#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:11:21 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286176 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/26/7062630.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_7062630
loop_
_publ_author_name
'Yuan, Zi-Yi'
'Zhang, Zheng-Qian'
'Liang, Jun-Rong'
'Lin, Chu-Yan'
'Peng, Dan-Li'
'Cui, Bao-Dong'
'Mou, Xue-Qing'
'Zhang, Yun'
'Chen, Yong-Zheng'
_publ_section_title
;
 A facile one-pot synthesis of
 N-acyl-1-cyano-1,2,3,4-tetrahydroisoquinoline via a photoredox and
 Reissert-type reaction from 1,2,3,4-tetrahydroisoquinolines
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15847
_journal_page_last               15851
_journal_paper_doi               10.1039/D3NJ02600K
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-21
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-17 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                102.299(15)
_cell_angle_beta                 97.775(15)
_cell_angle_gamma                99.273(14)
_cell_formula_units_Z            2
_cell_length_a                   7.1562(12)
_cell_length_b                   8.1948(14)
_cell_length_c                   9.4259(17)
_cell_measurement_reflns_used    1166
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      26.7510
_cell_measurement_theta_min      2.9030
_cell_volume                     524.71(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  18.00   1.00    1.99    --  -11.27 -77.00-150.00   95
  2  ω    -54.00  35.00   1.00    1.99    --   11.90 -57.00 -30.00   89
  3  ω    -16.00  84.00   1.00    1.99    --   11.90  57.00 120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0267095000
_diffrn_orient_matrix_UB_12      0.0528986000
_diffrn_orient_matrix_UB_13      0.0724910000
_diffrn_orient_matrix_UB_21      0.0549462000
_diffrn_orient_matrix_UB_22      0.0629253000
_diffrn_orient_matrix_UB_23      -0.0270227000
_diffrn_orient_matrix_UB_31      -0.0817050000
_diffrn_orient_matrix_UB_32      0.0374738000
_diffrn_orient_matrix_UB_33      -0.0116588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3302
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.115(12)
_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   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0566
_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)+(0.0599P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1239
_reflns_number_total             1845
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj02600k2.cif
_cod_data_source_block           c1
_cod_depositor_comments
'Adding full bibliography for 7062629--7062630.cif.'
_cod_original_cell_volume        524.71(16)
_cod_database_code               7062630
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 20.718
_oxdiff_exptl_absorpt_empirical_full_min 0.357
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 0.7384(2) 0.4716(2) 0.61828(19) 0.0432(5) Uani 1 1 d . . . . .
N1 N 0.2989(2) 0.0772(3) 0.4012(3) 0.0493(7) Uani 1 1 d . . . . .
N2 N 0.7618(2) 0.2697(2) 0.4221(2) 0.0290(5) Uani 1 1 d . . . . .
C1 C 0.7210(3) 0.2029(3) 0.1125(3) 0.0325(6) Uani 1 1 d . . . . .
C2 C 0.7110(3) 0.1878(3) -0.0373(3) 0.0428(7) Uani 1 1 d . . . . .
H2 H 0.810050 0.147292 -0.083869 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5611(3) 0.2299(3) -0.1208(3) 0.0445(7) Uani 1 1 d . . . . .
H3 H 0.557642 0.219749 -0.223493 0.053 Uiso 1 1 calc R U . . .
C4 C 0.4160(3) 0.2870(3) -0.0541(3) 0.0424(7) Uani 1 1 d . . . . .
H4 H 0.311340 0.314640 -0.111583 0.051 Uiso 1 1 calc R U . . .
C5 C 0.4212(3) 0.3044(3) 0.0959(3) 0.0349(6) Uani 1 1 d . . . . .
H5 H 0.320948 0.343910 0.141438 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5754(3) 0.2633(3) 0.1793(3) 0.0288(6) Uani 1 1 d . . . . .
C7 C 0.5795(2) 0.2908(3) 0.3441(2) 0.0287(6) Uani 1 1 d . . . . .
H7 H 0.562432 0.409807 0.383368 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4196(3) 0.1712(3) 0.3767(3) 0.0343(6) Uani 1 1 d . . . . .
C9 C 0.8867(3) 0.1559(3) 0.2031(3) 0.0395(6) Uani 1 1 d . . . . .
H9A H 0.918893 0.051146 0.146068 0.047 Uiso 1 1 calc R U . . .
H9B H 1.001179 0.248517 0.222576 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8382(3) 0.1269(3) 0.3480(3) 0.0336(6) Uani 1 1 d . . . . .
H10A H 0.741827 0.020202 0.329942 0.040 Uiso 1 1 calc R U . . .
H10B H 0.955202 0.115430 0.411297 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8252(3) 0.3644(3) 0.5621(3) 0.0295(6) Uani 1 1 d . . . . .
C12 C 1.0062(3) 0.3349(3) 0.6463(3) 0.0407(7) Uani 1 1 d . . . . .
H12A H 1.047773 0.423894 0.738113 0.061 Uiso 1 1 calc R U . . .
H12B H 1.107596 0.338417 0.586138 0.061 Uiso 1 1 calc R U . . .
H12C H 0.981106 0.223209 0.669494 0.061 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
C10 N2 C7 114.70(17) . . ?
C11 N2 C7 117.84(18) . . ?
C11 N2 C10 126.58(16) . . ?
C2 C1 C6 118.5(2) . . ?
C2 C1 C9 121.1(2) . . ?
C6 C1 C9 120.4(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.6(2) . . ?
C1 C6 C7 121.89(17) . . ?
C5 C6 C7 117.5(2) . . ?
N2 C7 C6 112.26(17) . . ?
N2 C7 H7 108.2 . . ?
N2 C7 C8 108.67(16) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 C6 111.19(17) . . ?
C8 C7 H7 108.2 . . ?
N1 C8 C7 178.7(2) . . ?
C1 C9 H9A 109.3 . . ?
C1 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C1 111.71(18) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
N2 C10 C9 109.65(17) . . ?
N2 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C11 N2 120.98(18) . . ?
O1 C11 C12 121.0(2) . . ?
N2 C11 C12 118.0(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 C11 1.227(3) . ?
N1 C8 1.144(3) . ?
N2 C7 1.463(2) . ?
N2 C10 1.455(3) . ?
N2 C11 1.356(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.393(3) . ?
C1 C9 1.515(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C6 C7 1.517(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.492(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.507(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C6 C7 N2 7.9(3) . . . . ?
C1 C6 C7 C8 -114.1(2) . . . . ?
C1 C9 C10 N2 -50.1(2) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C6 C7 -177.41(19) . . . . ?
C2 C1 C9 C10 -161.4(2) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 177.67(18) . . . . ?
C5 C6 C7 N2 -170.74(16) . . . . ?
C5 C6 C7 C8 67.3(2) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C1 C9 C10 18.9(3) . . . . ?
C7 N2 C10 C9 64.1(2) . . . . ?
C7 N2 C11 O1 -4.3(3) . . . . ?
C7 N2 C11 C12 176.13(17) . . . . ?
C9 C1 C2 C3 179.93(19) . . . . ?
C9 C1 C6 C5 -179.08(18) . . . . ?
C9 C1 C6 C7 2.3(3) . . . . ?
C10 N2 C7 C6 -41.6(2) . . . . ?
C10 N2 C7 C8 81.8(2) . . . . ?
C10 N2 C11 O1 -173.0(2) . . . . ?
C10 N2 C11 C12 7.5(3) . . . . ?
C11 N2 C7 C6 148.41(19) . . . . ?
C11 N2 C7 C8 -88.2(2) . . . . ?
C11 N2 C10 C9 -126.9(2) . . . . ?
