#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:57:29 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/98/1569833.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_1569833
loop_
_publ_author_name
'Khuntia, Rupkumar'
'Mahapatra, Sanat Kumar'
'Roy, Lisa'
'Chandra Pan, Subhas'
_publ_section_title
;
 Structurally divergent enantioselective synthesis of benzofuran fused
 azocine derivatives and spiro-cyclopentanone benzofurans enabled by
 sequential catalysis.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              10768
_journal_page_last               10776
_journal_paper_doi               10.1039/d3sc03239f
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration RSS
_chemical_formula_sum            'C37 H28 Cl3 N O4 S2'
_chemical_formula_weight         721.07
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2023-01-10 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.022(4)
_cell_length_b                   11.611(5)
_cell_length_c                   30.123(13)
_cell_measurement_reflns_used    9337
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.22
_cell_volume                     3505(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            95518
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0770
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1526P)²+3.2554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2148
_refine_ls_wR_factor_ref         0.2402
_reflns_number_gt                5074
_reflns_number_total             6128
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3sc03239f2.cif
_cod_data_source_block           rk-38-pph3-r_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569832--1569833.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1569833
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.32542(13) 0.30139(11) 0.65808(5) 0.0624(4) Uani 1 1 d . . .
S002 S 0.7986(3) 0.4248(2) 0.52242(7) 0.1109(8) Uani 1 1 d . . .
Cl03 Cl 0.0280(3) 0.8266(2) 0.64698(11) 0.1391(10) Uani 1 1 d . . .
O1 O 0.7993(3) 0.3918(3) 0.62787(11) 0.0527(8) Uani 1 1 d . . .
O005 O 0.7394(4) 0.7456(3) 0.66102(13) 0.0708(10) Uani 1 1 d . . .
N1 N 0.4514(4) 0.3905(3) 0.65064(14) 0.0529(9) Uani 1 1 d . . .
O007 O 0.3623(5) 0.2057(3) 0.68451(19) 0.0916(15) Uani 1 1 d . . .
Cl2 Cl 0.2083(5) 0.9863(4) 0.6121(2) 0.267(3) Uani 1 1 d . . .
O009 O 0.2667(5) 0.2813(5) 0.61590(16) 0.0938(15) Uani 1 1 d . . .
C2 C 0.5478(6) 0.3853(4) 0.52477(18) 0.0604(13) Uani 1 1 d . . .
H2 H 0.4577 0.3838 0.5321 0.072 Uiso 1 1 calc R . .
C00B C 0.7310(5) 0.6279(4) 0.59461(16) 0.0494(10) Uani 1 1 d . . .
H00B H 0.8235 0.6051 0.5888 0.059 Uiso 1 1 calc R . .
C3 C 0.7001(6) 0.7278(4) 0.56453(17) 0.0559(12) Uani 1 1 d . . .
C00D C 0.5698(5) 0.3572(4) 0.64056(14) 0.0449(10) Uani 1 1 d . . .
C00E C 0.6727(5) 0.4503(4) 0.63333(15) 0.0476(10) Uani 1 1 d . . .
C1 C 0.6875(5) 0.5458(4) 0.66764(14) 0.0482(10) Uani 1 1 d . . .
C00G C 0.6433(5) 0.4441(4) 0.74002(15) 0.0537(11) Uani 1 1 d . . .
C00H C 0.6691(5) 0.5429(4) 0.71165(16) 0.0536(11) Uani 1 1 d . . .
H00H H 0.6733 0.6137 0.7260 0.064 Uiso 1 1 calc R . .
C00I C 0.7198(5) 0.6525(4) 0.64425(16) 0.0508(11) Uani 1 1 d . . .
C00J C 0.6390(5) 0.2489(4) 0.63114(16) 0.0535(11) Uani 1 1 d . . .
C00K C 0.5569(6) 0.4554(5) 0.77592(18) 0.0672(14) Uani 1 1 d . . .
H00K H 0.5176 0.5263 0.7819 0.081 Uiso 1 1 calc R . .
C00L C 0.6445(5) 0.5192(4) 0.58976(15) 0.0478(10) Uani 1 1 d . . .
H00L H 0.5513 0.5444 0.5912 0.057 Uiso 1 1 calc R . .
C00M C 0.5988(7) 0.1344(4) 0.62753(19) 0.0688(15) Uani 1 1 d . . .
H00M H 0.5105 0.1127 0.6320 0.083 Uiso 1 1 calc R . .
C00N C 0.7714(5) 0.2775(4) 0.62376(16) 0.0555(12) Uani 1 1 d . . .
C00O C 0.0587(6) 0.5279(5) 0.7415(2) 0.0710(15) Uani 1 1 d . . .
C00P C 0.5291(7) 0.3617(6) 0.8029(2) 0.0763(16) Uani 1 1 d . . .
H00P H 0.4697 0.3694 0.8265 0.092 Uiso 1 1 calc R . .
C00Q C 0.5703(7) 0.7670(5) 0.5595(2) 0.0785(17) Uani 1 1 d . . .
H00Q H 0.5002 0.7292 0.5736 0.094 Uiso 1 1 calc R . .
C00R C 0.0484(6) 0.5298(6) 0.6960(2) 0.0819(18) Uani 1 1 d . . .
H00R H -0.0137 0.5784 0.6827 0.098 Uiso 1 1 calc R . .
C00S C 0.2309(6) 0.3862(5) 0.73520(19) 0.0632(13) Uani 1 1 d . . .
H00S H 0.2922 0.3373 0.7487 0.076 Uiso 1 1 calc R . .
Cl1 Cl 0.2019(6) 0.7529(9) 0.5835(3) 0.449(8) Uani 1 1 d . . .
C00U C 0.2208(5) 0.3894(4) 0.68958(17) 0.0542(11) Uani 1 1 d . . .
C00V C 0.1280(6) 0.4612(6) 0.6695(2) 0.0725(15) Uani 1 1 d . . .
H00V H 0.1196 0.4631 0.6388 0.087 Uiso 1 1 calc R . .
C00W C 0.7049(6) 0.3383(5) 0.73391(17) 0.0665(14) Uani 1 1 d . . .
H00W H 0.7662 0.3293 0.7110 0.080 Uiso 1 1 calc R . .
C00X C 0.5884(7) 0.2591(6) 0.7949(2) 0.0762(17) Uani 1 1 d . . .
H00X H 0.5684 0.1961 0.8128 0.091 Uiso 1 1 calc R . .
C00Y C 0.6579(7) 0.4494(4) 0.54863(16) 0.0646(14) Uani 1 1 d . . .
C00Z C 0.5459(10) 0.8627(6) 0.5334(3) 0.101(2) Uani 1 1 d . . .
H00Z H 0.4588 0.8890 0.5302 0.122 Uiso 1 1 calc R . .
C010 C 0.6959(9) 0.0543(5) 0.6170(2) 0.083(2) Uani 1 1 d . . .
H010 H 0.6719 -0.0226 0.6137 0.100 Uiso 1 1 calc R . .
C011 C 0.1507(7) 0.4551(6) 0.7605(2) 0.0763(16) Uani 1 1 d . . .
H011 H 0.1584 0.4528 0.7913 0.092 Uiso 1 1 calc R . .
C012 C 0.8002(7) 0.7828(5) 0.5427(2) 0.0721(15) Uani 1 1 d . . .
H012 H 0.8876 0.7563 0.5444 0.086 Uiso 1 1 calc R . .
C013 C 0.6430(13) 0.9174(7) 0.5129(3) 0.108(3) Uani 1 1 d . . .
H013 H 0.6235 0.9811 0.4954 0.129 Uiso 1 1 calc R . .
C014 C 0.8684(7) 0.1963(5) 0.61444(18) 0.0718(16) Uani 1 1 d . . .
H014 H 0.9574 0.2164 0.6105 0.086 Uiso 1 1 calc R . .
C015 C 0.8260(9) 0.0854(6) 0.6114(2) 0.086(2) Uani 1 1 d . . .
H015 H 0.8884 0.0283 0.6053 0.104 Uiso 1 1 calc R . .
C016 C -0.0258(8) 0.6075(8) 0.7683(3) 0.109(3) Uani 1 1 d . . .
H01A H -0.0820 0.5635 0.7877 0.163 Uiso 1 1 calc R . .
H01B H -0.0802 0.6531 0.7488 0.163 Uiso 1 1 calc R . .
H01C H 0.0305 0.6572 0.7856 0.163 Uiso 1 1 calc R . .
C017 C 0.6768(7) 0.2473(5) 0.7610(2) 0.0772(17) Uani 1 1 d . . .
H017 H 0.7184 0.1767 0.7562 0.093 Uiso 1 1 calc R . .
C018 C 0.7672(11) 0.8829(6) 0.5170(3) 0.096(2) Uani 1 1 d . . .
H018 H 0.8348 0.9239 0.5029 0.116 Uiso 1 1 calc R . .
C019 C 0.7353(18) 0.3437(9) 0.4848(3) 0.140(5) Uani 1 1 d . . .
H019 H 0.7851 0.3108 0.4620 0.168 Uiso 1 1 calc R . .
C01A C 0.610(2) 0.3286(10) 0.4892(4) 0.153(6) Uani 1 1 d . . .
H01D H 0.5618 0.2822 0.4697 0.183 Uiso 1 1 calc R . .
C5 C 0.1844(10) 0.8462(9) 0.6228(3) 0.116(3) Uani 1 1 d . . .
H5 H 0.2498 0.8255 0.6456 0.139 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
O007 S001 O009 118.9(3) . . ?
O007 S001 N1 111.6(3) . . ?
O009 S001 N1 107.4(3) . . ?
O007 S001 C00U 108.1(3) . . ?
O009 S001 C00U 109.5(3) . . ?
N1 S001 C00U 99.6(2) . . ?
C019 S002 C00Y 95.9(6) . . ?
C00N O1 C00E 106.7(4) . . ?
C00D N1 S001 123.4(3) . . ?
C01A C2 C00Y 105.7(8) . . ?
C3 C00B C00I 115.5(4) . . ?
C3 C00B C00L 117.4(4) . . ?
C00I C00B C00L 101.8(4) . . ?
C012 C3 C00Q 119.0(5) . . ?
C012 C3 C00B 120.2(5) . . ?
C00Q C3 C00B 120.8(5) . . ?
N1 C00D C00J 138.0(4) . . ?
N1 C00D C00E 116.7(4) . . ?
C00J C00D C00E 105.3(4) . . ?
O1 C00E C00D 106.2(3) . . ?
O1 C00E C1 109.4(4) . . ?
C00D C00E C1 119.3(4) . . ?
O1 C00E C00L 107.7(3) . . ?
C00D C00E C00L 111.3(4) . . ?
C1 C00E C00L 102.4(3) . . ?
C00H C1 C00I 122.0(4) . . ?
C00H C1 C00E 129.8(4) . . ?
C00I C1 C00E 108.2(4) . . ?
C00W C00G C00K 117.6(5) . . ?
C00W C00G C00H 122.8(5) . . ?
C00K C00G C00H 119.6(5) . . ?
C1 C00H C00G 128.8(4) . . ?
O005 C00I C1 126.3(4) . . ?
O005 C00I C00B 124.4(4) . . ?
C1 C00I C00B 109.2(4) . . ?
C00N C00J C00M 119.5(5) . . ?
C00N C00J C00D 106.2(4) . . ?
C00M C00J C00D 134.3(5) . . ?
C00P C00K C00G 120.5(6) . . ?
C00Y C00L C00B 118.4(4) . . ?
C00Y C00L C00E 113.9(4) . . ?
C00B C00L C00E 103.8(4) . . ?
C010 C00M C00J 117.2(6) . . ?
O1 C00N C014 122.6(5) . . ?
O1 C00N C00J 114.5(4) . . ?
C014 C00N C00J 122.9(5) . . ?
C00R C00O C011 118.5(6) . . ?
C00R C00O C016 119.2(6) . . ?
C011 C00O C016 122.3(6) . . ?
C00X C00P C00K 119.9(6) . . ?
C00Z C00Q C3 119.5(7) . . ?
C00O C00R C00V 121.5(6) . . ?
C011 C00S C00U 119.8(5) . . ?
C00S C00U C00V 120.0(5) . . ?
C00S C00U S001 118.8(4) . . ?
C00V C00U S001 121.2(4) . . ?
C00R C00V C00U 118.8(5) . . ?
C017 C00W C00G 121.0(6) . . ?
C00P C00X C017 120.6(6) . . ?
C00L C00Y C2 126.7(5) . . ?
C00L C00Y S002 125.0(4) . . ?
C2 C00Y S002 108.2(4) . . ?
C013 C00Z C00Q 121.6(8) . . ?
C015 C010 C00M 121.5(6) . . ?
C00S C011 C00O 121.4(6) . . ?
C3 C012 C018 118.2(7) . . ?
C018 C013 C00Z 120.7(7) . . ?
C015 C014 C00N 116.1(6) . . ?
C014 C015 C010 122.8(6) . . ?
C00X C017 C00W 120.4(6) . . ?
C013 C018 C012 121.0(7) . . ?
C01A C019 S002 113.4(8) . . ?
C019 C01A C2 116.9(9) . . ?
Cl1 C5 Cl2 119.6(8) . . ?
Cl1 C5 Cl03 108.5(5) . . ?
Cl2 C5 Cl03 109.6(6) . . ?
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
S001 O007 1.416(5) . ?
S001 O009 1.420(5) . ?
S001 N1 1.648(4) . ?
S001 C00U 1.745(5) . ?
S002 C019 1.604(14) . ?
S002 C00Y 1.641(7) . ?
Cl03 C5 1.743(10) . ?
O1 C00N 1.362(6) . ?
O1 C00E 1.448(5) . ?
O005 C00I 1.210(6) . ?
N1 C00D 1.284(6) . ?
Cl2 C5 1.676(11) . ?
C2 C01A 1.403(18) . ?
C2 C00Y 1.512(7) . ?
C00B C3 1.504(7) . ?
C00B C00I 1.527(7) . ?
C00B C00L 1.539(6) . ?
C3 C012 1.359(8) . ?
C3 C00Q 1.387(9) . ?
C00D C00J 1.464(6) . ?
C00D C00E 1.510(6) . ?
C00E C1 1.523(6) . ?
C00E C00L 1.563(6) . ?
C1 C00H 1.339(6) . ?
C1 C00I 1.462(7) . ?
C00G C00W 1.387(8) . ?
C00G C00K 1.391(7) . ?
C00G C00H 1.453(7) . ?
C00J C00N 1.386(8) . ?
C00J C00M 1.394(7) . ?
C00K C00P 1.386(9) . ?
C00L C00Y 1.487(7) . ?
C00M C010 1.383(9) . ?
C00N C014 1.383(7) . ?
C00O C00R 1.374(10) . ?
C00O C011 1.376(9) . ?
C00O C016 1.492(9) . ?
C00P C00X 1.353(9) . ?
C00Q C00Z 1.383(10) . ?
C00R C00V 1.381(9) . ?
C00S C011 1.367(9) . ?
C00S C00U 1.378(8) . ?
Cl1 C5 1.615(10) . ?
C00U C00V 1.388(8) . ?
C00W C017 1.364(9) . ?
C00X C017 1.360(10) . ?
C00Z C013 1.316(14) . ?
C010 C015 1.363(11) . ?
C012 C018 1.436(10) . ?
C013 C018 1.312(13) . ?
C014 C015 1.359(10) . ?
C019 C01A 1.276(19) . ?
