#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:26:34 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250101 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038073.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_4038073
loop_
_publ_author_name
'Outin, Johanne'
'Quellier, Pauline'
'Bélanger, Guillaume'
_publ_section_title
;
 Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich
 Cyclizations to Functionalized Benzoindolizidines and
 Benzoquinolizidines.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4712
_journal_page_last               4729
_journal_paper_doi               10.1021/acs.joc.9b03449
_journal_volume                  85
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H21 N1 O3'
_chemical_formula_sum            'C16 H21 N O3'
_chemical_formula_weight         275.34
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2014-07-21T08:34:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 113.6040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.3546(18)
_cell_length_b                   5.0780(3)
_cell_length_c                   20.1975(12)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.5583
_cell_measurement_theta_min      4.5565
_cell_measurement_wavelength     1.54186
_cell_volume                     2852.8(3)
_computing_cell_refinement       'SAINT V8.27B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      0.661714E-2
_diffrn_orient_matrix_UB_12      0.132578
_diffrn_orient_matrix_UB_13      0.394371E-1
_diffrn_orient_matrix_UB_21      -0.279806E-1
_diffrn_orient_matrix_UB_22      -0.680574E-1
_diffrn_orient_matrix_UB_23      0.91209E-2
_diffrn_orient_matrix_UB_31      0.215972E-1
_diffrn_orient_matrix_UB_32      -0.128793
_diffrn_orient_matrix_UB_33      0.357764E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7513
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         71.04
_diffrn_reflns_theta_min         4.56
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.2
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0080(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0445P)²+1.5156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                2502
_reflns_number_total             2700
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo9b03449_si_002.cif
_cod_data_source_block           cu_belanger_jo2_016d_0m
_cod_depositor_comments
'Adding full bibliography for 4038072--4038076.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038073
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C1 C 0.11477(5) 0.5432(3) -0.12158(6) 0.0443(3) Uani 1 1 d . . .
H1A H 0.1268 0.3665 -0.1268 0.053 Uiso 1 1 calc R . .
H1B H 0.1285 0.673 -0.1446 0.053 Uiso 1 1 calc R . .
C2 C 0.06045(5) 0.5476(3) -0.15915(6) 0.0386(3) Uani 1 1 d . . .
H2A H 0.0506 0.4934 -0.2102 0.046 Uiso 1 1 calc R . .
H2B H 0.0487 0.7292 -0.1586 0.046 Uiso 1 1 calc R . .
C3 C 0.03785(5) 0.3630(2) -0.12203(6) 0.0386(3) Uani 1 1 d . . .
H3A H 0.0439 0.1781 -0.1314 0.046 Uiso 1 1 calc R . .
H3B H 0.0026 0.391 -0.1422 0.046 Uiso 1 1 calc R . .
C4 C 0.05876(4) 0.4126(2) -0.04046(6) 0.0305(3) Uani 1 1 d . . .
H4 H 0.0471 0.2688 -0.0177 0.037 Uiso 1 1 calc R . .
C5 C 0.11409(4) 0.4018(2) -0.00819(6) 0.0306(3) Uani 1 1 d . . .
H5 H 0.124 0.2266 -0.0202 0.037 Uiso 1 1 calc R . .
C6 C 0.13659(4) 0.4350(2) 0.07370(6) 0.0283(3) Uani 1 1 d . . .
C7 C 0.11935(4) 0.2824(2) 0.11633(6) 0.0291(3) Uani 1 1 d . . .
H7 H 0.0942 0.1595 0.0936 0.035 Uiso 1 1 calc R . .
C8 C 0.13830(4) 0.3079(2) 0.19055(6) 0.0285(3) Uani 1 1 d . . .
C9 C 0.17493(4) 0.4937(2) 0.22422(6) 0.0293(3) Uani 1 1 d . . .
C10 C 0.19251(4) 0.6397(2) 0.18253(6) 0.0307(3) Uani 1 1 d . . .
H10 H 0.2175 0.7638 0.2052 0.037 Uiso 1 1 calc R . .
C11 C 0.17419(4) 0.6083(2) 0.10732(6) 0.0294(3) Uani 1 1 d . . .
C12 C 0.19660(4) 0.7581(3) 0.06403(6) 0.0363(3) Uani 1 1 d . . .
H12A H 0.1858 0.9437 0.0589 0.044 Uiso 1 1 calc R . .
H12B H 0.232 0.756 0.09 0.044 Uiso 1 1 calc R . .
C13 C 0.18273(4) 0.6372(3) -0.00991(7) 0.0422(3) Uani 1 1 d . . .
H13A H 0.1937 0.7517 -0.0399 0.051 Uiso 1 1 calc R . .
H13B H 0.1984 0.4633 -0.0054 0.051 Uiso 1 1 calc R . .
C14 C 0.04209(4) 0.6693(2) -0.02206(6) 0.0330(3) Uani 1 1 d . . .
H14 H 0.0617 0.7483 0.0227 0.04 Uiso 1 1 calc R . .
C15 C 0.08543(4) -0.0144(3) 0.20475(7) 0.0382(3) Uani 1 1 d . . .
H15A H 0.0567 0.0801 0.1724 0.057 Uiso 1 1 calc R . .
H15B H 0.0786 -0.1007 0.243 0.057 Uiso 1 1 calc R . .
H15C H 0.0944 -0.1473 0.1772 0.057 Uiso 1 1 calc R . .
C16 C 0.21926(5) 0.7352(3) 0.33116(7) 0.0407(3) Uani 1 1 d . . .
H16A H 0.2504 0.7203 0.3275 0.061 Uiso 1 1 calc R . .
H16B H 0.2243 0.7423 0.3822 0.061 Uiso 1 1 calc R . .
H16C H 0.203 0.8962 0.3067 0.061 Uiso 1 1 calc R . .
N1 N 0.13050(4) 0.6063(2) -0.04444(5) 0.0348(3) Uani 1 1 d . . .
O1 O 0.00612(3) 0.7833(2) -0.05909(5) 0.0467(3) Uani 1 1 d . . .
O2 O 0.12404(3) 0.16724(17) 0.23628(4) 0.0353(2) Uani 1 1 d . . .
O3 O 0.19033(3) 0.51246(17) 0.29775(4) 0.0366(2) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N1 C1 C2 110.75(10) . . ?
C1 C2 C3 111.02(10) . . ?
C2 C3 C4 110.73(10) . . ?
C14 C4 C3 111.98(10) . . ?
C14 C4 C5 110.21(9) . . ?
C3 C4 C5 111.20(10) . . ?
N1 C5 C6 111.63(10) . . ?
N1 C5 C4 107.11(9) . . ?
C6 C5 C4 113.20(9) . . ?
C11 C6 C7 119.06(10) . . ?
C11 C6 C5 121.70(10) . . ?
C7 C6 C5 119.23(10) . . ?
C8 C7 C6 121.21(11) . . ?
O2 C8 C7 125.29(10) . . ?
O2 C8 C9 115.21(9) . . ?
C7 C8 C9 119.49(10) . . ?
O3 C9 C10 125.22(10) . . ?
O3 C9 C8 115.51(10) . . ?
C10 C9 C8 119.27(10) . . ?
C9 C10 C11 121.17(11) . . ?
C6 C11 C10 119.69(10) . . ?
C6 C11 C12 120.65(10) . . ?
C10 C11 C12 119.64(10) . . ?
C13 C12 C11 110.84(11) . . ?
N1 C13 C12 109.57(10) . . ?
O1 C14 C4 125.45(11) . . ?
C13 N1 C5 110.96(9) . . ?
C13 N1 C1 111.03(9) . . ?
C5 N1 C1 110.08(10) . . ?
C8 O2 C15 117.52(9) . . ?
C9 O3 C16 116.52(9) . . ?
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
C1 N1 1.4705(15) . ?
C1 C2 1.5142(19) . ?
C2 C3 1.5241(18) . ?
C3 C4 1.5308(15) . ?
C4 C14 1.4982(16) . ?
C4 C5 1.5402(16) . ?
C5 N1 1.4676(15) . ?
C5 C6 1.5250(15) . ?
C6 C11 1.3845(16) . ?
C6 C7 1.4061(16) . ?
C7 C8 1.3800(15) . ?
C8 O2 1.3677(13) . ?
C8 C9 1.4084(16) . ?
C9 O3 1.3701(13) . ?
C9 C10 1.3796(16) . ?
C10 C11 1.4021(15) . ?
C11 C12 1.5107(15) . ?
C12 C13 1.5102(18) . ?
C13 N1 1.4624(16) . ?
C14 O1 1.1969(15) . ?
C15 O2 1.4255(14) . ?
C16 O3 1.4252(15) . ?
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
N1 C1 C2 C3 -55.45(15) . . . . ?
C1 C2 C3 C4 49.84(14) . . . . ?
C2 C3 C4 C14 71.01(13) . . . . ?
C2 C3 C4 C5 -52.78(13) . . . . ?
C14 C4 C5 N1 -65.10(11) . . . . ?
C3 C4 C5 N1 59.69(12) . . . . ?
C14 C4 C5 C6 58.38(12) . . . . ?
C3 C4 C5 C6 -176.83(9) . . . . ?
N1 C5 C6 C11 -11.01(14) . . . . ?
C4 C5 C6 C11 -131.97(11) . . . . ?
N1 C5 C6 C7 170.17(10) . . . . ?
C4 C5 C6 C7 49.22(14) . . . . ?
C11 C6 C7 C8 1.84(16) . . . . ?
C5 C6 C7 C8 -179.32(10) . . . . ?
C6 C7 C8 O2 -179.61(10) . . . . ?
C6 C7 C8 C9 1.25(17) . . . . ?
O2 C8 C9 O3 -1.58(14) . . . . ?
C7 C8 C9 O3 177.65(10) . . . . ?
O2 C8 C9 C10 178.27(10) . . . . ?
C7 C8 C9 C10 -2.50(16) . . . . ?
O3 C9 C10 C11 -179.47(10) . . . . ?
C8 C9 C10 C11 0.69(17) . . . . ?
C7 C6 C11 C10 -3.64(16) . . . . ?
C5 C6 C11 C10 177.55(10) . . . . ?
C7 C6 C11 C12 174.62(10) . . . . ?
C5 C6 C11 C12 -4.20(16) . . . . ?
C9 C10 C11 C6 2.41(17) . . . . ?
C9 C10 C11 C12 -175.86(10) . . . . ?
C6 C11 C12 C13 -15.85(15) . . . . ?
C10 C11 C12 C13 162.40(10) . . . . ?
C11 C12 C13 N1 51.30(14) . . . . ?
C3 C4 C14 O1 23.71(17) . . . . ?
C5 C4 C14 O1 148.05(12) . . . . ?
C12 C13 N1 C5 -69.40(14) . . . . ?
C12 C13 N1 C1 167.84(11) . . . . ?
C6 C5 N1 C13 47.17(13) . . . . ?
C4 C5 N1 C13 171.60(10) . . . . ?
C6 C5 N1 C1 170.48(9) . . . . ?
C4 C5 N1 C1 -65.09(12) . . . . ?
C2 C1 N1 C13 -172.38(12) . . . . ?
C2 C1 N1 C5 64.35(14) . . . . ?
C7 C8 O2 C15 -2.19(16) . . . . ?
C9 C8 O2 C15 176.99(10) . . . . ?
C10 C9 O3 C16 13.54(16) . . . . ?
C8 C9 O3 C16 -166.61(11) . . . . ?
