#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:26:34 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250101 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038072.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_4038072
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         'C13 H18 N2 O1'
_chemical_formula_sum            'C13 H18 N2 O'
_chemical_formula_weight         218.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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             2017-06-08T11:33:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.0350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6553(2)
_cell_length_b                   11.4000(3)
_cell_length_c                   11.0500(3)
_cell_measurement_reflns_used    7339
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.6428
_cell_measurement_theta_min      4.8451
_cell_measurement_wavelength     1.54186
_cell_volume                     1149.77(5)
_computing_cell_refinement       'SAINT V8.34A 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 0.995
_diffrn_measured_fraction_theta_max 0.989
_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      0.429503E-1
_diffrn_orient_matrix_UB_12      0.720689E-1
_diffrn_orient_matrix_UB_13      0.496974E-1
_diffrn_orient_matrix_UB_21      0.144456E-1
_diffrn_orient_matrix_UB_22      -0.434606E-1
_diffrn_orient_matrix_UB_23      0.818153E-1
_diffrn_orient_matrix_UB_31      0.997508E-1
_diffrn_orient_matrix_UB_32      -0.247373E-1
_diffrn_orient_matrix_UB_33      0.104691E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6120
_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         70.65
_diffrn_reflns_theta_min         4.85
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       newedle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0854P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1491
_reflns_number_gt                1628
_reflns_number_total             2185
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo9b03449_si_006.cif
_cod_data_source_block           cu_belanger_jo_129_0m
_cod_depositor_comments
'Adding full bibliography for 4038072--4038076.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.67776(17) 0.40763(16) 0.13620(17) 0.0263(4) Uani 1 1 d . . .
C2 C 0.80587(16) 0.47128(15) 0.11043(17) 0.0251(4) Uani 1 1 d . . .
C3 C 0.76638(16) 0.50970(16) -0.02601(18) 0.0285(4) Uani 1 1 d . . .
C4 C 0.67559(18) 0.46311(17) -0.14001(18) 0.0319(4) Uani 1 1 d . . .
H4 H 0.6208 0.3925 -0.1492 0.038 Uiso 1 1 calc R . .
C5 C 0.67867(19) 0.53857(18) -0.24005(19) 0.0356(5) Uani 1 1 d . . .
H5 H 0.6265 0.5282 -0.3285 0.043 Uiso 1 1 calc R . .
C6 C 0.77054(19) 0.62942(18) -0.18627(19) 0.0366(5) Uani 1 1 d . . .
H6 H 0.7928 0.694 -0.231 0.044 Uiso 1 1 calc R . .
C7 C 0.91698(18) 0.69220(17) 0.03756(19) 0.0344(5) Uani 1 1 d . . .
H7A H 0.8595 0.7624 0.0441 0.041 Uiso 1 1 calc R . .
H7B H 1.0005 0.7179 0.0107 0.041 Uiso 1 1 calc R . .
C8 C 0.97315(17) 0.63206(17) 0.16558(18) 0.0327(4) Uani 1 1 d . . .
H8A H 1.0477 0.5729 0.1642 0.039 Uiso 1 1 calc R . .
H8B H 1.02 0.6903 0.2329 0.039 Uiso 1 1 calc R . .
C9 C 0.89565(19) 0.53995(17) 0.32896(18) 0.0327(4) Uani 1 1 d . . .
H9A H 0.9355 0.6087 0.3841 0.039 Uiso 1 1 calc R . .
H9B H 0.9734 0.4796 0.3463 0.039 Uiso 1 1 calc R . .
C10 C 0.76500(19) 0.49134(17) 0.35964(19) 0.0337(5) Uani 1 1 d . . .
H10A H 0.794 0.4711 0.4517 0.04 Uiso 1 1 calc R . .
H10B H 0.6867 0.5513 0.3413 0.04 Uiso 1 1 calc R . .
C11 C 0.70868(18) 0.38324(16) 0.27968(17) 0.0307(4) Uani 1 1 d . . .
H11A H 0.6175 0.3564 0.2935 0.037 Uiso 1 1 calc R . .
H11B H 0.7821 0.3197 0.3075 0.037 Uiso 1 1 calc R . .
C12 C 0.64613(18) 0.28903(16) 0.06999(18) 0.0302(4) Uani 1 1 d . . .
C13 C 0.4902(2) 0.2480(2) 0.0302(2) 0.0446(5) Uani 1 1 d . . .
H13A H 0.4861 0.1641 0.0102 0.067 Uiso 1 1 calc R . .
H13B H 0.432 0.2917 -0.0458 0.067 Uiso 1 1 calc R . .
H13C H 0.4505 0.2616 0.1001 0.067 Uiso 1 1 calc R . .
N1 N 0.85159(14) 0.57475(13) 0.19456(14) 0.0277(4) Uani 1 1 d . . .
N2 N 0.82472(14) 0.61131(14) -0.05719(15) 0.0312(4) Uani 1 1 d . . .
O1 O 0.74309(13) 0.22897(12) 0.05591(14) 0.0395(4) Uani 1 1 d . . .
H1 H 0.5860(18) 0.4566(16) 0.1048(18) 0.025(5) Uiso 1 1 d . . .
H2 H 0.8909(18) 0.4181(16) 0.1322(17) 0.020(4) Uiso 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
C12 C1 C2 112.20(14) . . ?
C12 C1 C11 106.02(15) . . ?
C2 C1 C11 112.22(14) . . ?
N1 C2 C3 109.04(15) . . ?
N1 C2 C1 110.69(14) . . ?
C3 C2 C1 111.64(13) . . ?
N2 C3 C4 106.48(16) . . ?
N2 C3 C2 120.47(16) . . ?
C4 C3 C2 133.05(17) . . ?
C3 C4 C5 108.09(17) . . ?
C6 C5 C4 107.36(18) . . ?
N2 C6 C5 108.23(17) . . ?
N2 C7 C8 109.57(15) . . ?
N1 C8 C7 109.84(13) . . ?
N1 C9 C10 109.85(14) . . ?
C11 C10 C9 109.57(15) . . ?
C10 C11 C1 111.52(15) . . ?
O1 C12 C13 122.07(17) . . ?
O1 C12 C1 121.51(15) . . ?
C13 C12 C1 116.32(15) . . ?
C9 N1 C8 110.77(13) . . ?
C9 N1 C2 110.56(14) . . ?
C8 N1 C2 108.32(14) . . ?
C6 N2 C3 109.83(15) . . ?
C6 N2 C7 126.15(16) . . ?
C3 N2 C7 123.67(15) . . ?
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 C12 1.520(2) . ?
C1 C2 1.539(2) . ?
C1 C11 1.540(2) . ?
C2 N1 1.477(2) . ?
C2 C3 1.495(3) . ?
C3 N2 1.380(2) . ?
C3 C4 1.385(3) . ?
C4 C5 1.409(3) . ?
C5 C6 1.367(3) . ?
C6 N2 1.365(2) . ?
C7 N2 1.460(2) . ?
C7 C8 1.505(3) . ?
C8 N1 1.467(2) . ?
C9 N1 1.460(2) . ?
C9 C10 1.514(2) . ?
C10 C11 1.510(3) . ?
C12 O1 1.210(2) . ?
C12 C13 1.499(2) . ?
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
C12 C1 C2 N1 -169.39(14) . . . . ?
C11 C1 C2 N1 -50.14(18) . . . . ?
C12 C1 C2 C3 68.94(19) . . . . ?
C11 C1 C2 C3 -171.81(14) . . . . ?
N1 C2 C3 N2 24.57(19) . . . . ?
C1 C2 C3 N2 147.18(15) . . . . ?
N1 C2 C3 C4 -155.11(18) . . . . ?
C1 C2 C3 C4 -32.5(3) . . . . ?
N2 C3 C4 C5 -0.65(19) . . . . ?
C2 C3 C4 C5 179.06(16) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 N2 0.6(2) . . . . ?
N2 C7 C8 N1 -48.9(2) . . . . ?
N1 C9 C10 C11 61.94(19) . . . . ?
C9 C10 C11 C1 -53.32(19) . . . . ?
C12 C1 C11 C10 171.10(14) . . . . ?
C2 C1 C11 C10 48.30(19) . . . . ?
C2 C1 C12 O1 33.7(2) . . . . ?
C11 C1 C12 O1 -89.1(2) . . . . ?
C2 C1 C12 C13 -149.68(17) . . . . ?
C11 C1 C12 C13 87.50(19) . . . . ?
C10 C9 N1 C8 174.78(14) . . . . ?
C10 C9 N1 C2 -65.13(18) . . . . ?
C7 C8 N1 C9 -166.62(15) . . . . ?
C7 C8 N1 C2 71.96(18) . . . . ?
C3 C2 N1 C9 -178.14(12) . . . . ?
C1 C2 N1 C9 58.67(17) . . . . ?
C3 C2 N1 C8 -56.59(16) . . . . ?
C1 C2 N1 C8 -179.78(13) . . . . ?
C5 C6 N2 C3 -1.07(19) . . . . ?
C5 C6 N2 C7 -174.45(15) . . . . ?
C4 C3 N2 C6 1.06(19) . . . . ?
C2 C3 N2 C6 -178.69(14) . . . . ?
C4 C3 N2 C7 174.64(14) . . . . ?
C2 C3 N2 C7 -5.1(2) . . . . ?
C8 C7 N2 C6 -170.86(15) . . . . ?
C8 C7 N2 C3 16.6(2) . . . . ?
