#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:24:46 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158501.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_7158501
loop_
_publ_author_name
'McFadden, Timothy Patrick'
'Nwachukwu, Chideraa Iheanyi'
'Roberts, Andrew George'
_publ_section_title
;
 An amine template strategy to construct successive C-C bonds: synthesis
 of benzo[h]quinolines by a deaminative ring contraction cascade.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1379
_journal_page_last               1385
_journal_paper_doi               10.1039/d1ob02245h
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_common            deoxytoddaquinoline
_chemical_name_systematic
6-methyl-6,7-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]pyrido[2,3-e]azepine
_chemical_properties_physical    'Not sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-06-01 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                109.932(3)
_cell_angle_beta                 107.117(3)
_cell_angle_gamma                92.339(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6358(9)
_cell_length_b                   9.0784(11)
_cell_length_c                   9.7663(13)
_cell_measurement_reflns_used    4733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.79
_cell_measurement_theta_min      2.42
_cell_volume                     600.71(13)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18138
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.631
_diffrn_reflns_theta_min         2.676
_diffrn_source                   'Fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       irregular
_exptl_crystal_F_000             268
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methylene chloride'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0659P)²+0.0913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4242
_reflns_number_total             5526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02245h2.cif
_cod_data_source_block           20210324AR_0m
_cod_depositor_comments
'Adding full bibliography for 7158501--7158502.cif.'
_cod_database_code               7158501
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.972
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.04710(9) 0.12826(8) 0.33346(7) 0.01585(13) Uani 1 1 d . . . . .
O2 O 0.13498(9) 0.09074(8) 0.17628(7) 0.01650(13) Uani 1 1 d . . . . .
N3 N 0.41644(11) 0.19534(10) 0.87765(9) 0.01477(14) Uani 1 1 d . . . . .
N4 N 0.82584(10) 0.38650(9) 0.70667(8) 0.01218(13) Uani 1 1 d . . . . .
C5 C -0.04763(12) 0.04627(12) 0.17891(10) 0.01683(17) Uani 1 1 d . . . . .
H5A H -0.143382 0.077439 0.105086 0.020 Uiso 1 1 calc R U . . .
H5B H -0.074435 -0.069896 0.150376 0.020 Uiso 1 1 calc R U . . .
C6 C 0.13769(11) 0.15685(10) 0.42218(9) 0.01141(14) Uani 1 1 d . . . . .
C7 C 0.24730(12) 0.13575(10) 0.32767(9) 0.01156(14) Uani 1 1 d . . . . .
C8 C 0.43785(12) 0.15900(10) 0.38565(9) 0.01212(14) Uani 1 1 d . . . . .
H8 H 0.511299 0.143762 0.319989 0.015 Uiso 1 1 calc R U . . .
C9 C 0.51949(11) 0.20639(10) 0.54659(9) 0.01057(14) Uani 1 1 d . . . . .
C10 C 0.40841(11) 0.22832(10) 0.64191(9) 0.01074(14) Uani 1 1 d . . . . .
C11 C 0.21274(11) 0.20234(10) 0.57929(9) 0.01201(14) Uani 1 1 d . . . . .
H11 H 0.136811 0.215721 0.642856 0.014 Uiso 1 1 calc R U . . .
C12 C 0.49780(11) 0.27108(10) 0.80995(9) 0.01136(14) Uani 1 1 d . . . . .
C13 C 0.49737(13) 0.22930(12) 1.02886(10) 0.01674(16) Uani 1 1 d . . . . .
H13 H 0.440975 0.176494 1.077685 0.020 Uiso 1 1 calc R U . . .
C14 C 0.65903(13) 0.33728(12) 1.11844(10) 0.01700(17) Uani 1 1 d . . . . .
H14 H 0.712904 0.355763 1.224924 0.020 Uiso 1 1 calc R U . . .
C15 C 0.74012(12) 0.41772(11) 1.04840(10) 0.01532(16) Uani 1 1 d . . . . .
H15 H 0.849554 0.493532 1.107026 0.018 Uiso 1 1 calc R U . . .
C16 C 0.65914(11) 0.38589(10) 0.89140(9) 0.01209(14) Uani 1 1 d . . . . .
C17 C 0.73099(12) 0.47801(10) 0.81157(10) 0.01371(15) Uani 1 1 d . . . . .
H17A H 0.625675 0.515214 0.751991 0.016 Uiso 1 1 calc R U . . .
H17B H 0.818459 0.572874 0.890637 0.016 Uiso 1 1 calc R U . . .
C18 C 0.72757(11) 0.22280(10) 0.61712(10) 0.01225(14) Uani 1 1 d . . . . .
H18A H 0.753653 0.161427 0.685469 0.015 Uiso 1 1 calc R U . . .
H18B H 0.779338 0.174167 0.533273 0.015 Uiso 1 1 calc R U . . .
C19 C 0.84486(13) 0.46973(11) 0.60621(11) 0.01617(16) Uani 1 1 d . . . . .
H19A H 0.907904 0.409379 0.536116 0.024 Uiso 1 1 calc R U . . .
H19B H 0.721604 0.480297 0.546064 0.024 Uiso 1 1 calc R U . . .
H19C H 0.917830 0.575347 0.669087 0.024 Uiso 1 1 calc R U . . .
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
C6 O1 C5 104.08(6) . . ?
C7 O2 C5 104.09(6) . . ?
C13 N3 C12 117.47(8) . . ?
C19 N4 C17 109.09(7) . . ?
C19 N4 C18 111.60(7) . . ?
C17 N4 C18 111.59(6) . . ?
O1 C5 O2 106.67(7) . . ?
O1 C5 H5A 110.4 . . ?
O2 C5 H5A 110.4 . . ?
O1 C5 H5B 110.4 . . ?
O2 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C11 C6 O1 128.28(7) . . ?
C11 C6 C7 122.19(8) . . ?
O1 C6 C7 109.52(7) . . ?
C8 C7 O2 128.42(7) . . ?
C8 C7 C6 122.15(7) . . ?
O2 C7 C6 109.43(7) . . ?
C7 C8 C9 117.14(7) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C10 C9 C8 120.59(7) . . ?
C10 C9 C18 119.33(7) . . ?
C8 C9 C18 119.94(7) . . ?
C9 C10 C11 121.15(7) . . ?
C9 C10 C12 119.38(7) . . ?
C11 C10 C12 119.39(7) . . ?
C6 C11 C10 116.78(7) . . ?
C6 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
N3 C12 C16 123.12(7) . . ?
N3 C12 C10 116.42(7) . . ?
C16 C12 C10 120.46(7) . . ?
N3 C13 C14 123.80(8) . . ?
N3 C13 H13 118.1 . . ?
C14 C13 H13 118.1 . . ?
C13 C14 C15 118.41(8) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C16 119.32(8) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C12 117.84(8) . . ?
C15 C16 C17 121.88(7) . . ?
C12 C16 C17 120.14(7) . . ?
N4 C17 C16 113.89(7) . . ?
N4 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
N4 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
N4 C18 C9 115.53(7) . . ?
N4 C18 H18A 108.4 . . ?
C9 C18 H18A 108.4 . . ?
N4 C18 H18B 108.4 . . ?
C9 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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 C6 1.3807(10) . ?
O1 C5 1.4362(11) . ?
O2 C7 1.3790(10) . ?
O2 C5 1.4457(11) . ?
N3 C13 1.3397(11) . ?
N3 C12 1.3464(11) . ?
N4 C19 1.4612(11) . ?
N4 C17 1.4730(11) . ?
N4 C18 1.4741(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.3728(11) . ?
C6 C7 1.3915(11) . ?
C7 C8 1.3750(12) . ?
C8 C9 1.4087(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.4063(11) . ?
C9 C18 1.5125(12) . ?
C10 C11 1.4131(12) . ?
C10 C12 1.4813(11) . ?
C11 H11 0.9500 . ?
C12 C16 1.4106(12) . ?
C13 C14 1.3895(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.3919(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.3936(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.5057(12) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
C6 O1 C5 O2 -24.36(9) . . . . ?
C7 O2 C5 O1 23.83(9) . . . . ?
C5 O1 C6 C11 -165.45(9) . . . . ?
C5 O1 C6 C7 15.77(10) . . . . ?
C5 O2 C7 C8 165.94(9) . . . . ?
C5 O2 C7 C6 -14.20(9) . . . . ?
C11 C6 C7 C8 0.05(13) . . . . ?
O1 C6 C7 C8 178.92(8) . . . . ?
C11 C6 C7 O2 -179.82(8) . . . . ?
O1 C6 C7 O2 -0.96(10) . . . . ?
O2 C7 C8 C9 179.55(8) . . . . ?
C6 C7 C8 C9 -0.30(13) . . . . ?
C7 C8 C9 C10 0.01(12) . . . . ?
C7 C8 C9 C18 175.67(8) . . . . ?
C8 C9 C10 C11 0.52(12) . . . . ?
C18 C9 C10 C11 -175.16(7) . . . . ?
C8 C9 C10 C12 177.24(7) . . . . ?
C18 C9 C10 C12 1.56(12) . . . . ?
O1 C6 C11 C10 -178.17(8) . . . . ?
C7 C6 C11 C10 0.47(13) . . . . ?
C9 C10 C11 C6 -0.75(12) . . . . ?
C12 C10 C11 C6 -177.46(8) . . . . ?
C13 N3 C12 C16 -1.77(13) . . . . ?
C13 N3 C12 C10 178.43(8) . . . . ?
C9 C10 C12 N3 -137.08(8) . . . . ?
C11 C10 C12 N3 39.70(11) . . . . ?
C9 C10 C12 C16 43.11(12) . . . . ?
C11 C10 C12 C16 -140.11(9) . . . . ?
C12 N3 C13 C14 -0.02(14) . . . . ?
N3 C13 C14 C15 1.42(15) . . . . ?
C13 C14 C15 C16 -1.04(14) . . . . ?
C14 C15 C16 C12 -0.59(13) . . . . ?
C14 C15 C16 C17 175.00(8) . . . . ?
N3 C12 C16 C15 2.09(13) . . . . ?
C10 C12 C16 C15 -178.12(8) . . . . ?
N3 C12 C16 C17 -173.59(8) . . . . ?
C10 C12 C16 C17 6.21(12) . . . . ?
C19 N4 C17 C16 164.92(7) . . . . ?
C18 N4 C17 C16 41.14(10) . . . . ?
C15 C16 C17 N4 108.92(9) . . . . ?
C12 C16 C17 N4 -75.59(10) . . . . ?
C19 N4 C18 C9 -76.55(9) . . . . ?
C17 N4 C18 C9 45.80(10) . . . . ?
C10 C9 C18 N4 -74.41(10) . . . . ?
C8 C9 C18 N4 109.87(9) . . . . ?
