#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:51:40 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159326.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_7159326
loop_
_publ_author_name
'Wang, Yufeng'
'Li, Qiang'
'Song, Xiaopei'
'Wang, Jing'
'Yin, Xiangcong'
'Li, Shuai-Shuai'
'Wang, Liang'
_publ_section_title
;
 Chemoselective and diastereoselective construction of
 4-alkylidene-tetrahydroquinoline via a redox-neutral vinylogous
 cascade [1,7]-hydride transfer/6-endo-trig cyclization strategy.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4007
_journal_page_last               4012
_journal_paper_doi               10.1039/d3ob00223c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C22 H19 N3'
_chemical_formula_weight         325.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-22 deposited with the CCDC.	2023-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.392(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6563(6)
_cell_length_b                   9.6499(4)
_cell_length_c                   14.6371(7)
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6830
_cell_measurement_theta_min      3.6230
_cell_volume                     1731.56(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5821
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.219
_diffrn_reflns_theta_max         67.219
_diffrn_reflns_theta_min         4.140
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0097(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0658P)²+0.2027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1457
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2309
_reflns_number_total             3076
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00223c2.cif
_cod_data_source_block           exp_11675
_cod_depositor_comments          'Adding full bibliography for 7159326.cif.'
_cod_original_cell_volume        1731.55(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159326
_shelx_shelxl_version_number     2018/3
_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   0.878
_shelx_estimated_absorpt_t_max   0.903
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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
N1 N 0.50467(14) 1.08117(16) 0.62613(12) 0.0534(4) Uani 1 1 d . . . . .
N2 N 0.62930(18) 0.5160(2) 0.59236(16) 0.0766(6) Uani 1 1 d . . . . .
N3 N 0.37428(16) 0.5305(2) 0.73362(15) 0.0732(6) Uani 1 1 d . . . . .
C1 C 0.62444(15) 0.88570(19) 0.66880(12) 0.0450(4) Uani 1 1 d . . . . .
C2 C 0.72937(15) 0.8301(2) 0.68172(14) 0.0529(5) Uani 1 1 d . . . . .
H2 H 0.742643 0.740051 0.704232 0.064 Uiso 1 1 calc R U . . .
C3 C 0.81296(17) 0.9052(3) 0.66202(15) 0.0611(6) Uani 1 1 d . . . . .
H3 H 0.882153 0.866654 0.671081 0.073 Uiso 1 1 calc R U . . .
C4 C 0.79264(17) 1.0403(3) 0.62813(14) 0.0620(6) Uani 1 1 d . . . . .
H4 H 0.848623 1.090799 0.613151 0.074 Uiso 1 1 calc R U . . .
C5 C 0.69207(17) 1.1000(2) 0.61650(14) 0.0559(5) Uani 1 1 d . . . . .
H5 H 0.681058 1.190785 0.594937 0.067 Uiso 1 1 calc R U . . .
C6 C 0.60498(16) 1.02517(19) 0.63689(12) 0.0468(5) Uani 1 1 d . . . . .
C7 C 0.47322(19) 1.2212(2) 0.59405(17) 0.0632(6) Uani 1 1 d . . . . .
H7A H 0.490948 1.239901 0.534465 0.076 Uiso 1 1 calc R U . . .
H7B H 0.509618 1.288971 0.640185 0.076 Uiso 1 1 calc R U . . .
C8 C 0.35094(19) 1.2244(2) 0.58285(18) 0.0673(6) Uani 1 1 d . . . . .
H8A H 0.312161 1.203307 0.518454 0.081 Uiso 1 1 calc R U . . .
H8B H 0.327677 1.314511 0.599845 0.081 Uiso 1 1 calc R U . . .
C9 C 0.33120(19) 1.1130(2) 0.65037(17) 0.0657(6) Uani 1 1 d . . . . .
H9A H 0.345368 1.147816 0.714434 0.079 Uiso 1 1 calc R U . . .
H9B H 0.256989 1.078373 0.631509 0.079 Uiso 1 1 calc R U . . .
C10 C 0.41277(16) 1.0013(2) 0.64154(14) 0.0497(5) Uani 1 1 d . . . . .
H10 H 0.381791 0.947862 0.584184 0.060 Uiso 1 1 calc R U . . .
C11 C 0.45183(15) 0.89863(18) 0.72315(13) 0.0459(5) Uani 1 1 d . . . . .
H11 H 0.390298 0.840236 0.728494 0.055 Uiso 1 1 calc R U . . .
C12 C 0.49894(18) 0.9708(2) 0.81837(13) 0.0571(5) Uani 1 1 d . . . . .
H12A H 0.562056 1.024616 0.813574 0.069 Uiso 1 1 calc R U . . .
H12B H 0.444828 1.034976 0.830092 0.069 Uiso 1 1 calc R U . . .
C13 C 0.53240(15) 0.87479(19) 0.90188(13) 0.0460(5) Uani 1 1 d . . . . .
C14 C 0.63595(18) 0.8795(3) 0.96117(17) 0.0681(6) Uani 1 1 d . . . . .
H14 H 0.687764 0.939743 0.948287 0.082 Uiso 1 1 calc R U . . .
C15 C 0.6629(2) 0.7937(4) 1.0406(2) 0.0921(10) Uani 1 1 d . . . . .
H15 H 0.732376 0.798089 1.080923 0.110 Uiso 1 1 calc R U . . .
C16 C 0.5885(3) 0.7041(3) 1.0593(2) 0.0954(10) Uani 1 1 d . . . . .
H16 H 0.606959 0.646979 1.112031 0.115 Uiso 1 1 calc R U . . .
C17 C 0.4883(3) 0.6980(3) 1.0016(2) 0.0894(9) Uani 1 1 d . . . . .
H17 H 0.437641 0.635573 1.014027 0.107 Uiso 1 1 calc R U . . .
C18 C 0.45952(19) 0.7832(2) 0.92412(16) 0.0666(6) Uani 1 1 d . . . . .
H18 H 0.388967 0.778769 0.885796 0.080 Uiso 1 1 calc R U . . .
C19 C 0.53520(15) 0.80970(19) 0.69239(12) 0.0434(4) Uani 1 1 d . . . . .
C20 C 0.52240(15) 0.67010(19) 0.68141(13) 0.0457(5) Uani 1 1 d . . . . .
C21 C 0.58510(17) 0.58588(19) 0.63329(15) 0.0528(5) Uani 1 1 d . . . . .
C22 C 0.43942(17) 0.59502(19) 0.71121(15) 0.0522(5) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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 N1 C7 125.66(17) . . ?
C6 N1 C10 122.14(16) . . ?
C7 N1 C10 112.12(16) . . ?
C2 C1 C6 119.10(17) . . ?
C2 C1 C19 122.66(17) . . ?
C6 C1 C19 118.12(17) . . ?
C3 C2 C1 121.7(2) . . ?
C2 C3 C4 119.0(2) . . ?
C5 C4 C3 121.39(19) . . ?
C4 C5 C6 120.6(2) . . ?
N1 C6 C5 122.08(18) . . ?
N1 C6 C1 119.74(16) . . ?
C5 C6 C1 118.17(18) . . ?
N1 C7 C8 104.13(17) . . ?
C7 C8 C9 104.09(18) . . ?
C10 C9 C8 102.77(17) . . ?
N1 C10 C9 102.87(16) . . ?
N1 C10 C11 110.26(16) . . ?
C9 C10 C11 119.02(16) . . ?
C19 C11 C10 104.35(14) . . ?
C19 C11 C12 112.59(16) . . ?
C10 C11 C12 112.96(16) . . ?
C13 C12 C11 115.07(17) . . ?
C18 C13 C14 117.4(2) . . ?
C18 C13 C12 121.16(19) . . ?
C14 C13 C12 121.37(19) . . ?
C13 C14 C15 120.0(2) . . ?
C16 C15 C14 120.5(3) . . ?
C17 C16 C15 119.8(3) . . ?
C16 C17 C18 120.6(3) . . ?
C13 C18 C17 121.7(2) . . ?
C20 C19 C1 123.10(17) . . ?
C20 C19 C11 121.67(16) . . ?
C1 C19 C11 115.07(16) . . ?
C19 C20 C22 122.68(17) . . ?
C19 C20 C21 123.61(17) . . ?
C22 C20 C21 113.57(16) . . ?
N2 C21 C20 176.1(2) . . ?
N3 C22 C20 177.4(2) . . ?
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 C6 1.353(2) . ?
N1 C7 1.453(2) . ?
N1 C10 1.459(2) . ?
N2 C21 1.137(3) . ?
N3 C22 1.144(2) . ?
C1 C2 1.401(3) . ?
C1 C6 1.426(3) . ?
C1 C19 1.458(2) . ?
C2 C3 1.371(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.369(3) . ?
C5 C6 1.410(3) . ?
C7 C8 1.515(3) . ?
C8 C9 1.523(3) . ?
C9 C10 1.520(3) . ?
C10 C11 1.536(3) . ?
C11 C19 1.513(2) . ?
C11 C12 1.539(3) . ?
C12 C13 1.508(3) . ?
C13 C18 1.374(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.399(4) . ?
C15 C16 1.355(4) . ?
C16 C17 1.339(4) . ?
C17 C18 1.374(3) . ?
C19 C20 1.362(3) . ?
C20 C22 1.430(3) . ?
C20 C21 1.437(3) . ?
