#------------------------------------------------------------------------------
#$Date: 2024-05-05 04:35:58 +0300 (Sun, 05 May 2024) $
#$Revision: 291563 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/13/1571309.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_1571309
loop_
_publ_author_name
'Chaturvedi, Atul K.'
'Shukla, Rahul K.'
'Volla, Chandra M. R.'
_publ_section_title
;
 Rh(iii)-catalyzed sp³/sp²-C-H heteroarylations
 via cascade C-H activation and cyclization.
;
_journal_issue                   17
_journal_name_full               'Chemical science'
_journal_page_first              6544
_journal_page_last               6551
_journal_paper_doi               10.1039/d3sc06955a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C31 H24 N2 O2 S'
_chemical_formula_sum            'C31 H24 N2 O2 S'
_chemical_formula_weight         488.58
_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
_audit_creation_date             2023-01-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-04-27 deposited with the CCDC.	2024-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                88.421(2)
_cell_angle_beta                 69.933(2)
_cell_angle_gamma                76.069(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3547(2)
_cell_length_b                   11.5560(3)
_cell_length_c                   12.3884(3)
_cell_measurement_reflns_used    5458
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.6860
_cell_measurement_theta_min      3.7890
_cell_volume                     1218.69(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -191.00 -11.00   0.50    2.00    -- -101.00   0.00  36.00  360
  2  ω   -122.00  58.00   0.50    2.00    --  -32.00   0.00 108.00  360
  3  ω   -135.00 -11.00   0.50    2.00    -- -101.00  72.00 108.00  248
  4  ω   -135.00 -11.00   0.50    2.00    -- -101.00  72.00-108.00  248
  5  ω   -135.00 -13.00   0.50    2.00    -- -101.00  72.00  36.00  244
  6  ω   -189.00 -71.00   0.50    2.00    -- -101.00 -72.00-180.00  236
  7  ω    -66.00 -16.50   0.50    2.00    --  -32.00  72.00  36.00   99
  8  ω   -108.00 -17.00   0.50    2.00    -- -101.00  72.00 -36.00  182
  9  ω   -107.00 -18.00   0.50    2.00    -- -101.00  72.00-180.00  178
 10  ω    -53.00  -8.00   0.50    2.00    --  -32.00 -72.00-108.00   90
 11  ω   -187.00-132.50   0.50    2.00    -- -101.00 -72.00 108.00  109
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10290
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.744
_diffrn_reflns_theta_min         3.806
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0683
_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)+(0.1599P)²+0.1835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3808
_reflns_number_total             4601
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc06955a2.cif
_cod_data_source_block           cmrv-at-262_cu
_cod_depositor_comments
'Adding full bibliography for 1571308--1571309.cif.'
_cod_database_code               1571309
_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   0.957
_shelx_estimated_absorpt_t_min   0.761
_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 Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z)
2.c Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C)
;
_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
- Detector area scaling
;
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
S01 S 0.33920(7) 0.25764(5) 0.87975(5) 0.0329(2) Uani 1 1 d . . . . .
O002 O 0.1922(2) 0.32286(17) 0.87362(16) 0.0402(5) Uani 1 1 d . . . . .
O003 O 0.3438(2) 0.19460(18) 0.97994(15) 0.0454(5) Uani 1 1 d . . . . .
N004 N 0.4207(2) 0.15434(18) 0.76983(16) 0.0306(5) Uani 1 1 d . . . . .
N005 N 0.7017(3) 0.0896(2) 0.20961(18) 0.0368(5) Uani 1 1 d . . . . .
C006 C 0.6537(3) 0.0643(2) 0.6328(2) 0.0292(5) Uani 1 1 d . . . . .
C007 C 0.5485(3) 0.1267(2) 0.57573(19) 0.0273(5) Uani 1 1 d . . . . .
C008 C 0.2588(3) 0.2314(2) 0.6423(2) 0.0300(5) Uani 1 1 d . . . . .
C009 C 0.4108(3) 0.1797(2) 0.65826(19) 0.0284(5) Uani 1 1 d . . . . .
C00A C 0.5746(3) 0.0816(2) 0.7516(2) 0.0304(5) Uani 1 1 d . . . . .
C00B C 0.7382(3) 0.1796(2) 0.2566(2) 0.0314(5) Uani 1 1 d . . . . .
C00C C 0.5830(3) 0.1166(2) 0.44917(19) 0.0282(5) Uani 1 1 d . . . . .
H00A H 0.481981 0.133074 0.435389 0.034 Uiso 1 1 calc R . . . .
H00B H 0.639529 0.033141 0.420751 0.034 Uiso 1 1 calc R . . . .
C00D C 0.6791(3) 0.1987(2) 0.3785(2) 0.0289(5) Uani 1 1 d . . . . .
C00E C 0.1269(3) 0.1890(2) 0.7018(2) 0.0349(6) Uani 1 1 d . . . . .
H00E H 0.131771 0.132440 0.758343 0.042 Uiso 1 1 calc R . . . .
C00F C 0.7921(3) -0.0460(3) 0.7859(2) 0.0419(6) Uani 1 1 d . . . . .
H00F H 0.841100 -0.084332 0.837489 0.050 Uiso 1 1 calc R . . . .
C00G C 0.4662(3) 0.3529(2) 0.8523(2) 0.0329(5) Uani 1 1 d . . . . .
C00H C 0.7123(3) 0.2897(2) 0.4266(2) 0.0362(6) Uani 1 1 d . . . . .
H00H H 0.672932 0.303917 0.507904 0.043 Uiso 1 1 calc R . . . .
C00I C 0.6414(3) 0.0293(2) 0.8300(2) 0.0382(6) Uani 1 1 d . . . . .
H00I H 0.587225 0.043868 0.910551 0.046 Uiso 1 1 calc R . . . .
C00J C 0.8715(3) -0.0657(3) 0.6684(2) 0.0411(6) Uani 1 1 d . . . . .
H00J H 0.974025 -0.117258 0.640885 0.049 Uiso 1 1 calc R . . . .
C00K C 0.8046(3) -0.0120(2) 0.5902(2) 0.0348(6) Uani 1 1 d . . . . .
H00K H 0.859445 -0.026343 0.509713 0.042 Uiso 1 1 calc R . . . .
C00L C 0.8309(3) 0.2525(3) 0.1875(2) 0.0389(6) Uani 1 1 d . . . . .
C00M C -0.0107(3) 0.2293(3) 0.6788(2) 0.0417(6) Uani 1 1 d . . . . .
H00M H -0.100206 0.200513 0.719758 0.050 Uiso 1 1 calc R . . . .
C00N C 0.6577(4) 0.5101(3) 0.8117(3) 0.0546(9) Uani 1 1 d . . . . .
C00O C 0.5708(3) 0.3441(3) 0.9098(2) 0.0432(7) Uani 1 1 d . . . . .
H00O H 0.577494 0.284651 0.963571 0.052 Uiso 1 1 calc R . . . .
C00P C 0.8861(3) 0.2291(3) 0.0653(3) 0.0484(8) Uani 1 1 d . . . . .
H00P H 0.948730 0.275969 0.015702 0.058 Uiso 1 1 calc R . . . .
C00Q C 0.2491(3) 0.3131(2) 0.5596(2) 0.0379(6) Uani 1 1 d . . . . .
H00Q H 0.338212 0.342242 0.518403 0.046 Uiso 1 1 calc R . . . .
C00R C 0.4554(3) 0.4392(3) 0.7732(2) 0.0416(6) Uani 1 1 d . . . . .
H00R H 0.384090 0.443643 0.733196 0.050 Uiso 1 1 calc R . . . .
C00S C 0.1118(3) 0.3530(3) 0.5360(3) 0.0451(7) Uani 1 1 d . . . . .
H00S H 0.107023 0.408719 0.478736 0.054 Uiso 1 1 calc R . . . .
C00T C -0.0185(3) 0.3113(3) 0.5963(3) 0.0469(7) Uani 1 1 d . . . . .
H00T H -0.113394 0.338980 0.580975 0.056 Uiso 1 1 calc R . . . .
C00U C 0.8484(4) 0.1395(3) 0.0209(2) 0.0492(7) Uani 1 1 d . . . . .
H00U H 0.884827 0.122475 -0.059939 0.059 Uiso 1 1 calc R . . . .
C00V C 0.5503(4) 0.5189(3) 0.7533(3) 0.0528(8) Uani 1 1 d . . . . .
H00V H 0.542923 0.579186 0.700449 0.063 Uiso 1 1 calc R . . . .
C00W C 0.7555(4) 0.0731(3) 0.0958(2) 0.0461(7) Uani 1 1 d . . . . .
H00W H 0.728769 0.011580 0.063220 0.055 Uiso 1 1 calc R . . . .
C00X C 0.8619(3) 0.3445(3) 0.2408(3) 0.0485(7) Uani 1 1 d . . . . .
H00X H 0.923640 0.394254 0.195002 0.058 Uiso 1 1 calc R . . . .
C00Y C 0.8047(3) 0.3630(3) 0.3566(3) 0.0449(7) Uani 1 1 d . . . . .
H00Y H 0.826618 0.425634 0.391479 0.054 Uiso 1 1 calc R . . . .
C00Z C 0.6662(3) 0.4237(3) 0.8878(3) 0.0531(8) Uani 1 1 d . . . . .
H00Z H 0.739045 0.417590 0.926675 0.064 Uiso 1 1 calc R . . . .
C010 C 0.7615(5) 0.5966(5) 0.7902(4) 0.0892(16) Uani 1 1 d . . . . .
H01A H 0.724675 0.662274 0.746909 0.134 Uiso 1 1 calc GR . . . .
H01B H 0.869955 0.554952 0.745722 0.134 Uiso 1 1 calc GR . . . .
H01C H 0.757131 0.628677 0.863989 0.134 Uiso 1 1 calc GR . . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O002 S01 O003 119.79(12) . . ?
O002 S01 N004 107.42(10) . . ?
O002 S01 C00G 108.84(12) . . ?
O003 S01 N004 105.59(11) . . ?
O003 S01 C00G 109.18(12) . . ?
N004 S01 C00G 105.00(11) . . ?
C009 N004 S01 121.60(16) . . ?
C00A N004 S01 118.74(16) . . ?
C00A N004 C009 106.85(18) . . ?
C00W N005 C00B 117.7(2) . . ?
C00A C006 C007 108.3(2) . . ?
C00A C006 C00K 119.5(2) . . ?
C00K C006 C007 131.9(2) . . ?
C006 C007 C00C 124.2(2) . . ?
C009 C007 C006 107.7(2) . . ?
C009 C007 C00C 127.5(2) . . ?
C00E C008 C009 120.3(2) . . ?
C00Q C008 C009 120.5(2) . . ?
C00Q C008 C00E 118.8(2) . . ?
N004 C009 C008 121.91(19) . . ?
C007 C009 N004 109.7(2) . . ?
C007 C009 C008 126.9(2) . . ?
C006 C00A N004 107.5(2) . . ?
C00I C00A N004 130.0(2) . . ?
C00I C00A C006 122.4(2) . . ?
N005 C00B C00D 117.9(2) . . ?
N005 C00B C00L 121.9(2) . . ?
C00L C00B C00D 120.2(2) . . ?
C007 C00C C00D 115.75(19) . . ?
C00B C00D C00C 118.3(2) . . ?
C00H C00D C00B 118.6(2) . . ?
C00H C00D C00C 123.1(2) . . ?
C00M C00E C008 120.2(3) . . ?
C00J C00F C00I 121.2(2) . . ?
C00O C00G S01 120.8(2) . . ?
C00O C00G C00R 121.1(3) . . ?
C00R C00G S01 118.0(2) . . ?
C00D C00H C00Y 120.9(3) . . ?
C00A C00I C00F 117.2(2) . . ?
C00K C00J C00F 121.3(2) . . ?
C00J C00K C006 118.3(2) . . ?
C00B C00L C00P 117.4(3) . . ?
C00X C00L C00B 119.1(3) . . ?
C00X C00L C00P 123.4(3) . . ?
C00E C00M C00T 120.2(3) . . ?
C00V C00N C010 120.1(4) . . ?
C00Z C00N C00V 119.4(3) . . ?
C00Z C00N C010 120.6(4) . . ?
C00G C00O C00Z 118.9(3) . . ?
C00U C00P C00L 119.6(3) . . ?
C00S C00Q C008 121.1(3) . . ?
C00V C00R C00G 119.1(3) . . ?
C00Q C00S C00T 119.6(3) . . ?
C00S C00T C00M 120.1(3) . . ?
C00P C00U C00W 118.8(3) . . ?
C00R C00V C00N 119.9(3) . . ?
N005 C00W C00U 124.6(3) . . ?
C00Y C00X C00L 120.6(3) . . ?
C00X C00Y C00H 120.7(3) . . ?
C00N C00Z C00O 121.5(3) . . ?
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
S01 O002 1.4265(19) . ?
S01 O003 1.430(2) . ?
S01 N004 1.6732(19) . ?
S01 C00G 1.752(3) . ?
N004 C009 1.434(3) . ?
N004 C00A 1.426(3) . ?
N005 C00B 1.370(3) . ?
N005 C00W 1.326(3) . ?
C006 C007 1.448(3) . ?
C006 C00A 1.397(3) . ?
C006 C00K 1.400(3) . ?
C007 C009 1.353(3) . ?
C007 C00C 1.490(3) . ?
C008 C009 1.482(3) . ?
C008 C00E 1.397(3) . ?
C008 C00Q 1.385(4) . ?
C00A C00I 1.379(3) . ?
C00B C00D 1.422(3) . ?
C00B C00L 1.413(4) . ?
C00C C00D 1.516(3) . ?
C00D C00H 1.370(4) . ?
C00E C00M 1.382(4) . ?
C00F C00I 1.396(4) . ?
C00F C00J 1.385(4) . ?
C00G C00O 1.379(4) . ?
C00G C00R 1.390(4) . ?
C00H C00Y 1.420(4) . ?
C00J C00K 1.382(4) . ?
C00L C00P 1.432(4) . ?
C00L C00X 1.403(4) . ?
C00M C00T 1.383(4) . ?
C00N C00V 1.410(5) . ?
C00N C00Z 1.361(5) . ?
C00N C010 1.513(5) . ?
C00O C00Z 1.389(5) . ?
C00P C00U 1.355(5) . ?
C00Q C00S 1.382(4) . ?
C00R C00V 1.388(4) . ?
C00S C00T 1.384(4) . ?
C00U C00W 1.391(4) . ?
C00X C00Y 1.351(5) . ?
