#------------------------------------------------------------------------------
#$Date: 2022-06-06 03:54:05 +0200 (Mon 06 de Jun de 2022) $
#$Revision: 275800 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/14/7061493.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_7061493
loop_
_publ_author_name
'Zhang, Yahui'
'Chen, Yi'
'Guo, Mei'
'Sun, Ge'
'Que, Rongbin'
'Cui, Ranran'
'Gao, Yu'
'Chen, Haijun'
_publ_section_title
;
 Direct C--H functionalization of tetrahydro-γ-carbolines at the
 α-position
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9511
_journal_page_last               9514
_journal_paper_doi               10.1039/D2NJ00928E
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C24 H21 Cl2 N3 O2 S'
_chemical_formula_weight         486.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-08-14 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.848(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0746(18)
_cell_length_b                   11.3733(17)
_cell_length_c                   17.772(2)
_cell_measurement_reflns_used    4187
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.61
_cell_measurement_theta_min      2.61
_cell_volume                     2173.4(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0777
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15045
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         2.145
_exptl_absorpt_coefficient_mu    0.423
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         1.601
_refine_diff_density_min         -1.428
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3832
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0873
_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)+(0.0199P)²+13.8747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.1937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2760
_reflns_number_total             3832
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj00928e2.cif
_cod_data_source_block           20180810ZH_ZY_FZU000606016_0m_a
_cod_depositor_comments
'Adding full bibliography for 7061492--7061493.cif.'
_cod_original_cell_volume        2173.4(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7061493
_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   0.913
_shelx_estimated_absorpt_t_max   0.931
loop_
_space_group_symop_operation_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_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
C1 C 0.9207(7) 1.1732(6) 0.2552(4) 0.0462(17) Uani 1 1 d . . . . .
H1A H 0.916533 1.218446 0.301431 0.069 Uiso 1 1 calc R U . . .
H1B H 0.894692 1.223048 0.209147 0.069 Uiso 1 1 calc R U . . .
H1C H 1.006300 1.146502 0.259692 0.069 Uiso 1 1 calc R U . . .
C2 C 0.8359(6) 1.0685(5) 0.2479(3) 0.0320(14) Uani 1 1 d . . . . .
C3 C 0.8790(6) 0.9590(5) 0.2772(3) 0.0320(14) Uani 1 1 d . . . . .
H3 H 0.964616 0.948979 0.301400 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7995(5) 0.8654(5) 0.2717(3) 0.0275(13) Uani 1 1 d . . . . .
H4 H 0.830364 0.790669 0.291294 0.033 Uiso 1 1 calc R U . . .
C5 C 0.6748(5) 0.8795(5) 0.2378(3) 0.0231(12) Uani 1 1 d . . . . .
C6 C 0.6288(5) 0.9877(5) 0.2075(3) 0.0305(14) Uani 1 1 d . . . . .
H6 H 0.542831 0.997243 0.183890 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7099(6) 1.0808(5) 0.2121(3) 0.0321(14) Uani 1 1 d . . . . .
H7 H 0.679505 1.154652 0.190605 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4576(5) 0.8799(5) 0.3316(3) 0.0244(12) Uani 1 1 d . . . . .
H8A H 0.380982 0.880927 0.289255 0.029 Uiso 1 1 calc R U . . .
H8B H 0.505282 0.952479 0.327995 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4247(5) 0.8748(5) 0.4081(3) 0.0222(12) Uani 1 1 d . . . . .
C10 C 0.3287(5) 0.9362(5) 0.4342(3) 0.0225(12) Uani 1 1 d . . . . .
C11 C 0.2349(5) 1.0152(5) 0.4008(3) 0.0272(13) Uani 1 1 d . . . . .
H11 H 0.227515 1.042934 0.349433 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1529(6) 1.0525(5) 0.4434(3) 0.0327(14) Uani 1 1 d . . . . .
H12 H 0.087953 1.105414 0.420814 0.039 Uiso 1 1 calc R U . . .
C13 C 0.1641(6) 1.0133(5) 0.5198(3) 0.0323(14) Uani 1 1 d . . . . .
H13 H 0.106067 1.039637 0.547722 0.039 Uiso 1 1 calc R U . . .
C14 C 0.2575(6) 0.9374(5) 0.5548(3) 0.0308(14) Uani 1 1 d . . . . .
H14 H 0.265766 0.911975 0.606683 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3391(5) 0.8994(5) 0.5116(3) 0.0246(12) Uani 1 1 d . . . . .
C16 C 0.4840(5) 0.8047(5) 0.4667(3) 0.0279(13) Uani 1 1 d . . . . .
C17 C 0.5788(7) 0.7149(7) 0.4607(4) 0.050(2) Uani 1 1 d . . . . .
H17 H 0.531607 0.640462 0.444626 0.060 Uiso 1 1 calc R U . A 1
C18 C 0.6345(6) 0.7499(6) 0.3924(3) 0.0337(15) Uani 1 1 d . . . . .
H18A H 0.687841 0.820174 0.406339 0.040 Uiso 1 1 calc R U . . .
H18B H 0.686502 0.684912 0.380526 0.040 Uiso 1 1 calc R U . . .
N3 N 0.6655(6) 0.6886(6) 0.5282(3) 0.0305(15) Uani 0.75 1 d . . P B 1
H3A H 0.625272 0.682909 0.566188 0.037 Uiso 1 1 d R U . B 1
C20 C 0.7435(9) 0.5870(6) 0.5338(4) 0.054(2) Uani 1 1 d . . . . .
C21 C 0.7041(7) 0.4824(8) 0.4924(4) 0.060(2) Uani 1 1 d . . . . .
H21 H 0.623112 0.476507 0.459198 0.072 Uiso 1 1 calc R U . . .
C22 C 0.7883(7) 0.3858(7) 0.5014(4) 0.0481(18) Uani 1 1 d . . . . .
H22 H 0.764726 0.314176 0.474378 0.058 Uiso 1 1 calc R U . . .
C23 C 0.9044(6) 0.3986(5) 0.5501(3) 0.0342(14) Uani 1 1 d . . . . .
C24 C 0.9361(7) 0.5028(6) 0.5887(4) 0.0448(17) Uani 1 1 d . . . . .
C25 C 0.8564(8) 0.5939(6) 0.5812(4) 0.053(2) Uani 1 1 d . . . . .
H25 H 0.880911 0.663864 0.610073 0.064 Uiso 1 1 calc R U . . .
Cl1 Cl 1.00954(17) 0.28366(16) 0.56132(10) 0.0518(5) Uani 1 1 d . . . . .
Cl2 Cl 1.0829(2) 0.5205(2) 0.65072(13) 0.0734(7) Uani 1 1 d . . . . .
N1 N 0.5333(4) 0.7754(4) 0.3241(2) 0.0258(10) Uani 1 1 d . . . . .
N2 N 0.4340(4) 0.8202(4) 0.5296(2) 0.0301(12) Uani 1 1 d . . . . .
H2 H 0.459266 0.784495 0.574604 0.036 Uiso 1 1 calc R U . . .
O1 O 0.6352(4) 0.6552(4) 0.2410(2) 0.0396(11) Uani 1 1 d . . . . .
O2 O 0.4584(4) 0.7852(4) 0.1817(2) 0.0368(10) Uani 1 1 d . . . . .
S1 S 0.57099(14) 0.76401(13) 0.24055(8) 0.0287(4) Uani 1 1 d . . . . .
N3' N 0.5894(15) 0.6248(15) 0.4892(10) 0.020(4) Uani 0.25 1 d . U P B 2
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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 '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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.5(6) . . ?
C3 C2 C1 121.8(6) . . ?
C7 C2 C1 119.7(6) . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 S1 119.7(4) . . ?
C6 C5 S1 119.5(4) . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.1(5) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N1 C8 C9 108.6(4) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C16 C9 C10 107.4(4) . . ?
C16 C9 C8 123.1(5) . . ?
C10 C9 C8 129.5(5) . . ?
C11 C10 C15 118.9(5) . . ?
C11 C10 C9 135.1(5) . . ?
C15 C10 C9 106.0(5) . . ?
C12 C11 C10 119.0(5) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.0(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 121.3(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 117.6(5) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
N2 C15 C14 130.0(5) . . ?
N2 C15 C10 107.6(4) . . ?
C14 C15 C10 122.2(5) . . ?
C9 C16 N2 109.7(5) . . ?
C9 C16 C17 124.9(5) . . ?
N2 C16 C17 125.1(5) . . ?
N3' C17 C16 126.0(10) . . ?
N3 C17 C16 116.4(6) . . ?
N3' C17 C18 124.4(10) . . ?
N3 C17 C18 114.5(6) . . ?
C16 C17 C18 107.5(5) . . ?
N3 C17 H17 105.8 . . ?
C16 C17 H17 105.8 . . ?
C18 C17 H17 105.8 . . ?
N1 C18 C17 109.4(5) . . ?
N1 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
N1 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C17 N3 C20 121.2(6) . . ?
C17 N3 H3A 107.7 . . ?
C20 N3 H3A 106.9 . . ?
C25 C20 C21 120.4(7) . . ?
C25 C20 N3 117.1(8) . . ?
C21 C20 N3 122.5(8) . . ?
C25 C20 N3' 159.3(9) . . ?
C21 C20 N3' 79.9(8) . . ?
C20 C21 C22 118.6(7) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C23 C22 C21 118.6(7) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C24 C23 C22 119.6(6) . . ?
C24 C23 Cl1 120.7(5) . . ?
C22 C23 Cl1 119.7(5) . . ?
C25 C24 C23 122.2(7) . . ?
C25 C24 Cl2 117.6(6) . . ?
C23 C24 Cl2 120.2(5) . . ?
C20 C25 C24 120.7(8) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C18 N1 C8 114.9(4) . . ?
C18 N1 S1 115.0(4) . . ?
C8 N1 S1 114.7(3) . . ?
C15 N2 C16 109.3(4) . . ?
C15 N2 H2 125.3 . . ?
C16 N2 H2 125.3 . . ?
O1 S1 O2 119.5(3) . . ?
O1 S1 N1 107.4(2) . . ?
O2 S1 N1 106.2(2) . . ?
O1 S1 C5 108.7(3) . . ?
O2 S1 C5 108.2(3) . . ?
N1 S1 C5 106.1(2) . . ?
C17 N3' C20 114.1(13) . . ?
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 C2 1.503(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.389(8) . ?
C2 C7 1.395(8) . ?
C3 C4 1.370(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(8) . ?
C5 S1 1.754(6) . ?
C6 C7 1.379(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.479(7) . ?
C8 C9 1.491(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C16 1.350(7) . ?
C9 C10 1.439(7) . ?
C10 C11 1.394(7) . ?
C10 C15 1.416(7) . ?
C11 C12 1.382(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.405(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(8) . ?
C14 H14 0.9500 . ?
C15 N2 1.363(7) . ?
C16 N2 1.374(7) . ?
C16 C17 1.487(8) . ?
C17 N3' 1.136(18) . ?
C17 N3 1.378(9) . ?
C17 C18 1.540(8) . ?
C17 H17 1.0000 . ?
C18 N1 1.471(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N3 C20 1.432(9) . ?
N3 H3A 0.8951 . ?
C20 C25 1.332(11) . ?
C20 C21 1.413(11) . ?
C20 N3' 1.754(19) . ?
C21 C22 1.425(10) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.373(9) . ?
C23 Cl1 1.730(6) . ?
C24 C25 1.347(10) . ?
C24 Cl2 1.744(8) . ?
C25 H25 0.9500 . ?
N1 S1 1.641(4) . ?
N2 H2 0.8800 . ?
O1 S1 1.426(4) . ?
O2 S1 1.442(4) . ?
