#------------------------------------------------------------------------------
#$Date: 2022-08-06 13:56:09 +0200 (Sat 06 de Aug de 2022) $
#$Revision: 277123 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/16/7061620.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_7061620
loop_
_publ_author_name
'Merrett, James Theodore'
'Chen, Xiaoyu'
'Kyne, Sara Helen'
'Harode, Mandeep'
'Chan, Philip Wai Hong'
_publ_section_title
;
 Rhodium(i)-catalysed cycloisomerisation/6π electrocyclisation of
 5-(ethynylamino)pent-2-yn-1-yl esters to 2,3-dihydrobenzo[f]indoles
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13519
_journal_page_last               13523
_journal_paper_doi               10.1039/D2NJ01992B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C28 H24 Cl N O4 S'
_chemical_formula_sum            'C28 H24 Cl N O4 S'
_chemical_formula_weight         505.99
_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             2018-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-15 deposited with the CCDC.	2022-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                98.270(3)
_cell_angle_beta                 94.546(3)
_cell_angle_gamma                114.109(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8638(4)
_cell_length_b                   10.1729(3)
_cell_length_c                   13.2234(5)
_cell_measurement_reflns_used    4849
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     1184.47(8)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy Dualflex HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.473
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62171
_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    1.419
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0391
_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)+(0.0589P)²+0.4490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4138
_reflns_number_total             4849
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj01992b2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7061620.cif.'
_cod_database_code               7061620
_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   0.966
_shelx_estimated_absorpt_t_min   0.932
_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:
 C12(H12A,H12B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C23(H23), C25(H25), C15(H15), C22(H22), C19(H19),
 C21(H21), C17(H17), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S1 S 0.07507(4) 0.73416(4) 0.91424(3) 0.02078(12) Uani 1 1 d . . . . .
Cl1 Cl 0.41128(6) 0.94657(5) 0.31729(4) 0.03749(14) Uani 1 1 d . . . . .
O3 O -0.00177(13) 0.88487(12) 0.70586(9) 0.0226(3) Uani 1 1 d . . . . .
O1 O -0.00822(13) 0.65172(13) 0.98537(9) 0.0258(3) Uani 1 1 d . . . . .
O2 O 0.08262(14) 0.87665(13) 0.91155(9) 0.0255(3) Uani 1 1 d . . . . .
O4 O 0.22109(15) 1.07832(14) 0.76960(10) 0.0313(3) Uani 1 1 d . . . . .
N1 N -0.00649(15) 0.63153(15) 0.79672(11) 0.0215(3) Uani 1 1 d . . . . .
C9 C 0.06225(17) 0.68172(17) 0.70928(12) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.14481(18) 0.83017(18) 0.58042(12) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.11650(18) 0.58326(17) 0.66079(13) 0.0213(3) Uani 1 1 d . . . . .
C10 C 0.07075(18) 0.80003(17) 0.66781(13) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.20864(18) 0.73583(18) 0.53633(12) 0.0213(3) Uani 1 1 d . . . . .
C20 C 0.25895(18) 0.74733(18) 0.93312(13) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.18794(19) 0.60633(18) 0.57605(13) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.29149(19) 0.77560(19) 0.45389(13) 0.0252(4) Uani 1 1 d . . . . .
H2 H 0.337803 0.716688 0.424644 0.030 Uiso 1 1 calc R . . . .
C27 C 0.0873(2) 1.02459(18) 0.76154(13) 0.0253(4) Uani 1 1 d . . . . .
C14 C 0.37321(19) 0.49785(18) 0.60111(13) 0.0232(3) Uani 1 1 d . . . . .
C24 C 0.54756(19) 0.76156(19) 0.95837(13) 0.0265(4) Uani 1 1 d . . . . .
C6 C 0.2363(2) 0.98701(19) 0.45548(13) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.244293 1.069701 0.426623 0.032 Uiso 1 1 calc R . . . .
C5 C 0.15783(19) 0.95257(18) 0.53571(13) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.110707 1.012204 0.562295 0.029 Uiso 1 1 calc R . . . .
C23 C 0.5133(2) 0.8531(2) 0.90208(14) 0.0293(4) Uani 1 1 d . . . . .
H23 H 0.589899 0.920520 0.871964 0.035 Uiso 1 1 calc R . . . .
C1 C 0.3050(2) 0.89787(19) 0.41641(13) 0.0261(4) Uani 1 1 d . . . . .
C12 C -0.03107(19) 0.47392(18) 0.78550(14) 0.0246(4) Uani 1 1 d . . . . .
H12A H -0.135081 0.407420 0.752158 0.030 Uiso 1 1 calc R . . . .
H12B H -0.013461 0.450201 0.853959 0.030 Uiso 1 1 calc R . . . .
C11 C 0.0823(2) 0.45793(18) 0.71779(13) 0.0243(4) Uani 1 1 d . . . . .
H11A H 0.174060 0.467256 0.760509 0.029 Uiso 1 1 calc R . . . .
H11B H 0.038060 0.362235 0.669146 0.029 Uiso 1 1 calc R . . . .
C13 C 0.2434(2) 0.49589(18) 0.52974(13) 0.0249(4) Uani 1 1 d . . . . .
H13A H 0.276469 0.518231 0.462973 0.030 Uiso 1 1 calc R . . . .
H13B H 0.159693 0.396377 0.515870 0.030 Uiso 1 1 calc R . . . .
C25 C 0.4342(2) 0.6636(2) 1.00174(14) 0.0294(4) Uani 1 1 d . . . . .
H25 H 0.456201 0.601560 1.040969 0.035 Uiso 1 1 calc R . . . .
C15 C 0.3618(2) 0.37420(19) 0.63899(14) 0.0280(4) Uani 1 1 d . . . . .
H15 H 0.272953 0.285585 0.617858 0.034 Uiso 1 1 calc R . . . .
C22 C 0.3701(2) 0.84780(19) 0.88915(14) 0.0265(4) Uani 1 1 d . . . . .
H22 H 0.348307 0.911183 0.851213 0.032 Uiso 1 1 calc R . . . .
C19 C 0.5051(2) 0.62608(19) 0.63169(14) 0.0284(4) Uani 1 1 d . . . . .
H19 H 0.514742 0.711825 0.606421 0.034 Uiso 1 1 calc R . . . .
C21 C 0.2891(2) 0.6545(2) 0.98886(14) 0.0277(4) Uani 1 1 d . . . . .
H21 H 0.211943 0.585785 1.017801 0.033 Uiso 1 1 calc R . . . .
C17 C 0.6082(2) 0.5059(2) 0.73722(15) 0.0335(4) Uani 1 1 d . . . . .
H17 H 0.688078 0.509323 0.784269 0.040 Uiso 1 1 calc R . . . .
C16 C 0.4784(2) 0.3776(2) 0.70740(15) 0.0336(4) Uani 1 1 d . . . . .
H16 H 0.468723 0.292403 0.733391 0.040 Uiso 1 1 calc R . . . .
C26 C 0.7042(2) 0.7710(2) 0.97372(15) 0.0327(4) Uani 1 1 d . . . . .
H26A H 0.737864 0.761263 0.906411 0.049 Uiso 1 1 calc GR . . . .
H26B H 0.704714 0.691930 1.007956 0.049 Uiso 1 1 calc GR . . . .
H26C H 0.772188 0.866111 1.016778 0.049 Uiso 1 1 calc GR . . . .
C28 C -0.0091(2) 1.0924(2) 0.80614(15) 0.0332(4) Uani 1 1 d . . . . .
H28A H -0.090155 1.079359 0.752285 0.050 Uiso 1 1 calc GR . . . .
H28B H 0.052098 1.197426 0.832683 0.050 Uiso 1 1 calc GR . . . .
H28C H -0.052271 1.044922 0.862683 0.050 Uiso 1 1 calc GR . . . .
C18 C 0.6223(2) 0.6296(2) 0.69868(15) 0.0343(4) Uani 1 1 d . . . . .
H18 H 0.712587 0.717196 0.718230 0.041 Uiso 1 1 calc R . . . .
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
O1 S1 N1 105.45(7) . . ?
O1 S1 C20 108.74(8) . . ?
O2 S1 O1 119.53(7) . . ?
O2 S1 N1 106.66(7) . . ?
O2 S1 C20 108.73(8) . . ?
N1 S1 C20 107.05(7) . . ?
C27 O3 C10 117.37(13) . . ?
C9 N1 S1 117.88(11) . . ?
C9 N1 C12 105.75(12) . . ?
C12 N1 S1 114.65(11) . . ?
C8 C9 N1 110.77(14) . . ?
C10 C9 N1 128.78(15) . . ?
C10 C9 C8 120.30(15) . . ?
C10 C4 C3 119.63(15) . . ?
C5 C4 C10 121.45(15) . . ?
C5 C4 C3 118.92(15) . . ?
C9 C8 C11 109.01(14) . . ?
C7 C8 C9 122.47(15) . . ?
C7 C8 C11 128.51(15) . . ?
O3 C10 C4 119.68(14) . . ?
C9 C10 O3 120.60(15) . . ?
C9 C10 C4 119.56(15) . . ?
C4 C3 C7 119.69(15) . . ?
C2 C3 C4 117.97(15) . . ?
C2 C3 C7 122.34(15) . . ?
C22 C20 S1 119.32(13) . . ?
C21 C20 S1 119.19(13) . . ?
C21 C20 C22 121.46(16) . . ?
C8 C7 C3 118.02(15) . . ?
C8 C7 C13 118.90(15) . . ?
C3 C7 C13 123.08(15) . . ?
C1 C2 C3 120.47(16) . . ?
O3 C27 C28 109.94(15) . . ?
O4 C27 O3 122.60(16) . . ?
O4 C27 C28 127.45(17) . . ?
C15 C14 C13 121.14(16) . . ?
C15 C14 C19 118.67(17) . . ?
C19 C14 C13 120.17(16) . . ?
C23 C24 C26 120.86(16) . . ?
C25 C24 C23 118.44(16) . . ?
C25 C24 C26 120.68(17) . . ?
C5 C6 C1 118.73(16) . . ?
C6 C5 C4 121.73(16) . . ?
C22 C23 C24 121.52(16) . . ?
C2 C1 Cl1 119.47(14) . . ?
C2 C1 C6 122.03(16) . . ?
C6 C1 Cl1 118.50(13) . . ?
N1 C12 C11 105.75(13) . . ?
C8 C11 C12 103.05(13) . . ?
C7 C13 C14 111.89(13) . . ?
C24 C25 C21 121.29(17) . . ?
C14 C15 C16 121.12(17) . . ?
C23 C22 C20 118.42(16) . . ?
C18 C19 C14 120.49(17) . . ?
C20 C21 C25 118.86(16) . . ?
C16 C17 C18 120.11(18) . . ?
C17 C16 C15 119.45(18) . . ?
C17 C18 C19 120.15(18) . . ?
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
S1 O1 1.4316(12) . ?
S1 O2 1.4266(12) . ?
S1 N1 1.6737(14) . ?
S1 C20 1.7578(17) . ?
Cl1 C1 1.7442(17) . ?
O3 C10 1.3951(19) . ?
O3 C27 1.382(2) . ?
O4 C27 1.193(2) . ?
N1 C9 1.438(2) . ?
N1 C12 1.503(2) . ?
C9 C8 1.417(2) . ?
C9 C10 1.368(2) . ?
C4 C10 1.420(2) . ?
C4 C3 1.431(2) . ?
C4 C5 1.418(2) . ?
C8 C7 1.369(2) . ?
C8 C11 1.508(2) . ?
C3 C7 1.432(2) . ?
C3 C2 1.421(2) . ?
C20 C22 1.393(2) . ?
C20 C21 1.385(2) . ?
C7 C13 1.515(2) . ?
C2 C1 1.365(2) . ?
C27 C28 1.495(2) . ?
C14 C13 1.521(2) . ?
C14 C15 1.386(2) . ?
C14 C19 1.391(2) . ?
C24 C23 1.397(3) . ?
C24 C25 1.388(3) . ?
C24 C26 1.504(2) . ?
C6 C5 1.365(2) . ?
C6 C1 1.404(3) . ?
C23 C22 1.388(3) . ?
C12 C11 1.531(2) . ?
C25 C21 1.391(3) . ?
C15 C16 1.391(3) . ?
C19 C18 1.385(3) . ?
C17 C16 1.380(3) . ?
C17 C18 1.384(3) . ?
