# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_an13cult
_database_code_depnum_ccdc_archive 'CCDC 2045484'
loop_
_audit_author_name
_audit_author_address
'Herman Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2020-11-20 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
_audit_creation_date             2018-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'3-Butyl-2-phenyl-1-tosyl-4-((triisopropylsilyl)oxy)-1,2-dihydrobenzofuro [3,2-b]pyridine'
_chemical_formula_moiety         'C37 H47 N O4 S Si'
_chemical_formula_sum            'C37 H47 N O4 S Si'
_chemical_formula_weight         629.90
_chemical_melting_point          ?
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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.6691(10)
_cell_length_b                   10.8205(5)
_cell_length_c                   20.3333(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.297(7)
_cell_angle_gamma                90
_cell_volume                     3393.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9181
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5180
_cell_measurement_theta_min      4.3430
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91900
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18730
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.491
_diffrn_reflns_theta_min         4.342
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00 113.00   1.00   18.00    --  107.97-111.00-120.00   83
  2  ω    -64.00  29.00   1.00    6.00    --  -40.32  37.00-150.00   93
  3  ω   -122.00   6.00   1.00    6.00    --  -40.32 -19.00  30.00  128
  4  ω      1.00  66.00   1.00    6.00    --   40.32 -99.00  30.00   65
  5  ω     23.00  98.00   1.00    6.00    --   40.32-125.00 -60.00   75
  6  ω     80.00 178.00   1.00   18.00    --  107.97  45.00-180.00   98
  7  ω     25.00 169.00   1.00   18.00    --  107.97 -15.00  30.00  144
  8  ω     79.00 161.00   1.00   18.00    --  107.97  61.00-150.00   82
  9  ω    103.00 136.00   1.00   18.00    --  107.97 111.00 120.00   33
 10  ω    153.00 178.00   1.00   18.00    --  107.97 111.00 120.00   25
 11  ω     74.00 178.00   1.00   18.00    --  107.97  77.00  30.00  104
 12  ω     29.00 142.00   1.00   18.00    --  107.97 -77.00  60.00  113
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274187000
_diffrn_orient_matrix_UB_12      0.1300407000
_diffrn_orient_matrix_UB_13      0.0312237000
_diffrn_orient_matrix_UB_21      0.0789366000
_diffrn_orient_matrix_UB_22      -0.0044302000
_diffrn_orient_matrix_UB_23      -0.0217235000
_diffrn_orient_matrix_UB_31      -0.0546938000
_diffrn_orient_matrix_UB_32      0.0578122000
_diffrn_orient_matrix_UB_33      -0.0725604000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4992
_reflns_number_total             6094
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.46
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         6094
_refine_ls_number_restraints     179
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.005
_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)+(0.0780P)²+4.9360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1728
_refine_special_details          ?
_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. Restrained distances
 O4-C3 \\sim O4A-C3A
 with sigma of 0.02
 Si1-O4 \\sim Si1A-O4A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C47) \\sim Ueq, Uanis(C46A) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.002
Uanis(C49A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.002
Uanis(C41A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 Si1A, O4A, C2A, C3A, C37A, C38A, C39A, C40A, C42A, C43A, C44A, C45A, C46A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 Si1, O4, C1, C2, C3, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: Si1(0.6) Si1A(0.4) O4(0.6) O4A(0.4) H1A(0.6) H1B(0.4) C2(0.6)
 C2A(0.4) C3(0.6) C3A(0.4) C37(0.66667) H37A(0.66667) H37B(0.66667)
 C37A(0.33333) H37C(0.33333) H37D(0.33333) C38(0.66667) H38A(0.66667)
 H38B(0.66667) C38A(0.33333) H38C(0.33333) H38D(0.33333) C39(0.66667)
 H39A(0.66667) H39B(0.66667) C39A(0.33333) H39C(0.33333) H39D(0.33333)
 C40(0.66667) H40A(0.66667) H40B(0.66667) H40C(0.66667) C40A(0.33333)
 H40D(0.33333) H40E(0.33333) H40F(0.33333) C41(0.5) H41(0.5) C41A(0.5)
 H41A(0.5) C42(0.5) H42A(0.5) H42B(0.5) H42C(0.5) C42A(0.5) H42D(0.5) H42E(0.5)
 H42F(0.5) C43(0.5) H43A(0.5) H43B(0.5) H43C(0.5) C43A(0.5) H43D(0.5) H43E(0.5)
 H43F(0.5) C44(0.6) H44(0.6) C44A(0.4) H44A(0.4) C45(0.6) H45A(0.6) H45B(0.6)
 H45C(0.6) C45A(0.4) H45D(0.4) H45E(0.4) H45F(0.4) C46(0.6) H46A(0.6) H46B(0.6)
 H46C(0.6) C46A(0.4) H46D(0.4) H46E(0.4) H46F(0.4) C47(0.6) H47(0.6) C47A(0.4)
 H47A(0.4) C48(0.6) H48A(0.6) H48B(0.6) H48C(0.6) C48A(0.4) H48D(0.4) H48E(0.4)
 H48F(0.4) C49(0.6) H49A(0.6) H49B(0.6) H49C(0.6) C49A(0.4) H49D(0.4) H49E(0.4)
 H49F(0.4)
6.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B), C41(H41), C41A(H41A), C44(H44), C44A(H44A), C47(H47),
 C47A(H47A)
6.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C37A(H37C,H37D), C38(H38A,H38B), C38A(H38C,H38D), C39(H39A,
 H39B), C39A(H39C,H39D)
6.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C22(H22), C23(H23), C25(H25), C26(H26),
 C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
6.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C40(H40A,H40B,H40C), C40A(H40D,H40E,H40F), C42(H42A,H42B,
 H42C), C42A(H42D,H42E,H42F), C43(H43A,H43B,H43C), C43A(H43D,H43E,H43F),
 C45(H45A,H45B,H45C), C45A(H45D,H45E,H45F), C46(H46A,H46B,H46C), C46A(H46D,H46E,
 H46F), C48(H48A,H48B,H48C), C48A(H48D,H48E,H48F), C49(H49A,H49B,H49C),
 C49A(H49D,H49E,H49F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.70146(5) 0.66446(7) 0.21946(4) 0.0309(2) Uani 1 1 d . . . . .
Si1 Si 0.4099(2) 0.6751(3) 0.36645(16) 0.0296(6) Uani 0.6 1 d D U P A 1
Si1A Si 0.3947(3) 0.6969(4) 0.3469(2) 0.0220(8) Uani 0.4 1 d D U P A 2
O1 O 0.71006(14) 0.78002(19) 0.18872(12) 0.0345(5) Uani 1 1 d . . . . .
O2 O 0.74491(15) 0.5569(2) 0.20821(12) 0.0404(6) Uani 1 1 d . . . . .
O3 O 0.44491(14) 0.81560(19) 0.23004(12) 0.0345(5) Uani 1 1 d . . . . .
O4 O 0.4822(3) 0.6196(5) 0.3369(2) 0.0374(11) Uani 0.6 1 d D U P A 1
O4A O 0.4456(4) 0.5995(5) 0.3116(3) 0.0296(14) Uani 0.4 1 d D U P A 2
N1 N 0.59552(16) 0.6309(2) 0.18425(13) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.5692(2) 0.5057(3) 0.20072(17) 0.0341(7) Uani 1 1 d . U . . .
H1A H 0.6224 0.4534 0.2135 0.041 Uiso 0.6 1 calc R . P B 1
H1B H 0.6214 0.4513 0.2198 0.041 Uiso 0.4 1 calc R . P C 2
C2 C 0.5486(3) 0.5113(5) 0.2695(3) 0.0217(11) Uani 0.6 1 d . U P A 1
C2A C 0.5177(6) 0.4982(7) 0.2502(5) 0.0199(16) Uani 0.4 1 d . U P A 2
C3 C 0.5072(5) 0.6135(8) 0.2814(4) 0.0286(19) Uani 0.6 1 d D U P A 1
C3A C 0.4840(8) 0.5974(9) 0.2643(6) 0.021(3) Uani 0.4 1 d D U P A 2
C4 C 0.4944(2) 0.7140(3) 0.23157(16) 0.0313(6) Uani 1 1 d . . . . .
C5 C 0.54007(18) 0.7277(2) 0.18926(15) 0.0249(6) Uani 1 1 d . . . . .
C6 C 0.51950(17) 0.8475(2) 0.15659(14) 0.0232(5) Uani 1 1 d . . . . .
C7 C 0.46174(18) 0.8980(3) 0.18447(15) 0.0284(6) Uani 1 1 d . . . . .
C8 C 0.4257(2) 1.0138(3) 0.16856(17) 0.0331(7) Uani 1 1 d . . . . .
H8 H 0.3873 1.0448 0.1891 0.040 Uiso 1 1 calc R . . . .
C9 C 0.4485(2) 1.0830(3) 0.12088(16) 0.0322(6) Uani 1 1 d . . . . .
H9 H 0.4255 1.1638 0.1084 0.039 Uiso 1 1 calc R . . . .
C10 C 0.50504(19) 1.0352(3) 0.09082(15) 0.0291(6) Uani 1 1 d . . . . .
H10 H 0.5188 1.0840 0.0577 0.035 Uiso 1 1 calc R . . . .
C11 C 0.54133(18) 0.9188(2) 0.10821(14) 0.0252(6) Uani 1 1 d . . . . .
H11 H 0.5801 0.8879 0.0879 0.030 Uiso 1 1 calc R . . . .
C20 C 0.7985(2) 0.7371(3) 0.53528(17) 0.0411(8) Uani 1 1 d . . . . .
H20A H 0.8064 0.6569 0.5594 0.062 Uiso 1 1 calc GR . . . .
H20B H 0.7531 0.7838 0.5439 0.062 Uiso 1 1 calc GR . . . .
H20C H 0.8531 0.7835 0.5538 0.062 Uiso 1 1 calc GR . . . .
C21 C 0.77248(18) 0.7170(3) 0.45635(16) 0.0320(6) Uani 1 1 d . . . . .
C22 C 0.7860(2) 0.6040(3) 0.42948(17) 0.0373(7) Uani 1 1 d . . . . .
H22 H 0.8101 0.5374 0.4613 0.045 Uiso 1 1 calc R . . . .
C23 C 0.7650(2) 0.5863(3) 0.35722(18) 0.0377(7) Uani 1 1 d . . . . .
H23 H 0.7747 0.5088 0.3395 0.045 Uiso 1 1 calc R . . . .
C24 C 0.72935(18) 0.6851(3) 0.31126(16) 0.0295(6) Uani 1 1 d . . . . .
C25 C 0.71378(18) 0.7985(3) 0.33595(16) 0.0301(6) Uani 1 1 d . . . . .
H25 H 0.6887 0.8644 0.3039 0.036 Uiso 1 1 calc R . . . .
C26 C 0.73563(19) 0.8137(3) 0.40857(16) 0.0324(6) Uani 1 1 d . . . . .
H26 H 0.7254 0.8910 0.4261 0.039 Uiso 1 1 calc R . . . .
C31 C 0.5053(2) 0.4514(3) 0.13186(18) 0.0353(7) Uani 1 1 d . . . . .
C32 C 0.5378(2) 0.3957(3) 0.08471(18) 0.0355(7) Uani 1 1 d . . . . .
H32 H 0.5987 0.3895 0.0975 0.043 Uiso 1 1 calc R . . . .
C33 C 0.4826(2) 0.3499(3) 0.02004(19) 0.0402(7) Uani 1 1 d . . . . .
H33 H 0.5056 0.3123 -0.0113 0.048 Uiso 1 1 calc R . . . .
C34 C 0.3939(2) 0.3587(3) 0.0008(2) 0.0455(8) Uani 1 1 d . . . . .
H34 H 0.3557 0.3278 -0.0438 0.055 Uiso 1 1 calc R . . . .
C35 C 0.3608(2) 0.4130(3) 0.0473(2) 0.0485(9) Uani 1 1 d . . . . .
H35 H 0.2999 0.4189 0.0344 0.058 Uiso 1 1 calc R . . . .
C36 C 0.4166(2) 0.4586(3) 0.1126(2) 0.0422(8) Uani 1 1 d . . . . .
H36 H 0.3935 0.4950 0.1441 0.051 Uiso 1 1 calc R . . . .
C37 C 0.5679(3) 0.3999(4) 0.3171(2) 0.0299(9) Uani 0.6667 1 d . U P A 1
H37A H 0.5479 0.4171 0.3562 0.036 Uiso 0.6667 1 calc R . P A 1
H37B H 0.6316 0.3890 0.3387 0.036 Uiso 0.6667 1 calc R . P A 1
C37A C 0.5101(5) 0.3718(7) 0.2780(4) 0.0231(15) Uani 0.3333 1 d . U P A 2
H37C H 0.4891 0.3132 0.2377 0.028 Uiso 0.3333 1 calc R . P A 2
H37D H 0.4665 0.3746 0.3001 0.028 Uiso 0.3333 1 calc R . P A 2
C38 C 0.5276(3) 0.2779(4) 0.2823(3) 0.0385(11) Uani 0.6667 1 d . U P A 1
H38A H 0.5587 0.2480 0.2525 0.046 Uiso 0.6667 1 calc R . P A 1
H38B H 0.4664 0.2925 0.2508 0.046 Uiso 0.6667 1 calc R . P A 1
C38A C 0.5951(5) 0.3240(8) 0.3323(4) 0.0247(15) Uani 0.3333 1 d . U P A 2
H38C H 0.6361 0.3075 0.3087 0.030 Uiso 0.3333 1 calc R . P A 2
H38D H 0.6210 0.3875 0.3694 0.030 Uiso 0.3333 1 calc R . P A 2
C39 C 0.5309(4) 0.1772(5) 0.3367(3) 0.0443(12) Uani 0.6667 1 d . U P A 1
H39A H 0.5016 0.2084 0.3676 0.053 Uiso 0.6667 1 calc R . P A 1
H39B H 0.4982 0.1041 0.3109 0.053 Uiso 0.6667 1 calc R . P A 1
C39A C 0.5798(7) 0.2064(9) 0.3662(5) 0.0331(18) Uani 0.3333 1 d . U P A 2
H39C H 0.5528 0.1442 0.3286 0.040 Uiso 0.3333 1 calc R . P A 2
H39D H 0.5386 0.2239 0.3895 0.040 Uiso 0.3333 1 calc R . P A 2
C40 C 0.6217(4) 0.1374(6) 0.3830(3) 0.0450(12) Uani 0.6667 1 d . U P A 1
H40A H 0.6480 0.0941 0.3538 0.068 Uiso 0.6667 1 calc GR . P A 1
H40B H 0.6194 0.0819 0.4203 0.068 Uiso 0.6667 1 calc GR . P A 1
H40C H 0.6565 0.2103 0.4047 0.068 Uiso 0.6667 1 calc GR . P A 1
C40A C 0.6629(7) 0.1525(9) 0.4211(6) 0.034(2) Uani 0.3333 1 d . U P A 2
H40D H 0.7045 0.1365 0.3986 0.052 Uiso 0.3333 1 calc GR . P A 2
H40E H 0.6496 0.0750 0.4397 0.052 Uiso 0.3333 1 calc GR . P A 2
H40F H 0.6880 0.2114 0.4602 0.052 Uiso 0.3333 1 calc GR . P A 2
C41 C 0.4604(4) 0.8022(6) 0.4330(4) 0.0348(11) Uani 0.5 1 d . U P A 1
H41 H 0.4194 0.8217 0.4569 0.042 Uiso 0.5 1 calc R . P A 1
C41A C 0.4719(4) 0.8271(5) 0.3931(3) 0.0283(12) Uani 0.5 1 d . U P A 2
H41A H 0.4955 0.8588 0.3578 0.034 Uiso 0.5 1 calc R . P A 2
C42 C 0.5464(4) 0.7570(8) 0.4911(4) 0.0385(14) Uani 0.5 1 d . U P A 1
H42A H 0.5341 0.6899 0.5183 0.058 Uiso 0.5 1 calc GR . P A 1
H42B H 0.5740 0.8257 0.5231 0.058 Uiso 0.5 1 calc GR . P A 1
H42C H 0.5853 0.7270 0.4687 0.058 Uiso 0.5 1 calc GR . P A 1
C42A C 0.5498(5) 0.7883(7) 0.4575(4) 0.0424(17) Uani 0.5 1 d . U P A 2
H42D H 0.5880 0.8596 0.4761 0.064 Uiso 0.5 1 calc GR . P A 2
H42E H 0.5815 0.7232 0.4440 0.064 Uiso 0.5 1 calc GR . P A 2
H42F H 0.5304 0.7570 0.4943 0.064 Uiso 0.5 1 calc GR . P A 2
C43 C 0.4749(5) 0.9185(7) 0.3996(4) 0.0425(14) Uani 0.5 1 d . U P A 1
H43A H 0.5203 0.9049 0.3808 0.064 Uiso 0.5 1 calc GR . P A 1
H43B H 0.4930 0.9843 0.4354 0.064 Uiso 0.5 1 calc GR . P A 1
H43C H 0.4210 0.9426 0.3608 0.064 Uiso 0.5 1 calc GR . P A 1
C43A C 0.4251(5) 0.9366(6) 0.4107(4) 0.0367(14) Uani 0.5 1 d . U P A 2
H43D H 0.3957 0.9086 0.4417 0.055 Uiso 0.5 1 calc GR . P A 2
H43E H 0.3822 0.9703 0.3667 0.055 Uiso 0.5 1 calc GR . P A 2
H43F H 0.4674 1.0008 0.4351 0.055 Uiso 0.5 1 calc GR . P A 2
C44 C 0.3940(5) 0.5388(7) 0.4183(4) 0.0389(14) Uani 0.6 1 d . U P A 1
H44 H 0.4537 0.5083 0.4472 0.047 Uiso 0.6 1 calc R . P A 1
C44A C 0.3801(7) 0.5872(8) 0.4134(5) 0.0283(17) Uani 0.4 1 d . U P A 2
H44A H 0.4391 0.5520 0.4395 0.034 Uiso 0.4 1 calc R . P A 2
C45 C 0.3473(5) 0.4282(7) 0.3698(4) 0.0554(18) Uani 0.6 1 d . U P A 1
H45A H 0.2852 0.4462 0.3468 0.083 Uiso 0.6 1 calc GR . P A 1
H45B H 0.3556 0.3532 0.3987 0.083 Uiso 0.6 1 calc GR . P A 1
H45C H 0.3717 0.4156 0.3334 0.083 Uiso 0.6 1 calc GR . P A 1
C45A C 0.3239(7) 0.4750(8) 0.3773(5) 0.038(2) Uani 0.4 1 d . U P A 2
H45D H 0.2635 0.5014 0.3529 0.057 Uiso 0.4 1 calc GR . P A 2
H45E H 0.3271 0.4129 0.4133 0.057 Uiso 0.4 1 calc GR . P A 2
H45F H 0.3451 0.4392 0.3427 0.057 Uiso 0.4 1 calc GR . P A 2
C46 C 0.3522(5) 0.5631(8) 0.4709(4) 0.0561(16) Uani 0.6 1 d . U P A 1
H46A H 0.3852 0.6265 0.5047 0.084 Uiso 0.6 1 calc GR . P A 1
H46B H 0.3515 0.4867 0.4965 0.084 Uiso 0.6 1 calc GR . P A 1
H46C H 0.2926 0.5918 0.4456 0.084 Uiso 0.6 1 calc GR . P A 1
C46A C 0.3532(5) 0.6405(8) 0.4717(4) 0.0322(14) Uani 0.4 1 d . U P A 2
H46D H 0.3869 0.7154 0.4912 0.048 Uiso 0.4 1 calc GR . P A 2
H46E H 0.3643 0.5793 0.5097 0.048 Uiso 0.4 1 calc GR . P A 2
H46F H 0.2913 0.6608 0.4517 0.048 Uiso 0.4 1 calc GR . P A 2
C47 C 0.3089(6) 0.7299(8) 0.2943(5) 0.030(2) Uani 0.6 1 d . U P A 1
H47 H 0.3256 0.8068 0.2754 0.036 Uiso 0.6 1 calc R . P A 1
C47A C 0.2924(9) 0.7551(11) 0.2771(7) 0.025(3) Uani 0.4 1 d . . P A 2
H47A H 0.3077 0.8292 0.2549 0.030 Uiso 0.4 1 calc R . P A 2
C48 C 0.2368(7) 0.7717(12) 0.3237(7) 0.035(2) Uani 0.6 1 d . . P A 1
H48A H 0.2136 0.6987 0.3390 0.053 Uiso 0.6 1 calc GR . P A 1
H48B H 0.1897 0.8144 0.2860 0.053 Uiso 0.6 1 calc GR . P A 1
H48C H 0.2628 0.8276 0.3642 0.053 Uiso 0.6 1 calc GR . P A 1
C48A C 0.2300(16) 0.794(2) 0.3064(12) 0.048(5) Uani 0.4 1 d . . P A 2
H48D H 0.2090 0.7219 0.3242 0.072 Uiso 0.4 1 calc GR . P A 2
H48E H 0.1811 0.8349 0.2694 0.072 Uiso 0.4 1 calc GR . P A 2
H48F H 0.2576 0.8520 0.3456 0.072 Uiso 0.4 1 calc GR . P A 2
C49 C 0.2700(6) 0.6433(11) 0.2296(5) 0.051(3) Uani 0.6 1 d . . P A 1
H49A H 0.3122 0.6309 0.2073 0.076 Uiso 0.6 1 calc GR . P A 1
H49B H 0.2171 0.6804 0.1952 0.076 Uiso 0.6 1 calc GR . P A 1
H49C H 0.2559 0.5634 0.2453 0.076 Uiso 0.6 1 calc GR . P A 1
C49A C 0.2493(10) 0.6593(15) 0.2167(9) 0.041(4) Uani 0.4 1 d . U P A 2
H49D H 0.2943 0.6174 0.2050 0.061 Uiso 0.4 1 calc GR . P A 2
H49E H 0.2093 0.7019 0.1745 0.061 Uiso 0.4 1 calc GR . P A 2
H49F H 0.2173 0.5982 0.2328 0.061 Uiso 0.4 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.429(2) . ?
S1 O2 1.434(2) . ?
S1 N1 1.674(3) . ?
S1 C24 1.758(3) . ?
Si1 O4 1.650(5) . ?
Si1 C41 1.889(7) . ?
Si1 C44 1.889(8) . ?
Si1 C47 1.861(9) . ?
Si1A O4A 1.675(6) . ?
Si1A C41A 1.899(7) . ?
Si1A C44A 1.883(9) . ?
Si1A C47A 1.866(13) . ?
O3 C4 1.368(3) . ?
O3 C7 1.389(3) . ?
O4 C3 1.346(7) . ?
O4A C3A 1.343(9) . ?
N1 C1 1.501(4) . ?
N1 C5 1.426(3) . ?
C1 C2 1.562(6) . ?
C1 C2A 1.552(9) . ?
C1 C31 1.519(5) . ?
C2 C3 1.372(9) . ?
C2 C37 1.503(7) . ?
C2A C3A 1.293(12) . ?
C2A C37A 1.504(11) . ?
C3 C4 1.446(9) . ?
C3A C4 1.467(11) . ?
C4 C5 1.356(4) . ?
C5 C6 1.437(4) . ?
C6 C7 1.400(4) . ?
C6 C11 1.402(4) . ?
C7 C8 1.373(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.402(4) . ?
C10 C11 1.384(4) . ?
C20 C21 1.511(4) . ?
C21 C22 1.392(5) . ?
C21 C26 1.401(4) . ?
C22 C23 1.388(5) . ?
C23 C24 1.395(4) . ?
C24 C25 1.387(4) . ?
C25 C26 1.390(4) . ?
C31 C32 1.404(4) . ?
C31 C36 1.381(5) . ?
C32 C33 1.380(5) . ?
C33 C34 1.382(5) . ?
C34 C35 1.393(5) . ?
C35 C36 1.390(6) . ?
C37 C38 1.528(7) . ?
C37A C38A 1.517(11) . ?
C38 C39 1.539(6) . ?
C38A C39A 1.515(12) . ?
C39 C40 1.509(8) . ?
C39A C40A 1.527(13) . ?
C41 C42 1.551(9) . ?
C41 C43 1.492(10) . ?
C41A C42A 1.512(9) . ?
C41A C43A 1.534(9) . ?
C44 C45 1.558(10) . ?
C44 C46 1.505(9) . ?
C44A C45A 1.539(12) . ?
C44A C46A 1.531(11) . ?
C47 C48 1.598(19) . ?
C47 C49 1.543(13) . ?
C47A C48A 1.44(3) . ?
C47A C49A 1.56(2) . ?

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 O2 119.98(13) . . ?
O1 S1 N1 105.50(12) . . ?
O1 S1 C24 108.86(14) . . ?
O2 S1 N1 105.69(14) . . ?
O2 S1 C24 109.03(14) . . ?
N1 S1 C24 107.01(13) . . ?
O4 Si1 C41 109.7(3) . . ?
O4 Si1 C44 101.2(3) . . ?
O4 Si1 C47 113.3(4) . . ?
C44 Si1 C41 106.7(3) . . ?
C47 Si1 C41 110.9(4) . . ?
C47 Si1 C44 114.3(4) . . ?
O4A Si1A C41A 108.7(4) . . ?
O4A Si1A C44A 97.8(4) . . ?
O4A Si1A C47A 110.6(6) . . ?
C44A Si1A C41A 111.1(4) . . ?
C47A Si1A C41A 112.2(5) . . ?
C47A Si1A C44A 115.3(6) . . ?
C4 O3 C7 105.0(2) . . ?
C3 O4 Si1 145.6(5) . . ?
C3A O4A Si1A 140.7(6) . . ?
C1 N1 S1 116.79(19) . . ?
C5 N1 S1 114.67(19) . . ?
C5 N1 C1 113.2(2) . . ?
N1 C1 C2 110.3(3) . . ?
N1 C1 C2A 118.2(3) . . ?
N1 C1 C31 107.8(2) . . ?
C31 C1 C2 121.7(3) . . ?
C31 C1 C2A 102.1(4) . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 C37 122.2(5) . . ?
C37 C2 C1 118.6(4) . . ?
C3A C2A C1 119.6(7) . . ?
C3A C2A C37A 124.4(8) . . ?
C37A C2A C1 116.0(6) . . ?
O4 C3 C2 121.6(7) . . ?
O4 C3 C4 122.7(6) . . ?
C2 C3 C4 115.7(5) . . ?
O4A C3A C4 118.7(7) . . ?
C2A C3A O4A 122.6(9) . . ?
C2A C3A C4 118.5(7) . . ?
O3 C4 C3 123.3(4) . . ?
O3 C4 C3A 121.8(5) . . ?
C5 C4 O3 112.1(2) . . ?
C5 C4 C3 123.9(4) . . ?
C5 C4 C3A 125.0(4) . . ?
N1 C5 C6 132.6(2) . . ?
C4 C5 N1 120.0(2) . . ?
C4 C5 C6 107.4(2) . . ?
C7 C6 C5 104.2(2) . . ?
C7 C6 C11 118.1(2) . . ?
C11 C6 C5 137.7(3) . . ?
O3 C7 C6 111.3(2) . . ?
C8 C7 O3 124.2(3) . . ?
C8 C7 C6 124.5(3) . . ?
C7 C8 C9 116.5(3) . . ?
C8 C9 C10 120.9(3) . . ?
C11 C10 C9 121.7(3) . . ?
C10 C11 C6 118.4(3) . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 C26 118.5(3) . . ?
C26 C21 C20 120.2(3) . . ?
C23 C22 C21 121.6(3) . . ?
C22 C23 C24 118.4(3) . . ?
C23 C24 S1 119.2(2) . . ?
C25 C24 S1 119.1(2) . . ?
C25 C24 C23 121.7(3) . . ?
C24 C25 C26 118.7(3) . . ?
C25 C26 C21 121.2(3) . . ?
C32 C31 C1 118.6(3) . . ?
C36 C31 C1 122.7(3) . . ?
C36 C31 C32 118.7(3) . . ?
C33 C32 C31 121.0(3) . . ?
C32 C33 C34 120.0(3) . . ?
C33 C34 C35 119.6(4) . . ?
C36 C35 C34 120.3(3) . . ?
C31 C36 C35 120.5(3) . . ?
C2 C37 C38 116.5(4) . . ?
C2A C37A C38A 113.3(7) . . ?
C37 C38 C39 112.9(4) . . ?
C39A C38A C37A 110.2(7) . . ?
C40 C39 C38 113.8(5) . . ?
C38A C39A C40A 113.0(8) . . ?
C42 C41 Si1 110.4(5) . . ?
C43 C41 Si1 113.2(5) . . ?
C43 C41 C42 110.5(6) . . ?
C42A C41A Si1A 114.9(5) . . ?
C42A C41A C43A 111.0(5) . . ?
C43A C41A Si1A 112.3(4) . . ?
C45 C44 Si1 112.9(5) . . ?
C46 C44 Si1 117.4(5) . . ?
C46 C44 C45 109.2(6) . . ?
C45A C44A Si1A 112.1(6) . . ?
C46A C44A Si1A 118.4(6) . . ?
C46A C44A C45A 111.2(7) . . ?
C48 C47 Si1 112.3(7) . . ?
C49 C47 Si1 116.1(7) . . ?
C49 C47 C48 111.0(8) . . ?
C48A C47A Si1A 112.3(11) . . ?
C48A C47A C49A 109.3(15) . . ?
C49A C47A Si1A 112.9(9) . . ?

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
S1 N1 C1 C2 90.4(3) . . . . ?
S1 N1 C1 C2A 110.4(4) . . . . ?
S1 N1 C1 C31 -134.6(2) . . . . ?
S1 N1 C5 C4 -112.3(3) . . . . ?
S1 N1 C5 C6 67.8(4) . . . . ?
S1 C24 C25 C26 179.7(2) . . . . ?
Si1 O4 C3 C2 -148.5(8) . . . . ?
Si1 O4 C3 C4 32.9(14) . . . . ?
Si1A O4A C3A C2A -179.7(8) . . . . ?
Si1A O4A C3A C4 5.4(18) . . . . ?
O1 S1 N1 C1 172.8(2) . . . . ?
O1 S1 N1 C5 -51.3(2) . . . . ?
O1 S1 C24 C23 -150.3(2) . . . . ?
O1 S1 C24 C25 31.0(3) . . . . ?
O2 S1 N1 C1 44.7(2) . . . . ?
O2 S1 N1 C5 -179.35(19) . . . . ?
O2 S1 C24 C23 -17.7(3) . . . . ?
O2 S1 C24 C25 163.5(2) . . . . ?
O3 C4 C5 N1 179.9(3) . . . . ?
O3 C4 C5 C6 -0.2(4) . . . . ?
O3 C7 C8 C9 -178.8(3) . . . . ?
O4 Si1 C41 C42 -51.7(6) . . . . ?
O4 Si1 C41 C43 72.7(5) . . . . ?
O4 Si1 C44 C45 -68.8(6) . . . . ?
O4 Si1 C44 C46 162.8(6) . . . . ?
O4 Si1 C47 C48 174.8(6) . . . . ?
O4 Si1 C47 C49 45.6(9) . . . . ?
O4 C3 C4 O3 -10.0(10) . . . . ?
O4 C3 C4 C5 159.2(6) . . . . ?
O4A Si1A C41A C42A -66.3(6) . . . . ?
O4A Si1A C41A C43A 165.7(5) . . . . ?
O4A Si1A C44A C45A -61.6(8) . . . . ?
O4A Si1A C44A C46A 166.8(7) . . . . ?
O4A Si1A C47A C48A 155.5(12) . . . . ?
O4A Si1A C47A C49A 31.4(12) . . . . ?
O4A C3A C4 O3 -20.4(12) . . . . ?
O4A C3A C4 C5 172.4(7) . . . . ?
N1 S1 C24 C23 96.2(3) . . . . ?
N1 S1 C24 C25 -82.6(3) . . . . ?
N1 C1 C2 C3 38.0(6) . . . . ?
N1 C1 C2 C37 -147.3(4) . . . . ?
N1 C1 C2A C3A 13.7(11) . . . . ?
N1 C1 C2A C37A -166.9(5) . . . . ?
N1 C1 C31 C32 80.9(3) . . . . ?
N1 C1 C31 C36 -96.7(3) . . . . ?
N1 C5 C6 C7 -179.1(3) . . . . ?
N1 C5 C6 C11 0.9(6) . . . . ?
C1 N1 C5 C4 25.2(4) . . . . ?
C1 N1 C5 C6 -154.7(3) . . . . ?
C1 C2 C3 O4 175.0(6) . . . . ?
C1 C2 C3 C4 -6.3(9) . . . . ?
C1 C2 C37 C38 -54.6(6) . . . . ?
C1 C2A C3A O4A -173.8(8) . . . . ?
C1 C2A C3A C4 1.2(14) . . . . ?
C1 C2A C37A C38A 70.4(9) . . . . ?
C1 C31 C32 C33 -177.1(3) . . . . ?
C1 C31 C36 C35 176.7(3) . . . . ?
C2 C1 C31 C32 -150.4(3) . . . . ?
C2 C1 C31 C36 32.1(5) . . . . ?
C2 C3 C4 O3 171.4(5) . . . . ?
C2 C3 C4 C5 -19.4(9) . . . . ?
C2 C37 C38 C39 -165.5(4) . . . . ?
C2A C1 C31 C32 -153.9(4) . . . . ?
C2A C1 C31 C36 28.6(4) . . . . ?
C2A C3A C4 O3 164.5(8) . . . . ?
C2A C3A C4 C5 -2.8(13) . . . . ?
C2A C37A C38A C39A 171.2(7) . . . . ?
C3 C2 C37 C38 119.9(7) . . . . ?
C3 C4 C5 N1 9.6(6) . . . . ?
C3 C4 C5 C6 -170.5(5) . . . . ?
C3A C2A C37A C38A -110.2(11) . . . . ?
C3A C4 C5 N1 -11.7(7) . . . . ?
C3A C4 C5 C6 168.1(6) . . . . ?
C4 O3 C7 C6 1.3(3) . . . . ?
C4 O3 C7 C8 -179.1(3) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C4 C5 C6 C11 -179.0(3) . . . . ?
C5 N1 C1 C2 -46.1(4) . . . . ?
C5 N1 C1 C2A -26.1(5) . . . . ?
C5 N1 C1 C31 88.9(3) . . . . ?
C5 C6 C7 O3 -1.5(3) . . . . ?
C5 C6 C7 C8 179.0(3) . . . . ?
C5 C6 C11 C10 -179.7(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 O3 C4 C3 169.7(5) . . . . ?
C7 O3 C4 C3A -169.4(6) . . . . ?
C7 O3 C4 C5 -0.7(3) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C9 C10 C11 C6 0.7(4) . . . . ?
C11 C6 C7 O3 178.5(2) . . . . ?
C11 C6 C7 C8 -1.0(4) . . . . ?
C20 C21 C22 C23 -177.7(3) . . . . ?
C20 C21 C26 C25 177.9(3) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C22 C21 C26 C25 -0.8(4) . . . . ?
C22 C23 C24 S1 -179.5(2) . . . . ?
C22 C23 C24 C25 -0.8(5) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C24 S1 N1 C1 -71.4(2) . . . . ?
C24 S1 N1 C5 64.5(2) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
C26 C21 C22 C23 1.0(5) . . . . ?
C31 C1 C2 C3 -89.7(6) . . . . ?
C31 C1 C2 C37 85.0(5) . . . . ?
C31 C1 C2A C3A -104.3(9) . . . . ?
C31 C1 C2A C37A 75.1(7) . . . . ?
C31 C32 C33 C34 0.1(5) . . . . ?
C32 C31 C36 C35 -0.8(4) . . . . ?
C32 C33 C34 C35 -0.5(5) . . . . ?
C33 C34 C35 C36 0.2(5) . . . . ?
C34 C35 C36 C31 0.5(5) . . . . ?
C36 C31 C32 C33 0.5(4) . . . . ?
C37 C2 C3 O4 0.5(11) . . . . ?
C37 C2 C3 C4 179.2(5) . . . . ?
C37 C38 C39 C40 -64.7(6) . . . . ?
C37A C2A C3A O4A 6.9(17) . . . . ?
C37A C2A C3A C4 -178.2(8) . . . . ?
C37A C38A C39A C40A 179.5(8) . . . . ?
C41 Si1 O4 C3 -107.8(10) . . . . ?
C41 Si1 C44 C45 176.4(5) . . . . ?
C41 Si1 C44 C46 48.1(6) . . . . ?
C41 Si1 C47 C48 -61.2(8) . . . . ?
C41 Si1 C47 C49 169.6(7) . . . . ?
C41A Si1A O4A C3A -60.1(12) . . . . ?
C41A Si1A C44A C45A -175.2(6) . . . . ?
C41A Si1A C44A C46A 53.2(8) . . . . ?
C41A Si1A C47A C48A -82.9(14) . . . . ?
C41A Si1A C47A C49A 153.0(10) . . . . ?
C44 Si1 O4 C3 139.7(9) . . . . ?
C44 Si1 C41 C42 57.2(6) . . . . ?
C44 Si1 C41 C43 -178.4(5) . . . . ?
C44 Si1 C47 C48 59.5(8) . . . . ?
C44 Si1 C47 C49 -69.7(9) . . . . ?
C44A Si1A O4A C3A -175.6(12) . . . . ?
C44A Si1A C41A C42A 40.3(7) . . . . ?
C44A Si1A C41A C43A -87.7(6) . . . . ?
C44A Si1A C47A C48A 45.7(14) . . . . ?
C44A Si1A C47A C49A -78.4(12) . . . . ?
C47 Si1 O4 C3 16.8(11) . . . . ?
C47 Si1 C41 C42 -177.7(6) . . . . ?
C47 Si1 C41 C43 -53.3(7) . . . . ?
C47 Si1 C44 C45 53.4(7) . . . . ?
C47 Si1 C44 C46 -74.9(7) . . . . ?
C47A Si1A O4A C3A 63.5(13) . . . . ?
C47A Si1A C41A C42A 171.1(7) . . . . ?
C47A Si1A C41A C43A 43.1(7) . . . . ?
C47A Si1A C44A C45A 55.6(9) . . . . ?
C47A Si1A C44A C46A -76.0(9) . . . . ?

_olex2_date_sample_data_collection 2018-07-26
_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 1.817
_oxdiff_exptl_absorpt_empirical_full_min 0.798
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qf20cult
_database_code_depnum_ccdc_archive 'CCDC 2079165'
loop_
_audit_author_name
_audit_author_address
'Herman Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2021-04-21 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
_audit_creation_date             2021-02-18
_audit_creation_method           
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'Trans-3-Butyl-3-chloro-2-(4-chlorophenyl)-1-tosyl-2,3-dihydrobenzofuro [3,2-b]pyridin-4(1H)-one'
_chemical_formula_moiety         'C28 H25 Cl2 N O4 S'
_chemical_formula_sum            'C28 H25 Cl2 N O4 S'
_chemical_formula_weight         542.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H18 O4 Cl N2'
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'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7086(4)
_cell_length_b                   10.8936(5)
_cell_length_c                   11.8325(6)
_cell_angle_alpha                78.430(4)
_cell_angle_beta                 66.115(4)
_cell_angle_gamma                79.274(3)
_cell_volume                     1227.97(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5581
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      76.4320
_cell_measurement_theta_min      4.1270
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.543
_exptl_absorpt_coefficient_mu    3.481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8055
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.618
_diffrn_reflns_theta_min         4.126
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     86.00 177.00   1.00    3.00    --  113.00  30.00 -60.00   91
  2  ω   -114.00 -14.00   1.00    1.00    --  -39.95 -37.00 -90.00  100
  3  ω    -87.00  -6.00   1.00    1.00    --  -39.95 125.00   0.00   81
  4  ω   -114.00 -27.00   1.00    1.00    --  -39.95 -37.00-180.00   87
  5  ω      6.00  47.00   1.00    1.00    --   39.95 -99.00 150.00   41
  6  ω     52.00  94.00   1.00    1.00    --   39.95-125.00 -90.00   42
  7  ω     40.00 109.00   1.00    3.00    --  113.00-111.00-180.00   69
  8  ω     75.00 138.00   1.00    3.00    --  113.00 -77.00-150.00   63
  9  ω     37.00 144.00   1.00    3.00    --  113.00 -30.00 -90.00  107
 10  ω     53.00 107.00   1.00    3.00    --  113.00-111.00  30.00   54
 11  ω     40.00 141.00   1.00    3.00    --  113.00 -61.00 150.00  101
 12  ω     35.00  61.00   1.00    3.00    --  113.00-111.00 120.00   26
 13  ω     82.00 108.00   1.00    3.00    --  113.00-111.00 120.00   26
 14  ω     59.00 178.00   1.00    3.00    --  113.00  15.00-120.00  119
 15  ω     42.00  68.00   1.00    3.00    --  113.00 -77.00-150.00   26
 16  ω     50.00 136.00   1.00    3.00    --  113.00 -61.00   0.00   86
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0078304000
_diffrn_orient_matrix_UB_12      -0.0589662000
_diffrn_orient_matrix_UB_13      -0.1045648000
_diffrn_orient_matrix_UB_21      -0.0130660000
_diffrn_orient_matrix_UB_22      0.1325454000
_diffrn_orient_matrix_UB_23      -0.0730278000
_diffrn_orient_matrix_UB_31      0.1576915000
_diffrn_orient_matrix_UB_32      -0.0090468000
_diffrn_orient_matrix_UB_33      -0.0664094000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4578
_reflns_number_total             4967
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-beta (Bourhis et al., 2015)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.043
_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)+(0.0362P)²+0.4481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0747
_refine_special_details          ?
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.44907(3) 0.49413(3) 0.36495(3) 0.01526(8) Uani 1 1 d . . . . .
Cl2 Cl -0.19514(3) 0.35705(3) 0.16459(3) 0.02197(9) Uani 1 1 d . . . . .
S1 S 0.51765(3) 0.25852(3) 0.11013(3) 0.01165(8) Uani 1 1 d . . . . .
O1 O 0.57337(10) 0.37483(9) 0.04755(9) 0.01544(19) Uani 1 1 d . . . . .
O2 O 0.60668(10) 0.14937(9) 0.13149(9) 0.0158(2) Uani 1 1 d . . . . .
O3 O 0.25138(9) 0.14710(9) 0.56859(9) 0.01384(19) Uani 1 1 d . . . . .
O4 O 0.15688(11) 0.40339(10) 0.59246(10) 0.0205(2) Uani 1 1 d . . . . .
N1 N 0.40269(11) 0.28725(10) 0.25000(10) 0.0114(2) Uani 1 1 d . . . . .
C1 C 0.31708(13) 0.03932(12) 0.51797(13) 0.0132(2) Uani 1 1 d . . . . .
C2 C 0.30880(14) -0.07975(13) 0.58761(13) 0.0156(3) Uani 1 1 d . . . . .
H2 H 0.2566 -0.0917 0.6749 0.019 Uiso 1 1 calc R U . . .
C3 C 0.38048(14) -0.18028(13) 0.52344(14) 0.0169(3) Uani 1 1 d . . . . .
H3 H 0.3766 -0.2638 0.5669 0.020 Uiso 1 1 calc R U . . .
C4 C 0.45912(14) -0.16015(13) 0.39432(14) 0.0161(3) Uani 1 1 d . . . . .
H4 H 0.5085 -0.2307 0.3527 0.019 Uiso 1 1 calc R U . . .
C5 C 0.46663(13) -0.04078(13) 0.32621(13) 0.0145(3) Uani 1 1 d . . . . .
H5 H 0.5204 -0.0293 0.2392 0.017 Uiso 1 1 calc R U . . .
C6 C 0.39277(13) 0.06367(12) 0.38856(12) 0.0124(2) Uani 1 1 d . . . . .
C7 C 0.36847(13) 0.20003(12) 0.35952(12) 0.0115(2) Uani 1 1 d . . . . .
C8 C 0.28545(13) 0.24311(12) 0.47035(12) 0.0129(2) Uani 1 1 d . . . . .
C9 C 0.23183(13) 0.37139(12) 0.49141(13) 0.0134(2) Uani 1 1 d . . . . .
C10 C 0.28283(13) 0.46678(12) 0.37196(12) 0.0117(2) Uani 1 1 d . . . . .
C11 C 0.31035(13) 0.40798(12) 0.25359(12) 0.0111(2) Uani 1 1 d . . . . .
H11 H 0.3613 0.4678 0.1801 0.013 Uiso 1 1 calc R U . . .
C12 C 0.17847(13) 0.39338(12) 0.23829(12) 0.0122(2) Uani 1 1 d . . . . .
C13 C 0.12695(14) 0.49027(12) 0.16678(13) 0.0149(3) Uani 1 1 d . . . . .
H13 H 0.1724 0.5640 0.1315 0.018 Uiso 1 1 calc R U . . .
C14 C 0.01037(14) 0.48129(13) 0.14602(13) 0.0159(3) Uani 1 1 d . . . . .
H14 H -0.0250 0.5489 0.0987 0.019 Uiso 1 1 calc R U . . .
C15 C -0.05327(13) 0.37248(13) 0.19521(13) 0.0156(3) Uani 1 1 d . . . . .
C16 C -0.00369(15) 0.27392(14) 0.26550(15) 0.0209(3) Uani 1 1 d . . . . .
H16 H -0.0481 0.1995 0.2987 0.025 Uiso 1 1 calc R U . . .
C17 C 0.11180(15) 0.28484(14) 0.28710(14) 0.0191(3) Uani 1 1 d . . . . .
H17 H 0.1458 0.2175 0.3357 0.023 Uiso 1 1 calc R U . . .
C18 C 0.18760(13) 0.59061(12) 0.38314(13) 0.0138(2) Uani 1 1 d . . . . .
H18A H 0.1696 0.6176 0.4639 0.017 Uiso 1 1 calc R U . . .
H18B H 0.0986 0.5748 0.3850 0.017 Uiso 1 1 calc R U . . .
C19 C 0.24141(14) 0.69953(12) 0.27870(13) 0.0155(3) Uani 1 1 d . . . . .
H19A H 0.3165 0.7308 0.2894 0.019 Uiso 1 1 calc R U . . .
H19B H 0.2800 0.6678 0.1971 0.019 Uiso 1 1 calc R U . . .
C20 C 0.12860(16) 0.80886(13) 0.27839(14) 0.0208(3) Uani 1 1 d . . . . .
H20A H 0.1618 0.8659 0.1985 0.025 Uiso 1 1 calc R U . . .
H20B H 0.0471 0.7746 0.2827 0.025 Uiso 1 1 calc R U . . .
C21 C 0.08514(16) 0.88511(15) 0.38579(16) 0.0260(3) Uani 1 1 d . . . . .
H21A H 0.0156 0.9552 0.3781 0.039 Uiso 1 1 calc R U . . .
H21B H 0.1654 0.9185 0.3830 0.039 Uiso 1 1 calc R U . . .
H21C H 0.0465 0.8306 0.4653 0.039 Uiso 1 1 calc R U . . .
C22 C 0.42014(13) 0.22614(13) 0.03292(12) 0.0135(2) Uani 1 1 d . . . . .
C23 C 0.38815(14) 0.32002(13) -0.05298(13) 0.0161(3) Uani 1 1 d . . . . .
H23 H 0.4251 0.3982 -0.0752 0.019 Uiso 1 1 calc R U . . .
C24 C 0.30119(15) 0.29794(14) -0.10604(13) 0.0180(3) Uani 1 1 d . . . . .
H24 H 0.2807 0.3610 -0.1663 0.022 Uiso 1 1 calc R U . . .
C25 C 0.24364(14) 0.18497(14) -0.07227(13) 0.0177(3) Uani 1 1 d . . . . .
C26 C 0.27943(15) 0.09151(14) 0.01298(14) 0.0190(3) Uani 1 1 d . . . . .
H26 H 0.2429 0.0131 0.0350 0.023 Uiso 1 1 calc R U . . .
C27 C 0.36676(15) 0.11078(13) 0.06582(13) 0.0172(3) Uani 1 1 d . . . . .
H27 H 0.3901 0.0465 0.1237 0.021 Uiso 1 1 calc R U . . .
C28 C 0.14412(17) 0.16348(16) -0.12513(16) 0.0262(3) Uani 1 1 d . . . . .
H28A H 0.0499 0.1775 -0.0641 0.039 Uiso 1 1 calc R U . . .
H28B H 0.1632 0.0766 -0.1438 0.039 Uiso 1 1 calc R U . . .
H28C H 0.1546 0.2224 -0.2019 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cl1 C10 1.8256(13) . ?
Cl2 C15 1.7416(13) . ?
S1 O1 1.4342(10) . ?
S1 O2 1.4280(10) . ?
S1 N1 1.6634(11) . ?
S1 C22 1.7574(13) . ?
O3 C1 1.3659(16) . ?
O3 C8 1.3745(16) . ?
O4 C9 1.2170(17) . ?
N1 C7 1.4027(17) . ?
N1 C11 1.4879(16) . ?
C1 C2 1.3872(19) . ?
C1 C6 1.4086(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.409(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3831(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.4119(18) . ?
C6 C7 1.4547(17) . ?
C7 C8 1.3704(18) . ?
C8 C9 1.4386(18) . ?
C9 C10 1.5404(18) . ?
C10 C11 1.5538(17) . ?
C10 C18 1.5256(17) . ?
C11 H11 1.0000 . ?
C11 C12 1.5345(17) . ?
C12 C13 1.3918(18) . ?
C12 C17 1.3956(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3899(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3824(19) . ?
C15 C16 1.383(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3899(19) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5352(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5311(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.524(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.3896(19) . ?
C22 C27 1.3959(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(2) . ?
C25 C26 1.399(2) . ?
C25 C28 1.508(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(2) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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 106.46(6) . . ?
O1 S1 C22 107.70(6) . . ?
O2 S1 O1 119.75(6) . . ?
O2 S1 N1 106.27(6) . . ?
O2 S1 C22 110.96(6) . . ?
N1 S1 C22 104.57(6) . . ?
C1 O3 C8 105.11(10) . . ?
C7 N1 S1 125.94(9) . . ?
C7 N1 C11 116.72(10) . . ?
C11 N1 S1 116.28(9) . . ?
O3 C1 C2 123.10(12) . . ?
O3 C1 C6 112.28(11) . . ?
C2 C1 C6 124.62(13) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 116.61(13) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.68(12) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.02(13) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.69(13) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 117.36(12) . . ?
C1 C6 C7 103.97(11) . . ?
C5 C6 C7 138.67(13) . . ?
N1 C7 C6 135.30(12) . . ?
C8 C7 N1 118.44(12) . . ?
C8 C7 C6 106.12(11) . . ?
O3 C8 C9 119.68(12) . . ?
C7 C8 O3 112.51(11) . . ?
C7 C8 C9 127.79(12) . . ?
O4 C9 C8 124.57(13) . . ?
O4 C9 C10 122.66(12) . . ?
C8 C9 C10 112.75(11) . . ?
C9 C10 Cl1 103.05(8) . . ?
C9 C10 C11 111.52(10) . . ?
C11 C10 Cl1 107.20(8) . . ?
C18 C10 Cl1 109.27(9) . . ?
C18 C10 C9 111.35(11) . . ?
C18 C10 C11 113.79(11) . . ?
N1 C11 C10 110.58(10) . . ?
N1 C11 H11 106.7 . . ?
N1 C11 C12 112.19(10) . . ?
C10 C11 H11 106.7 . . ?
C12 C11 C10 113.38(10) . . ?
C12 C11 H11 106.7 . . ?
C13 C12 C11 118.42(11) . . ?
C13 C12 C17 118.37(12) . . ?
C17 C12 C11 123.12(12) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.31(12) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.02(13) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 Cl2 119.59(11) . . ?
C14 C15 C16 121.06(13) . . ?
C16 C15 Cl2 119.33(11) . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.34(13) . . ?
C17 C16 H16 120.3 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.88(13) . . ?
C16 C17 H17 119.6 . . ?
C10 C18 H18A 108.4 . . ?
C10 C18 H18B 108.4 . . ?
C10 C18 C19 115.47(11) . . ?
H18A C18 H18B 107.5 . . ?
C19 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 C18 112.25(11) . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.73(12) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 S1 119.17(10) . . ?
C23 C22 C27 120.91(13) . . ?
C27 C22 S1 119.71(11) . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.08(13) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.12(13) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 118.46(13) . . ?
C24 C25 C28 121.12(14) . . ?
C26 C25 C28 120.42(13) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 C25 121.40(13) . . ?
C27 C26 H26 119.3 . . ?
C22 C27 H27 120.5 . . ?
C26 C27 C22 118.99(13) . . ?
C26 C27 H27 120.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
Cl1 C10 C11 N1 59.61(11) . . . . ?
Cl1 C10 C11 C12 -173.39(9) . . . . ?
Cl1 C10 C18 C19 56.99(13) . . . . ?
Cl2 C15 C16 C17 178.26(12) . . . . ?
S1 N1 C7 C6 -13.7(2) . . . . ?
S1 N1 C7 C8 171.23(10) . . . . ?
S1 N1 C11 C10 -142.44(9) . . . . ?
S1 N1 C11 C12 89.90(11) . . . . ?
S1 C22 C23 C24 -174.54(10) . . . . ?
S1 C22 C27 C26 173.80(11) . . . . ?
O1 S1 N1 C7 -149.51(10) . . . . ?
O1 S1 N1 C11 42.73(10) . . . . ?
O1 S1 C22 C23 -12.40(13) . . . . ?
O1 S1 C22 C27 172.76(11) . . . . ?
O2 S1 N1 C7 -20.81(12) . . . . ?
O2 S1 N1 C11 171.43(9) . . . . ?
O2 S1 C22 C23 -145.24(11) . . . . ?
O2 S1 C22 C27 39.91(13) . . . . ?
O3 C1 C2 C3 179.75(12) . . . . ?
O3 C1 C6 C5 179.21(11) . . . . ?
O3 C1 C6 C7 -0.43(14) . . . . ?
O3 C8 C9 O4 0.5(2) . . . . ?
O3 C8 C9 C10 178.76(11) . . . . ?
O4 C9 C10 Cl1 94.02(13) . . . . ?
O4 C9 C10 C11 -151.29(13) . . . . ?
O4 C9 C10 C18 -23.00(18) . . . . ?
N1 S1 C22 C23 100.58(11) . . . . ?
N1 S1 C22 C27 -74.27(12) . . . . ?
N1 C7 C8 O3 175.32(10) . . . . ?
N1 C7 C8 C9 -3.4(2) . . . . ?
N1 C11 C12 C13 -141.04(12) . . . . ?
N1 C11 C12 C17 35.46(18) . . . . ?
C1 O3 C8 C7 0.84(14) . . . . ?
C1 O3 C8 C9 179.64(11) . . . . ?
C1 C2 C3 C4 1.07(19) . . . . ?
C1 C6 C7 N1 -174.63(14) . . . . ?
C1 C6 C7 C8 0.89(14) . . . . ?
C2 C1 C6 C5 -0.87(19) . . . . ?
C2 C1 C6 C7 179.49(12) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 0.98(18) . . . . ?
C4 C5 C6 C7 -179.56(14) . . . . ?
C5 C6 C7 N1 5.9(3) . . . . ?
C5 C6 C7 C8 -178.62(15) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C6 C7 C8 O3 -1.10(15) . . . . ?
C6 C7 C8 C9 -179.79(12) . . . . ?
C7 N1 C11 C10 48.64(14) . . . . ?
C7 N1 C11 C12 -79.02(14) . . . . ?
C7 C8 C9 O4 179.07(14) . . . . ?
C7 C8 C9 C10 -2.64(19) . . . . ?
C8 O3 C1 C2 179.87(12) . . . . ?
C8 O3 C1 C6 -0.21(14) . . . . ?
C8 C9 C10 Cl1 -84.30(11) . . . . ?
C8 C9 C10 C11 30.38(15) . . . . ?
C8 C9 C10 C18 158.67(11) . . . . ?
C9 C10 C11 N1 -52.48(13) . . . . ?
C9 C10 C11 C12 74.52(13) . . . . ?
C9 C10 C18 C19 170.17(11) . . . . ?
C10 C11 C12 C13 92.81(14) . . . . ?
C10 C11 C12 C17 -90.69(15) . . . . ?
C10 C18 C19 C20 166.25(11) . . . . ?
C11 N1 C7 C6 154.05(14) . . . . ?
C11 N1 C7 C8 -21.06(17) . . . . ?
C11 C10 C18 C19 -62.77(15) . . . . ?
C11 C12 C13 C14 177.99(12) . . . . ?
C11 C12 C17 C16 -176.86(13) . . . . ?
C12 C13 C14 C15 -1.5(2) . . . . ?
C13 C12 C17 C16 -0.4(2) . . . . ?
C13 C14 C15 Cl2 -177.32(11) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C12 -0.4(2) . . . . ?
C17 C12 C13 C14 1.3(2) . . . . ?
C18 C10 C11 N1 -179.46(10) . . . . ?
C18 C10 C11 C12 -52.46(14) . . . . ?
C18 C19 C20 C21 72.46(16) . . . . ?
C22 S1 N1 C7 96.64(11) . . . . ?
C22 S1 N1 C11 -71.12(10) . . . . ?
C22 C23 C24 C25 1.5(2) . . . . ?
C23 C22 C27 C26 -1.0(2) . . . . ?
C23 C24 C25 C26 -2.5(2) . . . . ?
C23 C24 C25 C28 177.04(13) . . . . ?
C24 C25 C26 C27 1.8(2) . . . . ?
C25 C26 C27 C22 -0.1(2) . . . . ?
C27 C22 C23 C24 0.2(2) . . . . ?
C28 C25 C26 C27 -177.77(14) . . . . ?

_olex2_date_sample_data_collection 2021-02-10
_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 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.809
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qf19cult
_database_code_depnum_ccdc_archive 'CCDC 2079164'
loop_
_audit_author_name
_audit_author_address
'Herman Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2021-04-21 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
_audit_creation_date             2021-02-18
_audit_creation_method           
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'Trans-3-Bromo-3-butyl-2-(4-chlorophenyl)-1-tosyl-2,3-dihydrobenzofuro [3,2-b]pyridin-4(1H)-one'
_chemical_formula_moiety         'C28 H25 Br Cl N O4 S'
_chemical_formula_sum            'C28 H25 Br Cl N O4 S'
_chemical_formula_weight         586.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cl C20 H18 O4 N'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7962(5)
_cell_length_b                   10.9702(4)
_cell_length_c                   11.8384(5)
_cell_angle_alpha                78.442(4)
_cell_angle_beta                 65.815(4)
_cell_angle_gamma                79.502(4)
_cell_volume                     1245.21(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6217
_cell_measurement_temperature    99.97(16)
_cell_measurement_theta_max      76.4630
_cell_measurement_theta_min      4.1500
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.478
_exptl_absorpt_coefficient_mu    4.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.955
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7889
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.815
_diffrn_reflns_theta_min         4.134
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -129.00  49.00   1.00    1.00    --  -39.95   0.00 -60.00  178
  2  ω     28.00  55.00   1.00    1.00    --   39.95-125.00  60.00   27
  3  ω     30.00  76.00   1.00    1.00    --   39.95-125.00 -30.00   46
  4  ω     32.00  59.00   1.00    1.00    --   39.95-125.00-120.00   27
  5  ω     27.00  85.00   1.00    1.00    --   39.95-125.00 150.00   58
  6  ω     71.00 109.00   1.00    2.00    --  113.00-111.00 120.00   38
  7  ω     40.00 140.00   1.00    2.00    --  113.00 -61.00-150.00  100
  8  ω     87.00 175.00   1.00    2.00    --  113.00  30.00 -60.00   88
  9  ω    142.00 168.00   1.00    2.00    --  113.00  30.00 150.00   26
 10  ω     84.00 120.00   1.00    2.00    --  113.00  30.00 150.00   36
 11  ω     36.00  82.00   1.00    2.00    --  113.00-111.00  90.00   46
 12  ω     40.00  66.00   1.00    2.00    --  113.00-111.00 120.00   26
 13  ω     90.00 178.00   1.00    2.00    --  113.00  45.00-180.00   88
 14  ω     65.00 109.00   1.00    2.00    --  113.00-111.00-120.00   44
 15  ω     35.00 107.00   1.00    2.00    --  113.00-111.00  30.00   72
 16  ω     98.00 175.00   1.00    2.00    --  113.00  45.00-120.00   77
 17  ω     40.00 143.00   1.00    2.00    --  113.00 -61.00  90.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0997724000
_diffrn_orient_matrix_UB_12      0.0515198000
_diffrn_orient_matrix_UB_13      -0.0657079000
_diffrn_orient_matrix_UB_21      -0.0778680000
_diffrn_orient_matrix_UB_22      -0.1159095000
_diffrn_orient_matrix_UB_23      0.0623230000
_diffrn_orient_matrix_UB_31      -0.0936027000
_diffrn_orient_matrix_UB_32      0.0686855000
_diffrn_orient_matrix_UB_33      0.1120534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4803
_reflns_number_total             5020
_reflns_odcompleteness_completeness 98.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.5439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0588
_refine_special_details          ?
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.45577(2) 0.49571(2) 0.36790(2) 0.01374(5) Uani 1 1 d . . . . .
Cl1 Cl -0.19170(4) 0.35393(4) 0.16316(4) 0.02168(9) Uani 1 1 d . . . . .
S1 S 0.51595(3) 0.26046(3) 0.10923(3) 0.01082(7) Uani 1 1 d . . . . .
O1 O 0.57114(11) 0.37617(10) 0.04689(9) 0.0147(2) Uani 1 1 d . . . . .
O2 O 0.60448(11) 0.15273(10) 0.13063(10) 0.0151(2) Uani 1 1 d . . . . .
O3 O 0.24871(11) 0.14917(9) 0.56833(9) 0.0132(2) Uani 1 1 d . . . . .
O4 O 0.15140(12) 0.40294(10) 0.59244(10) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.40021(12) 0.28876(11) 0.24923(11) 0.0105(2) Uani 1 1 d . . . . .
C1 C 0.31508(15) 0.04258(14) 0.51762(14) 0.0127(3) Uani 1 1 d . . . . .
C2 C 0.30730(15) -0.07564(14) 0.58716(14) 0.0155(3) Uani 1 1 d . . . . .
H2 H 0.2551 -0.0878 0.6747 0.019 Uiso 1 1 calc R U . . .
C3 C 0.37933(16) -0.17513(14) 0.52276(15) 0.0169(3) Uani 1 1 d . . . . .
H3 H 0.3756 -0.2580 0.5663 0.020 Uiso 1 1 calc R U . . .
C4 C 0.45793(16) -0.15484(14) 0.39360(15) 0.0162(3) Uani 1 1 d . . . . .
H4 H 0.5075 -0.2247 0.3519 0.019 Uiso 1 1 calc R U . . .
C5 C 0.46522(15) -0.03668(14) 0.32558(14) 0.0139(3) Uani 1 1 d . . . . .
H5 H 0.5192 -0.0252 0.2384 0.017 Uiso 1 1 calc R U . . .
C6 C 0.39112(14) 0.06687(13) 0.38772(13) 0.0117(3) Uani 1 1 d . . . . .
C7 C 0.36578(14) 0.20200(13) 0.35896(13) 0.0109(3) Uani 1 1 d . . . . .
C8 C 0.28174(14) 0.24444(13) 0.46993(13) 0.0118(3) Uani 1 1 d . . . . .
C9 C 0.22701(15) 0.37183(14) 0.49120(13) 0.0125(3) Uani 1 1 d . . . . .
C10 C 0.27775(14) 0.46627(13) 0.37173(13) 0.0108(3) Uani 1 1 d . . . . .
C11 C 0.30773(14) 0.40795(13) 0.25273(13) 0.0102(3) Uani 1 1 d . . . . .
H11 H 0.3583 0.4680 0.1793 0.012 Uiso 1 1 calc R U . . .
C12 C 0.17770(14) 0.39196(13) 0.23732(13) 0.0112(3) Uani 1 1 d . . . . .
C13 C 0.12551(15) 0.48901(14) 0.16723(14) 0.0144(3) Uani 1 1 d . . . . .
H13 H 0.1695 0.5632 0.1333 0.017 Uiso 1 1 calc R U . . .
C14 C 0.01053(15) 0.47907(14) 0.14630(14) 0.0153(3) Uani 1 1 d . . . . .
H14 H -0.0251 0.5464 0.0999 0.018 Uiso 1 1 calc R U . . .
C15 C -0.05145(15) 0.37020(15) 0.19370(14) 0.0152(3) Uani 1 1 d . . . . .
C16 C -0.00117(17) 0.27159(15) 0.26243(15) 0.0197(3) Uani 1 1 d . . . . .
H16 H -0.0443 0.1968 0.2944 0.024 Uiso 1 1 calc R U . . .
C17 C 0.11279(16) 0.28336(15) 0.28393(15) 0.0179(3) Uani 1 1 d . . . . .
H17 H 0.1472 0.2161 0.3313 0.021 Uiso 1 1 calc R U . . .
C18 C 0.18382(15) 0.58953(13) 0.38277(13) 0.0126(3) Uani 1 1 d . . . . .
H18A H 0.1645 0.6157 0.4642 0.015 Uiso 1 1 calc R U . . .
H18B H 0.0960 0.5743 0.3833 0.015 Uiso 1 1 calc R U . . .
C19 C 0.23964(15) 0.69798(13) 0.27902(14) 0.0149(3) Uani 1 1 d . . . . .
H19A H 0.3139 0.7282 0.2909 0.018 Uiso 1 1 calc R U . . .
H19B H 0.2790 0.6670 0.1970 0.018 Uiso 1 1 calc R U . . .
C20 C 0.12894(17) 0.80731(15) 0.27815(16) 0.0204(3) Uani 1 1 d . . . . .
H20A H 0.1636 0.8642 0.1984 0.024 Uiso 1 1 calc R U . . .
H20B H 0.0481 0.7741 0.2814 0.024 Uiso 1 1 calc R U . . .
C21 C 0.08474(18) 0.88240(17) 0.38638(18) 0.0263(4) Uani 1 1 d . . . . .
H21A H 0.0147 0.9509 0.3797 0.039 Uiso 1 1 calc R U . . .
H21B H 0.1638 0.9170 0.3831 0.039 Uiso 1 1 calc R U . . .
H21C H 0.0473 0.8275 0.4658 0.039 Uiso 1 1 calc R U . . .
C22 C 0.41998(15) 0.22694(14) 0.03205(13) 0.0126(3) Uani 1 1 d . . . . .
C23 C 0.38567(16) 0.32091(14) -0.05151(14) 0.0158(3) Uani 1 1 d . . . . .
H23 H 0.4208 0.3994 -0.0727 0.019 Uiso 1 1 calc R U . . .
C24 C 0.29914(16) 0.29836(15) -0.10368(14) 0.0181(3) Uani 1 1 d . . . . .
H24 H 0.2767 0.3616 -0.1621 0.022 Uiso 1 1 calc R U . . .
C25 C 0.24485(16) 0.18486(15) -0.07185(14) 0.0172(3) Uani 1 1 d . . . . .
C26 C 0.28257(17) 0.09137(15) 0.01121(14) 0.0183(3) Uani 1 1 d . . . . .
H26 H 0.2479 0.0127 0.0322 0.022 Uiso 1 1 calc R U . . .
C27 C 0.36953(17) 0.11140(14) 0.06334(14) 0.0168(3) Uani 1 1 d . . . . .
H27 H 0.3944 0.0472 0.1197 0.020 Uiso 1 1 calc R U . . .
C28 C 0.14598(19) 0.16239(18) -0.12359(17) 0.0259(4) Uani 1 1 d . . . . .
H28A H 0.0523 0.1773 -0.0625 0.039 Uiso 1 1 calc R U . . .
H28B H 0.1640 0.0757 -0.1405 0.039 Uiso 1 1 calc R U . . .
H28C H 0.1573 0.2196 -0.2014 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Br1 C10 1.9872(14) . ?
Cl1 C15 1.7401(15) . ?
S1 O1 1.4321(11) . ?
S1 O2 1.4287(11) . ?
S1 N1 1.6651(12) . ?
S1 C22 1.7587(15) . ?
O3 C1 1.3655(18) . ?
O3 C8 1.3726(17) . ?
O4 C9 1.2165(19) . ?
N1 C7 1.4033(18) . ?
N1 C11 1.4901(17) . ?
C1 C2 1.386(2) . ?
C1 C6 1.411(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.412(2) . ?
C6 C7 1.4542(19) . ?
C7 C8 1.371(2) . ?
C8 C9 1.444(2) . ?
C9 C10 1.5358(19) . ?
C10 C11 1.5527(18) . ?
C10 C18 1.5285(19) . ?
C11 H11 1.0000 . ?
C11 C12 1.5320(19) . ?
C12 C13 1.396(2) . ?
C12 C17 1.392(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(2) . ?
C15 C16 1.386(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5351(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.533(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.525(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.390(2) . ?
C22 C27 1.392(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(2) . ?
C25 C26 1.399(2) . ?
C25 C28 1.506(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(2) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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 106.34(6) . . ?
O1 S1 C22 107.97(7) . . ?
O2 S1 O1 119.67(6) . . ?
O2 S1 N1 106.50(6) . . ?
O2 S1 C22 110.88(7) . . ?
N1 S1 C22 104.30(6) . . ?
C1 O3 C8 105.13(11) . . ?
C7 N1 S1 125.74(10) . . ?
C7 N1 C11 116.72(11) . . ?
C11 N1 S1 116.47(9) . . ?
O3 C1 C2 123.19(13) . . ?
O3 C1 C6 112.41(12) . . ?
C2 C1 C6 124.40(14) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 C1 116.70(14) . . ?
C3 C2 H2 121.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.70(14) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.01(14) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.87(14) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 117.30(13) . . ?
C1 C6 C7 103.69(12) . . ?
C5 C6 C7 139.02(14) . . ?
N1 C7 C6 135.18(13) . . ?
C8 C7 N1 118.37(13) . . ?
C8 C7 C6 106.32(12) . . ?
O3 C8 C9 119.65(12) . . ?
C7 C8 O3 112.45(12) . . ?
C7 C8 C9 127.90(13) . . ?
O4 C9 C8 124.51(13) . . ?
O4 C9 C10 122.89(13) . . ?
C8 C9 C10 112.58(12) . . ?
C9 C10 Br1 101.76(9) . . ?
C9 C10 C11 111.90(11) . . ?
C11 C10 Br1 107.47(9) . . ?
C18 C10 Br1 108.95(9) . . ?
C18 C10 C9 111.62(11) . . ?
C18 C10 C11 114.26(11) . . ?
N1 C11 C10 110.69(11) . . ?
N1 C11 H11 106.9 . . ?
N1 C11 C12 112.23(11) . . ?
C10 C11 H11 106.9 . . ?
C12 C11 C10 112.94(11) . . ?
C12 C11 H11 106.9 . . ?
C13 C12 C11 118.20(13) . . ?
C17 C12 C11 123.53(13) . . ?
C17 C12 C13 118.19(13) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.19(14) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.22(14) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 Cl1 119.77(12) . . ?
C14 C15 C16 120.97(14) . . ?
C16 C15 Cl1 119.23(12) . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.21(14) . . ?
C17 C16 H16 120.4 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.21(14) . . ?
C16 C17 H17 119.4 . . ?
C10 C18 H18A 108.4 . . ?
C10 C18 H18B 108.4 . . ?
C10 C18 C19 115.40(12) . . ?
H18A C18 H18B 107.5 . . ?
C19 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 C18 112.31(12) . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.77(14) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 S1 118.91(11) . . ?
C23 C22 C27 120.97(14) . . ?
C27 C22 S1 119.86(11) . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.01(14) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.18(14) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 118.56(15) . . ?
C24 C25 C28 121.28(15) . . ?
C26 C25 C28 120.15(15) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.19(15) . . ?
C27 C26 H26 119.4 . . ?
C22 C27 H27 120.5 . . ?
C26 C27 C22 119.05(14) . . ?
C26 C27 H27 120.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
Br1 C10 C11 N1 58.74(12) . . . . ?
Br1 C10 C11 C12 -174.47(9) . . . . ?
Br1 C10 C18 C19 57.33(14) . . . . ?
Cl1 C15 C16 C17 178.31(13) . . . . ?
S1 N1 C7 C6 -13.4(2) . . . . ?
S1 N1 C7 C8 171.39(11) . . . . ?
S1 N1 C11 C10 -142.86(10) . . . . ?
S1 N1 C11 C12 89.96(12) . . . . ?
S1 C22 C23 C24 -174.00(11) . . . . ?
S1 C22 C27 C26 173.36(12) . . . . ?
O1 S1 N1 C7 -149.35(12) . . . . ?
O1 S1 N1 C11 42.93(11) . . . . ?
O1 S1 C22 C23 -14.03(14) . . . . ?
O1 S1 C22 C27 171.64(12) . . . . ?
O2 S1 N1 C7 -20.68(13) . . . . ?
O2 S1 N1 C11 171.61(10) . . . . ?
O2 S1 C22 C23 -146.93(11) . . . . ?
O2 S1 C22 C27 38.73(14) . . . . ?
O3 C1 C2 C3 179.53(13) . . . . ?
O3 C1 C6 C5 179.37(12) . . . . ?
O3 C1 C6 C7 -0.50(16) . . . . ?
O3 C8 C9 O4 -0.1(2) . . . . ?
O3 C8 C9 C10 178.38(12) . . . . ?
O4 C9 C10 Br1 94.07(15) . . . . ?
O4 C9 C10 C11 -151.47(14) . . . . ?
O4 C9 C10 C18 -22.00(19) . . . . ?
N1 S1 C22 C23 98.80(12) . . . . ?
N1 S1 C22 C27 -75.54(13) . . . . ?
N1 C7 C8 O3 175.84(12) . . . . ?
N1 C7 C8 C9 -3.4(2) . . . . ?
N1 C11 C12 C13 -142.22(13) . . . . ?
N1 C11 C12 C17 34.34(18) . . . . ?
C1 O3 C8 C7 0.34(16) . . . . ?
C1 O3 C8 C9 179.68(12) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C1 C6 C7 N1 -174.95(15) . . . . ?
C1 C6 C7 C8 0.67(15) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C1 C6 C7 179.32(14) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 -179.19(16) . . . . ?
C5 C6 C7 N1 5.2(3) . . . . ?
C5 C6 C7 C8 -179.15(17) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C6 C7 C8 O3 -0.65(16) . . . . ?
C6 C7 C8 C9 -179.92(14) . . . . ?
C7 N1 C11 C10 48.29(16) . . . . ?
C7 N1 C11 C12 -78.89(14) . . . . ?
C7 C8 C9 O4 179.15(15) . . . . ?
C7 C8 C9 C10 -2.4(2) . . . . ?
C8 O3 C1 C2 -179.70(13) . . . . ?
C8 O3 C1 C6 0.13(15) . . . . ?
C8 C9 C10 Br1 -84.41(12) . . . . ?
C8 C9 C10 C11 30.05(16) . . . . ?
C8 C9 C10 C18 159.53(12) . . . . ?
C9 C10 C11 N1 -52.16(15) . . . . ?
C9 C10 C11 C12 74.63(14) . . . . ?
C9 C10 C18 C19 168.91(12) . . . . ?
C10 C11 C12 C13 91.81(15) . . . . ?
C10 C11 C12 C17 -91.63(16) . . . . ?
C10 C18 C19 C20 166.47(12) . . . . ?
C11 N1 C7 C6 154.29(15) . . . . ?
C11 N1 C7 C8 -20.93(18) . . . . ?
C11 C10 C18 C19 -62.87(16) . . . . ?
C11 C12 C13 C14 177.98(13) . . . . ?
C11 C12 C17 C16 -177.00(14) . . . . ?
C12 C13 C14 C15 -1.3(2) . . . . ?
C13 C12 C17 C16 -0.4(2) . . . . ?
C13 C14 C15 Cl1 -177.53(11) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C15 C16 C17 C12 -0.3(2) . . . . ?
C17 C12 C13 C14 1.2(2) . . . . ?
C18 C10 C11 N1 179.76(11) . . . . ?
C18 C10 C11 C12 -53.45(16) . . . . ?
C18 C19 C20 C21 72.59(17) . . . . ?
C22 S1 N1 C7 96.66(12) . . . . ?
C22 S1 N1 C11 -71.06(11) . . . . ?
C22 C23 C24 C25 1.2(2) . . . . ?
C23 C22 C27 C26 -0.9(2) . . . . ?
C23 C24 C25 C26 -2.1(2) . . . . ?
C23 C24 C25 C28 177.12(15) . . . . ?
C24 C25 C26 C27 1.5(2) . . . . ?
C25 C26 C27 C22 0.0(2) . . . . ?
C27 C22 C23 C24 0.3(2) . . . . ?
C28 C25 C26 C27 -177.73(15) . . . . ?

_olex2_date_sample_data_collection 2021-02-17
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.857
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexane'
