19) 0.92669(7) 0.0224(3) Uani 1 1 d . . .
C1 C 0.11548(9) 0.0164(2) 0.95682(8) 0.0224(4) Uani 1 1 d . . .
C2 C 0.13983(8) -0.1571(2) 0.92079(9) 0.0209(4) Uani 1 1 d . . .
C3 C 0.16325(8) -0.2967(2) 0.96564(9) 0.0257(4) Uani 1 1 d . . .
H3A H 0.1639 -0.2752 1.0147 0.031 Uiso 1 1 calc R . .
C4 C 0.18543(9) -0.4651(3) 0.94027(9) 0.0285(4) Uani 1 1 d . . .
H4A H 0.2014 -0.5577 0.9717 0.034 Uiso 1 1 calc R . .
C5 C 0.18428(9) -0.4987(2) 0.86887(9) 0.0269(4) Uani 1 1 d . . .
H5A H 0.1970 -0.6163 0.8512 0.032 Uiso 1 1 calc R . .
C6 C 0.16444(8) -0.3591(2) 0.82352(9) 0.0232(4) Uani 1 1 d . . .
H6A H 0.1651 -0.3818 0.7745 0.028 Uiso 1 1 calc R . .
C7 C 0.14336(8) -0.1852(2) 0.84767(8) 0.0195(3) Uani 1 1 d . . .
C8 C 0.13184(8) -0.0381(2) 0.79486(8) 0.0197(3) Uani 1 1 d . . .
C9 C 0.17970(8) -0.0242(2) 0.73881(8) 0.0209(4) Uani 1 1 d . . .
H9A H 0.2187 -0.1079 0.7362 0.025 Uiso 1 1 calc R . .
C10 C 0.17206(9) 0.1086(2) 0.68665(8) 0.0213(4) Uani 1 1 d . . .
C11 C 0.11500(9) 0.2306(2) 0.69215(9) 0.0260(4) Uani 1 1 d . . .
H11A H 0.1086 0.3225 0.6574 0.031 Uiso 1 1 calc R . .
C12 C 0.06735(9) 0.2198(2) 0.74780(9) 0.0260(4) Uani 1 1 d . . .
H12A H 0.0290 0.3054 0.7506 0.031 Uiso 1 1 calc R . .
C13 C 0.07454(8) 0.0864(2) 0.79939(8) 0.0208(4) Uani 1 1 d . . .
C14 C 0.02461(8) 0.0657(2) 0.86119(8) 0.0211(4) Uani 1 1 d . . .
H14A H 0.0081 -0.0648 0.8640 0.025 Uiso 1 1 calc R . .
C15 C -0.04065(9) 0.1935(2) 0.86365(9) 0.0270(4) Uani 1 1 d . . .
H15A H -0.0562 0.2281 0.8158 0.032 Uiso 1 1 calc R . .
H15B H -0.0812 0.1342 0.8883 0.032 Uiso 1 1 calc R . .
C16 C -0.01391(10) 0.3612(2) 0.90401(10) 0.0311(4) Uani 1 1 d . . .
H16A H 0.0150 0.4429 0.8736 0.037 Uiso 1 1 calc R . .
H16B H -0.0543 0.4322 0.9240 0.037 Uiso 1 1 calc R . .
C17 C 0.03154(9) 0.2761(2) 0.96118(9) 0.0277(4) Uani 1 1 d . . .
H17A H 0.0693 0.3620 0.9769 0.033 Uiso 1 1 calc R . .
H17B H 0.0019 0.2400 1.0019 0.033 Uiso 1 1 calc R . .
C18 C 0.22360(10) 0.1182(2) 0.62594(9) 0.0276(4) Uani 1 1 d . . .
H18A H 0.2098 0.2193 0.5948 0.041 Uiso 1 1 calc R . .
H18B H 0.2223 0.0020 0.6000 0.041 Uiso 1 1 calc R . .
H18C H 0.2721 0.1395 0.6436 0.041 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 C17 121.45(14) . . ?
C1 N1 C14 125.97(13) . . ?
C17 N1 C14 112.32(13) . . ?
O1 C1 N1 121.21(16) . . ?
O1 C1 C2 120.72(15) . . ?
N1 C1 C2 117.94(14) . . ?
C3 C2 C7 119.03(15) . . ?
C3 C2 C1 115.02(15) . . ?
C7 C2 C1 125.90(15) . . ?
C4 C3 C2 121.55(16) . . ?
C3 C4 C5 119.78(16) . . ?
C6 C5 C4 119.37(16) . . ?
C5 C6 C7 122.05(15) . . ?
C6 C7 C2 117.95(14) . . ?
C6 C7 C8 117.84(14) . . ?
C2 C7 C8 124.02(14) . . ?
C9 C8 C13 119.20(15) . . ?
C9 C8 C7 118.60(14) . . ?
C13 C8 C7 122.20(14) . . ?
C10 C9 C8 122.08(15) . . ?
C11 C10 C9 117.80(15) . . ?
C11 C10 C18 121.15(15) . . ?
C9 C10 C18 121.04(15) . . ?
C12 C11 C10 120.86(15) . . ?
C11 C12 C13 121.36(16) . . ?
C12 C13 C8 118.69(15) . . ?
C12 C13 C14 124.29(14) . . ?
C8 C13 C14 117.01(14) . . ?
N1 C14 C13 109.86(12) . . ?
N1 C14 C15 102.19(12) . . ?
C13 C14 C15 117.02(14) . . ?
C16 C15 C14 103.85(14) . . ?
C17 C16 C15 102.74(14) . . ?
N1 C17 C16 103.07(13) . . ?
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
O1 C1 1.2341(19) . ?
N1 C1 1.346(2) . ?
N1 C17 1.469(2) . ?
N1 C14 1.480(2) . ?
C1 C2 1.507(2) . ?
C2 C3 1.398(2) . ?
C2 C7 1.412(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.385(3) . ?
C5 C6 1.385(2) . ?
C6 C7 1.402(2) . ?
C7 C8 1.486(2) . ?
C8 C9 1.398(2) . ?
C8 C13 1.405(2) . ?
C9 C10 1.394(2) . ?
C10 C11 1.391(2) . ?
C10 C18 1.508(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.511(2) . ?
C14 C15 1.534(2) . ?
C15 C16 1.526(2) . ?
C16 C17 1.515(3) . ?
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
C17 N1 C1 O1 -1.1(2) . . . . ?
C14 N1 C1 O1 -174.84(15) . . . . ?
C17 N1 C1 C2 174.78(14) . . . . ?
C14 N1 C1 C2 1.1(2) . . . . ?
O1 C1 C2 C3 28.2(2) . . . . ?
N1 C1 C2 C3 -147.68(15) . . . . ?
O1 C1 C2 C7 -149.10(16) . . . . ?
N1 C1 C2 C7 35.0(2) . . . . ?
C7 C2 C3 C4 -4.1(2) . . . . ?
C1 C2 C3 C4 178.34(15) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 3.4(3) . . . . ?
C4 C5 C6 C7 -1.9(3) . . . . ?
C5 C6 C7 C2 -2.6(2) . . . . ?
C5 C6 C7 C8 172.54(14) . . . . ?
C3 C2 C7 C6 5.5(2) . . . . ?
C1 C2 C7 C6 -177.24(15) . . . . ?
C3 C2 C7 C8 -169.33(14) . . . . ?
C1 C2 C7 C8 7.9(2) . . . . ?
C6 C7 C8 C9 -40.6(2) . . . . ?
C2 C7 C8 C9 134.27(16) . . . . ?
C6 C7 C8 C13 139.22(16) . . . . ?
C2 C7 C8 C13 -45.9(2) . . . . ?
C13 C8 C9 C10 -0.6(2) . . . . ?
C7 C8 C9 C10 179.19(15) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C8 C9 C10 C18 -178.76(15) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C18 C10 C11 C12 179.35(16) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?
C11 C12 C13 C14 -179.68(16) . . . . ?
C9 C8 C13 C12 0.0(2) . . . . ?
C7 C8 C13 C12 -179.83(15) . . . . ?
C9 C8 C13 C14 -179.75(14) . . . . ?
C7 C8 C13 C14 0.4(2) . . . . ?
C1 N1 C14 C13 -69.52(19) . . . . ?
C17 N1 C14 C13 116.26(14) . . . . ?
C1 N1 C14 C15 165.57(15) . . . . ?
C17 N1 C14 C15 -8.65(17) . . . . ?
C12 C13 C14 N1 -111.75(17) . . . . ?
C8 C13 C14 N1 67.96(18) . . . . ?
C12 C13 C14 C15 4.1(2) . . . . ?
C8 C13 C14 C15 -176.18(14) . . . . ?
N1 C14 C15 C16 29.78(16) . . . . ?
C13 C14 C15 C16 -90.24(16) . . . . ?
C14 C15 C16 C17 -40.16(17) . . . . ?
C1 N1 C17 C16 169.44(15) . . . . ?
C14 N1 C17 C16 -16.04(17) . . . . ?
C15 C16 C17 N1 34.04(16) . . . . ?
