# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_18085_a
_audit_block_doi                 10.5517/ccdc.csd.cc22bnvy
_database_code_depnum_ccdc_archive 'CCDC 1916880'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N2, C6 H4 N O5 S'
_chemical_formula_sum            'C27 H27 N3 O5 S'
_chemical_formula_weight         505.57

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5893(7)
_cell_length_b                   13.5028(11)
_cell_length_c                   23.829(2)
_cell_angle_alpha                95.198(5)
_cell_angle_beta                 92.280(6)
_cell_angle_gamma                99.555(7)
_cell_volume                     2394.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9786
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      68.38

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.579
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4716
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58061
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.335
_diffrn_reflns_theta_max         68.824
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8756
_reflns_number_gt                7904
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+1.4267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8756
_refine_ls_number_parameters     655
_refine_ls_number_restraints     1184
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.69377(6) 0.39526(3) 0.12366(2) 0.02322(11) Uani 1 1 d . U . . .
O1 O 1.0286(2) 0.79678(9) 0.30158(5) 0.0360(3) Uani 1 1 d . U . . .
N1 N 0.80997(19) 1.03677(10) 0.53034(5) 0.0209(3) Uani 1 1 d . U . . .
C1 C 0.7580(2) 1.02092(14) 0.58740(7) 0.0263(4) Uani 1 1 d . U . . .
H1A H 0.628868 1.019512 0.589365 0.039 Uiso 1 1 calc R U . . .
H1B H 0.822493 1.076008 0.613868 0.039 Uiso 1 1 calc R U . . .
H1C H 0.787579 0.956556 0.597386 0.039 Uiso 1 1 calc R U . . .
C2 C 0.8981(2) 1.13705(12) 0.52054(7) 0.0245(4) Uani 1 1 d . U . . .
H2A H 0.985939 1.131777 0.491848 0.037 Uiso 1 1 calc R U . . .
H2B H 0.958951 1.171361 0.555766 0.037 Uiso 1 1 calc R U . . .
H2C H 0.808831 1.175754 0.507383 0.037 Uiso 1 1 calc R U . . .
N2 N 0.2105(2) 0.46920(12) 0.07129(6) 0.0288(3) Uani 1 1 d . U . . .
O2 O 1.0196(2) 0.68057(10) 0.35831(5) 0.0424(4) Uani 1 1 d . U . . .
O3 O 0.51742(18) 0.35227(11) 0.13927(7) 0.0439(4) Uani 1 1 d . U . . .
N3 N 0.9936(2) 0.70863(11) 0.31167(6) 0.0256(3) Uani 1 1 d . U . . .
C3 C 0.7353(2) 0.96957(12) 0.48626(7) 0.0183(3) Uani 1 1 d . U . . .
O4 O 0.81687(17) 0.32437(9) 0.12344(5) 0.0297(3) Uani 1 1 d . U . . .
C4 C 0.7711(2) 0.98592(12) 0.42974(7) 0.0209(3) Uani 1 1 d . U . . .
H4 H 0.842006 1.047308 0.421708 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7040(2) 0.91373(13) 0.38632(7) 0.0237(3) Uani 1 1 d . U . . .
H5 H 0.732308 0.925427 0.348738 0.028 Uiso 1 1 calc R U . . .
O5 O 0.6939(3) 0.44709(10) 0.07349(6) 0.0576(5) Uani 1 1 d . U . . .
C6 C 0.5942(2) 0.82260(13) 0.39629(7) 0.0254(4) Uani 1 1 d . U . . .
C7 C 0.5561(2) 0.80879(13) 0.45181(7) 0.0249(4) Uani 1 1 d . U . . .
H7 H 0.480779 0.748585 0.459505 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6232(2) 0.87875(12) 0.49589(7) 0.0228(3) Uani 1 1 d . U . . .
H8 H 0.594278 0.866188 0.533303 0.027 Uiso 1 1 calc R U . . .
C9 C 0.5145(2) 0.74482(14) 0.35239(7) 0.0269(4) Uani 1 1 d . U . . .
H9 H 0.442024 0.687123 0.364411 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4442(2) 0.66698(14) 0.25397(8) 0.0284(4) Uani 1 1 d . U . . .
S11 S 0.78243(5) -0.10070(3) 0.11329(2) 0.01762(10) Uani 1 1 d . U . . .
O11 O 1.0320(2) 0.30433(10) 0.29747(6) 0.0436(4) Uani 1 1 d . U . . .
N11 N 0.80097(19) 0.54205(10) 0.52452(6) 0.0204(3) Uani 1 1 d . U . . .
C10 C 0.5320(2) 0.74557(14) 0.29738(8) 0.0281(4) Uani 1 1 d . U . . .
H10 H 0.607739 0.801725 0.284965 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4581(2) 0.68486(14) 0.19846(7) 0.0286(4) Uani 1 1 d . U . . .
H12 H 0.524955 0.746586 0.189218 0.034 Uiso 1 1 calc R U . . .
N12 N 0.23614(18) -0.05320(11) 0.07879(5) 0.0220(3) Uani 1 1 d . U . . .
O12 O 1.0185(2) 0.18743(10) 0.35425(5) 0.0369(3) Uani 1 1 d . U . . .
C13 C 0.3744(2) 0.61282(13) 0.15499(7) 0.0262(4) Uani 1 1 d . U . . .
N13 N 1.0033(2) 0.21563(11) 0.30697(6) 0.0275(3) Uani 1 1 d . U . . .
O13 O 0.59238(16) -0.13421(10) 0.11699(5) 0.0300(3) Uani 1 1 d . U . . .
C14 C 0.2782(2) 0.51955(13) 0.16843(7) 0.0262(4) Uani 1 1 d . U . . .
O14 O 0.88750(16) -0.17865(8) 0.12318(5) 0.0216(2) Uani 1 1 d . U . . .
C15 C 0.2655(2) 0.50081(14) 0.22564(8) 0.0294(4) Uani 1 1 d . U . . .
H15 H 0.202327 0.438533 0.235452 0.035 Uiso 1 1 calc R U . . .
O15 O 0.82697(17) -0.05089(9) 0.06282(5) 0.0259(3) Uani 1 1 d . U . . .
C16 C 0.3458(2) 0.57376(15) 0.26685(7) 0.0296(4) Uani 1 1 d . U . . .
H16 H 0.335108 0.561417 0.305288 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3030(3) 0.55861(14) 0.05711(8) 0.0313(4) Uani 1 1 d . U . . .
H18 H 0.310288 0.570489 0.018517 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3839(3) 0.63008(14) 0.09760(8) 0.0315(4) Uani 1 1 d . U . . .
H17 H 0.447268 0.692018 0.087394 0.038 Uiso 1 1 calc R U . . .
C19 C 0.1986(2) 0.44901(14) 0.12452(8) 0.0279(4) Uani 1 1 d . U . . .
H19 H 0.135055 0.385792 0.132877 0.033 Uiso 1 1 calc R U . . .
C20 C 0.1294(3) 0.39142(15) 0.02526(8) 0.0358(5) Uani 1 1 d . U . . .
H20A H 0.022700 0.349593 0.038790 0.043 Uiso 1 1 calc R U . . .
H20B H 0.089743 0.425069 -0.007053 0.043 Uiso 1 1 calc R U . . .
C21 C 0.2564(3) 0.32628(19) 0.00646(10) 0.0524(6) Uani 1 1 d . U . . .
H21A H 0.201531 0.278937 -0.025509 0.079 Uiso 1 1 calc R U . . .
H21B H 0.287955 0.288494 0.037522 0.079 Uiso 1 1 calc R U . . .
H21C H 0.364626 0.367842 -0.005208 0.079 Uiso 1 1 calc R U . . .
C22 C 0.9179(2) 0.63245(12) 0.26554(6) 0.0198(3) Uani 1 1 d . U . . .
C23 C 0.9113(2) 0.66085(12) 0.21131(7) 0.0204(3) Uani 1 1 d . U . . .
H23 H 0.954067 0.728449 0.204095 0.025 Uiso 1 1 calc R U . . .
C24 C 0.8410(2) 0.58862(12) 0.16784(7) 0.0206(3) Uani 1 1 d . U . . .
H24 H 0.834969 0.606093 0.130162 0.025 Uiso 1 1 calc R U . . .
C25 C 0.7794(2) 0.49043(12) 0.17950(7) 0.0195(3) Uani 1 1 d . U . . .
C26 C 0.7865(2) 0.46371(12) 0.23453(7) 0.0226(3) Uani 1 1 d . U . . .
H26 H 0.742755 0.396356 0.241963 0.027 Uiso 1 1 calc R U . . .
C27 C 0.8571(2) 0.53489(12) 0.27814(7) 0.0222(3) Uani 1 1 d . U . . .
H27 H 0.863903 0.517597 0.315842 0.027 Uiso 1 1 calc R U . . .
C31 C 0.8528(2) 0.50182(13) 0.57613(7) 0.0228(3) Uani 1 1 d . U . . .
H31A H 0.751429 0.454654 0.587779 0.034 Uiso 1 1 calc R U . . .
H31B H 0.887933 0.557302 0.605982 0.034 Uiso 1 1 calc R U . . .
H31C H 0.953810 0.466386 0.569409 0.034 Uiso 1 1 calc R U . . .
C32 C 0.7752(2) 0.64635(12) 0.52791(7) 0.0238(3) Uani 1 1 d . U . . .
H32A H 0.820782 0.676932 0.494447 0.036 Uiso 1 1 calc R U . . .
H32B H 0.840003 0.683437 0.561862 0.036 Uiso 1 1 calc R U . . .
H32C H 0.647320 0.649200 0.529718 0.036 Uiso 1 1 calc R U . . .
C33 C 0.7356(2) 0.47791(12) 0.47803(6) 0.0186(3) Uani 1 1 d . U . . .
C34 C 0.6499(2) 0.51141(12) 0.43138(7) 0.0214(3) Uani 1 1 d . U . . .
H34 H 0.634251 0.579903 0.432418 0.026 Uiso 1 1 calc R U . . .
C35 C 0.5886(2) 0.44559(13) 0.38430(7) 0.0240(3) Uani 1 1 d . U . . .
H35 H 0.531440 0.470385 0.353606 0.029 Uiso 1 1 calc R U . . .
C36 C 0.6071(2) 0.34436(13) 0.37995(7) 0.0232(3) Uani 1 1 d . U . . .
C37 C 0.6948(2) 0.31188(12) 0.42603(7) 0.0226(3) Uani 1 1 d . U . . .
H37 H 0.712660 0.243708 0.424262 0.027 Uiso 1 1 calc R U . . .
C38 C 0.7557(2) 0.37548(12) 0.47366(7) 0.0208(3) Uani 1 1 d . U . . .
H38 H 0.812428 0.350026 0.504199 0.025 Uiso 1 1 calc R U . . .
C39 C 0.5343(2) 0.27830(14) 0.32949(7) 0.0260(4) Uani 1 1 d . U . . .
H39 H 0.487287 0.309554 0.299447 0.031 Uiso 1 1 calc R U . . .
C40 C 0.5271(2) 0.17892(14) 0.32132(7) 0.0260(4) Uani 1 1 d . U . . .
H40 H 0.573962 0.147372 0.351270 0.031 Uiso 1 1 calc R U . . .
C41 C 0.4536(2) 0.11339(14) 0.27041(7) 0.0250(4) Uani 1 1 d . U . . .
C42 C 0.4227(2) 0.15048(14) 0.21887(7) 0.0259(4) Uani 1 1 d . U . . .
H42 H 0.446989 0.221101 0.215985 0.031 Uiso 1 1 calc R U . . .
C43 C 0.3558(2) 0.08401(13) 0.17116(7) 0.0233(3) Uani 1 1 d . U . . .
C44 C 0.3191(2) -0.02078(13) 0.17657(7) 0.0220(3) Uani 1 1 d . U . . .
C45 C 0.3495(2) -0.05730(14) 0.22935(7) 0.0264(4) Uani 1 1 d . U . . .
H45 H 0.323223 -0.127589 0.233109 0.032 Uiso 1 1 calc R U . . .
C46 C 0.4162(2) 0.00847(14) 0.27443(7) 0.0266(4) Uani 1 1 d . U . . .
H46 H 0.438303 -0.016613 0.309562 0.032 Uiso 1 1 calc R U . . .
C47 C 0.3273(2) 0.11644(14) 0.11682(7) 0.0261(4) Uani 1 1 d . U . . .
H47 H 0.350312 0.186352 0.111892 0.031 Uiso 1 1 calc R U . . .
C48 C 0.2676(2) 0.04811(13) 0.07206(7) 0.0243(4) Uani 1 1 d . U . . .
H48 H 0.247461 0.070295 0.036004 0.029 Uiso 1 1 calc R U . . .
C49 C 0.2600(2) -0.08647(13) 0.12860(7) 0.0226(3) Uani 1 1 d . U . . .
H49 H 0.236043 -0.157024 0.131719 0.027 Uiso 1 1 calc R U . . .
C50 C 0.1812(2) -0.12613(13) 0.02823(7) 0.0258(4) Uani 1 1 d . U . . .
H50A H 0.089423 -0.101730 0.004950 0.031 Uiso 1 1 calc R U . . .
H50B H 0.127165 -0.192153 0.040300 0.031 Uiso 1 1 calc R U . . .
C51 C 0.3385(2) -0.13940(14) -0.00675(7) 0.0266(4) Uani 1 1 d . U . . .
H51A H 0.300828 -0.192920 -0.037523 0.040 Uiso 1 1 calc R U . . .
H51B H 0.433797 -0.157858 0.017086 0.040 Uiso 1 1 calc R U . . .
H51C H 0.383135 -0.076044 -0.022542 0.040 Uiso 1 1 calc R U . . .
C52 C 0.9475(2) 0.13857(12) 0.25931(7) 0.0215(3) Uani 1 1 d . U . . .
C53 C 0.8973(2) 0.16858(12) 0.20784(7) 0.0238(3) Uani 1 1 d . U . . .
H53 H 0.898265 0.237833 0.203289 0.029 Uiso 1 1 calc R U . . .
C54 C 0.8459(2) 0.09533(12) 0.16331(7) 0.0215(3) Uani 1 1 d . U . . .
H54 H 0.810348 0.113756 0.127568 0.026 Uiso 1 1 calc R U . . .
C55 C 0.8463(2) -0.00529(12) 0.17092(6) 0.0168(3) Uani 1 1 d . U . . .
C56 C 0.8966(2) -0.03349(12) 0.22303(7) 0.0207(3) Uani 1 1 d . U . . .
H56 H 0.895759 -0.102686 0.227722 0.025 Uiso 1 1 calc R U . . .
C57 C 0.9478(2) 0.03877(12) 0.26798(6) 0.0207(3) Uani 1 1 d . U . . .
H57 H 0.982301 0.020476 0.303864 0.025 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
S1 O5 1.4389(14) . ?
S1 O4 1.4441(13) . ?
S1 O3 1.4447(15) . ?
S1 C25 1.7854(16) . ?
O1 N3 1.2237(19) . ?
N1 C3 1.363(2) . ?
N1 C2 1.451(2) . ?
N1 C1 1.455(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C19 1.325(2) . ?
N2 C18 1.370(3) . ?
N2 C20 1.486(2) . ?
O2 N3 1.2252(19) . ?
N3 C22 1.4648(19) . ?
C3 C4 1.414(2) . ?
C3 C8 1.414(2) . ?
C4 C5 1.375(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(3) . ?
C6 C9 1.450(2) . ?
C7 C8 1.368(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.324(3) . ?
C9 H9 0.9500 . ?
C11 C12 1.371(3) . ?
C11 C16 1.419(3) . ?
C11 C10 1.467(2) . ?
S11 O13 1.4469(13) . ?
S11 O14 1.4519(12) . ?
S11 O15 1.4546(12) . ?
S11 C55 1.7889(15) . ?
O11 N13 1.225(2) . ?
N11 C33 1.365(2) . ?
N11 C32 1.449(2) . ?
N11 C31 1.454(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.408(2) . ?
C12 H12 0.9500 . ?
N12 C49 1.323(2) . ?
N12 C48 1.374(2) . ?
N12 C50 1.4845(19) . ?
O12 N13 1.2287(19) . ?
C13 C17 1.411(3) . ?
C13 C14 1.417(3) . ?
N13 C52 1.467(2) . ?
C14 C19 1.395(2) . ?
C14 C15 1.413(3) . ?
C15 C16 1.372(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C17 1.352(3) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.466(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.382(2) . ?
C22 C27 1.385(2) . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(2) . ?
C26 C27 1.376(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C38 1.412(2) . ?
C33 C34 1.412(2) . ?
C34 C35 1.380(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.402(2) . ?
C36 C39 1.462(2) . ?
C37 C38 1.374(2) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.330(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.467(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.393(2) . ?
C41 C46 1.411(3) . ?
C42 C43 1.405(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.415(3) . ?
C43 C47 1.424(2) . ?
C44 C49 1.392(2) . ?
C44 C45 1.416(2) . ?
C45 C46 1.354(2) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C48 1.356(2) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
C50 C51 1.508(2) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 C57 1.382(2) . ?
C52 C53 1.385(2) . ?
C53 C54 1.380(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.387(2) . ?
C54 H54 0.9500 . ?
C55 C56 1.389(2) . ?
C56 C57 1.379(2) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?

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
O5 S1 O4 113.53(10) . . ?
O5 S1 O3 114.05(11) . . ?
O4 S1 O3 112.59(8) . . ?
O5 S1 C25 105.36(8) . . ?
O4 S1 C25 104.82(7) . . ?
O3 S1 C25 105.39(8) . . ?
C3 N1 C2 120.46(13) . . ?
C3 N1 C1 119.75(14) . . ?
C2 N1 C1 117.35(13) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C19 N2 C18 121.76(15) . . ?
C19 N2 C20 119.59(16) . . ?
C18 N2 C20 118.59(16) . . ?
O1 N3 O2 123.43(14) . . ?
O1 N3 C22 118.37(13) . . ?
O2 N3 C22 118.20(14) . . ?
N1 C3 C4 121.72(15) . . ?
N1 C3 C8 120.64(14) . . ?
C4 C3 C8 117.60(14) . . ?
C5 C4 C3 120.56(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.52(16) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 117.27(15) . . ?
C7 C6 C9 118.32(16) . . ?
C5 C6 C9 124.38(16) . . ?
C8 C7 C6 122.39(16) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C3 120.62(15) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C10 C9 C6 127.00(18) . . ?
C10 C9 H9 116.5 . . ?
C6 C9 H9 116.5 . . ?
C12 C11 C16 118.73(16) . . ?
C12 C11 C10 118.25(17) . . ?
C16 C11 C10 123.03(16) . . ?
O13 S11 O14 112.87(8) . . ?
O13 S11 O15 113.41(8) . . ?
O14 S11 O15 113.62(7) . . ?
O13 S11 C55 105.52(7) . . ?
O14 S11 C55 105.10(7) . . ?
O15 S11 C55 105.29(7) . . ?
C33 N11 C32 119.81(13) . . ?
C33 N11 C31 119.96(13) . . ?
C32 N11 C31 118.23(13) . . ?
C9 C10 C11 125.49(18) . . ?
C9 C10 H10 117.3 . . ?
C11 C10 H10 117.3 . . ?
C11 C12 C13 120.78(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C49 N12 C48 121.47(14) . . ?
C49 N12 C50 119.91(15) . . ?
C48 N12 C50 118.58(14) . . ?
C12 C13 C17 121.92(18) . . ?
C12 C13 C14 119.89(17) . . ?
C17 C13 C14 118.20(16) . . ?
O11 N13 O12 123.67(14) . . ?
O11 N13 C52 118.28(14) . . ?
O12 N13 C52 118.05(14) . . ?
C19 C14 C15 122.03(18) . . ?
C19 C14 C13 118.71(16) . . ?
C15 C14 C13 119.26(16) . . ?
C16 C15 C14 119.11(18) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 122.21(17) . . ?
C15 C16 H16 118.9 . . ?
C11 C16 H16 118.9 . . ?
C17 C18 N2 120.53(17) . . ?
C17 C18 H18 119.7 . . ?
N2 C18 H18 119.7 . . ?
C18 C17 C13 120.08(18) . . ?
C18 C17 H17 120.0 . . ?
C13 C17 H17 120.0 . . ?
N2 C19 C14 120.73(17) . . ?
N2 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C21 C20 N2 111.57(16) . . ?
C21 C20 H20A 109.3 . . ?
N2 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
N2 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 122.88(14) . . ?
C23 C22 N3 118.59(14) . . ?
C27 C22 N3 118.53(14) . . ?
C24 C23 C22 118.43(15) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C23 C24 C25 119.66(14) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.88(14) . . ?
C24 C25 S1 120.31(12) . . ?
C26 C25 S1 118.80(12) . . ?
C27 C26 C25 120.00(15) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 118.15(14) . . ?
C26 C27 H27 120.9 . . ?
C22 C27 H27 120.9 . . ?
N11 C31 H31A 109.5 . . ?
N11 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N11 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N11 C32 H32A 109.5 . . ?
N11 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N11 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N11 C33 C38 121.38(14) . . ?
N11 C33 C34 121.72(14) . . ?
C38 C33 C34 116.87(14) . . ?
C35 C34 C33 120.64(15) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 122.69(15) . . ?
C34 C35 H35 118.7 . . ?
C36 C35 H35 118.7 . . ?
C35 C36 C37 116.43(15) . . ?
C35 C36 C39 119.71(15) . . ?
C37 C36 C39 123.85(16) . . ?
C38 C37 C36 122.14(15) . . ?
C38 C37 H37 118.9 . . ?
C36 C37 H37 118.9 . . ?
C37 C38 C33 121.22(15) . . ?
C37 C38 H38 119.4 . . ?
C33 C38 H38 119.4 . . ?
C40 C39 C36 126.69(16) . . ?
C40 C39 H39 116.7 . . ?
C36 C39 H39 116.7 . . ?
C39 C40 C41 126.17(17) . . ?
C39 C40 H40 116.9 . . ?
C41 C40 H40 116.9 . . ?
C42 C41 C46 119.47(15) . . ?
C42 C41 C40 122.79(17) . . ?
C46 C41 C40 117.73(15) . . ?
C41 C42 C43 120.36(17) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C42 C43 C44 118.84(15) . . ?
C42 C43 C47 123.28(17) . . ?
C44 C43 C47 117.86(15) . . ?
C49 C44 C43 118.49(15) . . ?
C49 C44 C45 121.28(16) . . ?
C43 C44 C45 120.18(15) . . ?
C46 C45 C44 119.66(17) . . ?
C46 C45 H45 120.2 . . ?
C44 C45 H45 120.2 . . ?
C45 C46 C41 121.48(16) . . ?
C45 C46 H46 119.3 . . ?
C41 C46 H46 119.3 . . ?
C48 C47 C43 120.39(17) . . ?
C48 C47 H47 119.8 . . ?
C43 C47 H47 119.8 . . ?
C47 C48 N12 120.07(15) . . ?
C47 C48 H48 120.0 . . ?
N12 C48 H48 120.0 . . ?
N12 C49 C44 121.71(16) . . ?
N12 C49 H49 119.1 . . ?
C44 C49 H49 119.1 . . ?
N12 C50 C51 111.35(13) . . ?
N12 C50 H50A 109.4 . . ?
C51 C50 H50A 109.4 . . ?
N12 C50 H50B 109.4 . . ?
C51 C50 H50B 109.4 . . ?
H50A C50 H50B 108.0 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C57 C52 C53 122.91(15) . . ?
C57 C52 N13 118.14(14) . . ?
C53 C52 N13 118.95(15) . . ?
C54 C53 C52 118.33(15) . . ?
C54 C53 H53 120.8 . . ?
C52 C53 H53 120.8 . . ?
C53 C54 C55 119.79(14) . . ?
C53 C54 H54 120.1 . . ?
C55 C54 H54 120.1 . . ?
C54 C55 C56 120.79(14) . . ?
C54 C55 S11 120.17(12) . . ?
C56 C55 S11 119.05(12) . . ?
C57 C56 C55 120.12(15) . . ?
C57 C56 H56 119.9 . . ?
C55 C56 H56 119.9 . . ?
C56 C57 C52 118.07(14) . . ?
C56 C57 H57 121.0 . . ?
C52 C57 H57 121.0 . . ?

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_18129_a
_audit_block_doi                 10.5517/ccdc.csd.cc22bny1
_database_code_depnum_ccdc_archive 'CCDC 1916883'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 I N2'
_chemical_formula_weight         430.31

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'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.7754(6)
_cell_length_b                   8.5188(5)
_cell_length_c                   35.3048(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3842.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      68.40

_exptl_crystal_description       Shards
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    13.107
_shelx_estimated_absorpt_T_min   0.118
_shelx_estimated_absorpt_T_max   0.478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0284
_exptl_absorpt_correction_T_max  0.1326
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37866
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.503
_diffrn_reflns_theta_max         68.745
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3542
_reflns_number_gt                3053
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+7.3338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3542
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
I1 I 0.91004(2) 0.42428(4) 0.59491(2) 0.04450(13) Uani 1 1 d . . . . .
C1 C 0.8148(5) 0.0779(9) 0.20976(16) 0.079(2) Uani 1 1 d . . . . .
H1A H 0.840264 0.059793 0.183939 0.119 Uiso 1 1 calc R U . . .
H1B H 0.746245 0.129265 0.208763 0.119 Uiso 1 1 calc R U . . .
H1C H 0.808383 -0.022842 0.222978 0.119 Uiso 1 1 calc R U . . .
N1 N 0.8879(3) 0.1772(7) 0.22983(12) 0.0622(13) Uani 1 1 d . . . . .
N2 N 0.5537(3) 0.4219(5) 0.57269(10) 0.0421(8) Uani 1 1 d . . . . .
C2 C 0.9694(5) 0.2549(8) 0.20872(15) 0.0675(15) Uani 1 1 d . . . . .
H2A H 0.969251 0.216579 0.182551 0.101 Uiso 1 1 calc R U . . .
H2B H 1.037340 0.232667 0.220400 0.101 Uiso 1 1 calc R U . . .
H2C H 0.956869 0.368449 0.208853 0.101 Uiso 1 1 calc R U . . .
C4 C 0.9318(4) 0.3275(6) 0.28602(13) 0.0476(11) Uani 1 1 d . . . . .
H4 H 0.991113 0.370801 0.273625 0.057 Uiso 1 1 calc R U . . .
C3 C 0.8669(4) 0.2217(6) 0.26655(13) 0.0495(11) Uani 1 1 d . . . . .
C5 C 0.9103(4) 0.3692(6) 0.32290(14) 0.0482(11) Uani 1 1 d . . . . .
H5 H 0.956044 0.439914 0.335503 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8234(4) 0.3110(6) 0.34238(12) 0.0451(11) Uani 1 1 d . . . . .
C7 C 0.7602(4) 0.2051(6) 0.32308(14) 0.0519(12) Uani 1 1 d . . . . .
H7 H 0.700728 0.162744 0.335567 0.062 Uiso 1 1 calc R U . . .
C9 C 0.8045(4) 0.3630(6) 0.38110(13) 0.0441(10) Uani 1 1 d . . . . .
H9 H 0.854658 0.431937 0.391962 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7811(4) 0.1595(7) 0.28644(14) 0.0549(12) Uani 1 1 d . . . . .
H8 H 0.736853 0.085004 0.274417 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7225(4) 0.3223(6) 0.40282(12) 0.0450(11) Uani 1 1 d . . . . .
H10 H 0.671323 0.256828 0.391362 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7035(3) 0.3678(6) 0.44218(12) 0.0416(10) Uani 1 1 d . . . . .
C12 C 0.7751(3) 0.4614(5) 0.46386(12) 0.0413(10) Uani 1 1 d . . . . .
H12 H 0.837375 0.498644 0.452220 0.050 Uiso 1 1 calc R U . . .
C13 C 0.7558(3) 0.4980(6) 0.50085(12) 0.0411(10) Uani 1 1 d . . . . .
H13 H 0.804356 0.560193 0.514645 0.049 Uiso 1 1 calc R U . . .
C14 C 0.6634(3) 0.4434(5) 0.51868(12) 0.0386(9) Uani 1 1 d . . . . .
C15 C 0.5922(3) 0.3471(5) 0.49771(13) 0.0396(10) Uani 1 1 d . . . . .
C16 C 0.6141(3) 0.3150(6) 0.45963(13) 0.0422(10) Uani 1 1 d . . . . .
H16 H 0.565459 0.254725 0.445384 0.051 Uiso 1 1 calc R U . . .
C17 C 0.6395(3) 0.4776(5) 0.55639(12) 0.0389(9) Uani 1 1 d . . . . .
H17 H 0.685701 0.542097 0.570646 0.047 Uiso 1 1 calc R U . . .
C18 C 0.5027(3) 0.2903(5) 0.51674(13) 0.0429(10) Uani 1 1 d . . . . .
H18 H 0.453989 0.225981 0.503599 0.051 Uiso 1 1 calc R U . . .
C19 C 0.4857(4) 0.3265(5) 0.55336(13) 0.0450(11) Uani 1 1 d . . . . .
H19 H 0.425919 0.285545 0.565953 0.054 Uiso 1 1 calc R U . . .
C20 C 0.5315(4) 0.4633(6) 0.61273(13) 0.0483(11) Uani 1 1 d . . . . .
H20A H 0.458734 0.432940 0.619035 0.058 Uiso 1 1 calc R U . . .
H20B H 0.537893 0.578259 0.616059 0.058 Uiso 1 1 calc R U . . .
C21 C 0.6060(4) 0.3813(7) 0.63928(14) 0.0540(13) Uani 1 1 d . . . . .
H21A H 0.602609 0.267801 0.634990 0.081 Uiso 1 1 calc R U . . .
H21B H 0.586339 0.404488 0.665523 0.081 Uiso 1 1 calc R U . . .
H21C H 0.677406 0.418487 0.634582 0.081 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
C1 N1 1.446(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N1 C3 1.377(6) . ?
N1 C2 1.441(7) . ?
N2 C17 1.326(6) . ?
N2 C19 1.372(6) . ?
N2 C20 1.484(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 C5 1.377(7) . ?
C4 C3 1.404(7) . ?
C4 H4 0.9500 . ?
C3 C8 1.406(7) . ?
C5 C6 1.397(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(7) . ?
C6 C9 1.457(6) . ?
C7 C8 1.377(7) . ?
C7 H7 0.9500 . ?
C9 C10 1.343(7) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.463(6) . ?
C10 H10 0.9500 . ?
C11 C16 1.373(6) . ?
C11 C12 1.435(6) . ?
C12 C13 1.365(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.416(6) . ?
C13 H13 0.9500 . ?
C14 C17 1.397(6) . ?
C14 C15 1.431(6) . ?
C15 C16 1.400(6) . ?
C15 C18 1.412(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.347(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.507(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N1 C2 120.1(5) . . ?
C3 N1 C1 119.8(4) . . ?
C2 N1 C1 118.8(4) . . ?
C17 N2 C19 121.3(4) . . ?
C17 N2 C20 119.1(4) . . ?
C19 N2 C20 119.5(4) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C3 C4 121.5(5) . . ?
N1 C3 C8 121.2(5) . . ?
C4 C3 C8 117.2(4) . . ?
C4 C5 C6 122.1(5) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C7 C6 C5 116.8(4) . . ?
C7 C6 C9 124.2(4) . . ?
C5 C6 C9 119.0(4) . . ?
C8 C7 C6 122.1(5) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C10 C9 C6 125.9(5) . . ?
C10 C9 H9 117.1 . . ?
C6 C9 H9 117.1 . . ?
C7 C8 C3 120.9(5) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C9 C10 C11 127.1(5) . . ?
C9 C10 H10 116.4 . . ?
C11 C10 H10 116.4 . . ?
C16 C11 C12 118.2(4) . . ?
C16 C11 C10 118.5(4) . . ?
C12 C11 C10 123.2(4) . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C17 C14 C13 122.5(4) . . ?
C17 C14 C15 118.3(4) . . ?
C13 C14 C15 119.2(4) . . ?
C16 C15 C18 123.5(4) . . ?
C16 C15 C14 118.8(4) . . ?
C18 C15 C14 117.7(4) . . ?
C11 C16 C15 122.2(4) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
N2 C17 C14 121.3(4) . . ?
N2 C17 H17 119.4 . . ?
C14 C17 H17 119.4 . . ?
C19 C18 C15 120.6(4) . . ?
C19 C18 H18 119.7 . . ?
C15 C18 H18 119.7 . . ?
C18 C19 N2 120.7(4) . . ?
C18 C19 H19 119.6 . . ?
N2 C19 H19 119.6 . . ?
N2 C20 C21 111.2(4) . . ?
N2 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N2 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.982
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_18107_a
_audit_block_doi                 10.5517/ccdc.csd.cc22bnwz
_database_code_depnum_ccdc_archive 'CCDC 1916881'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 N2, C6 H4 N O5 S, 0.5(H2 O0.96)'
_chemical_formula_sum            'C26 H26 N3 O5.48 S'
_chemical_formula_weight         500.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   38.437(2)
_cell_length_b                   7.1832(5)
_cell_length_c                   20.0502(13)
_cell_angle_alpha                90
_cell_angle_beta                 121.085(3)
_cell_angle_gamma                90
_cell_volume                     4740.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8599
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      68.31

_exptl_crystal_description       Plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             2103
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    1.605
_shelx_estimated_absorpt_T_min   0.608
_shelx_estimated_absorpt_T_max   0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3892
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27089
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.410
_diffrn_reflns_theta_max         68.529
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4364
_reflns_number_gt                3683
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0692P)²+7.6107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     328
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.42707(2) 0.86915(8) 0.31318(3) 0.02785(17) Uani 1 1 d . . . . .
O1 O 0.43915(5) 0.8442(2) 0.25582(9) 0.0350(4) Uani 1 1 d . . . . .
N1 N 0.93960(6) 0.9318(3) 0.55898(12) 0.0378(5) Uani 1 1 d . . . . .
C1 C 0.95195(7) 0.9507(4) 0.50221(16) 0.0381(6) Uani 1 1 d . . . . .
H1A H 0.935137 0.869693 0.457548 0.057 Uiso 1 1 calc R U . . .
H1B H 0.980542 0.914834 0.525988 0.057 Uiso 1 1 calc R U . . .
H1C H 0.948529 1.080334 0.484673 0.057 Uiso 1 1 calc R U . . .
O2 O 0.41285(5) 1.0562(2) 0.31390(10) 0.0337(4) Uani 1 1 d . . . . .
N2 N 0.58014(5) 1.0392(3) 0.46945(11) 0.0299(4) Uani 1 1 d . . . . .
C2 C 0.97069(7) 0.9178(4) 0.64080(15) 0.0396(6) Uani 1 1 d . . . . .
H2A H 0.997383 0.905082 0.646049 0.059 Uiso 1 1 calc R U . . .
H2B H 0.965380 0.808613 0.663524 0.059 Uiso 1 1 calc R U . . .
H2C H 0.970318 1.030248 0.668101 0.059 Uiso 1 1 calc R U . . .
N3 N 0.28814(5) 0.3575(3) 0.23555(11) 0.0301(4) Uani 1 1 d . . . . .
O3 O 0.45702(4) 0.8012(2) 0.39004(9) 0.0338(4) Uani 1 1 d . . . . .
C3 C 0.89984(7) 0.9593(3) 0.53780(14) 0.0295(5) Uani 1 1 d . . . . .
C4 C 0.88694(7) 0.9267(3) 0.59105(14) 0.0304(5) Uani 1 1 d . . . . .
H4 H 0.906265 0.890571 0.642903 0.036 Uiso 1 1 calc R U . . .
O4 O 0.29359(5) 0.1897(2) 0.23446(10) 0.0373(4) Uani 1 1 d . . . . .
O5 O 0.25665(5) 0.4250(3) 0.22610(11) 0.0401(4) Uani 1 1 d . . . . .
C5 C 0.84682(7) 0.9462(3) 0.56910(13) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.839018 0.922187 0.606170 0.035 Uiso 1 1 calc R U . . .
C6 C 0.81706(6) 1.0007(3) 0.49343(13) 0.0283(5) Uani 1 1 d . . . . .
O6 O 0.500000 1.0610(4) 0.250000 0.0408(10) Uani 0.959(11) 2 d DS T P . .
HO6 H 0.5144(9) 0.994(4) 0.2407(19) 0.049 Uiso 1 1 d D U . . .
C7 C 0.83010(7) 1.0363(3) 0.44132(13) 0.0293(5) Uani 1 1 d . . . . .
H7 H 0.810777 1.075641 0.389956 0.035 Uiso 1 1 calc R U . . .
C8 C 0.87025(7) 1.0160(3) 0.46205(14) 0.0302(5) Uani 1 1 d . . . . .
H8 H 0.877935 1.040557 0.424844 0.036 Uiso 1 1 calc R U . . .
C9 C 0.77422(7) 1.0212(3) 0.46769(14) 0.0293(5) Uani 1 1 d . . . . .
H9 H 0.756721 1.064221 0.415988 0.035 Uiso 1 1 calc R U . . .
C10 C 0.75715(6) 0.9850(3) 0.51018(14) 0.0293(5) Uani 1 1 d . . . . .
H10 H 0.774637 0.939621 0.561491 0.035 Uiso 1 1 calc R U . . .
C11 C 0.71461(6) 1.0083(3) 0.48559(13) 0.0284(5) Uani 1 1 d . . . . .
C12 C 0.70205(7) 0.9717(3) 0.53763(13) 0.0291(5) Uani 1 1 d . . . . .
H12 H 0.721373 0.930216 0.588661 0.035 Uiso 1 1 calc R U . . .
C13 C 0.66139(7) 0.9945(3) 0.51669(13) 0.0284(5) Uani 1 1 d . . . . .
C14 C 0.63236(6) 1.0532(3) 0.43990(13) 0.0280(5) Uani 1 1 d . . . . .
C15 C 0.64521(7) 1.0891(3) 0.38645(13) 0.0297(5) Uani 1 1 d . . . . .
H15 H 0.626057 1.128205 0.334941 0.036 Uiso 1 1 calc R U . . .
C16 C 0.68489(7) 1.0676(3) 0.40870(13) 0.0298(5) Uani 1 1 d . . . . .
H16 H 0.693095 1.092710 0.372291 0.036 Uiso 1 1 calc R U . . .
C17 C 0.64737(7) 0.9621(3) 0.56840(14) 0.0313(5) Uani 1 1 d . . . . .
H17 H 0.665974 0.924035 0.620371 0.038 Uiso 1 1 calc R U . . .
C18 C 0.60750(7) 0.9850(3) 0.54437(14) 0.0313(5) Uani 1 1 d . . . . .
H18 H 0.598469 0.963213 0.579760 0.038 Uiso 1 1 calc R U . . .
C19 C 0.59196(7) 1.0730(3) 0.41917(14) 0.0302(5) Uani 1 1 d . . . . .
H19 H 0.572437 1.111697 0.367820 0.036 Uiso 1 1 calc R U . . .
C20 C 0.53670(7) 1.0533(4) 0.44513(15) 0.0365(6) Uani 1 1 d . . . . .
H20A H 0.522786 1.137521 0.400444 0.055 Uiso 1 1 calc R U . . .
H20B H 0.534427 1.101853 0.488400 0.055 Uiso 1 1 calc R U . . .
H20C H 0.524152 0.929691 0.430462 0.055 Uiso 1 1 calc R U . . .
C21 C 0.38448(6) 0.7192(3) 0.28346(12) 0.0278(5) Uani 1 1 d . . . . .
C22 C 0.38991(6) 0.5278(3) 0.28363(13) 0.0293(5) Uani 1 1 d . . . . .
H22 H 0.415424 0.478947 0.295326 0.035 Uiso 1 1 calc R U . . .
C23 C 0.35805(7) 0.4081(3) 0.26670(13) 0.0296(5) Uani 1 1 d . . . . .
H23 H 0.361296 0.277030 0.266701 0.035 Uiso 1 1 calc R U . . .
C24 C 0.32136(6) 0.4854(3) 0.24981(13) 0.0281(5) Uani 1 1 d . . . . .
C25 C 0.31490(6) 0.6745(3) 0.24810(13) 0.0289(5) Uani 1 1 d . . . . .
H25 H 0.289204 0.722546 0.235693 0.035 Uiso 1 1 calc R U . . .
C26 C 0.34693(6) 0.7927(3) 0.26501(13) 0.0284(5) Uani 1 1 d . . . . .
H26 H 0.343334 0.923712 0.264036 0.034 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
S1 O3 1.4513(17) . ?
S1 O2 1.4537(17) . ?
S1 O1 1.4567(16) . ?
S1 C21 1.785(2) . ?
N1 C3 1.373(3) . ?
N1 C1 1.448(3) . ?
N1 C2 1.451(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C19 1.325(3) . ?
N2 C18 1.372(3) . ?
N2 C20 1.482(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 O5 1.224(2) . ?
N3 O4 1.226(3) . ?
N3 C24 1.476(3) . ?
C3 C8 1.408(3) . ?
C3 C4 1.410(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(3) . ?
C6 C9 1.457(3) . ?
O6 HO6 0.826(19) . ?
O6 HO6 0.826(19) 2_655 ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.342(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.454(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 C16 1.430(3) . ?
C12 C13 1.403(3) . ?
C12 H12 0.9500 . ?
C13 C17 1.413(3) . ?
C13 C14 1.421(3) . ?
C14 C19 1.392(3) . ?
C14 C15 1.416(3) . ?
C15 C16 1.359(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.359(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.390(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
O3 S1 O2 113.35(10) . . ?
O3 S1 O1 113.29(10) . . ?
O2 S1 O1 113.36(10) . . ?
O3 S1 C21 103.86(10) . . ?
O2 S1 C21 106.05(10) . . ?
O1 S1 C21 105.86(10) . . ?
C3 N1 C1 120.5(2) . . ?
C3 N1 C2 119.7(2) . . ?
C1 N1 C2 118.83(18) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 N2 C18 121.01(19) . . ?
C19 N2 C20 120.5(2) . . ?
C18 N2 C20 118.43(19) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O5 N3 O4 123.4(2) . . ?
O5 N3 C24 118.09(19) . . ?
O4 N3 C24 118.48(18) . . ?
N1 C3 C8 121.7(2) . . ?
N1 C3 C4 120.8(2) . . ?
C8 C3 C4 117.5(2) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 116.92(19) . . ?
C7 C6 C9 119.6(2) . . ?
C5 C6 C9 123.5(2) . . ?
HO6 O6 HO6 109(5) . 2_655 ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C3 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C10 C9 C6 126.1(2) . . ?
C10 C9 H9 116.9 . . ?
C6 C9 H9 116.9 . . ?
C9 C10 C11 126.6(2) . . ?
C9 C10 H10 116.7 . . ?
C11 C10 H10 116.7 . . ?
C12 C11 C16 118.3(2) . . ?
C12 C11 C10 119.5(2) . . ?
C16 C11 C10 122.2(2) . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C17 123.3(2) . . ?
C12 C13 C14 119.3(2) . . ?
C17 C13 C14 117.4(2) . . ?
C19 C14 C15 121.8(2) . . ?
C19 C14 C13 119.0(2) . . ?
C15 C14 C13 119.2(2) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 121.6(2) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C18 C17 C13 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C17 H17 119.7 . . ?
C17 C18 N2 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
N2 C18 H18 119.7 . . ?
N2 C19 C14 121.5(2) . . ?
N2 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 120.5(2) . . ?
C22 C21 S1 119.03(16) . . ?
C26 C21 S1 120.31(18) . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 118.1(2) . . ?
C24 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?
C25 C24 C23 123.3(2) . . ?
C25 C24 N3 118.80(19) . . ?
C23 C24 N3 117.9(2) . . ?
C24 C25 C26 118.1(2) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C25 C26 C21 120.0(2) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_18142_a
_audit_block_doi                 10.5517/ccdc.csd.cc22bnz2
_database_code_depnum_ccdc_archive 'CCDC 1916884'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N2, C6 H4 Cl O3 S'
_chemical_formula_sum            'C27 H27 Cl N2 O3 S'
_chemical_formula_weight         495.01

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0643(5)
_cell_length_b                   10.0456(6)
_cell_length_c                   14.7344(9)
_cell_angle_alpha                95.018(3)
_cell_angle_beta                 96.726(3)
_cell_angle_gamma                92.402(3)
_cell_volume                     1179.24(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      68.52

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.529
_shelx_estimated_absorpt_T_min   0.703
_shelx_estimated_absorpt_T_max   0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6415
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25621
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.033
_diffrn_reflns_theta_max         68.512
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4313
_reflns_number_gt                4032
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.8839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4313
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.66797(5) 0.79151(4) 0.16769(3) 0.01526(11) Uani 1 1 d . . . . .
Cl1 Cl 1.30741(5) 0.91994(4) 0.45454(3) 0.02341(12) Uani 1 1 d . . . . .
N1 N -0.11184(19) 0.73705(15) 0.87376(10) 0.0216(3) Uani 1 1 d . . . . .
C1 C -0.1082(2) 0.87668(19) 0.91011(13) 0.0256(4) Uani 1 1 d . . . . .
H1A H 0.008124 0.911068 0.925644 0.038 Uiso 1 1 calc R U . . .
H1B H -0.165373 0.883996 0.965331 0.038 Uiso 1 1 calc R U . . .
H1C H -0.164892 0.929028 0.863827 0.038 Uiso 1 1 calc R U . . .
N2 N 0.55854(17) 0.24828(14) 0.16013(9) 0.0164(3) Uani 1 1 d . . . . .
C2 C -0.1560(2) 0.63635(19) 0.93313(12) 0.0240(4) Uani 1 1 d . . . . .
H2A H -0.224739 0.563476 0.896561 0.036 Uiso 1 1 calc R U . . .
H2B H -0.219177 0.676865 0.980370 0.036 Uiso 1 1 calc R U . . .
H2C H -0.053932 0.600829 0.962481 0.036 Uiso 1 1 calc R U . . .
O003 O 0.52683(15) 0.82083(12) 0.21773(8) 0.0209(3) Uani 1 1 d . . . . .
C3 C -0.0325(2) 0.70196(17) 0.79814(11) 0.0159(3) Uani 1 1 d . . . . .
O004 O 0.69125(15) 0.88421(12) 0.09923(8) 0.0200(3) Uani 1 1 d . . . . .
C4 C -0.0085(2) 0.56667(17) 0.76983(11) 0.0180(3) Uani 1 1 d . . . . .
H4 H -0.044192 0.498401 0.805021 0.022 Uiso 1 1 calc R U . . .
O005 O 0.67030(16) 0.65203(12) 0.13237(8) 0.0229(3) Uani 1 1 d . . . . .
C5 C 0.0655(2) 0.53221(17) 0.69218(11) 0.0169(3) Uani 1 1 d . . . . .
H5 H 0.078411 0.440318 0.674609 0.020 Uiso 1 1 calc R U . . .
C6 C 0.12242(19) 0.62853(17) 0.63832(11) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.1015(2) 0.76212(17) 0.66781(11) 0.0168(3) Uani 1 1 d . . . . .
H7 H 0.140239 0.830078 0.633280 0.020 Uiso 1 1 calc R U . . .
C8 C 0.0268(2) 0.79925(17) 0.74516(11) 0.0174(3) Uani 1 1 d . . . . .
H8 H 0.015451 0.891370 0.762721 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2023(2) 0.59696(17) 0.55617(11) 0.0166(3) Uani 1 1 d . . . . .
H9 H 0.237794 0.671196 0.526207 0.020 Uiso 1 1 calc R U . . .
C10 C 0.2318(2) 0.47596(18) 0.51763(11) 0.0181(3) Uani 1 1 d . . . . .
H10 H 0.195901 0.400406 0.546171 0.022 Uiso 1 1 calc R U . . .
C11 C 0.3145(2) 0.45060(17) 0.43542(11) 0.0171(3) Uani 1 1 d . . . . .
C12 C 0.3422(2) 0.32084(17) 0.40354(12) 0.0183(3) Uani 1 1 d . . . . .
H12 H 0.309124 0.249205 0.436641 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4183(2) 0.29213(17) 0.32299(12) 0.0170(3) Uani 1 1 d . . . . .
C14 C 0.4677(2) 0.39980(17) 0.27485(11) 0.0168(3) Uani 1 1 d . . . . .
C15 C 0.4428(2) 0.53313(17) 0.30796(12) 0.0179(3) Uani 1 1 d . . . . .
H15 H 0.478031 0.605584 0.276209 0.021 Uiso 1 1 calc R U . . .
C16 C 0.3683(2) 0.55688(17) 0.38553(12) 0.0181(3) Uani 1 1 d . . . . .
H16 H 0.351537 0.646626 0.407137 0.022 Uiso 1 1 calc R U . . .
C17 C 0.4470(2) 0.16154(17) 0.28657(12) 0.0200(4) Uani 1 1 d . . . . .
H17 H 0.418645 0.087044 0.318278 0.024 Uiso 1 1 calc R U . . .
C18 C 0.5144(2) 0.14152(17) 0.20699(12) 0.0198(4) Uani 1 1 d . . . . .
H18 H 0.531717 0.052960 0.183017 0.024 Uiso 1 1 calc R U . . .
C19 C 0.5400(2) 0.37276(17) 0.19332(11) 0.0173(3) Uani 1 1 d . . . . .
H19 H 0.576099 0.444945 0.161593 0.021 Uiso 1 1 calc R U . . .
C20 C 0.6251(2) 0.21299(17) 0.07139(11) 0.0195(4) Uani 1 1 d . . . . .
H20A H 0.538246 0.157698 0.029897 0.023 Uiso 1 1 calc R U . . .
H20B H 0.722709 0.157660 0.082997 0.023 Uiso 1 1 calc R U . . .
C21 C 0.6771(2) 0.33144(19) 0.02340(12) 0.0234(4) Uani 1 1 d . . . . .
H21A H 0.723757 0.300049 -0.032663 0.035 Uiso 1 1 calc R U . . .
H21B H 0.761897 0.387806 0.064148 0.035 Uiso 1 1 calc R U . . .
H21C H 0.579603 0.383558 0.007481 0.035 Uiso 1 1 calc R U . . .
C22 C 0.8491(2) 0.82072(16) 0.25018(11) 0.0152(3) Uani 1 1 d . . . . .
C23 C 1.0070(2) 0.81738(16) 0.22113(11) 0.0173(3) Uani 1 1 d . . . . .
H23 H 1.017269 0.796093 0.157995 0.021 Uiso 1 1 calc R U . . .
C24 C 1.1497(2) 0.84480(17) 0.28340(12) 0.0189(3) Uani 1 1 d . . . . .
H24 H 1.257717 0.843373 0.263775 0.023 Uiso 1 1 calc R U . . .
C25 C 1.1301(2) 0.87443(16) 0.37527(12) 0.0185(3) Uani 1 1 d . . . . .
C26 C 0.9748(2) 0.87224(17) 0.40623(12) 0.0195(4) Uani 1 1 d . . . . .
H26 H 0.965100 0.888177 0.469855 0.023 Uiso 1 1 calc R U . . .
C27 C 0.8334(2) 0.84642(16) 0.34292(11) 0.0176(3) Uani 1 1 d . . . . .
H27 H 0.725589 0.846297 0.362945 0.021 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
S1 O005 1.4531(13) . ?
S1 O003 1.4534(12) . ?
S1 O004 1.4539(12) . ?
S1 C22 1.7841(17) . ?
Cl1 C25 1.7544(17) . ?
N1 C3 1.376(2) . ?
N1 C2 1.454(2) . ?
N1 C1 1.455(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C19 1.323(2) . ?
N2 C18 1.382(2) . ?
N2 C20 1.491(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.405(2) . ?
C3 C4 1.414(2) . ?
C4 C5 1.376(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(2) . ?
C6 C9 1.454(2) . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.339(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.458(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 C16 1.429(2) . ?
C12 C13 1.412(2) . ?
C12 H12 0.9500 . ?
C13 C17 1.412(2) . ?
C13 C14 1.413(2) . ?
C14 C19 1.406(2) . ?
C14 C15 1.415(2) . ?
C15 C16 1.360(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.352(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.506(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.390(2) . ?
C22 C23 1.391(2) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(2) . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
O005 S1 O003 113.79(7) . . ?
O005 S1 O004 113.24(7) . . ?
O003 S1 O004 113.00(7) . . ?
O005 S1 C22 105.25(7) . . ?
O003 S1 C22 105.62(7) . . ?
O004 S1 C22 104.86(7) . . ?
C3 N1 C2 120.27(15) . . ?
C3 N1 C1 119.74(14) . . ?
C2 N1 C1 117.58(14) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 N2 C18 120.78(14) . . ?
C19 N2 C20 123.50(14) . . ?
C18 N2 C20 115.71(14) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C8 121.30(15) . . ?
N1 C3 C4 121.55(15) . . ?
C8 C3 C4 117.15(15) . . ?
C5 C4 C3 121.14(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.95(15) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 116.57(15) . . ?
C7 C6 C9 119.53(15) . . ?
C5 C6 C9 123.89(15) . . ?
C8 C7 C6 122.59(15) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C3 120.58(15) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C10 C9 C6 127.86(16) . . ?
C10 C9 H9 116.1 . . ?
C6 C9 H9 116.1 . . ?
C9 C10 C11 125.36(16) . . ?
C9 C10 H10 117.3 . . ?
C11 C10 H10 117.3 . . ?
C12 C11 C16 118.16(15) . . ?
C12 C11 C10 120.02(15) . . ?
C16 C11 C10 121.82(16) . . ?
C11 C12 C13 121.65(15) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C17 C13 C12 123.99(15) . . ?
C17 C13 C14 117.50(15) . . ?
C12 C13 C14 118.50(16) . . ?
C19 C14 C13 119.22(15) . . ?
C19 C14 C15 120.52(15) . . ?
C13 C14 C15 120.25(15) . . ?
C16 C15 C14 119.58(15) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 121.83(16) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
C18 C17 C13 120.63(16) . . ?
C18 C17 H17 119.7 . . ?
C13 C17 H17 119.7 . . ?
C17 C18 N2 120.80(16) . . ?
C17 C18 H18 119.6 . . ?
N2 C18 H18 119.6 . . ?
N2 C19 C14 120.98(15) . . ?
N2 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
N2 C20 C21 114.49(14) . . ?
N2 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
N2 C20 H20B 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 119.97(16) . . ?
C27 C22 S1 120.51(13) . . ?
C23 C22 S1 119.52(13) . . ?
C24 C23 C22 120.66(15) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 118.13(16) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C26 C25 C24 122.15(16) . . ?
C26 C25 Cl1 118.68(13) . . ?
C24 C25 Cl1 119.15(13) . . ?
C25 C26 C27 118.92(16) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C26 C27 C22 120.07(15) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?

_refine_diff_density_max         0.500
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_18186_a
_audit_block_doi                 10.5517/ccdc.csd.cc22bp15
_database_code_depnum_ccdc_archive 'CCDC 1916886'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 N3 O6 S'
_chemical_formula_weight         509.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.8624(4)
_cell_length_b                   8.1056(2)
_cell_length_c                   17.3004(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.784(2)
_cell_angle_gamma                90
_cell_volume                     2341.84(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      5.16
_cell_measurement_theta_max      68.15

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    1.651
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.439773
_exptl_absorpt_correction_T_max  0.584905
_exptl_absorpt_process_details   'twinabs 2008/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4287
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.646
_diffrn_reflns_theta_max         68.518
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4287
_reflns_number_gt                3358
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+1.1687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4287
_refine_ls_number_parameters     334
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.13712(3) 0.19645(7) 0.17239(3) 0.02066(17) Uani 1 1 d . . . . .
O1 O 0.14091(11) 0.1180(3) 0.24847(12) 0.0327(4) Uani 1 1 d . . . . .
N1 N 0.86860(11) 0.1245(3) 0.53904(12) 0.0213(4) Uani 1 1 d . . . . .
C1 C 0.90157(15) -0.0280(3) 0.58183(16) 0.0288(6) Uani 1 1 d . . . . .
H1A H 0.876689 -0.122239 0.546559 0.043 Uiso 1 1 calc R U . . .
H1B H 0.890691 -0.034432 0.633431 0.043 Uiso 1 1 calc R U . . .
H1C H 0.959541 -0.030268 0.594343 0.043 Uiso 1 1 calc R U . . .
O2 O 0.10481(10) 0.0862(2) 0.10141(11) 0.0336(5) Uani 1 1 d . . . . .
N2 N 0.13092(12) 0.6426(3) 0.28730(12) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.91192(14) 0.1900(3) 0.48839(15) 0.0249(5) Uani 1 1 d . . . . .
H2A H 0.894715 0.132078 0.435215 0.037 Uiso 1 1 calc R U . . .
H2B H 0.969543 0.173711 0.517026 0.037 Uiso 1 1 calc R U . . .
H2C H 0.900589 0.308050 0.478926 0.037 Uiso 1 1 calc R U . . .
N3 N 0.47530(12) 0.2965(3) 0.19283(13) 0.0301(5) Uani 1 1 d . . . . .
O3 O 0.10040(10) 0.3572(2) 0.15875(11) 0.0290(4) Uani 1 1 d . . . . .
C3 C 0.78849(14) 0.1592(3) 0.51948(14) 0.0204(5) Uani 1 1 d . . . . .
O4 O 0.52943(11) 0.2389(3) 0.25230(12) 0.0446(6) Uani 1 1 d . . . . .
C4 C 0.74818(15) 0.2755(3) 0.45852(15) 0.0239(5) Uani 1 1 d . . . . .
H4 H 0.776485 0.331571 0.429166 0.029 Uiso 1 1 calc R U . . .
O5 O 0.48716(11) 0.3763(3) 0.13780(12) 0.0358(5) Uani 1 1 d . . . . .
C5 C 0.66755(15) 0.3093(3) 0.44069(15) 0.0279(6) Uani 1 1 d . . . . .
H5 H 0.641791 0.387364 0.398730 0.033 Uiso 1 1 calc R U . . .
C6 C 0.62295(15) 0.2317(3) 0.48268(16) 0.0277(6) Uani 1 1 d . . . . .
C7 C 0.66338(15) 0.1181(3) 0.54298(15) 0.0259(5) Uani 1 1 d . . . . .
H7 H 0.634989 0.064059 0.572859 0.031 Uiso 1 1 calc R U . . .
C8 C 0.74314(14) 0.0804(3) 0.56136(15) 0.0232(5) Uani 1 1 d . . . . .
H8 H 0.767988 0.000526 0.602679 0.028 Uiso 1 1 calc R U . . .
C9 C 0.53808(16) 0.2635(3) 0.46744(17) 0.0298(6) Uani 1 1 d . . . . .
H9 H 0.513651 0.200112 0.498203 0.036 Uiso 1 1 calc R U . . .
C10 C 0.49219(16) 0.3733(3) 0.41429(16) 0.0292(6) Uani 1 1 d . . . . .
H10 H 0.516660 0.434964 0.382976 0.035 Uiso 1 1 calc R U . . .
C11 C 0.40802(15) 0.4083(3) 0.39936(16) 0.0279(6) Uani 1 1 d . . . . .
C12 C 0.37052(14) 0.5220(3) 0.33978(16) 0.0261(5) Uani 1 1 d . . . . .
H12 H 0.400029 0.574441 0.310579 0.031 Uiso 1 1 calc R U . . .
C13 C 0.28976(14) 0.5633(3) 0.32063(15) 0.0218(5) Uani 1 1 d . . . . .
C14 C 0.24536(13) 0.4864(3) 0.36402(14) 0.0200(5) Uani 1 1 d . . . . .
C15 C 0.28359(15) 0.3685(3) 0.42585(16) 0.0262(5) Uani 1 1 d . . . . .
H15 H 0.254557 0.315572 0.455406 0.031 Uiso 1 1 calc R U . . .
C16 C 0.36268(16) 0.3309(3) 0.44286(16) 0.0287(6) Uani 1 1 d . . . . .
H16 H 0.387950 0.251764 0.484453 0.034 Uiso 1 1 calc R U . . .
C17 C 0.24929(16) 0.6817(3) 0.25947(15) 0.0273(6) Uani 1 1 d . . . . .
H17 H 0.277223 0.734965 0.228904 0.033 Uiso 1 1 calc R U . . .
C18 C 0.17196(16) 0.7193(3) 0.24421(15) 0.0267(6) Uani 1 1 d . . . . .
H18 H 0.145880 0.799354 0.203427 0.032 Uiso 1 1 calc R U . . .
C19 C 0.16523(14) 0.5303(3) 0.34458(14) 0.0214(5) Uani 1 1 d . . . . .
H19 H 0.134714 0.478724 0.372949 0.026 Uiso 1 1 calc R U . . .
C20 C 0.04579(15) 0.6850(4) 0.26955(17) 0.0327(6) Uani 1 1 d . . . . .
H20A H 0.024406 0.742048 0.216227 0.049 Uiso 1 1 calc R U . . .
H20B H 0.041552 0.757236 0.313240 0.049 Uiso 1 1 calc R U . . .
H20C H 0.015073 0.583856 0.267418 0.049 Uiso 1 1 calc R U . . .
O1S O -0.03711(12) -0.0950(2) 0.07869(12) 0.0320(4) Uani 1 1 d D . . . .
HO1S H 0.0043(14) -0.033(3) 0.0863(19) 0.038 Uiso 1 1 d D U . . .
HO2S H -0.0566(17) -0.116(4) 0.0263(12) 0.038 Uiso 1 1 d D U . . .
C21 C 0.39204(14) 0.2699(3) 0.18743(15) 0.0226(5) Uani 1 1 d . . . . .
C22 C 0.33317(15) 0.3669(3) 0.13375(15) 0.0259(5) Uani 1 1 d . . . . .
H22 H 0.345702 0.446616 0.099922 0.031 Uiso 1 1 calc R U . . .
C23 C 0.25545(14) 0.3454(3) 0.13037(15) 0.0229(5) Uani 1 1 d . . . . .
H23 H 0.213675 0.411292 0.094208 0.028 Uiso 1 1 calc R U . . .
C24 C 0.23820(13) 0.2268(3) 0.18003(14) 0.0190(5) Uani 1 1 d . . . . .
C25 C 0.29912(15) 0.1312(3) 0.23397(15) 0.0229(5) Uani 1 1 d . . . . .
H25 H 0.287031 0.050803 0.267739 0.028 Uiso 1 1 calc R U . . .
C26 C 0.37752(14) 0.1534(3) 0.23842(15) 0.0242(5) Uani 1 1 d . . . . .
H26 H 0.419923 0.090180 0.275479 0.029 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
S1 O3 1.4399(18) . ?
S1 O1 1.4417(18) . ?
S1 O2 1.4618(18) . ?
S1 C24 1.780(2) . ?
N1 C3 1.378(3) . ?
N1 C1 1.454(3) . ?
N1 C2 1.459(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C19 1.325(3) . ?
N2 C18 1.367(3) . ?
N2 C20 1.481(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 O4 1.227(3) . ?
N3 O5 1.230(3) . ?
N3 C21 1.473(3) . ?
C3 C4 1.407(3) . ?
C3 C8 1.416(3) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(4) . ?
C6 C9 1.466(4) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.332(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.460(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(4) . ?
C11 C16 1.431(4) . ?
C12 C13 1.401(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.415(3) . ?
C13 C17 1.421(4) . ?
C14 C19 1.395(3) . ?
C14 C15 1.417(3) . ?
C15 C16 1.371(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.346(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1S HO1S 0.866(18) . ?
O1S HO2S 0.865(18) . ?
C21 C22 1.376(4) . ?
C21 C26 1.379(4) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(3) . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
O3 S1 O1 114.82(11) . . ?
O3 S1 O2 113.23(11) . . ?
O1 S1 O2 111.96(12) . . ?
O3 S1 C24 106.16(11) . . ?
O1 S1 C24 105.99(11) . . ?
O2 S1 C24 103.57(10) . . ?
C3 N1 C1 119.8(2) . . ?
C3 N1 C2 120.3(2) . . ?
C1 N1 C2 114.18(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 N2 C18 121.7(2) . . ?
C19 N2 C20 118.9(2) . . ?
C18 N2 C20 119.4(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 N3 O5 123.3(2) . . ?
O4 N3 C21 118.4(2) . . ?
O5 N3 C21 118.4(2) . . ?
N1 C3 C4 122.1(2) . . ?
N1 C3 C8 121.0(2) . . ?
C4 C3 C8 116.9(2) . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.1(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 116.6(2) . . ?
C7 C6 C9 118.8(2) . . ?
C5 C6 C9 124.7(2) . . ?
C8 C7 C6 122.7(2) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C3 120.9(2) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C10 C9 C6 125.8(3) . . ?
C10 C9 H9 117.1 . . ?
C6 C9 H9 117.1 . . ?
C9 C10 C11 126.5(3) . . ?
C9 C10 H10 116.8 . . ?
C11 C10 H10 116.8 . . ?
C12 C11 C16 118.3(2) . . ?
C12 C11 C10 117.5(2) . . ?
C16 C11 C10 124.1(3) . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 C17 123.1(2) . . ?
C14 C13 C17 117.3(2) . . ?
C19 C14 C13 118.7(2) . . ?
C19 C14 C15 122.2(2) . . ?
C13 C14 C15 119.1(2) . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.5(2) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C18 C17 C13 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C13 C17 H17 119.5 . . ?
C17 C18 N2 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
N2 C18 H18 119.9 . . ?
N2 C19 C14 121.2(2) . . ?
N2 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
HO1S O1S HO2S 106(3) . . ?
C22 C21 C26 123.5(2) . . ?
C22 C21 N3 118.2(2) . . ?
C26 C21 N3 118.3(2) . . ?
C21 C22 C23 118.2(2) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C22 C23 C24 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 S1 120.29(18) . . ?
C23 C24 S1 119.31(18) . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C21 C26 C25 118.0(2) . . ?
C21 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?

_refine_diff_density_max         0.641
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_18172_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc22bp04
_database_code_depnum_ccdc_archive 'CCDC 1916885'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N2, C9 H11 O3 S'
_chemical_formula_sum            'C30 H34 N2 O3 S'
_chemical_formula_weight         502.65

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6019(5)
_cell_length_b                   10.1226(6)
_cell_length_c                   15.5819(8)
_cell_angle_alpha                95.347(4)
_cell_angle_beta                 104.070(4)
_cell_angle_gamma                105.448(4)
_cell_volume                     1250.29(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5695
_cell_measurement_theta_min      4.60
_cell_measurement_theta_max      70.21

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    1.431
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.464553
_exptl_absorpt_correction_T_max  0.585904
_exptl_absorpt_process_details   'twinabs 2008/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4760
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.966
_diffrn_reflns_theta_max         71.187
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4760
_reflns_number_gt                4268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+1.3605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4760
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.49039(6) 0.22967(5) 0.34033(3) 0.02197(14) Uani 1 1 d . . . . .
O1 O -0.4948(2) 0.12753(15) 0.40016(10) 0.0309(4) Uani 1 1 d . . . . .
N1 N 1.1309(2) 0.41396(17) 0.91839(11) 0.0219(4) Uani 1 1 d . . . . .
C1 C 1.2034(2) 0.3113(2) 0.95559(14) 0.0261(4) Uani 1 1 d . . . . .
H1A H 1.169991 0.227903 0.909975 0.039 Uiso 1 1 calc R U . . .
H1B H 1.163314 0.287041 1.007477 0.039 Uiso 1 1 calc R U . . .
H1C H 1.326120 0.349378 0.974569 0.039 Uiso 1 1 calc R U . . .
O2 O -0.65449(19) 0.2149(2) 0.28219(11) 0.0396(4) Uani 1 1 d . . . . .
N2 N -0.4573(2) 0.29247(17) 0.58645(10) 0.0205(3) Uani 1 1 d . . . . .
C2 C 1.2413(3) 0.5510(2) 0.92160(14) 0.0269(4) Uani 1 1 d . . . . .
H2A H 1.214432 0.578794 0.862480 0.040 Uiso 1 1 calc R U . . .
H2B H 1.358126 0.549460 0.938245 0.040 Uiso 1 1 calc R U . . .
H2C H 1.226039 0.617683 0.966244 0.040 Uiso 1 1 calc R U . . .
C3 C 0.9604(2) 0.3865(2) 0.88971(12) 0.0197(4) Uani 1 1 d . . . . .
O3 O -0.40501(19) 0.37060(15) 0.38728(10) 0.0309(3) Uani 1 1 d . . . . .
C4 C 0.8853(3) 0.4881(2) 0.85966(13) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.954417 0.579482 0.861704 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7125(3) 0.4569(2) 0.82720(13) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.665761 0.527473 0.807160 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6051(2) 0.3244(2) 0.82317(13) 0.0219(4) Uani 1 1 d . . . . .
C7 C 0.6791(2) 0.2251(2) 0.85468(13) 0.0237(4) Uani 1 1 d . . . . .
H7 H 0.608996 0.134562 0.853678 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8511(2) 0.2538(2) 0.88738(13) 0.0222(4) Uani 1 1 d . . . . .
H8 H 0.896445 0.183137 0.908577 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4220(2) 0.2841(2) 0.78697(13) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.362281 0.191735 0.789871 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3296(2) 0.3621(2) 0.75043(13) 0.0219(4) Uani 1 1 d . . . . .
H10 H 0.387886 0.454871 0.747676 0.026 Uiso 1 1 calc R U . . .
C11 C 0.1472(2) 0.3181(2) 0.71429(12) 0.0191(4) Uani 1 1 d . . . . .
C12 C 0.0679(2) 0.4145(2) 0.68490(13) 0.0218(4) Uani 1 1 d . . . . .
H12 H 0.133008 0.507296 0.686879 0.026 Uiso 1 1 calc R U . . .
C13 C -0.1094(2) 0.3765(2) 0.65190(12) 0.0205(4) Uani 1 1 d . . . . .
C14 C -0.2052(2) 0.2367(2) 0.64597(12) 0.0199(4) Uani 1 1 d . . . . .
C15 C -0.1237(2) 0.1384(2) 0.67519(13) 0.0217(4) Uani 1 1 d . . . . .
H15 H -0.187336 0.044639 0.671614 0.026 Uiso 1 1 calc R U . . .
C16 C 0.0465(2) 0.1786(2) 0.70851(13) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.099923 0.111703 0.728556 0.025 Uiso 1 1 calc R U . . .
C17 C -0.1980(3) 0.4728(2) 0.62684(13) 0.0237(4) Uani 1 1 d . . . . .
H17 H -0.137859 0.567867 0.631660 0.028 Uiso 1 1 calc R U . . .
C18 C -0.3677(3) 0.4305(2) 0.59609(13) 0.0228(4) Uani 1 1 d . . . . .
H18 H -0.425604 0.496685 0.580979 0.027 Uiso 1 1 calc R U . . .
C19 C -0.3809(2) 0.1991(2) 0.61092(12) 0.0206(4) Uani 1 1 d . . . . .
H19 H -0.445673 0.104931 0.604731 0.025 Uiso 1 1 calc R U . . .
C20 C -0.6418(2) 0.2554(2) 0.54365(13) 0.0213(4) Uani 1 1 d . . . . .
H20A H -0.660715 0.268755 0.480213 0.026 Uiso 1 1 calc R U . . .
H20B H -0.687321 0.320277 0.574201 0.026 Uiso 1 1 calc R U . . .
C21 C -0.7380(3) 0.1088(2) 0.54641(14) 0.0269(4) Uani 1 1 d . . . . .
H21A H -0.858398 0.094285 0.520856 0.040 Uiso 1 1 calc R U . . .
H21B H -0.716709 0.093109 0.608768 0.040 Uiso 1 1 calc R U . . .
H21C H -0.701509 0.043400 0.511406 0.040 Uiso 1 1 calc R U . . .
C22 C -0.3594(2) 0.19160(19) 0.27290(13) 0.0190(4) Uani 1 1 d . . . . .
C23 C -0.4162(2) 0.15478(19) 0.17923(13) 0.0200(4) Uani 1 1 d . . . . .
C24 C -0.3063(2) 0.12145(19) 0.13408(13) 0.0213(4) Uani 1 1 d . . . . .
H24 H -0.345013 0.093958 0.070725 0.026 Uiso 1 1 calc R U . . .
C25 C -0.1438(2) 0.12670(19) 0.17744(13) 0.0210(4) Uani 1 1 d . . . . .
C26 C -0.0889(2) 0.16668(19) 0.27009(13) 0.0207(4) Uani 1 1 d . . . . .
H26 H 0.022996 0.172019 0.300812 0.025 Uiso 1 1 calc R U . . .
C27 C -0.1927(2) 0.19917(19) 0.31938(13) 0.0192(4) Uani 1 1 d . . . . .
C28 C -0.1205(2) 0.2445(2) 0.41942(13) 0.0248(4) Uani 1 1 d . . . . .
H28A H -0.005067 0.239688 0.437327 0.037 Uiso 1 1 calc R U . . .
H28B H -0.188860 0.182976 0.450183 0.037 Uiso 1 1 calc R U . . .
H28C H -0.120811 0.340253 0.435816 0.037 Uiso 1 1 calc R U . . .
C29 C -0.5873(3) 0.1509(2) 0.12219(14) 0.0280(5) Uani 1 1 d . . . . .
H29A H -0.593088 0.130126 0.058582 0.042 Uiso 1 1 calc R U . . .
H29B H -0.605636 0.241383 0.134592 0.042 Uiso 1 1 calc R U . . .
H29C H -0.674006 0.078640 0.136395 0.042 Uiso 1 1 calc R U . . .
C30 C -0.0270(3) 0.0935(2) 0.12653(15) 0.0282(5) Uani 1 1 d . . . . .
H30A H -0.088870 0.059409 0.063160 0.042 Uiso 1 1 calc R U . . .
H30B H 0.018301 0.021886 0.151640 0.042 Uiso 1 1 calc R U . . .
H30C H 0.065439 0.177695 0.131660 0.042 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
S1 O2 1.4408(16) . ?
S1 O3 1.4477(16) . ?
S1 O1 1.4546(15) . ?
S1 C22 1.8035(19) . ?
N1 C3 1.367(2) . ?
N1 C1 1.444(2) . ?
N1 C2 1.446(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C19 1.322(2) . ?
N2 C18 1.379(3) . ?
N2 C20 1.492(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.411(3) . ?
C3 C8 1.411(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 C9 1.466(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.333(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.459(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 C16 1.428(3) . ?
C12 C13 1.417(3) . ?
C12 H12 0.9500 . ?
C13 C17 1.416(3) . ?
C13 C14 1.416(3) . ?
C14 C19 1.407(3) . ?
C14 C15 1.410(3) . ?
C15 C16 1.361(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.353(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.505(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.401(3) . ?
C22 C27 1.419(3) . ?
C23 C24 1.397(3) . ?
C23 C29 1.511(3) . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 C30 1.506(3) . ?
C26 C27 1.392(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.507(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
O2 S1 O3 112.68(10) . . ?
O2 S1 O1 112.11(10) . . ?
O3 S1 O1 112.84(9) . . ?
O2 S1 C22 108.86(9) . . ?
O3 S1 C22 105.34(9) . . ?
O1 S1 C22 104.35(8) . . ?
C3 N1 C1 120.39(16) . . ?
C3 N1 C2 120.64(16) . . ?
C1 N1 C2 118.60(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 N2 C18 121.00(17) . . ?
C19 N2 C20 122.82(17) . . ?
C18 N2 C20 116.12(15) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 121.89(18) . . ?
N1 C3 C8 121.27(17) . . ?
C4 C3 C8 116.84(17) . . ?
C5 C4 C3 121.16(19) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.74(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 117.06(18) . . ?
C7 C6 C9 118.71(18) . . ?
C5 C6 C9 124.22(18) . . ?
C8 C7 C6 122.24(19) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C3 120.93(18) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C10 C9 C6 127.43(19) . . ?
C10 C9 H9 116.3 . . ?
C6 C9 H9 116.3 . . ?
C9 C10 C11 125.99(19) . . ?
C9 C10 H10 117.0 . . ?
C11 C10 H10 117.0 . . ?
C12 C11 C16 118.43(17) . . ?
C12 C11 C10 119.20(18) . . ?
C16 C11 C10 122.38(17) . . ?
C11 C12 C13 120.73(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C17 C13 C14 117.51(18) . . ?
C17 C13 C12 123.18(18) . . ?
C14 C13 C12 119.28(17) . . ?
C19 C14 C15 121.35(18) . . ?
C19 C14 C13 118.88(17) . . ?
C15 C14 C13 119.78(18) . . ?
C16 C15 C14 119.69(18) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 122.06(18) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
C18 C17 C13 120.59(19) . . ?
C18 C17 H17 119.7 . . ?
C13 C17 H17 119.7 . . ?
C17 C18 N2 120.70(18) . . ?
C17 C18 H18 119.6 . . ?
N2 C18 H18 119.6 . . ?
N2 C19 C14 121.18(18) . . ?
N2 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
N2 C20 C21 114.26(16) . . ?
N2 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
N2 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 120.30(17) . . ?
C23 C22 S1 122.97(14) . . ?
C27 C22 S1 116.73(14) . . ?
C24 C23 C22 118.12(17) . . ?
C24 C23 C29 116.83(17) . . ?
C22 C23 C29 125.04(18) . . ?
C25 C24 C23 122.93(18) . . ?
C25 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
C24 C25 C26 117.93(17) . . ?
C24 C25 C30 121.62(18) . . ?
C26 C25 C30 120.44(18) . . ?
C25 C26 C27 122.12(17) . . ?
C25 C26 H26 118.9 . . ?
C27 C26 H26 118.9 . . ?
C26 C27 C22 118.57(17) . . ?
C26 C27 C28 118.21(17) . . ?
C22 C27 C28 123.21(17) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 109.5 . . ?
C23 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C23 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_18115_a
_audit_block_doi                 10.5517/ccdc.csd.cc22bnx0
_database_code_depnum_ccdc_archive 'CCDC 1916882'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N2, C6 H4 N O5 S'
_chemical_formula_sum            'C27 H27 N3 O5 S'
_chemical_formula_weight         505.57

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2165(3)
_cell_length_b                   9.5708(5)
_cell_length_c                   15.9375(7)
_cell_angle_alpha                97.645(4)
_cell_angle_beta                 92.675(4)
_cell_angle_gamma                93.859(3)
_cell_volume                     1237.38(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      68.43

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    1.528
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3653
_exptl_absorpt_correction_T_max  0.4672
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28506
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         68.492
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4530
_reflns_number_gt                4280
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+1.8491P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4530
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.26652(6) 0.16873(6) 0.84603(3) 0.02333(17) Uani 1 1 d . . . . .
O1 O 0.0087(3) 0.1500(2) 0.53387(11) 0.0379(4) Uani 1 1 d . . . . .
N1 N 1.1459(2) 0.3366(2) 0.13968(12) 0.0255(4) Uani 1 1 d . . . . .
C1 C 1.1619(3) 0.1965(3) 0.09497(15) 0.0272(5) Uani 1 1 d . . . . .
H1A H 1.054200 0.144604 0.086190 0.041 Uiso 1 1 calc R U . . .
H1B H 1.234831 0.145746 0.128556 0.041 Uiso 1 1 calc R U . . .
H1C H 1.207497 0.204531 0.039927 0.041 Uiso 1 1 calc R U . . .
O2 O -0.2433(3) 0.0681(2) 0.53412(13) 0.0466(5) Uani 1 1 d . . . . .
N2 N 0.3758(2) 0.6784(2) 0.82220(11) 0.0222(4) Uani 1 1 d . . . . .
C2 C 1.1850(3) 0.4586(3) 0.09728(15) 0.0291(5) Uani 1 1 d . . . . .
H2A H 1.233660 0.428022 0.043515 0.044 Uiso 1 1 calc R U . . .
H2B H 1.262862 0.525072 0.133513 0.044 Uiso 1 1 calc R U . . .
H2C H 1.085070 0.505024 0.086167 0.044 Uiso 1 1 calc R U . . .
N3 N -0.1111(3) 0.1129(2) 0.57046(14) 0.0325(5) Uani 1 1 d . . . . .
O3 O 0.2621(2) 0.05834(18) 0.90024(10) 0.0288(4) Uani 1 1 d . . . . .
C3 C 1.0694(3) 0.3525(2) 0.21455(13) 0.0191(4) Uani 1 1 d . . . . .
O4 O 0.2755(2) 0.31063(19) 0.89259(11) 0.0342(4) Uani 1 1 d . . . . .
C4 C 1.0365(3) 0.4872(2) 0.25491(14) 0.0210(5) Uani 1 1 d . . . . .
H4 H 1.071948 0.569148 0.231122 0.025 Uiso 1 1 calc R U . . .
C5 C 0.9539(3) 0.5012(2) 0.32818(14) 0.0214(5) Uani 1 1 d . . . . .
H5 H 0.933818 0.593312 0.353982 0.026 Uiso 1 1 calc R U . . .
O5 O 0.3841(2) 0.1512(2) 0.78137(11) 0.0319(4) Uani 1 1 d . . . . .
C6 C 0.8982(3) 0.3844(2) 0.36616(13) 0.0205(5) Uani 1 1 d . . . . .
C8 C 1.0173(3) 0.2350(2) 0.25363(14) 0.0219(5) Uani 1 1 d . . . . .
H8 H 1.039932 0.142799 0.229110 0.026 Uiso 1 1 calc R U . . .
C7 C 0.9341(3) 0.2518(2) 0.32689(14) 0.0220(5) Uani 1 1 d . . . . .
H7 H 0.900048 0.170352 0.351532 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8055(3) 0.3949(3) 0.44181(14) 0.0237(5) Uani 1 1 d . . . . .
H9 H 0.767622 0.308405 0.459881 0.028 Uiso 1 1 calc R U . . .
C10 C 0.7682(3) 0.5130(3) 0.48846(14) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.807167 0.599978 0.471397 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6725(3) 0.5204(3) 0.56374(15) 0.0259(5) Uani 1 1 d . . . . .
C12 C 0.6430(3) 0.6510(3) 0.60465(15) 0.0262(5) Uani 1 1 d . . . . .
H12 H 0.685007 0.733302 0.583194 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5510(3) 0.6661(3) 0.67854(15) 0.0251(5) Uani 1 1 d . . . . .
C14 C 0.4943(3) 0.5409(3) 0.70964(15) 0.0254(5) Uani 1 1 d . . . . .
C15 C 0.5213(3) 0.4059(3) 0.66692(15) 0.0269(5) Uani 1 1 d . . . . .
H15 H 0.480300 0.322716 0.687752 0.032 Uiso 1 1 calc R U . . .
C16 C 0.6069(3) 0.3968(3) 0.59566(15) 0.0264(5) Uani 1 1 d . . . . .
H16 H 0.623527 0.306277 0.566347 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5154(3) 0.7958(3) 0.72121(16) 0.0294(5) Uani 1 1 d . . . . .
H17 H 0.552519 0.880862 0.701224 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4279(3) 0.8008(3) 0.79111(16) 0.0287(5) Uani 1 1 d . . . . .
H18 H 0.401898 0.889706 0.819248 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4056(3) 0.5528(3) 0.78402(15) 0.0260(5) Uani 1 1 d . . . . .
H19 H 0.367591 0.470147 0.806394 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2854(3) 0.6935(3) 0.90088(14) 0.0243(5) Uani 1 1 d . . . . .
H20A H 0.218104 0.604708 0.903893 0.029 Uiso 1 1 calc R U . . .
H20B H 0.210974 0.770398 0.899414 0.029 Uiso 1 1 calc R U . . .
C21 C 0.4000(3) 0.7260(4) 0.97838(16) 0.0416(7) Uani 1 1 d . . . . .
H21A H 0.473254 0.649638 0.980168 0.062 Uiso 1 1 calc R U . . .
H21B H 0.336883 0.734418 1.029248 0.062 Uiso 1 1 calc R U . . .
H21C H 0.464676 0.815215 0.976255 0.062 Uiso 1 1 calc R U . . .
C22 C 0.0710(3) 0.1501(2) 0.79039(14) 0.0206(5) Uani 1 1 d . . . . .
C23 C 0.0588(3) 0.1360(2) 0.70286(14) 0.0223(5) Uani 1 1 d . . . . .
H23 H 0.153500 0.134822 0.670876 0.027 Uiso 1 1 calc R U . . .
C24 C -0.0963(3) 0.1237(2) 0.66329(15) 0.0250(5) Uani 1 1 d . . . . .
C25 C -0.2370(3) 0.1249(2) 0.70762(17) 0.0277(5) Uani 1 1 d . . . . .
H25 H -0.341593 0.115924 0.678545 0.033 Uiso 1 1 calc R U . . .
C26 C -0.2223(3) 0.1395(2) 0.79520(17) 0.0273(5) Uani 1 1 d . . . . .
H26 H -0.317260 0.140801 0.826986 0.033 Uiso 1 1 calc R U . . .
C27 C -0.0688(3) 0.1521(2) 0.83654(15) 0.0242(5) Uani 1 1 d . . . . .
H27 H -0.058899 0.162211 0.896704 0.029 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
S1 O5 1.4466(18) . ?
S1 O3 1.4507(17) . ?
S1 O4 1.4539(19) . ?
S1 C22 1.785(2) . ?
O1 N3 1.223(3) . ?
N1 C3 1.370(3) . ?
N1 C1 1.449(3) . ?
N1 C2 1.450(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O2 N3 1.230(3) . ?
N2 C19 1.317(3) . ?
N2 C18 1.381(3) . ?
N2 C20 1.483(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C24 1.468(3) . ?
C3 C8 1.408(3) . ?
C3 C4 1.411(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 C9 1.451(3) . ?
C8 C7 1.377(3) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.330(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.462(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(3) . ?
C11 C16 1.431(3) . ?
C12 C13 1.426(3) . ?
C12 H12 0.9500 . ?
C13 C17 1.389(4) . ?
C13 C14 1.415(3) . ?
C14 C15 1.415(3) . ?
C14 C19 1.416(3) . ?
C15 C16 1.359(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.351(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.503(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.382(3) . ?
C22 C27 1.393(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(4) . ?
C25 C26 1.383(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.385(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
O5 S1 O3 113.76(10) . . ?
O5 S1 O4 113.43(11) . . ?
O3 S1 O4 113.52(11) . . ?
O5 S1 C22 105.64(10) . . ?
O3 S1 C22 105.14(10) . . ?
O4 S1 C22 104.13(10) . . ?
C3 N1 C1 120.10(19) . . ?
C3 N1 C2 120.05(19) . . ?
C1 N1 C2 118.96(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 N2 C18 121.6(2) . . ?
C19 N2 C20 120.9(2) . . ?
C18 N2 C20 117.5(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 N3 O2 123.9(2) . . ?
O1 N3 C24 118.0(2) . . ?
O2 N3 C24 118.1(2) . . ?
N1 C3 C8 121.4(2) . . ?
N1 C3 C4 121.4(2) . . ?
C8 C3 C4 117.2(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C7 C6 C5 116.6(2) . . ?
C7 C6 C9 119.6(2) . . ?
C5 C6 C9 123.8(2) . . ?
C7 C8 C3 120.9(2) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C10 C9 C6 126.8(2) . . ?
C10 C9 H9 116.6 . . ?
C6 C9 H9 116.6 . . ?
C9 C10 C11 125.6(2) . . ?
C9 C10 H10 117.2 . . ?
C11 C10 H10 117.2 . . ?
C12 C11 C16 118.9(2) . . ?
C12 C11 C10 118.6(2) . . ?
C16 C11 C10 122.5(2) . . ?
C11 C12 C13 121.6(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C17 C13 C14 118.9(2) . . ?
C17 C13 C12 123.8(2) . . ?
C14 C13 C12 117.4(2) . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 C19 120.0(2) . . ?
C13 C14 C19 118.6(2) . . ?
C16 C15 C14 119.1(2) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C11 121.6(2) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C18 C17 C13 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C13 C17 H17 120.0 . . ?
C17 C18 N2 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
N2 C18 H18 119.6 . . ?
N2 C19 C14 120.0(2) . . ?
N2 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
N2 C20 C21 111.38(19) . . ?
N2 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N2 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 120.5(2) . . ?
C23 C22 S1 120.44(17) . . ?
C27 C22 S1 119.01(18) . . ?
C22 C23 C24 117.8(2) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 H23 121.1 . . ?
C25 C24 C23 122.8(2) . . ?
C25 C24 N3 118.8(2) . . ?
C23 C24 N3 118.4(2) . . ?
C24 C25 C26 118.6(2) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 120.4(2) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?

_refine_diff_density_max         0.948
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_18138_a
_database_code_depnum_ccdc_archive 'CCDC 1867834'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2018-09-14 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N O, C7 H7 O3 S'
_chemical_formula_sum            'C26 H25 N O4 S'
_chemical_formula_weight         447.53

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.9488(3)
_cell_length_b                   8.1027(4)
_cell_length_c                   9.9927(5)
_cell_angle_alpha                104.045(3)
_cell_angle_beta                 97.177(3)
_cell_angle_gamma                93.047(3)
_cell_volume                     539.49(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7410
_cell_measurement_theta_min      4.61
_cell_measurement_theta_max      68.28

_exptl_crystal_description       Shards
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.615
_shelx_estimated_absorpt_T_min   0.615
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6207
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18617
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.608
_diffrn_reflns_theta_max         68.341
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3795
_reflns_number_gt                3559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.931

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.1008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.017(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3795
_refine_ls_number_parameters     292
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.19914(12) 0.19394(10) 0.19568(8) 0.0193(2) Uani 1 1 d . . . . .
O1 O -0.3356(3) 0.9324(3) 0.7868(2) 0.0223(6) Uani 1 1 d . . . . .
N1 N 1.1683(4) 0.0751(4) 0.5937(3) 0.0197(6) Uani 1 1 d . . . . .
C1 C -0.3312(5) 1.0251(5) 0.9290(4) 0.0250(8) Uani 1 1 d . . . . .
H1A H -0.212966 1.103694 0.958493 0.038 Uiso 1 1 calc R U . . .
H1B H -0.331869 0.944844 0.988197 0.038 Uiso 1 1 calc R U . . .
H1C H -0.445898 1.090267 0.937539 0.038 Uiso 1 1 calc R U . . .
C2 C -0.1840(5) 0.8350(4) 0.7582(4) 0.0187(7) Uani 1 1 d . . . . .
O2 O 1.3370(4) 0.2476(3) 0.3234(3) 0.0248(6) Uani 1 1 d . . . . .
O3 O 1.2871(4) 0.1894(3) 0.0708(3) 0.0268(6) Uani 1 1 d . . . . .
C3 C -0.1895(5) 0.7489(4) 0.6167(4) 0.0203(8) Uani 1 1 d . . . . .
H3 H -0.295661 0.759306 0.550308 0.024 Uiso 1 1 calc R U . . .
C4 C -0.0448(5) 0.6516(4) 0.5744(3) 0.0185(7) Uani 1 1 d . . . . .
H4 H -0.050148 0.595294 0.478684 0.022 Uiso 1 1 calc R U . . .
O4 O 1.0790(4) 0.0384(3) 0.1893(2) 0.0228(6) Uani 1 1 d . . . . .
C5 C 0.1144(5) 0.6329(4) 0.6717(3) 0.0168(7) Uani 1 1 d . . . . .
C6 C 0.1168(5) 0.7181(4) 0.8138(4) 0.0168(7) Uani 1 1 d . . . . .
C7 C -0.0339(5) 0.8199(4) 0.8561(4) 0.0175(7) Uani 1 1 d . . . . .
H7 H -0.031352 0.877228 0.951347 0.021 Uiso 1 1 calc R U . . .
C9 C 0.4178(5) 0.5129(4) 0.7276(4) 0.0184(7) Uani 1 1 d . . . . .
C8 C 0.2669(5) 0.5331(4) 0.6311(4) 0.0195(8) Uani 1 1 d . . . . .
H8 H 0.265843 0.478656 0.535370 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4200(5) 0.5983(4) 0.8701(4) 0.0211(8) Uani 1 1 d . . . . .
H10 H 0.523644 0.585481 0.937451 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2761(5) 0.6980(4) 0.9117(3) 0.0196(7) Uani 1 1 d . . . . .
H11 H 0.281860 0.755175 1.007263 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5707(5) 0.4067(4) 0.6786(4) 0.0191(7) Uani 1 1 d . . . . .
H12 H 0.558946 0.359046 0.580943 0.023 Uiso 1 1 calc R U . . .
C13 C 0.7252(5) 0.3690(4) 0.7558(4) 0.0204(8) Uani 1 1 d . . . . .
H13 H 0.738418 0.412200 0.854125 0.024 Uiso 1 1 calc R U . . .
C14 C 0.8748(5) 0.2654(4) 0.6979(4) 0.0192(7) Uani 1 1 d . . . . .
C15 C 0.8703(5) 0.1955(4) 0.5545(4) 0.0189(7) Uani 1 1 d . . . . .
H15 H 0.764222 0.212888 0.491041 0.023 Uiso 1 1 calc R U . . .
C16 C 1.0163(5) 0.1029(4) 0.5050(4) 0.0190(7) Uani 1 1 d . . . . .
H16 H 1.011437 0.057503 0.407471 0.023 Uiso 1 1 calc R U . . .
C17 C 1.1749(5) 0.1386(5) 0.7320(4) 0.0215(8) Uani 1 1 d . . . . .
H17 H 1.280281 0.116228 0.793503 0.026 Uiso 1 1 calc R U . . .
C18 C 1.0338(5) 0.2341(5) 0.7857(4) 0.0215(8) Uani 1 1 d . . . . .
H18 H 1.043759 0.279639 0.883578 0.026 Uiso 1 1 calc R U . . .
C19 C 1.3217(5) -0.0247(5) 0.5342(4) 0.0258(8) Uani 1 1 d . . . . .
H19A H 1.268394 -0.142730 0.491062 0.039 Uiso 1 1 calc R U . . .
H19B H 1.428949 -0.023259 0.608215 0.039 Uiso 1 1 calc R U . . .
H19C H 1.370068 0.025478 0.463499 0.039 Uiso 1 1 calc R U . . .
C20 C 1.0352(5) 0.3563(4) 0.2042(3) 0.0174(7) Uani 1 1 d . . . . .
C21 C 1.1011(6) 0.5159(5) 0.1906(4) 0.0238(8) Uani 1 1 d . . . . .
H21 H 1.231440 0.535520 0.174909 0.029 Uiso 1 1 calc R U . . .
C22 C 0.9788(6) 0.6462(4) 0.1998(4) 0.0243(8) Uani 1 1 d . . . . .
H22 H 1.026134 0.754784 0.191190 0.029 Uiso 1 1 calc R U . . .
C23 C 0.7865(5) 0.6193(5) 0.2216(4) 0.0221(8) Uani 1 1 d . . . . .
C24 C 0.7186(5) 0.4587(5) 0.2311(4) 0.0207(8) Uani 1 1 d . . . . .
H24 H 0.586980 0.437765 0.243384 0.025 Uiso 1 1 calc R U . . .
C25 C 0.8424(5) 0.3287(4) 0.2227(4) 0.0208(8) Uani 1 1 d . . . . .
H25 H 0.794556 0.219494 0.229657 0.025 Uiso 1 1 calc R U . . .
C26 C 0.6577(6) 0.7647(5) 0.2376(4) 0.0266(8) Uani 1 1 d . . . . .
H26A H 0.694799 0.841273 0.181060 0.040 Uiso 1 1 calc R U . . .
H26B H 0.672985 0.828090 0.335760 0.040 Uiso 1 1 calc R U . . .
H26C H 0.521601 0.719339 0.206493 0.040 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
S1 O3 1.450(2) . ?
S1 O2 1.455(3) . ?
S1 O4 1.458(2) . ?
S1 C20 1.779(4) . ?
O1 C2 1.367(4) . ?
O1 C1 1.433(4) . ?
N1 C17 1.346(5) . ?
N1 C16 1.356(5) . ?
N1 C19 1.470(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.370(5) . ?
C2 C3 1.412(5) . ?
C3 C4 1.357(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(5) . ?
C4 H4 0.9500 . ?
C5 C8 1.408(5) . ?
C5 C6 1.417(4) . ?
C6 C7 1.410(5) . ?
C6 C11 1.426(5) . ?
C7 H7 0.9500 . ?
C9 C8 1.378(5) . ?
C9 C10 1.422(5) . ?
C9 C12 1.460(5) . ?
C8 H8 0.9500 . ?
C10 C11 1.361(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.335(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.459(5) . ?
C13 H13 0.9500 . ?
C14 C18 1.397(5) . ?
C14 C15 1.403(5) . ?
C15 C16 1.365(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.363(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.389(5) . ?
C20 C21 1.392(5) . ?
C21 C22 1.383(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.395(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(5) . ?
C23 C26 1.507(5) . ?
C24 C25 1.388(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
O3 S1 O2 113.48(15) . . ?
O3 S1 O4 113.78(15) . . ?
O2 S1 O4 112.38(14) . . ?
O3 S1 C20 105.32(15) . . ?
O2 S1 C20 105.62(15) . . ?
O4 S1 C20 105.28(15) . . ?
C2 O1 C1 116.3(3) . . ?
C17 N1 C16 119.8(3) . . ?
C17 N1 C19 122.1(3) . . ?
C16 N1 C19 118.2(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 124.3(3) . . ?
O1 C2 C3 115.1(3) . . ?
C7 C2 C3 120.7(3) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C8 C5 C6 119.9(3) . . ?
C8 C5 C4 122.0(3) . . ?
C6 C5 C4 118.0(3) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 C11 121.4(3) . . ?
C5 C6 C11 118.0(3) . . ?
C2 C7 C6 119.2(3) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C8 C9 C10 118.8(3) . . ?
C8 C9 C12 118.4(3) . . ?
C10 C9 C12 122.7(3) . . ?
C9 C8 C5 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C5 C8 H8 119.4 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 C9 127.2(3) . . ?
C13 C12 H12 116.4 . . ?
C9 C12 H12 116.4 . . ?
C12 C13 C14 123.7(3) . . ?
C12 C13 H13 118.1 . . ?
C14 C13 H13 118.1 . . ?
C18 C14 C15 116.8(3) . . ?
C18 C14 C13 120.2(3) . . ?
C15 C14 C13 123.0(3) . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N1 C16 C15 120.6(3) . . ?
N1 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N1 C17 C18 121.5(3) . . ?
N1 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C14 120.5(3) . . ?
C17 C18 H18 119.8 . . ?
C14 C18 H18 119.8 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.7(3) . . ?
C25 C20 S1 122.1(3) . . ?
C21 C20 S1 119.1(3) . . ?
C22 C21 C20 120.7(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 119.0(3) . . ?
C24 C23 C26 121.2(3) . . ?
C22 C23 C26 119.8(3) . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_18132_1_a
_database_code_depnum_ccdc_archive 'CCDC 1867835'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2018-09-14 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N O, C6 H4 N O5 S'
_chemical_formula_sum            'C25 H22 N2 O6 S'
_chemical_formula_weight         478.50

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.1520(2)
_cell_length_b                   7.9596(3)
_cell_length_c                   9.8172(3)
_cell_angle_alpha                102.972(2)
_cell_angle_beta                 96.957(2)
_cell_angle_gamma                91.888(2)
_cell_volume                     539.55(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9808
_cell_measurement_theta_min      5.71
_cell_measurement_theta_max      68.23

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             250
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    1.743
_shelx_estimated_absorpt_T_min   0.640
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4820
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27337
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.663
_diffrn_reflns_theta_max         68.289
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             3810
_reflns_number_gt                3748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.935

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.0885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1776 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.006(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3810
_refine_ls_number_parameters     309
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.20567(8) 0.79821(7) 0.22061(6) 0.01620(15) Uani 1 1 d . . . . .
O1 O 1.3332(3) 0.0693(2) 0.6281(2) 0.0237(4) Uani 1 1 d . . . . .
N1 N -0.1607(3) 0.9236(3) 0.8213(2) 0.0216(5) Uani 1 1 d . . . . .
C1 C 1.3328(4) -0.0232(4) 0.4846(3) 0.0268(6) Uani 1 1 d . . . . .
H1A H 1.322221 0.057936 0.422756 0.040 Uiso 1 1 calc R U . . .
H1B H 1.225339 -0.108878 0.457618 0.040 Uiso 1 1 calc R U . . .
H1C H 1.450468 -0.081978 0.475521 0.040 Uiso 1 1 calc R U . . .
O2 O -0.3333(2) 0.7364(2) 0.0900(2) 0.0213(4) Uani 1 1 d . . . . .
N2 N 0.3575(3) 0.2530(3) 0.1640(2) 0.0209(5) Uani 1 1 d . . . . .
C2 C 1.1821(4) 0.1648(3) 0.6554(3) 0.0201(6) Uani 1 1 d . . . . .
C3 C 1.1862(4) 0.2540(3) 0.7978(3) 0.0206(6) Uani 1 1 d . . . . .
H3 H 1.290821 0.245982 0.865128 0.025 Uiso 1 1 calc R U . . .
O3 O -0.1038(3) 0.9613(2) 0.2269(2) 0.0214(4) Uani 1 1 d . . . . .
O4 O -0.2917(2) 0.7925(2) 0.3457(2) 0.0236(4) Uani 1 1 d . . . . .
C4 C 1.0411(4) 0.3511(3) 0.8388(3) 0.0216(6) Uani 1 1 d . . . . .
H4 H 1.045603 0.409902 0.934887 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8830(4) 0.3664(3) 0.7409(3) 0.0190(6) Uani 1 1 d . . . . .
O5 O 0.3054(3) 0.1089(3) 0.1733(3) 0.0335(5) Uani 1 1 d . . . . .
O6 O 0.5118(3) 0.2868(3) 0.1310(3) 0.0341(5) Uani 1 1 d . . . . .
C6 C 0.8810(4) 0.2776(3) 0.5972(3) 0.0183(5) Uani 1 1 d . . . . .
C8 C 0.7228(4) 0.2946(3) 0.4994(3) 0.0220(6) Uani 1 1 d . . . . .
H8 H 0.716752 0.234858 0.403443 0.026 Uiso 1 1 calc R U . . .
C7 C 1.0318(4) 0.1764(3) 0.5561(3) 0.0195(5) Uani 1 1 d . . . . .
H7 H 1.029953 0.116489 0.460552 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5800(4) 0.3947(3) 0.5407(3) 0.0224(6) Uani 1 1 d . . . . .
H9 H 0.477396 0.405411 0.472670 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5815(4) 0.4834(3) 0.6836(3) 0.0200(6) Uani 1 1 d . . . . .
C11 C 0.7321(4) 0.4659(3) 0.7812(3) 0.0203(5) Uani 1 1 d . . . . .
H11 H 0.733161 0.522335 0.877465 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4316(4) 0.5917(3) 0.7338(3) 0.0213(6) Uani 1 1 d . . . . .
H12 H 0.444884 0.641327 0.832170 0.026 Uiso 1 1 calc R U . . .
C13 C 0.2775(4) 0.6290(3) 0.6568(3) 0.0220(6) Uani 1 1 d . . . . .
H13 H 0.263172 0.584137 0.557632 0.026 Uiso 1 1 calc R U . . .
C14 C 0.1303(4) 0.7339(3) 0.7154(3) 0.0201(5) Uani 1 1 d . . . . .
C15 C 0.1387(4) 0.8121(3) 0.8597(3) 0.0214(6) Uani 1 1 d . . . . .
H15 H 0.246612 0.801446 0.923160 0.026 Uiso 1 1 calc R U . . .
C16 C -0.0070(4) 0.9031(3) 0.9091(3) 0.0214(6) Uani 1 1 d . . . . .
H16 H -0.000197 0.952959 1.007171 0.026 Uiso 1 1 calc R U . . .
C17 C -0.1714(4) 0.8528(4) 0.6817(3) 0.0227(6) Uani 1 1 d . . . . .
H17 H -0.278915 0.869060 0.620091 0.027 Uiso 1 1 calc R U . . .
C18 C -0.0305(4) 0.7585(3) 0.6278(3) 0.0229(6) Uani 1 1 d . . . . .
H18 H -0.041948 0.708808 0.529465 0.028 Uiso 1 1 calc R U . . .
C19 C -0.3149(4) 1.0226(4) 0.8814(3) 0.0273(6) Uani 1 1 d . . . . .
H19A H -0.419775 1.019751 0.806629 0.041 Uiso 1 1 calc R U . . .
H19B H -0.268303 1.142549 0.922862 0.041 Uiso 1 1 calc R U . . .
H19C H -0.358569 0.970896 0.954505 0.041 Uiso 1 1 calc R U . . .
C20 C -0.0289(4) 0.6429(3) 0.2138(3) 0.0165(5) Uani 1 1 d . . . . .
C21 C -0.0812(4) 0.4779(3) 0.2294(3) 0.0189(5) Uani 1 1 d . . . . .
H21 H -0.204869 0.453463 0.248671 0.023 Uiso 1 1 calc R U . . .
C22 C 0.0466(4) 0.3503(3) 0.2167(3) 0.0191(5) Uani 1 1 d . . . . .
H22 H 0.012520 0.237545 0.226168 0.023 Uiso 1 1 calc R U . . .
C23 C 0.2264(4) 0.3926(3) 0.1897(3) 0.0173(5) Uani 1 1 d . . . . .
C24 C 0.2844(4) 0.5557(3) 0.1787(3) 0.0184(5) Uani 1 1 d . . . . .
H24 H 0.409688 0.580865 0.162891 0.022 Uiso 1 1 calc R U . . .
C25 C 0.1539(4) 0.6818(3) 0.1915(3) 0.0171(5) Uani 1 1 d . . . . .
H25 H 0.189891 0.795293 0.184821 0.021 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
S1 O4 1.4472(18) . ?
S1 O3 1.4532(18) . ?
S1 O2 1.4569(19) . ?
S1 C20 1.793(3) . ?
O1 C2 1.361(3) . ?
O1 C1 1.435(3) . ?
N1 C16 1.351(4) . ?
N1 C17 1.351(4) . ?
N1 C19 1.480(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 O5 1.221(3) . ?
N2 O6 1.224(3) . ?
N2 C23 1.476(3) . ?
C2 C7 1.381(4) . ?
C2 C3 1.415(4) . ?
C3 C4 1.361(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(4) . ?
C4 H4 0.9500 . ?
C5 C11 1.403(4) . ?
C5 C6 1.427(4) . ?
C6 C7 1.412(4) . ?
C6 C8 1.423(4) . ?
C8 C9 1.360(4) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.421(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(4) . ?
C10 C12 1.460(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.340(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.458(4) . ?
C13 H13 0.9500 . ?
C14 C18 1.397(4) . ?
C14 C15 1.407(4) . ?
C15 C16 1.364(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.364(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.388(3) . ?
C20 C21 1.400(3) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(4) . ?
C24 C25 1.388(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
O4 S1 O3 114.29(11) . . ?
O4 S1 O2 113.45(11) . . ?
O3 S1 O2 113.15(11) . . ?
O4 S1 C20 105.16(11) . . ?
O3 S1 C20 105.10(11) . . ?
O2 S1 C20 104.44(11) . . ?
C2 O1 C1 116.1(2) . . ?
C16 N1 C17 119.7(2) . . ?
C16 N1 C19 118.7(2) . . ?
C17 N1 C19 121.6(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O5 N2 O6 123.2(2) . . ?
O5 N2 C23 118.5(2) . . ?
O6 N2 C23 118.2(2) . . ?
O1 C2 C7 124.6(2) . . ?
O1 C2 C3 114.8(2) . . ?
C7 C2 C3 120.5(2) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C11 C5 C4 122.1(2) . . ?
C11 C5 C6 119.9(2) . . ?
C4 C5 C6 118.0(2) . . ?
C7 C6 C8 122.1(2) . . ?
C7 C6 C5 120.1(2) . . ?
C8 C6 C5 117.7(2) . . ?
C9 C8 C6 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C6 C8 H8 119.4 . . ?
C2 C7 C6 119.7(2) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 C12 118.0(2) . . ?
C9 C10 C12 123.5(3) . . ?
C10 C11 C5 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C5 C11 H11 119.3 . . ?
C13 C12 C10 127.4(3) . . ?
C13 C12 H12 116.3 . . ?
C10 C12 H12 116.3 . . ?
C12 C13 C14 124.2(3) . . ?
C12 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C18 C14 C15 116.6(2) . . ?
C18 C14 C13 120.2(2) . . ?
C15 C14 C13 123.2(2) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N1 C16 C15 121.3(2) . . ?
N1 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
N1 C17 C18 121.1(2) . . ?
N1 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C14 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C14 C18 H18 119.6 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 120.2(2) . . ?
C25 C20 S1 121.85(19) . . ?
C21 C20 S1 117.95(19) . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 117.8(2) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C24 C23 C22 123.3(2) . . ?
C24 C23 N2 118.7(2) . . ?
C22 C23 N2 117.9(2) . . ?
C23 C24 C25 117.9(2) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 H24 121.1 . . ?
C20 C25 C24 120.4(2) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_18155_a
_database_code_depnum_ccdc_archive 'CCDC 1960841'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N O, C10 H7 O3 S'
_chemical_formula_sum            'C28 H27 N O4 S'
_chemical_formula_weight         473.56

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'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7501(6)
_cell_length_b                   10.9056(6)
_cell_length_c                   11.4648(6)
_cell_angle_alpha                77.261(3)
_cell_angle_beta                 79.382(4)
_cell_angle_gamma                81.917(3)
_cell_volume                     1162.32(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9715
_cell_measurement_theta_min      4.18
_cell_measurement_theta_max      68.33

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    1.530
_shelx_estimated_absorpt_T_min   0.541
_shelx_estimated_absorpt_T_max   0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4832
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45091
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.004
_diffrn_reflns_theta_max         68.295
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4229
_reflns_number_gt                4044
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.5219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4229
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.04815(3) 0.60217(3) 0.23124(2) 0.01349(10) Uani 1 1 d . . . . .
N1 N 0.62591(11) 0.32413(9) 0.08902(9) 0.0155(2) Uani 1 1 d . . . . .
O1 O 0.59437(9) 1.37680(8) 0.46225(8) 0.0195(2) Uani 1 1 d . . . . .
C1 C 0.70770(14) 1.44039(12) 0.47616(13) 0.0224(3) Uani 1 1 d . . . . .
H1A H 0.765287 1.465796 0.397018 0.034 Uiso 1 1 calc R U . . .
H1B H 0.765510 1.383287 0.531025 0.034 Uiso 1 1 calc R U . . .
H1C H 0.669747 1.515536 0.509934 0.034 Uiso 1 1 calc R U . . .
O2 O -0.05664(9) 0.63339(8) 0.33009(8) 0.0204(2) Uani 1 1 d . . . . .
C2 C 0.62752(13) 1.26861(11) 0.41875(11) 0.0158(3) Uani 1 1 d . . . . .
O3 O -0.00133(9) 0.63480(8) 0.11434(8) 0.01804(19) Uani 1 1 d . . . . .
C3 C 0.51291(13) 1.20659(12) 0.41362(11) 0.0167(3) Uani 1 1 d . . . . .
H3 H 0.420236 1.241851 0.438736 0.020 Uiso 1 1 calc R U . . .
C4 C 0.53358(13) 1.09514(11) 0.37251(11) 0.0166(3) Uani 1 1 d . . . . .
H4 H 0.454717 1.054139 0.370004 0.020 Uiso 1 1 calc R U . . .
O4 O 0.18254(9) 0.64856(8) 0.22638(8) 0.0198(2) Uani 1 1 d . . . . .
C5 C 0.66940(13) 1.04062(11) 0.33408(11) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.78198(13) 1.10504(12) 0.33824(11) 0.0176(3) Uani 1 1 d . . . . .
H6 H 0.874653 1.070746 0.311736 0.021 Uiso 1 1 calc R U . . .
C7 C 0.76288(13) 1.21779(12) 0.37991(11) 0.0171(3) Uani 1 1 d . . . . .
H7 H 0.841399 1.259557 0.381803 0.021 Uiso 1 1 calc R U . . .
C8 C 0.69596(13) 0.92177(12) 0.29121(11) 0.0176(3) Uani 1 1 d . . . . .
H8 H 0.791280 0.893030 0.266501 0.021 Uiso 1 1 calc R U . . .
C9 C 0.59914(14) 0.84875(12) 0.28314(11) 0.0173(3) Uani 1 1 d . . . . .
H9 H 0.502988 0.874660 0.307988 0.021 Uiso 1 1 calc R U . . .
C10 C 0.63485(13) 0.73347(11) 0.23862(11) 0.0167(3) Uani 1 1 d . . . . .
H10 H 0.731151 0.708185 0.213647 0.020 Uiso 1 1 calc R U . . .
C11 C 0.53924(13) 0.65904(12) 0.23028(11) 0.0170(3) Uani 1 1 d . . . . .
H11 H 0.443454 0.683559 0.257968 0.020 Uiso 1 1 calc R U . . .
C12 C 0.57206(13) 0.54431(11) 0.18211(10) 0.0150(2) Uani 1 1 d . . . . .
C13 C 0.46471(13) 0.47178(12) 0.18069(11) 0.0176(3) Uani 1 1 d . . . . .
H13 H 0.370586 0.498120 0.211837 0.021 Uiso 1 1 calc R U . . .
C14 C 0.49390(13) 0.36336(12) 0.13491(11) 0.0172(3) Uani 1 1 d . . . . .
H14 H 0.419760 0.315114 0.135584 0.021 Uiso 1 1 calc R U . . .
C15 C 0.70882(13) 0.50065(12) 0.13334(11) 0.0167(3) Uani 1 1 d . . . . .
H15 H 0.785160 0.546649 0.131842 0.020 Uiso 1 1 calc R U . . .
C16 C 0.73213(13) 0.39237(12) 0.08816(11) 0.0172(3) Uani 1 1 d . . . . .
H16 H 0.824986 0.364226 0.055365 0.021 Uiso 1 1 calc R U . . .
C17 C 0.66377(14) 0.20780(12) 0.03683(12) 0.0201(3) Uani 1 1 d . . . . .
H17A H 0.736029 0.152520 0.079814 0.024 Uiso 1 1 calc R U . . .
H17B H 0.706121 0.232395 -0.049218 0.024 Uiso 1 1 calc R U . . .
C18 C 0.54288(15) 0.13297(12) 0.04395(12) 0.0234(3) Uani 1 1 d . . . . .
H18A H 0.472770 0.185146 -0.002052 0.035 Uiso 1 1 calc R U . . .
H18B H 0.500166 0.107628 0.128788 0.035 Uiso 1 1 calc R U . . .
H18C H 0.577041 0.057435 0.009751 0.035 Uiso 1 1 calc R U . . .
C19 C 0.08250(12) 0.43343(11) 0.26234(11) 0.0142(2) Uani 1 1 d . . . . .
C20 C 0.08796(12) 0.36548(11) 0.17405(11) 0.0155(2) Uani 1 1 d . . . . .
H20 H 0.072716 0.408176 0.095099 0.019 Uiso 1 1 calc R U . . .
C21 C 0.11626(12) 0.23161(12) 0.19957(11) 0.0162(3) Uani 1 1 d . . . . .
C22 C 0.14009(13) 0.16922(12) 0.31827(12) 0.0174(3) Uani 1 1 d . . . . .
C23 C 0.13317(13) 0.24274(12) 0.40744(11) 0.0181(3) Uani 1 1 d . . . . .
H23 H 0.148628 0.201848 0.486820 0.022 Uiso 1 1 calc R U . . .
C24 C 0.10462(12) 0.37160(12) 0.38119(11) 0.0164(3) Uani 1 1 d . . . . .
H24 H 0.099630 0.419364 0.442122 0.020 Uiso 1 1 calc R U . . .
C25 C 0.11692(13) 0.15818(12) 0.11117(12) 0.0205(3) Uani 1 1 d . . . . .
H25 H 0.101564 0.198828 0.031697 0.025 Uiso 1 1 calc R U . . .
C26 C 0.13968(14) 0.02875(13) 0.14030(13) 0.0242(3) Uani 1 1 d . . . . .
H26 H 0.138535 -0.019521 0.080959 0.029 Uiso 1 1 calc R U . . .
C27 C 0.16477(14) -0.03353(12) 0.25725(14) 0.0247(3) Uani 1 1 d . . . . .
H27 H 0.181158 -0.123126 0.275973 0.030 Uiso 1 1 calc R U . . .
C28 C 0.16550(14) 0.03507(12) 0.34377(13) 0.0220(3) Uani 1 1 d . . . . .
H28 H 0.183261 -0.007601 0.422051 0.026 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
S1 O2 1.4456(9) . ?
S1 O4 1.4571(9) . ?
S1 O3 1.4612(9) . ?
S1 C19 1.7908(12) . ?
N1 C14 1.3458(17) . ?
N1 C16 1.3550(16) . ?
N1 C17 1.4918(15) . ?
O1 C2 1.3558(15) . ?
O1 C1 1.4340(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.3906(18) . ?
C2 C3 1.4015(17) . ?
C3 C4 1.3743(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4073(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3971(17) . ?
C5 C8 1.4587(17) . ?
C6 C7 1.3917(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.3454(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.4341(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3480(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.4491(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4022(17) . ?
C12 C15 1.4077(18) . ?
C13 C14 1.3707(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3657(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.5058(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.3698(17) . ?
C19 C24 1.4213(17) . ?
C20 C21 1.4218(17) . ?
C20 H20 0.9500 . ?
C21 C25 1.4222(18) . ?
C21 C22 1.4257(18) . ?
C22 C23 1.4189(18) . ?
C22 C28 1.4224(18) . ?
C23 C24 1.3701(18) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.3727(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.411(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.369(2) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

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
O2 S1 O4 113.30(5) . . ?
O2 S1 O3 113.41(5) . . ?
O4 S1 O3 112.61(5) . . ?
O2 S1 C19 106.02(5) . . ?
O4 S1 C19 105.16(5) . . ?
O3 S1 C19 105.41(5) . . ?
C14 N1 C16 119.72(10) . . ?
C14 N1 C17 123.45(10) . . ?
C16 N1 C17 116.83(10) . . ?
C2 O1 C1 117.65(10) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 125.22(11) . . ?
O1 C2 C3 115.22(11) . . ?
C7 C2 C3 119.55(11) . . ?
C4 C3 C2 120.49(11) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.23(11) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 117.31(11) . . ?
C6 C5 C8 119.74(11) . . ?
C4 C5 C8 122.95(11) . . ?
C7 C6 C5 122.18(12) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C2 C7 C6 119.23(11) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C5 126.60(12) . . ?
C9 C8 H8 116.7 . . ?
C5 C8 H8 116.7 . . ?
C8 C9 C10 122.82(12) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C11 C10 C9 123.58(12) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C10 C11 C12 124.71(12) . . ?
C10 C11 H11 117.6 . . ?
C12 C11 H11 117.6 . . ?
C13 C12 C15 116.64(11) . . ?
C13 C12 C11 120.09(11) . . ?
C15 C12 C11 123.26(11) . . ?
C14 C13 C12 120.81(11) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N1 C14 C13 121.06(11) . . ?
N1 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C12 120.22(11) . . ?
C16 C15 H15 119.9 . . ?
C12 C15 H15 119.9 . . ?
N1 C16 C15 121.54(11) . . ?
N1 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
N1 C17 C18 114.73(11) . . ?
N1 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
N1 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 120.72(11) . . ?
C20 C19 S1 121.05(9) . . ?
C24 C19 S1 118.23(9) . . ?
C19 C20 C21 120.56(11) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C25 121.80(12) . . ?
C20 C21 C22 118.95(11) . . ?
C25 C21 C22 119.22(11) . . ?
C23 C22 C28 122.49(12) . . ?
C23 C22 C21 118.87(11) . . ?
C28 C22 C21 118.61(12) . . ?
C24 C23 C22 121.24(11) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C19 119.65(11) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C26 C25 C21 120.21(12) . . ?
C26 C25 H25 119.9 . . ?
C21 C25 H25 119.9 . . ?
C25 C26 C27 120.86(12) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C28 C27 C26 120.05(12) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C22 121.04(12) . . ?
C27 C28 H28 119.5 . . ?
C22 C28 H28 119.5 . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_18143_a
_database_code_depnum_ccdc_archive 'CCDC 1960837'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_SHFSU01_18143_a             
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: Due to the whole molecule disorder present the refinement does not converge tightly.
;
_vrf_PLAT080_18143_a             
;
PROBLEM: Maximum Shift/Error ............................       0.78 Why ?
RESPONSE: Due to the whole molecule disorder present the refinement does not converge tightly.
;
# Added during the CSD deposition process: Tuesday 22 October 2019 07:27 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H30 N2 O4 S'
_chemical_formula_weight         478.59

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1028(5)
_cell_length_b                   10.3242(6)
_cell_length_c                   13.4088(7)
_cell_angle_alpha                101.539(2)
_cell_angle_beta                 108.960(2)
_cell_angle_gamma                106.377(2)
_cell_volume                     1201.70(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      68.38

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.494
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4389
_exptl_absorpt_correction_T_max  0.521
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20694
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.681
_diffrn_reflns_theta_max         68.408
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4406
_reflns_number_gt                4195
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device,Highly disorder structure
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0865P)²+1.5320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4406
_refine_ls_number_parameters     503
_refine_ls_number_restraints     1403
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.784
_refine_ls_shift/su_mean         0.014

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
N1 N 1.243(2) 0.8047(17) 0.0520(17) 0.047(3) Uani 0.584(7) 1 d D U P A 1
C1 C 1.275(2) 0.6766(17) 0.0291(17) 0.076(5) Uani 0.584(7) 1 d D U P A 1
H1A H 1.181255 0.596005 -0.021370 0.114 Uiso 0.584(7) 1 calc R U P A 1
H1B H 1.317996 0.657736 0.098939 0.114 Uiso 0.584(7) 1 calc R U P A 1
H1C H 1.347122 0.689342 -0.005749 0.114 Uiso 0.584(7) 1 calc R U P A 1
C2 C 1.307(2) 0.9207(17) 0.0154(18) 0.067(4) Uani 0.584(7) 1 d D U P A 1
H2A H 1.374853 0.898424 -0.016924 0.100 Uiso 0.584(7) 1 calc R U P A 1
H2B H 1.362811 1.008573 0.079140 0.100 Uiso 0.584(7) 1 calc R U P A 1
H2C H 1.225166 0.933494 -0.040794 0.100 Uiso 0.584(7) 1 calc R U P A 1
C3 C 1.136(4) 0.806(2) 0.094(3) 0.028(3) Uani 0.584(7) 1 d D U P A 1
C4 C 1.092(3) 0.9234(19) 0.113(2) 0.029(2) Uani 0.584(7) 1 d D U P A 1
H4 H 1.137714 1.006003 0.097062 0.035 Uiso 0.584(7) 1 calc R U P A 1
C5 C 0.9824(13) 0.9201(11) 0.1541(11) 0.0254(18) Uani 0.584(7) 1 d D U P A 1
H5 H 0.953688 1.000266 0.163898 0.030 Uiso 0.584(7) 1 calc R U P A 1
C6 C 0.9130(9) 0.8050(8) 0.1818(7) 0.0241(16) Uani 0.584(7) 1 d D U P A 1
C7 C 0.9608(14) 0.6905(10) 0.1683(11) 0.0279(18) Uani 0.584(7) 1 d D U P A 1
H7 H 0.919198 0.611438 0.189686 0.034 Uiso 0.584(7) 1 calc R U P A 1
C8 C 1.067(2) 0.6897(17) 0.125(2) 0.029(2) Uani 0.584(7) 1 d D U P A 1
H8 H 1.095287 0.609009 0.114961 0.035 Uiso 0.584(7) 1 calc R U P A 1
C9 C 0.7948(5) 0.8038(6) 0.2219(3) 0.0304(12) Uani 0.584(7) 1 d D U P A 1
H9 H 0.748552 0.719916 0.236203 0.036 Uiso 0.584(7) 1 calc R U P A 1
C10 C 0.7445(5) 0.9121(5) 0.2408(3) 0.0315(12) Uani 0.584(7) 1 d D U P A 1
H10 H 0.790865 0.995559 0.226012 0.038 Uiso 0.584(7) 1 calc R U P A 1
C11 C 0.6265(5) 0.9130(8) 0.2815(4) 0.0294(12) Uani 0.584(7) 1 d D U P A 1
C12 C 0.5557(7) 0.8064(7) 0.3153(5) 0.0298(12) Uani 0.584(7) 1 d D U P A 1
H12 H 0.584859 0.726479 0.314396 0.036 Uiso 0.584(7) 1 calc R U P A 1
C13 C 0.4382(12) 0.8140(10) 0.3518(10) 0.0304(13) Uani 0.584(7) 1 d D U P A 1
C14 C 0.404(2) 0.9392(17) 0.356(2) 0.0324(11) Uani 0.584(7) 1 d D U P A 1
C15 C 0.4746(11) 1.0483(9) 0.3222(10) 0.0304(15) Uani 0.584(7) 1 d D U P A 1
H15 H 0.447726 1.129518 0.323649 0.036 Uiso 0.584(7) 1 calc R U P A 1
C16 C 0.5845(5) 1.0338(7) 0.2864(4) 0.0292(11) Uani 0.584(7) 1 d D U P A 1
H16 H 0.634565 1.107798 0.263997 0.035 Uiso 0.584(7) 1 calc R U P A 1
C17 C 0.3639(13) 0.7107(12) 0.3847(10) 0.0367(19) Uani 0.584(7) 1 d D U P A 1
H17 H 0.386027 0.626932 0.382352 0.044 Uiso 0.584(7) 1 calc R U P A 1
C18 C 0.2614(15) 0.7283(14) 0.4195(13) 0.035(2) Uani 0.584(7) 1 d D U P A 1
H18 H 0.212145 0.655732 0.443448 0.042 Uiso 0.584(7) 1 calc R U P A 1
C19 C 0.285(4) 0.948(3) 0.391(4) 0.0293(13) Uani 0.584(7) 1 d D U P A 1
H19 H 0.253271 1.026330 0.390514 0.035 Uiso 0.584(7) 1 calc R U P A 1
N2 N 0.220(2) 0.8436(18) 0.424(2) 0.0227(19) Uani 0.584(7) 1 d D U P A 1
C20 C 0.0987(18) 0.8466(15) 0.4608(16) 0.029(2) Uani 0.584(7) 1 d D U P A 1
H20A H 0.079550 0.933889 0.457321 0.043 Uiso 0.584(7) 1 calc R U P A 1
H20B H 0.128959 0.844656 0.537517 0.043 Uiso 0.584(7) 1 calc R U P A 1
H20C H 0.006649 0.763367 0.412049 0.043 Uiso 0.584(7) 1 calc R U P A 1
N1A N 1.249(3) 0.794(2) 0.065(2) 0.028(3) Uani 0.416(7) 1 d D U P A 2
C1A C 1.277(2) 0.6628(16) 0.0461(17) 0.032(2) Uani 0.416(7) 1 d D U P A 2
H1AA H 1.200253 0.593840 -0.025329 0.048 Uiso 0.416(7) 1 calc R U P A 2
H1AB H 1.273226 0.623268 0.106210 0.048 Uiso 0.416(7) 1 calc R U P A 2
H1AC H 1.377309 0.682544 0.044759 0.048 Uiso 0.416(7) 1 calc R U P A 2
C2A C 1.312(3) 0.8921(18) 0.0131(19) 0.035(3) Uani 0.416(7) 1 d D U P A 2
H2AA H 1.403511 0.881125 0.009230 0.052 Uiso 0.416(7) 1 calc R U P A 2
H2AB H 1.336737 0.990213 0.057389 0.052 Uiso 0.416(7) 1 calc R U P A 2
H2AC H 1.237543 0.871232 -0.062308 0.052 Uiso 0.416(7) 1 calc R U P A 2
C3A C 1.141(5) 0.810(3) 0.101(5) 0.024(3) Uani 0.416(7) 1 d D U P A 2
C4A C 1.108(4) 0.935(2) 0.104(3) 0.026(3) Uani 0.416(7) 1 d D U P A 2
H4A H 1.157117 1.004288 0.077628 0.032 Uiso 0.416(7) 1 calc R U P A 2
C5A C 1.0037(18) 0.9556(14) 0.1444(15) 0.023(2) Uani 0.416(7) 1 d D U P A 2
H5A H 0.986711 1.042116 0.148920 0.028 Uiso 0.416(7) 1 calc R U P A 2
C6A C 0.9240(12) 0.8558(12) 0.1786(10) 0.024(2) Uani 0.416(7) 1 d D U P A 2
C7A C 0.9526(16) 0.7316(14) 0.1736(14) 0.023(2) Uani 0.416(7) 1 d D U P A 2
H7A H 0.896524 0.660396 0.195256 0.027 Uiso 0.416(7) 1 calc R U P A 2
C8A C 1.061(3) 0.708(2) 0.138(3) 0.025(3) Uani 0.416(7) 1 d D U P A 2
H8A H 1.080809 0.623822 0.138722 0.030 Uiso 0.416(7) 1 calc R U P A 2
C9A C 0.8164(7) 0.8912(9) 0.2192(5) 0.0341(16) Uani 0.416(7) 1 d D U P A 2
H9A H 0.809964 0.981067 0.218413 0.041 Uiso 0.416(7) 1 calc R U P A 2
C10A C 0.7285(6) 0.8161(6) 0.2563(5) 0.0267(15) Uani 0.416(7) 1 d D U P A 2
H10A H 0.738038 0.727320 0.257066 0.032 Uiso 0.416(7) 1 calc R U P A 2
C11A C 0.6211(7) 0.8420(9) 0.2957(5) 0.0207(14) Uani 0.416(7) 1 d D U P A 2
C12A C 0.5374(10) 0.7519(11) 0.3369(8) 0.0437(19) Uani 0.416(7) 1 d D U P A 2
H12A H 0.553732 0.667129 0.343294 0.052 Uiso 0.416(7) 1 calc R U P A 2
C13A C 0.4223(18) 0.7887(16) 0.3707(15) 0.0304(13) Uani 0.416(7) 1 d D U P A 2
C14A C 0.398(4) 0.914(3) 0.358(4) 0.0324(11) Uani 0.416(7) 1 d D U P A 2
C15A C 0.4862(17) 1.0088(15) 0.3224(15) 0.038(2) Uani 0.416(7) 1 d D U P A 2
H15A H 0.476957 1.097146 0.319526 0.045 Uiso 0.416(7) 1 calc R U P A 2
C16A C 0.5862(9) 0.9649(12) 0.2924(6) 0.0370(18) Uani 0.416(7) 1 d D U P A 2
H16A H 0.642232 1.027004 0.264361 0.044 Uiso 0.416(7) 1 calc R U P A 2
C17A C 0.3343(18) 0.6980(15) 0.4045(14) 0.033(2) Uani 0.416(7) 1 d D U P A 2
H17A H 0.347510 0.611212 0.408098 0.040 Uiso 0.416(7) 1 calc R U P A 2
C18A C 0.2311(19) 0.7289(16) 0.4322(17) 0.025(2) Uani 0.416(7) 1 d D U P A 2
H18A H 0.170723 0.663587 0.455695 0.030 Uiso 0.416(7) 1 calc R U P A 2
C19A C 0.288(6) 0.947(4) 0.395(6) 0.0293(13) Uani 0.416(7) 1 d D U P A 2
H19A H 0.273468 1.034000 0.395665 0.035 Uiso 0.416(7) 1 calc R U P A 2
N2A N 0.208(3) 0.853(3) 0.428(3) 0.020(2) Uani 0.416(7) 1 d D U P A 2
C20A C 0.093(3) 0.879(2) 0.465(2) 0.025(3) Uani 0.416(7) 1 d D U P A 2
H20D H 0.089869 0.972059 0.462359 0.038 Uiso 0.416(7) 1 calc R U P A 2
H20E H 0.117961 0.877210 0.542098 0.038 Uiso 0.416(7) 1 calc R U P A 2
H20F H -0.006297 0.804216 0.416632 0.038 Uiso 0.416(7) 1 calc R U P A 2
S1 S 0.12076(7) 0.30001(6) 0.39346(5) 0.0300(2) Uani 1 1 d . U . B 2
O1 O 0.1530(3) 0.1913(2) 0.4380(2) 0.0527(6) Uani 1 1 d . U . B 2
O2 O -0.0374(2) 0.2603(2) 0.32191(18) 0.0450(5) Uani 1 1 d . U . B 2
O3 O 0.1790(2) 0.4377(2) 0.47834(17) 0.0448(5) Uani 1 1 d . U . B 2
C21 C 0.4725(3) 0.3926(4) 0.1060(3) 0.0484(7) Uani 1 1 d . U . B 2
H21A H 0.419665 0.315924 0.034278 0.073 Uiso 1 1 calc R U . B 2
H21B H 0.573463 0.392870 0.144014 0.073 Uiso 1 1 calc R U . B 2
H21C H 0.481218 0.484425 0.093658 0.073 Uiso 1 1 calc R U . B 2
C22 C 0.3848(3) 0.3686(3) 0.1771(2) 0.0315(5) Uani 1 1 d . U . B 2
C23 C 0.4546(3) 0.3737(3) 0.2866(2) 0.0358(6) Uani 1 1 d . U . B 2
H23 H 0.559923 0.393358 0.317645 0.043 Uiso 1 1 calc R U . B 2
C24 C 0.3732(3) 0.3506(3) 0.3510(2) 0.0316(5) Uani 1 1 d . U . B 2
H24 H 0.422118 0.352473 0.425248 0.038 Uiso 1 1 calc R U . B 2
C25 C 0.2210(3) 0.3250(2) 0.30743(19) 0.0247(5) Uani 1 1 d . U . B 2
C26 C 0.1501(3) 0.3230(3) 0.1998(2) 0.0309(5) Uani 1 1 d . U . B 2
H26 H 0.045757 0.307608 0.170206 0.037 Uiso 1 1 calc R U . B 2
C27 C 0.2318(3) 0.3437(3) 0.1350(2) 0.0334(6) Uani 1 1 d . U . B 2
H27 H 0.182271 0.340649 0.060560 0.040 Uiso 1 1 calc R U . B 2
O1S O 0.1535(3) 0.5140(3) 0.68321(18) 0.0463(5) Uani 1 1 d D . . C 2
HO1S H 0.157(4) 0.487(4) 0.622(2) 0.064(12) Uiso 1 1 d D . . D 2
HO2S H 0.118(4) 0.577(3) 0.678(3) 0.068(12) Uiso 1 1 d D . . E 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
N1 C3 1.373(8) . ?
N1 C1 1.446(10) . ?
N1 C2 1.447(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.411(9) . ?
C3 C8 1.414(9) . ?
C4 C5 1.381(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(8) . ?
C6 C9 1.458(7) . ?
C7 C8 1.384(9) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.364(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.466(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(8) . ?
C11 C16 1.423(8) . ?
C12 C13 1.439(8) . ?
C12 H12 0.9500 . ?
C13 C17 1.359(9) . ?
C13 C14 1.423(8) . ?
C14 C15 1.396(8) . ?
C14 C19 1.447(8) . ?
C15 C16 1.377(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.307(9) . ?
C17 H17 0.9500 . ?
C18 N2 1.363(9) . ?
C18 H18 0.9500 . ?
C19 N2 1.325(9) . ?
C19 H19 0.9500 . ?
N2 C20 1.473(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1A C3A 1.365(11) . ?
N1A C1A 1.449(11) . ?
N1A C2A 1.457(10) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A C4A 1.416(12) . ?
C3A C8A 1.419(11) . ?
C4A C5A 1.378(11) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.372(10) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.386(11) . ?
C6A C9A 1.463(9) . ?
C7A C8A 1.384(12) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C9A C10A 1.300(10) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.418(8) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.396(9) . ?
C11A C16A 1.414(10) . ?
C12A C13A 1.492(11) . ?
C12A H12A 0.9500 . ?
C13A C17A 1.354(11) . ?
C13A C14A 1.417(11) . ?
C14A C15A 1.394(11) . ?
C14A C19A 1.452(12) . ?
C15A C16A 1.356(11) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A C18A 1.312(11) . ?
C17A H17A 0.9500 . ?
C18A N2A 1.377(11) . ?
C18A H18A 0.9500 . ?
C19A N2A 1.325(11) . ?
C19A H19A 0.9500 . ?
N2A C20A 1.469(11) . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
S1 O1 1.439(2) . ?
S1 O3 1.452(2) . ?
S1 O2 1.455(2) . ?
S1 C25 1.776(2) . ?
C21 C22 1.508(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.386(4) . ?
C22 C23 1.389(4) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(3) . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
O1S HO1S 0.830(19) . ?
O1S HO2S 0.829(19) . ?

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
C3 N1 C1 118.9(11) . . ?
C3 N1 C2 120.8(10) . . ?
C1 N1 C2 119.6(10) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 122.6(9) . . ?
N1 C3 C8 121.2(9) . . ?
C4 C3 C8 116.1(8) . . ?
C5 C4 C3 121.0(9) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 122.8(8) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C7 116.8(6) . . ?
C5 C6 C9 121.1(6) . . ?
C7 C6 C9 122.1(6) . . ?
C8 C7 C6 121.5(8) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C3 121.7(9) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
C10 C9 C6 126.1(5) . . ?
C10 C9 H9 117.0 . . ?
C6 C9 H9 117.0 . . ?
C9 C10 C11 126.8(5) . . ?
C9 C10 H10 116.6 . . ?
C11 C10 H10 116.6 . . ?
C12 C11 C16 118.7(4) . . ?
C12 C11 C10 124.5(6) . . ?
C16 C11 C10 116.7(5) . . ?
C11 C12 C13 121.0(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C17 C13 C14 119.8(6) . . ?
C17 C13 C12 123.2(6) . . ?
C14 C13 C12 117.0(6) . . ?
C15 C14 C13 122.7(7) . . ?
C15 C14 C19 119.3(8) . . ?
C13 C14 C19 117.8(7) . . ?
C16 C15 C14 117.5(6) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C11 122.9(5) . . ?
C15 C16 H16 118.5 . . ?
C11 C16 H16 118.5 . . ?
C18 C17 C13 119.0(8) . . ?
C18 C17 H17 120.5 . . ?
C13 C17 H17 120.5 . . ?
C17 C18 N2 124.5(9) . . ?
C17 C18 H18 117.7 . . ?
N2 C18 H18 117.7 . . ?
N2 C19 C14 118.2(9) . . ?
N2 C19 H19 120.8 . . ?
C14 C19 H19 120.8 . . ?
C19 N2 C18 120.5(9) . . ?
C19 N2 C20 120.8(9) . . ?
C18 N2 C20 118.7(8) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3A N1A C1A 123.2(12) . . ?
C3A N1A C2A 119.9(13) . . ?
C1A N1A C2A 114.6(10) . . ?
N1A C1A H1AA 109.5 . . ?
N1A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
N1A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N1A C2A H2AA 109.5 . . ?
N1A C2A H2AB 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
N1A C2A H2AC 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N1A C3A C4A 119.8(12) . . ?
N1A C3A C8A 123.0(12) . . ?
C4A C3A C8A 117.1(11) . . ?
C5A C4A C3A 120.5(12) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.7 . . ?
C6A C5A C4A 122.2(11) . . ?
C6A C5A H5A 118.9 . . ?
C4A C5A H5A 118.9 . . ?
C5A C6A C7A 118.0(8) . . ?
C5A C6A C9A 116.6(9) . . ?
C7A C6A C9A 125.3(9) . . ?
C8A C7A C6A 121.9(10) . . ?
C8A C7A H7A 119.0 . . ?
C6A C7A H7A 119.0 . . ?
C7A C8A C3A 120.1(12) . . ?
C7A C8A H8A 120.0 . . ?
C3A C8A H8A 120.0 . . ?
C10A C9A C6A 128.6(8) . . ?
C10A C9A H9A 115.7 . . ?
C6A C9A H9A 115.7 . . ?
C9A C10A C11A 132.0(7) . . ?
C9A C10A H10A 114.0 . . ?
C11A C10A H10A 114.0 . . ?
C12A C11A C16A 113.8(7) . . ?
C12A C11A C10A 125.5(7) . . ?
C16A C11A C10A 120.7(7) . . ?
C11A C12A C13A 120.0(8) . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C17A C13A C14A 120.6(9) . . ?
C17A C13A C12A 120.4(9) . . ?
C14A C13A C12A 118.7(9) . . ?
C15A C14A C13A 121.8(10) . . ?
C15A C14A C19A 121.6(11) . . ?
C13A C14A C19A 116.3(11) . . ?
C16A C15A C14A 114.8(10) . . ?
C16A C15A H15A 122.6 . . ?
C14A C15A H15A 122.6 . . ?
C15A C16A C11A 130.8(9) . . ?
C15A C16A H16A 114.6 . . ?
C11A C16A H16A 114.6 . . ?
C18A C17A C13A 120.5(9) . . ?
C18A C17A H17A 119.7 . . ?
C13A C17A H17A 119.7 . . ?
C17A C18A N2A 121.9(10) . . ?
C17A C18A H18A 119.0 . . ?
N2A C18A H18A 119.0 . . ?
N2A C19A C14A 119.0(13) . . ?
N2A C19A H19A 120.4 . . ?
C14A C19A H19A 120.4 . . ?
C19A N2A C18A 121.3(12) . . ?
C19A N2A C20A 121.7(12) . . ?
C18A N2A C20A 117.1(11) . . ?
N2A C20A H20D 109.5 . . ?
N2A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
N2A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
O1 S1 O3 113.02(14) . . ?
O1 S1 O2 114.16(14) . . ?
O3 S1 O2 111.24(13) . . ?
O1 S1 C25 106.27(11) . . ?
O3 S1 C25 105.38(11) . . ?
O2 S1 C25 105.98(11) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 118.2(2) . . ?
C27 C22 C21 120.4(2) . . ?
C23 C22 C21 121.3(2) . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.0(2) . . ?
C24 C25 S1 118.77(18) . . ?
C26 C25 S1 121.19(18) . . ?
C25 C26 C27 119.7(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 121.1(2) . . ?
C22 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
HO1S O1S HO2S 105(4) . . ?

_refine_diff_density_max         1.070
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_18148_a
_database_code_depnum_ccdc_archive 'CCDC 1960838'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 N O, C10 H7 O3 S'
_chemical_formula_sum            'C27 H25 N O4 S'
_chemical_formula_weight         459.54

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6916(4)
_cell_length_b                   10.6359(5)
_cell_length_c                   11.1871(5)
_cell_angle_alpha                78.992(2)
_cell_angle_beta                 79.976(2)
_cell_angle_gamma                89.669(2)
_cell_volume                     1114.21(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      4.24
_cell_measurement_theta_max      68.47

_exptl_crystal_description       Blocks
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.224
_exptl_absorpt_coefficient_mu    1.580
_shelx_estimated_absorpt_T_min   0.591
_shelx_estimated_absorpt_T_max   0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4813
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49750
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.090
_diffrn_reflns_theta_max         68.571
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4089
_reflns_number_gt                3997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.5071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4089
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.95347(3) -0.10821(3) 0.27701(2) 0.01266(10) Uani 1 1 d . . . . .
N1 N 0.59136(11) -0.22566(10) 0.56839(9) 0.0171(2) Uani 1 1 d . . . . .
O1 O 0.57426(9) 0.85766(8) 0.95574(8) 0.0197(2) Uani 1 1 d . . . . .
C1 C 0.68626(14) 0.93280(13) 0.97823(13) 0.0231(3) Uani 1 1 d . . . . .
H1A H 0.753119 0.959933 0.901081 0.035 Uiso 1 1 calc R U . . .
H1B H 0.734131 0.881229 1.040192 0.035 Uiso 1 1 calc R U . . .
H1C H 0.647965 1.008513 1.008766 0.035 Uiso 1 1 calc R U . . .
O2 O 0.81239(9) -0.16248(8) 0.29155(8) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.60896(13) 0.74832(12) 0.91305(11) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.74490(13) 0.70588(12) 0.88665(12) 0.0177(3) Uani 1 1 d . . . . .
H3 H 0.822058 0.753685 0.898816 0.021 Uiso 1 1 calc R U . . .
O3 O 1.00774(9) -0.13082(8) 0.39278(8) 0.01758(19) Uani 1 1 d . . . . .
C4 C 0.76627(13) 0.59284(12) 0.84233(11) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.859359 0.564740 0.823462 0.021 Uiso 1 1 calc R U . . .
O4 O 1.04997(9) -0.14215(8) 0.17481(8) 0.0198(2) Uani 1 1 d . . . . .
C5 C 0.65575(13) 0.51884(12) 0.82447(11) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.51925(13) 0.56453(12) 0.85149(11) 0.0183(3) Uani 1 1 d . . . . .
H6 H 0.441799 0.516894 0.839630 0.022 Uiso 1 1 calc R U . . .
C7 C 0.49631(13) 0.67665(12) 0.89463(11) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.403497 0.705832 0.912108 0.021 Uiso 1 1 calc R U . . .
C8 C 0.68567(13) 0.39928(12) 0.78108(11) 0.0183(3) Uani 1 1 d . . . . .
H8 H 0.781637 0.379662 0.760749 0.022 Uiso 1 1 calc R U . . .
C9 C 0.59105(13) 0.31393(12) 0.76692(11) 0.0186(3) Uani 1 1 d . . . . .
H9 H 0.494449 0.331511 0.786890 0.022 Uiso 1 1 calc R U . . .
C10 C 0.62784(13) 0.19779(12) 0.72333(11) 0.0179(3) Uani 1 1 d . . . . .
H10 H 0.724080 0.179288 0.702573 0.022 Uiso 1 1 calc R U . . .
C11 C 0.52971(13) 0.11400(12) 0.71095(11) 0.0173(3) Uani 1 1 d . . . . .
H11 H 0.434473 0.134148 0.734659 0.021 Uiso 1 1 calc R U . . .
C12 C 0.55597(13) -0.00346(12) 0.66500(11) 0.0155(3) Uani 1 1 d . . . . .
C13 C 0.69051(13) -0.04658(12) 0.62353(11) 0.0167(3) Uani 1 1 d . . . . .
H13 H 0.771448 0.000747 0.628553 0.020 Uiso 1 1 calc R U . . .
C14 C 0.70485(13) -0.15594(12) 0.57626(11) 0.0173(3) Uani 1 1 d . . . . .
H14 H 0.796063 -0.183744 0.548342 0.021 Uiso 1 1 calc R U . . .
C15 C 0.46089(13) -0.18826(12) 0.60936(11) 0.0182(3) Uani 1 1 d . . . . .
H15 H 0.381946 -0.238573 0.604882 0.022 Uiso 1 1 calc R U . . .
C16 C 0.44100(13) -0.07939(12) 0.65702(11) 0.0176(3) Uani 1 1 d . . . . .
H16 H 0.348494 -0.054639 0.685092 0.021 Uiso 1 1 calc R U . . .
C17 C 0.61111(15) -0.34192(12) 0.51492(13) 0.0225(3) Uani 1 1 d . . . . .
H17A H 0.678034 -0.323064 0.436894 0.034 Uiso 1 1 calc R U . . .
H17B H 0.521086 -0.370543 0.499354 0.034 Uiso 1 1 calc R U . . .
H17C H 0.647361 -0.409611 0.572884 0.034 Uiso 1 1 calc R U . . .
C18 C 0.93273(12) 0.06084(11) 0.23884(11) 0.0132(2) Uani 1 1 d . . . . .
C19 C 0.91028(12) 0.11494(12) 0.11796(11) 0.0149(2) Uani 1 1 d . . . . .
H19 H 0.912010 0.062340 0.058001 0.018 Uiso 1 1 calc R U . . .
C20 C 0.88617(12) 0.24278(12) 0.08785(11) 0.0160(3) Uani 1 1 d . . . . .
H20 H 0.871473 0.278524 0.006649 0.019 Uiso 1 1 calc R U . . .
C21 C 0.88276(12) 0.32304(12) 0.17625(11) 0.0153(2) Uani 1 1 d . . . . .
C22 C 0.90699(12) 0.26847(12) 0.29700(11) 0.0146(2) Uani 1 1 d . . . . .
C23 C 0.93208(12) 0.13523(12) 0.32629(11) 0.0142(2) Uani 1 1 d . . . . .
H23 H 0.948411 0.097762 0.406564 0.017 Uiso 1 1 calc R U . . .
C24 C 0.85938(13) 0.45633(12) 0.14753(12) 0.0191(3) Uani 1 1 d . . . . .
H24 H 0.841622 0.493461 0.067626 0.023 Uiso 1 1 calc R U . . .
C25 C 0.86198(14) 0.53228(13) 0.23305(13) 0.0217(3) Uani 1 1 d . . . . .
H25 H 0.847285 0.621580 0.212029 0.026 Uiso 1 1 calc R U . . .
C26 C 0.88654(14) 0.47775(13) 0.35266(13) 0.0214(3) Uani 1 1 d . . . . .
H26 H 0.888240 0.530979 0.411635 0.026 Uiso 1 1 calc R U . . .
C27 C 0.90800(13) 0.34885(12) 0.38485(12) 0.0181(3) Uani 1 1 d . . . . .
H27 H 0.923519 0.313390 0.465858 0.022 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
S1 O4 1.4469(9) . ?
S1 O2 1.4578(9) . ?
S1 O3 1.4589(9) . ?
S1 C18 1.7855(12) . ?
N1 C15 1.3525(17) . ?
N1 C14 1.3548(16) . ?
N1 C17 1.4708(16) . ?
O1 C2 1.3583(15) . ?
O1 C1 1.4360(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.3912(18) . ?
C2 C7 1.4012(18) . ?
C3 C4 1.3868(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3968(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.4096(18) . ?
C5 C8 1.4557(18) . ?
C6 C7 1.3725(19) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.3436(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.4336(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3493(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.4441(18) . ?
C11 H11 0.9500 . ?
C12 C16 1.4052(17) . ?
C12 C13 1.4105(17) . ?
C13 C14 1.3636(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3636(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.3698(17) . ?
C18 C19 1.4181(17) . ?
C19 C20 1.3658(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.4208(18) . ?
C20 H20 0.9500 . ?
C21 C24 1.4184(18) . ?
C21 C22 1.4234(17) . ?
C22 C27 1.4217(18) . ?
C22 C23 1.4217(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3684(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.4129(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.3736(19) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
O4 S1 O2 113.56(5) . . ?
O4 S1 O3 113.30(5) . . ?
O2 S1 O3 112.48(5) . . ?
O4 S1 C18 106.44(5) . . ?
O2 S1 C18 104.39(5) . . ?
O3 S1 C18 105.72(5) . . ?
C15 N1 C14 120.08(11) . . ?
C15 N1 C17 120.36(11) . . ?
C14 N1 C17 119.56(11) . . ?
C2 O1 C1 117.29(10) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.83(11) . . ?
O1 C2 C7 115.44(11) . . ?
C3 C2 C7 119.73(12) . . ?
C4 C3 C2 119.11(12) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 122.32(12) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 117.29(12) . . ?
C4 C5 C8 119.32(11) . . ?
C6 C5 C8 123.39(12) . . ?
C7 C6 C5 121.14(12) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 120.40(11) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C9 C8 C5 126.47(12) . . ?
C9 C8 H8 116.8 . . ?
C5 C8 H8 116.8 . . ?
C8 C9 C10 123.61(12) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C11 C10 C9 121.89(12) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 126.08(12) . . ?
C10 C11 H11 117.0 . . ?
C12 C11 H11 117.0 . . ?
C16 C12 C13 116.85(12) . . ?
C16 C12 C11 118.70(11) . . ?
C13 C12 C11 124.43(11) . . ?
C14 C13 C12 120.25(11) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N1 C14 C13 121.18(11) . . ?
N1 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
N1 C15 C16 120.97(11) . . ?
N1 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C12 120.65(12) . . ?
C15 C16 H16 119.7 . . ?
C12 C16 H16 119.7 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 120.97(11) . . ?
C23 C18 S1 120.54(9) . . ?
C19 C18 S1 118.42(9) . . ?
C20 C19 C18 119.91(11) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.93(11) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C24 C21 C20 122.29(11) . . ?
C24 C21 C22 118.80(11) . . ?
C20 C21 C22 118.89(11) . . ?
C27 C22 C23 121.51(11) . . ?
C27 C22 C21 119.25(11) . . ?
C23 C22 C21 119.23(11) . . ?
C18 C23 C22 120.05(11) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C21 121.06(12) . . ?
C25 C24 H24 119.5 . . ?
C21 C24 H24 119.5 . . ?
C24 C25 C26 119.93(12) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 120.91(12) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C22 120.04(12) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_18153_a
_database_code_depnum_ccdc_archive 'CCDC 1960840'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N O, C6 H4 N O5 S'
_chemical_formula_sum            'C24 H24 N2 O6 S'
_chemical_formula_weight         468.51

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   6.7363(3)
_cell_length_b                   8.1126(4)
_cell_length_c                   39.4951(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2158.36(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      68.28

_exptl_crystal_description       Needles
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.373
_exptl_crystal_size_min          0.136
_exptl_absorpt_coefficient_mu    1.726
_shelx_estimated_absorpt_T_min   0.539
_shelx_estimated_absorpt_T_max   0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4433
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22725
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         68.274
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3952
_reflns_number_gt                3897
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0267P)²+0.8001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1586 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.017(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3952
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 -0.31054(7) 0.92374(6) 0.56108(2) 0.01447(13) Uani 1 1 d . . . . .
O1 O 1.3376(3) 0.1659(2) 0.73883(4) 0.0238(4) Uani 1 1 d . . . . .
N1 N -0.1567(3) 0.4740(2) 0.53850(4) 0.0148(4) Uani 1 1 d . . . . .
C1 C 1.3658(4) 0.0329(3) 0.76223(6) 0.0273(5) Uani 1 1 d . . . . .
H1A H 1.353427 -0.072376 0.750247 0.041 Uiso 1 1 calc R U . . .
H1B H 1.265078 0.039135 0.780082 0.041 Uiso 1 1 calc R U . . .
H1C H 1.498281 0.041015 0.772359 0.041 Uiso 1 1 calc R U . . .
O2 O -0.1875(3) 0.9623(2) 0.53198(4) 0.0243(4) Uani 1 1 d . . . . .
N2 N 0.2447(3) 0.7864(2) 0.67644(5) 0.0189(4) Uani 1 1 d . . . . .
C2 C 1.1620(4) 0.1724(3) 0.72183(5) 0.0179(5) Uani 1 1 d . . . . .
O3 O -0.4318(2) 1.0604(2) 0.57285(4) 0.0219(4) Uani 1 1 d . . . . .
C3 C 1.0054(3) 0.0641(3) 0.72604(5) 0.0189(5) Uani 1 1 d . . . . .
H3 H 1.014738 -0.023954 0.741819 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8340(3) 0.0855(3) 0.70690(5) 0.0184(4) Uani 1 1 d . . . . .
H4 H 0.726692 0.010896 0.709859 0.022 Uiso 1 1 calc R U . . .
O4 O -0.4237(2) 0.77209(19) 0.55708(4) 0.0207(3) Uani 1 1 d . . . . .
C5 C 0.8150(3) 0.2137(3) 0.68340(5) 0.0158(4) Uani 1 1 d . . . . .
O5 O 0.4159(3) 0.8397(2) 0.67519(4) 0.0291(4) Uani 1 1 d . . . . .
O6 O 0.1811(3) 0.7043(2) 0.70008(4) 0.0265(4) Uani 1 1 d . . . . .
C6 C 0.9759(3) 0.3224(3) 0.68005(5) 0.0173(5) Uani 1 1 d . . . . .
H6 H 0.966858 0.411576 0.664529 0.021 Uiso 1 1 calc R U . . .
C7 C 1.1459(3) 0.3026(3) 0.69876(5) 0.0181(5) Uani 1 1 d . . . . .
H7 H 1.253114 0.377496 0.696026 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6320(3) 0.2301(3) 0.66389(5) 0.0182(5) Uani 1 1 d . . . . .
H8 H 0.536376 0.145045 0.666547 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5844(4) 0.3536(3) 0.64245(5) 0.0171(5) Uani 1 1 d . . . . .
H9 H 0.674989 0.442349 0.639740 0.021 Uiso 1 1 calc R U . . .
C10 C 0.4017(3) 0.3561(3) 0.62355(5) 0.0164(5) Uani 1 1 d . . . . .
H10 H 0.309455 0.269339 0.627256 0.020 Uiso 1 1 calc R U . . .
C11 C 0.3534(3) 0.4738(3) 0.60090(5) 0.0163(4) Uani 1 1 d . . . . .
H11 H 0.443413 0.562780 0.597989 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1729(3) 0.4741(2) 0.58059(5) 0.0144(4) Uani 1 1 d . . . . .
C13 C 0.0094(3) 0.3726(3) 0.58701(5) 0.0160(5) Uani 1 1 d . . . . .
H13 H 0.010396 0.301878 0.606181 0.019 Uiso 1 1 calc R U . . .
C14 C -0.1520(3) 0.3741(3) 0.56596(5) 0.0160(4) Uani 1 1 d . . . . .
H14 H -0.261828 0.304375 0.570656 0.019 Uiso 1 1 calc R U . . .
C15 C -0.0039(3) 0.5753(3) 0.53175(5) 0.0163(4) Uani 1 1 d . . . . .
H15 H -0.009763 0.645363 0.512498 0.020 Uiso 1 1 calc R U . . .
C16 C 0.1602(3) 0.5790(3) 0.55222(5) 0.0162(4) Uani 1 1 d . . . . .
H16 H 0.265977 0.652659 0.547278 0.019 Uiso 1 1 calc R U . . .
C17 C -0.3259(3) 0.4621(3) 0.51456(5) 0.0184(4) Uani 1 1 d . . . . .
H17A H -0.344021 0.568865 0.502809 0.022 Uiso 1 1 calc R U . . .
H17B H -0.449204 0.437155 0.527198 0.022 Uiso 1 1 calc R U . . .
C18 C -0.2868(3) 0.3275(3) 0.48879(5) 0.0171(4) Uani 1 1 d . . . . .
H18A H -0.398604 0.320995 0.472969 0.026 Uiso 1 1 calc R U . . .
H18B H -0.271577 0.221664 0.500468 0.026 Uiso 1 1 calc R U . . .
H18C H -0.164943 0.352797 0.476270 0.026 Uiso 1 1 calc R U . . .
C19 C -0.1414(3) 0.8840(2) 0.59506(5) 0.0147(4) Uani 1 1 d . . . . .
C20 C -0.2133(3) 0.8096(3) 0.62439(5) 0.0178(5) Uani 1 1 d . . . . .
H20 H -0.349489 0.780033 0.625929 0.021 Uiso 1 1 calc R U . . .
C21 C -0.0874(3) 0.7786(3) 0.65124(5) 0.0176(4) Uani 1 1 d . . . . .
H21 H -0.135147 0.727998 0.671339 0.021 Uiso 1 1 calc R U . . .
C22 C 0.1105(3) 0.8233(3) 0.64812(5) 0.0159(4) Uani 1 1 d . . . . .
C23 C 0.1852(3) 0.8993(3) 0.61944(5) 0.0173(4) Uani 1 1 d . . . . .
H23 H 0.320946 0.930624 0.618209 0.021 Uiso 1 1 calc R U . . .
C24 C 0.0580(3) 0.9287(3) 0.59265(5) 0.0165(4) Uani 1 1 d . . . . .
H24 H 0.106470 0.979233 0.572591 0.020 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
S1 O2 1.4509(16) . ?
S1 O3 1.4532(17) . ?
S1 O4 1.4557(16) . ?
S1 C19 1.790(2) . ?
O1 C2 1.361(3) . ?
O1 C1 1.433(3) . ?
N1 C15 1.344(3) . ?
N1 C14 1.354(3) . ?
N1 C17 1.484(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 O6 1.224(3) . ?
N2 O5 1.233(3) . ?
N2 C22 1.469(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.399(3) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(3) . ?
C5 C8 1.460(3) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.350(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.439(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.348(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.457(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(3) . ?
C12 C16 1.410(3) . ?
C13 C14 1.369(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.370(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.516(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.394(3) . ?
C19 C24 1.395(3) . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(3) . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
O2 S1 O3 114.19(10) . . ?
O2 S1 O4 113.29(10) . . ?
O3 S1 O4 112.65(10) . . ?
O2 S1 C19 105.61(10) . . ?
O3 S1 C19 104.78(9) . . ?
O4 S1 C19 105.22(10) . . ?
C2 O1 C1 117.55(18) . . ?
C15 N1 C14 120.46(18) . . ?
C15 N1 C17 120.11(17) . . ?
C14 N1 C17 119.30(18) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6 N2 O5 123.3(2) . . ?
O6 N2 C22 118.45(19) . . ?
O5 N2 C22 118.28(19) . . ?
O1 C2 C3 125.37(19) . . ?
O1 C2 C7 114.7(2) . . ?
C3 C2 C7 119.9(2) . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 C8 119.7(2) . . ?
C6 C5 C8 122.99(19) . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C5 126.8(2) . . ?
C9 C8 H8 116.6 . . ?
C5 C8 H8 116.6 . . ?
C8 C9 C10 122.6(2) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C11 C10 C9 124.1(2) . . ?
C11 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C10 C11 C12 124.6(2) . . ?
C10 C11 H11 117.7 . . ?
C12 C11 H11 117.7 . . ?
C13 C12 C16 116.9(2) . . ?
C13 C12 C11 123.79(19) . . ?
C16 C12 C11 119.3(2) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N1 C14 C13 120.7(2) . . ?
N1 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N1 C15 C16 120.96(19) . . ?
N1 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C12 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
C12 C16 H16 119.8 . . ?
N1 C17 C18 109.94(17) . . ?
N1 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
N1 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 120.3(2) . . ?
C20 C19 S1 118.69(17) . . ?
C24 C19 S1 121.03(16) . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 118.4(2) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C23 C22 C21 122.6(2) . . ?
C23 C22 N2 119.3(2) . . ?
C21 C22 N2 118.1(2) . . ?
C24 C23 C22 118.5(2) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C19 120.0(2) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_18144_a
_database_code_depnum_ccdc_archive 'CCDC 1960848'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N O, C6 H4 N O5 S'
_chemical_formula_sum            'C25 H22 N2 O6 S'
_chemical_formula_weight         478.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.6595(7)
_cell_length_b                   6.4297(2)
_cell_length_c                   17.8266(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.903(2)
_cell_angle_gamma                90
_cell_volume                     2177.57(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4929
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      67.90

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.727
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4368
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25706
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         69.732
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4016
_reflns_number_gt                3319
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.7493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4016
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1015
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.38897(2) 0.31248(7) 0.58240(3) 0.01847(13) Uani 1 1 d . . . . .
N1 N 0.56274(8) 0.0030(2) 0.64824(9) 0.0189(3) Uani 1 1 d . . . . .
O1 O 0.98076(7) 1.5581(2) 0.88886(8) 0.0268(3) Uani 1 1 d . . . . .
C1 C 0.99042(10) 1.6845(3) 0.82618(12) 0.0276(5) Uani 1 1 d . . . . .
H1A H 1.008375 1.598479 0.790130 0.041 Uiso 1 1 calc R U . . .
H1B H 1.024221 1.795482 0.846827 0.041 Uiso 1 1 calc R U . . .
H1C H 0.945261 1.746016 0.798748 0.041 Uiso 1 1 calc R U . . .
O2 O 0.42862(7) 0.2702(2) 0.52562(8) 0.0279(3) Uani 1 1 d . . . . .
N2 N 0.13535(8) 0.3457(3) 0.40544(9) 0.0240(4) Uani 1 1 d . . . . .
C2 C 0.93755(10) 1.3893(3) 0.86924(11) 0.0220(4) Uani 1 1 d . . . . .
O3 O 0.41651(7) 0.2076(2) 0.65595(8) 0.0257(3) Uani 1 1 d . . . . .
C3 C 0.89307(9) 1.3565(3) 0.79703(11) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.891377 1.453510 0.756381 0.026 Uiso 1 1 calc R U . . .
C4 C 0.84971(9) 1.1771(3) 0.78353(11) 0.0193(4) Uani 1 1 d . . . . .
O4 O 0.37536(7) 0.5322(2) 0.58981(8) 0.0237(3) Uani 1 1 d . . . . .
C5 C 0.85308(9) 1.0303(3) 0.84398(11) 0.0201(4) Uani 1 1 d . . . . .
O5 O 0.14277(7) 0.5354(2) 0.40575(9) 0.0307(3) Uani 1 1 d . . . . .
C6 C 0.90079(10) 1.0696(3) 0.91693(11) 0.0248(4) Uani 1 1 d . . . . .
H6 H 0.904477 0.972259 0.957859 0.030 Uiso 1 1 calc R U . . .
O6 O 0.08630(7) 0.2545(3) 0.36173(9) 0.0387(4) Uani 1 1 d . . . . .
C7 C 0.94149(10) 1.2440(3) 0.92965(11) 0.0248(4) Uani 1 1 d . . . . .
H7 H 0.972616 1.267905 0.979284 0.030 Uiso 1 1 calc R U . . .
C8 C 0.80259(9) 1.1383(3) 0.71001(11) 0.0215(4) Uani 1 1 d . . . . .
H8 H 0.800056 1.234185 0.668819 0.026 Uiso 1 1 calc R U . . .
C9 C 0.76099(9) 0.9661(3) 0.69755(11) 0.0212(4) Uani 1 1 d . . . . .
H9 H 0.729407 0.944918 0.647986 0.025 Uiso 1 1 calc R U . . .
C10 C 0.76384(9) 0.8175(3) 0.75714(11) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.80956(10) 0.8519(3) 0.82890(11) 0.0219(4) Uani 1 1 d . . . . .
H11 H 0.811887 0.753432 0.869206 0.026 Uiso 1 1 calc R U . . .
C12 C 0.72036(10) 0.6304(3) 0.74474(11) 0.0221(4) Uani 1 1 d . . . . .
H12 H 0.722663 0.545650 0.788983 0.026 Uiso 1 1 calc R U . . .
C13 C 0.67760(10) 0.5653(3) 0.67777(11) 0.0213(4) Uani 1 1 d . . . . .
H13 H 0.673702 0.649578 0.633092 0.026 Uiso 1 1 calc R U . . .
C14 C 0.63669(9) 0.3743(3) 0.66874(11) 0.0199(4) Uani 1 1 d . . . . .
C15 C 0.62171(10) 0.2679(3) 0.73128(11) 0.0258(4) Uani 1 1 d . . . . .
H15 H 0.637138 0.323930 0.782148 0.031 Uiso 1 1 calc R U . . .
C16 C 0.58527(10) 0.0849(3) 0.72008(11) 0.0242(4) Uani 1 1 d . . . . .
H16 H 0.575702 0.014737 0.763147 0.029 Uiso 1 1 calc R U . . .
C17 C 0.61098(9) 0.2859(3) 0.59512(11) 0.0205(4) Uani 1 1 d . . . . .
H17 H 0.618425 0.354484 0.550702 0.025 Uiso 1 1 calc R U . . .
C18 C 0.57523(9) 0.1014(3) 0.58678(11) 0.0200(4) Uani 1 1 d . . . . .
H18 H 0.558943 0.041852 0.536582 0.024 Uiso 1 1 calc R U . . .
C19 C 0.51933(10) -0.1880(3) 0.63733(12) 0.0235(4) Uani 1 1 d . . . . .
H19A H 0.469595 -0.150245 0.628470 0.035 Uiso 1 1 calc R U . . .
H19B H 0.533541 -0.275022 0.683882 0.035 Uiso 1 1 calc R U . . .
H19C H 0.526092 -0.265296 0.592418 0.035 Uiso 1 1 calc R U . . .
C20 C 0.30494(9) 0.1980(3) 0.54154(10) 0.0177(4) Uani 1 1 d . . . . .
C21 C 0.25261(9) 0.3173(3) 0.49338(10) 0.0194(4) Uani 1 1 d . . . . .
H21 H 0.260334 0.459566 0.483781 0.023 Uiso 1 1 calc R U . . .
C22 C 0.18880(9) 0.2223(3) 0.45978(11) 0.0207(4) Uani 1 1 d . . . . .
C23 C 0.17384(10) 0.0188(3) 0.47393(11) 0.0243(4) Uani 1 1 d . . . . .
H23 H 0.128997 -0.040076 0.450975 0.029 Uiso 1 1 calc R U . . .
C24 C 0.22653(10) -0.0967(3) 0.52283(11) 0.0244(4) Uani 1 1 d . . . . .
H24 H 0.217613 -0.236724 0.534418 0.029 Uiso 1 1 calc R U . . .
C25 C 0.29214(10) -0.0100(3) 0.55502(11) 0.0218(4) Uani 1 1 d . . . . .
H25 H 0.328523 -0.092868 0.586401 0.026 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
S1 O3 1.4497(13) . ?
S1 O4 1.4503(14) . ?
S1 O2 1.4532(14) . ?
S1 C20 1.7841(18) . ?
N1 C18 1.341(2) . ?
N1 C16 1.350(2) . ?
N1 C19 1.480(2) . ?
O1 C2 1.367(2) . ?
O1 C1 1.433(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 O6 1.222(2) . ?
N2 O5 1.228(2) . ?
N2 C22 1.466(2) . ?
C2 C3 1.374(3) . ?
C2 C7 1.413(3) . ?
C3 C4 1.418(3) . ?
C3 H3 0.9500 . ?
C4 C8 1.419(3) . ?
C4 C5 1.421(3) . ?
C5 C11 1.415(3) . ?
C5 C6 1.417(3) . ?
C6 C7 1.362(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.361(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.419(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(3) . ?
C10 C12 1.459(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.338(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.454(3) . ?
C13 H13 0.9500 . ?
C14 C17 1.400(3) . ?
C14 C15 1.402(3) . ?
C15 C16 1.365(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.367(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.389(3) . ?
C20 C25 1.393(3) . ?
C21 C22 1.385(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
O3 S1 O4 113.93(8) . . ?
O3 S1 O2 113.60(8) . . ?
O4 S1 O2 112.98(9) . . ?
O3 S1 C20 105.58(8) . . ?
O4 S1 C20 105.43(8) . . ?
O2 S1 C20 104.15(8) . . ?
C18 N1 C16 120.44(17) . . ?
C18 N1 C19 120.31(16) . . ?
C16 N1 C19 119.08(16) . . ?
C2 O1 C1 116.68(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6 N2 O5 123.53(17) . . ?
O6 N2 C22 118.39(17) . . ?
O5 N2 C22 118.07(16) . . ?
O1 C2 C3 124.44(18) . . ?
O1 C2 C7 114.92(17) . . ?
C3 C2 C7 120.64(18) . . ?
C2 C3 C4 119.61(18) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C8 121.40(18) . . ?
C3 C4 C5 120.20(17) . . ?
C8 C4 C5 118.40(17) . . ?
C11 C5 C6 122.98(18) . . ?
C11 C5 C4 119.11(17) . . ?
C6 C5 C4 117.91(18) . . ?
C7 C6 C5 121.44(19) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 120.18(18) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C4 121.07(18) . . ?
C9 C8 H8 119.5 . . ?
C4 C8 H8 119.5 . . ?
C8 C9 C10 121.30(17) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 118.49(18) . . ?
C11 C10 C12 119.31(18) . . ?
C9 C10 C12 122.20(17) . . ?
C10 C11 C5 121.63(18) . . ?
C10 C11 H11 119.2 . . ?
C5 C11 H11 119.2 . . ?
C13 C12 C10 127.02(19) . . ?
C13 C12 H12 116.5 . . ?
C10 C12 H12 116.5 . . ?
C12 C13 C14 124.44(19) . . ?
C12 C13 H13 117.8 . . ?
C14 C13 H13 117.8 . . ?
C17 C14 C15 116.64(18) . . ?
C17 C14 C13 120.17(18) . . ?
C15 C14 C13 123.18(17) . . ?
C16 C15 C14 120.91(18) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
N1 C16 C15 120.45(18) . . ?
N1 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C14 120.37(18) . . ?
C18 C17 H17 119.8 . . ?
C14 C17 H17 119.8 . . ?
N1 C18 C17 121.15(17) . . ?
N1 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 119.92(17) . . ?
C21 C20 S1 119.03(15) . . ?
C25 C20 S1 121.01(14) . . ?
C22 C21 C20 117.90(18) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
C23 C22 C21 123.48(18) . . ?
C23 C22 N2 118.97(17) . . ?
C21 C22 N2 117.54(17) . . ?
C22 C23 C24 117.63(18) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C23 C24 C25 120.67(19) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 120.30(18) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_19130_a
_database_code_depnum_ccdc_archive 'CCDC 1962606'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 N O4 S'
_chemical_formula_weight         423.51

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8320(6)
_cell_length_b                   6.6710(5)
_cell_length_c                   36.675(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.170(5)
_cell_angle_gamma                90
_cell_volume                     2152.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6601
_cell_measurement_theta_min      4.84
_cell_measurement_theta_max      68.05

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    1.586
_shelx_estimated_absorpt_T_min   0.717
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4518
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18602
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         68.321
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3937
_reflns_number_gt                3451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+1.2230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3937
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.75086(5) -0.70600(7) 0.80792(2) 0.01907(14) Uani 1 1 d . . . . .
O1 O 0.71569(16) 1.6714(2) 0.53227(4) 0.0308(3) Uani 1 1 d . . . . .
N1 N 0.74608(16) 0.0067(2) 0.72106(4) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.5928(2) 1.8033(3) 0.52142(6) 0.0311(5) Uani 1 1 d . . . . .
H1A H 0.629240 1.912479 0.506609 0.047 Uiso 1 1 calc R U . . .
H1B H 0.552001 1.859193 0.543233 0.047 Uiso 1 1 calc R U . . .
H1C H 0.512617 1.729035 0.506962 0.047 Uiso 1 1 calc R U . . .
O2 O 0.87864(14) -0.8081(2) 0.79381(3) 0.0235(3) Uani 1 1 d . . . . .
C2 C 0.6842(2) 1.5106(3) 0.55355(5) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.5444(2) 1.4693(3) 0.56599(5) 0.0247(4) Uani 1 1 d . . . . .
H3 H 0.460660 1.556505 0.560228 0.030 Uiso 1 1 calc R U . . .
O3 O 0.74238(15) -0.4942(2) 0.79900(4) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.60751(14) -0.8123(2) 0.80000(3) 0.0254(3) Uani 1 1 d . . . . .
C4 C 0.5278(2) 1.2984(3) 0.58706(5) 0.0236(4) Uani 1 1 d . . . . .
H4 H 0.431254 1.270977 0.595472 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6469(2) 1.1662(3) 0.59626(5) 0.0200(4) Uani 1 1 d . . . . .
C6 C 0.7882(2) 1.2140(3) 0.58371(5) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.872735 1.128512 0.589764 0.028 Uiso 1 1 calc R U . . .
C7 C 0.8065(2) 1.3818(3) 0.56286(5) 0.0259(4) Uani 1 1 d . . . . .
H7 H 0.903214 1.410698 0.554683 0.031 Uiso 1 1 calc R U . . .
C8 C 0.6230(2) 0.9870(3) 0.61784(5) 0.0212(4) Uani 1 1 d . . . . .
H8 H 0.523184 0.966424 0.624826 0.025 Uiso 1 1 calc R U . . .
C9 C 0.7277(2) 0.8479(3) 0.62890(5) 0.0201(4) Uani 1 1 d . . . . .
H9 H 0.828494 0.865409 0.622353 0.024 Uiso 1 1 calc R U . . .
C10 C 0.6951(2) 0.6744(3) 0.65006(5) 0.0194(4) Uani 1 1 d . . . . .
H10 H 0.593811 0.653164 0.655962 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8026(2) 0.5412(3) 0.66180(5) 0.0192(4) Uani 1 1 d . . . . .
H11 H 0.903196 0.567034 0.655786 0.023 Uiso 1 1 calc R U . . .
C12 C 0.7792(2) 0.3608(3) 0.68288(4) 0.0173(4) Uani 1 1 d . . . . .
C13 C 0.6372(2) 0.3002(3) 0.69351(5) 0.0190(4) Uani 1 1 d . . . . .
H13 H 0.550221 0.381800 0.687709 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6236(2) 0.1243(3) 0.71217(5) 0.0183(4) Uani 1 1 d . . . . .
H14 H 0.526800 0.084389 0.718958 0.022 Uiso 1 1 calc R U . . .
C15 C 0.8847(2) 0.0613(3) 0.71199(4) 0.0192(4) Uani 1 1 d . . . . .
H15 H 0.970053 -0.021580 0.718761 0.023 Uiso 1 1 calc R U . . .
C16 C 0.9036(2) 0.2354(3) 0.69308(5) 0.0189(4) Uani 1 1 d . . . . .
H16 H 1.001968 0.271710 0.686800 0.023 Uiso 1 1 calc R U . . .
C17 C 0.7289(2) -0.1770(3) 0.74273(5) 0.0214(4) Uani 1 1 d . . . . .
H17A H 0.636441 -0.247906 0.733279 0.032 Uiso 1 1 calc R U . . .
H17B H 0.721653 -0.140996 0.768418 0.032 Uiso 1 1 calc R U . . .
H17C H 0.817324 -0.263959 0.740875 0.032 Uiso 1 1 calc R U . . .
C18 C 0.78767(19) -0.7164(3) 0.85666(5) 0.0189(4) Uani 1 1 d . . . . .
C19 C 0.8126(2) -0.5434(3) 0.87723(5) 0.0251(4) Uani 1 1 d . . . . .
H19 H 0.810299 -0.416182 0.865559 0.030 Uiso 1 1 calc R U . . .
C20 C 0.8410(2) -0.5573(3) 0.91528(5) 0.0290(5) Uani 1 1 d . . . . .
H20 H 0.857482 -0.438243 0.929295 0.035 Uiso 1 1 calc R U . . .
C21 C 0.8457(2) -0.7406(3) 0.93291(5) 0.0288(5) Uani 1 1 d . . . . .
C22 C 0.8201(2) -0.9121(3) 0.91170(5) 0.0281(4) Uani 1 1 d . . . . .
H22 H 0.822590 -1.039398 0.923340 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7909(2) -0.9017(3) 0.87398(5) 0.0234(4) Uani 1 1 d . . . . .
H23 H 0.773205 -1.020779 0.860038 0.028 Uiso 1 1 calc R U . . .
C24 C 0.8800(3) -0.7557(4) 0.97418(6) 0.0429(6) Uani 1 1 d . . . . .
H24A H 0.989210 -0.777061 0.980082 0.064 Uiso 1 1 calc R U . . .
H24B H 0.823536 -0.868580 0.983420 0.064 Uiso 1 1 calc R U . . .
H24C H 0.849251 -0.631271 0.985649 0.064 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
S1 O3 1.4510(14) . ?
S1 O2 1.4527(13) . ?
S1 O4 1.4575(13) . ?
S1 C18 1.7894(18) . ?
O1 C2 1.370(2) . ?
O1 C1 1.426(2) . ?
N1 C15 1.347(2) . ?
N1 C14 1.352(2) . ?
N1 C17 1.475(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.381(3) . ?
C2 C7 1.398(3) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 C8 1.459(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.346(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.437(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.343(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.455(2) . ?
C11 H11 0.9500 . ?
C12 C16 1.405(2) . ?
C12 C13 1.405(2) . ?
C13 C14 1.369(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.385(3) . ?
C18 C23 1.389(3) . ?
C19 C20 1.398(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(3) . ?
C21 C24 1.520(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
O3 S1 O2 113.72(8) . . ?
O3 S1 O4 113.76(8) . . ?
O2 S1 O4 112.94(8) . . ?
O3 S1 C18 105.31(9) . . ?
O2 S1 C18 105.10(8) . . ?
O4 S1 C18 104.86(8) . . ?
C2 O1 C1 116.98(15) . . ?
C15 N1 C14 120.54(15) . . ?
C15 N1 C17 119.82(15) . . ?
C14 N1 C17 119.55(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.30(17) . . ?
O1 C2 C7 115.33(17) . . ?
C3 C2 C7 119.36(17) . . ?
C2 C3 C4 119.27(18) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 122.56(18) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 116.83(17) . . ?
C4 C5 C8 120.52(17) . . ?
C6 C5 C8 122.65(17) . . ?
C7 C6 C5 121.34(18) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 120.62(18) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C9 C8 C5 126.80(17) . . ?
C9 C8 H8 116.6 . . ?
C5 C8 H8 116.6 . . ?
C8 C9 C10 123.54(17) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C11 C10 C9 122.42(17) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 125.96(17) . . ?
C10 C11 H11 117.0 . . ?
C12 C11 H11 117.0 . . ?
C16 C12 C13 116.80(16) . . ?
C16 C12 C11 119.23(16) . . ?
C13 C12 C11 123.96(16) . . ?
C14 C13 C12 120.39(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N1 C14 C13 120.90(16) . . ?
N1 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N1 C15 C16 120.61(16) . . ?
N1 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C12 120.74(16) . . ?
C15 C16 H16 119.6 . . ?
C12 C16 H16 119.6 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 119.78(17) . . ?
C19 C18 S1 121.14(14) . . ?
C23 C18 S1 119.08(14) . . ?
C18 C19 C20 119.58(19) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 121.35(19) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 118.01(18) . . ?
C20 C21 C24 121.3(2) . . ?
C22 C21 C24 120.7(2) . . ?
C23 C22 C21 121.59(19) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C18 119.69(19) . . ?
C22 C23 H23 120.2 . . ?
C18 C23 H23 120.2 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_18161_a
_database_code_depnum_ccdc_archive 'CCDC 1960847'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Cl N O4 S'
_chemical_formula_weight         457.95

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   6.8059(2)
_cell_length_b                   7.9943(3)
_cell_length_c                   39.4102(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2144.25(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      68.31

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.756
_shelx_estimated_absorpt_T_min   0.599
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4552
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24305
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         4.488
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3930
_reflns_number_gt                3790
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.4210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.023(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3930
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 -0.28354(8) 0.07834(7) 0.43766(2) 0.01631(14) Uani 1 1 d . . . . .
Cl1 Cl 0.32591(10) 0.20506(9) 0.32051(2) 0.02872(17) Uani 1 1 d . . . . .
O1 O 1.3452(3) 0.8180(2) 0.26017(5) 0.0251(4) Uani 1 1 d . . . . .
N1 N -0.1322(3) 0.5224(2) 0.46214(5) 0.0162(4) Uani 1 1 d . . . . .
C1 C 1.3725(4) 0.9503(3) 0.23622(7) 0.0274(6) Uani 1 1 d . . . . .
H1A H 1.507711 0.947724 0.227678 0.041 Uiso 1 1 calc R U . . .
H1B H 1.347693 1.058021 0.247292 0.041 Uiso 1 1 calc R U . . .
H1C H 1.280868 0.935878 0.217260 0.041 Uiso 1 1 calc R U . . .
O2 O -0.4022(3) -0.0633(2) 0.42670(5) 0.0227(4) Uani 1 1 d . . . . .
C2 C 1.1695(4) 0.8114(3) 0.27660(6) 0.0200(5) Uani 1 1 d . . . . .
C3 C 1.1528(4) 0.6847(3) 0.30098(6) 0.0198(5) Uani 1 1 d . . . . .
H3 H 1.259251 0.610003 0.304661 0.024 Uiso 1 1 calc R U . . .
O3 O -0.1667(3) 0.0446(2) 0.46777(5) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.9830(4) 0.6679(3) 0.31961(6) 0.0185(5) Uani 1 1 d . . . . .
H4 H 0.973932 0.581619 0.336113 0.022 Uiso 1 1 calc R U . . .
O4 O -0.3973(3) 0.2322(2) 0.44003(5) 0.0220(4) Uani 1 1 d . . . . .
C5 C 0.8220(4) 0.7764(3) 0.31468(6) 0.0185(5) Uani 1 1 d . . . . .
C6 C 0.8420(4) 0.9004(3) 0.28985(6) 0.0221(5) Uani 1 1 d . . . . .
H6 H 0.735492 0.974769 0.285902 0.027 Uiso 1 1 calc R U . . .
C7 C 1.0120(4) 0.9183(3) 0.27081(6) 0.0219(5) Uani 1 1 d . . . . .
H7 H 1.020779 1.002903 0.253951 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5944(4) 0.6432(3) 0.35684(6) 0.0185(5) Uani 1 1 d . . . . .
H9 H 0.684389 0.553909 0.360202 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6417(4) 0.7641(3) 0.33434(6) 0.0204(5) Uani 1 1 d . . . . .
H8 H 0.547308 0.850077 0.331007 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4143(4) 0.6433(3) 0.37596(6) 0.0193(5) Uani 1 1 d . . . . .
H10 H 0.323076 0.731336 0.372217 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3687(4) 0.5247(3) 0.39889(6) 0.0176(5) Uani 1 1 d . . . . .
H11 H 0.458385 0.434685 0.401659 0.021 Uiso 1 1 calc R U . . .
C12 C 0.1925(4) 0.5243(3) 0.41972(6) 0.0165(5) Uani 1 1 d . . . . .
C13 C 0.1829(4) 0.4205(3) 0.44839(6) 0.0174(5) Uani 1 1 d . . . . .
H13 H 0.289277 0.347641 0.453418 0.021 Uiso 1 1 calc R U . . .
C14 C 0.0214(4) 0.4231(3) 0.46923(6) 0.0178(5) Uani 1 1 d . . . . .
H14 H 0.018240 0.353990 0.488833 0.021 Uiso 1 1 calc R U . . .
C15 C -0.1311(4) 0.6211(3) 0.43433(6) 0.0174(5) Uani 1 1 d . . . . .
H15 H -0.241984 0.689281 0.429486 0.021 Uiso 1 1 calc R U . . .
C16 C 0.0275(4) 0.6242(3) 0.41305(6) 0.0174(5) Uani 1 1 d . . . . .
H16 H 0.025973 0.694444 0.393607 0.021 Uiso 1 1 calc R U . . .
C17 C -0.2989(4) 0.5333(3) 0.48624(6) 0.0198(5) Uani 1 1 d . . . . .
H17A H -0.312933 0.426038 0.498547 0.024 Uiso 1 1 calc R U . . .
H17B H -0.422228 0.554316 0.473606 0.024 Uiso 1 1 calc R U . . .
C18 C -0.2641(4) 0.6737(3) 0.51139(6) 0.0188(5) Uani 1 1 d . . . . .
H18A H -0.246934 0.779322 0.499111 0.028 Uiso 1 1 calc R U . . .
H18B H -0.145522 0.649847 0.524654 0.028 Uiso 1 1 calc R U . . .
H18C H -0.377162 0.682782 0.526673 0.028 Uiso 1 1 calc R U . . .
C19 C 0.1557(4) 0.1655(3) 0.35277(7) 0.0204(5) Uani 1 1 d . . . . .
C20 C 0.2208(4) 0.0955(3) 0.38285(6) 0.0203(5) Uani 1 1 d . . . . .
H20 H 0.355006 0.066056 0.385763 0.024 Uiso 1 1 calc R U . . .
C21 C 0.0860(4) 0.0695(3) 0.40858(6) 0.0184(5) Uani 1 1 d . . . . .
H21 H 0.127902 0.021717 0.429422 0.022 Uiso 1 1 calc R U . . .
C22 C -0.1107(4) 0.1128(3) 0.40422(6) 0.0169(5) Uani 1 1 d . . . . .
C23 C -0.1729(4) 0.1812(3) 0.37358(6) 0.0205(5) Uani 1 1 d . . . . .
H23 H -0.307209 0.209572 0.370473 0.025 Uiso 1 1 calc R U . . .
C24 C -0.0400(4) 0.2079(3) 0.34767(6) 0.0223(5) Uani 1 1 d . . . . .
H24 H -0.081730 0.254521 0.326704 0.027 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
S1 O3 1.4536(19) . ?
S1 O4 1.4561(17) . ?
S1 O2 1.4565(19) . ?
S1 C22 1.788(3) . ?
Cl1 C19 1.749(3) . ?
O1 C2 1.361(3) . ?
O1 C1 1.430(3) . ?
N1 C14 1.342(3) . ?
N1 C15 1.351(3) . ?
N1 C17 1.482(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.390(4) . ?
C2 C3 1.401(3) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(3) . ?
C5 C8 1.455(3) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C8 1.350(4) . ?
C9 C10 1.439(3) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.346(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.453(3) . ?
C11 H11 0.9500 . ?
C12 C16 1.403(3) . ?
C12 C13 1.403(3) . ?
C13 C14 1.372(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.367(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.516(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.384(4) . ?
C19 C24 1.389(4) . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(3) . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
O3 S1 O4 113.26(11) . . ?
O3 S1 O2 113.65(12) . . ?
O4 S1 O2 112.39(11) . . ?
O3 S1 C22 105.69(11) . . ?
O4 S1 C22 105.50(11) . . ?
O2 S1 C22 105.43(11) . . ?
C2 O1 C1 117.2(2) . . ?
C14 N1 C15 120.7(2) . . ?
C14 N1 C17 119.8(2) . . ?
C15 N1 C17 119.3(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 125.1(2) . . ?
O1 C2 C3 115.2(2) . . ?
C7 C2 C3 119.7(2) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 117.2(2) . . ?
C6 C5 C8 120.2(2) . . ?
C4 C5 C8 122.7(2) . . ?
C7 C6 C5 122.2(2) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C2 119.4(2) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C8 C9 C10 123.1(2) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C9 C8 C5 126.8(2) . . ?
C9 C8 H8 116.6 . . ?
C5 C8 H8 116.6 . . ?
C11 C10 C9 123.2(2) . . ?
C11 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C10 C11 C12 124.8(2) . . ?
C10 C11 H11 117.6 . . ?
C12 C11 H11 117.6 . . ?
C16 C12 C13 116.7(2) . . ?
C16 C12 C11 123.6(2) . . ?
C13 C12 C11 119.7(2) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N1 C14 C13 120.6(2) . . ?
N1 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N1 C15 C16 120.8(2) . . ?
N1 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C12 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C12 C16 H16 119.8 . . ?
N1 C17 C18 110.0(2) . . ?
N1 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
N1 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 122.0(2) . . ?
C20 C19 Cl1 118.9(2) . . ?
C24 C19 Cl1 119.1(2) . . ?
C21 C20 C19 118.4(2) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.8(2) . . ?
C23 C22 S1 120.01(19) . . ?
C21 C22 S1 120.21(19) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 118.9(2) . . ?
C23 C24 H24 120.5 . . ?
C19 C24 H24 120.5 . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_19146_a
_database_code_depnum_ccdc_archive 'CCDC 1973431'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-12-21 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 O6 S'
_chemical_formula_weight         492.53

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.085(3)
_cell_length_b                   7.315(2)
_cell_length_c                   22.030(7)
_cell_angle_alpha                90.112(9)
_cell_angle_beta                 96.227(10)
_cell_angle_gamma                92.400(18)
_cell_volume                     1134.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9685
_cell_measurement_theta_min      4.03
_cell_measurement_theta_max      68.41

_exptl_crystal_description       Blocks
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.674
_shelx_estimated_absorpt_T_min   0.725
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4288
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48398
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.017
_diffrn_reflns_theta_max         68.624
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4138
_reflns_number_gt                3796
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+0.7847P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4138
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S001 S 1.23831(5) 0.24923(5) 0.87306(2) 0.01379(11) Uani 1 1 d . . . . .
N1 N 1.04449(18) 0.73538(17) 0.92025(6) 0.0151(3) Uani 1 1 d . . . . .
O1 O 0.00677(15) 0.20321(16) 0.43312(5) 0.0208(3) Uani 1 1 d . . . . .
C1 C -0.1965(2) 0.1906(2) 0.43070(8) 0.0221(4) Uani 1 1 d . . . . .
H1A H -0.251800 0.170512 0.388361 0.033 Uiso 1 1 calc R U . . .
H1B H -0.241909 0.304540 0.446224 0.033 Uiso 1 1 calc R U . . .
H1C H -0.234752 0.088064 0.455873 0.033 Uiso 1 1 calc R U . . .
O2 O 1.15707(15) 0.30432(16) 0.92767(5) 0.0220(3) Uani 1 1 d . . . . .
N2 N 0.58808(18) -0.02836(18) 0.69505(6) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.1072(2) 0.2430(2) 0.48815(7) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.3045(2) 0.2639(2) 0.48768(7) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.359578 0.246002 0.450789 0.021 Uiso 1 1 calc R U . . .
O3 O 1.33178(15) 0.39895(15) 0.84330(5) 0.0203(2) Uani 1 1 d . . . . .
C4 C 0.4191(2) 0.3102(2) 0.54058(7) 0.0175(3) Uani 1 1 d . . . . .
H4 H 0.552587 0.323934 0.539514 0.021 Uiso 1 1 calc R U . . .
O4 O 1.35399(15) 0.08994(15) 0.88206(5) 0.0193(2) Uani 1 1 d . . . . .
C5 C 0.3430(2) 0.3375(2) 0.59589(7) 0.0154(3) Uani 1 1 d . . . . .
O5 O 0.43324(16) -0.06277(18) 0.71373(5) 0.0270(3) Uani 1 1 d . . . . .
O6 O 0.61809(16) -0.04999(17) 0.64197(5) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.1472(2) 0.3078(2) 0.59573(7) 0.0174(3) Uani 1 1 d . . . . .
H6 H 0.092654 0.319297 0.633008 0.021 Uiso 1 1 calc R U . . .
C7 C 0.0291(2) 0.2619(2) 0.54275(7) 0.0177(3) Uani 1 1 d . . . . .
H7 H -0.103960 0.243685 0.544008 0.021 Uiso 1 1 calc R U . . .
C8 C 0.4573(2) 0.4023(2) 0.65184(7) 0.0168(3) Uani 1 1 d . . . . .
H8 H 0.397136 0.399261 0.688328 0.020 Uiso 1 1 calc R U . . .
C9 C 0.6386(2) 0.4653(2) 0.65641(7) 0.0172(3) Uani 1 1 d . . . . .
H9 H 0.699644 0.464447 0.620102 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7524(2) 0.5354(2) 0.71180(7) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.9408(2) 0.6047(2) 0.70641(7) 0.0166(3) Uani 1 1 d . . . . .
H11 H 0.985577 0.607308 0.667282 0.020 Uiso 1 1 calc R U . . .
C12 C 1.0589(2) 0.6675(2) 0.75578(7) 0.0161(3) Uani 1 1 d . . . . .
H12 H 1.184995 0.710068 0.751116 0.019 Uiso 1 1 calc R U . . .
C13 C 0.9920(2) 0.6686(2) 0.81396(7) 0.0146(3) Uani 1 1 d . . . . .
C14 C 0.8039(2) 0.6034(2) 0.82023(7) 0.0154(3) Uani 1 1 d . . . . .
C15 C 0.6860(2) 0.5363(2) 0.76847(7) 0.0165(3) Uani 1 1 d . . . . .
H15 H 0.560340 0.491573 0.772661 0.020 Uiso 1 1 calc R U . . .
C16 C 0.7432(2) 0.6071(2) 0.87939(7) 0.0186(3) Uani 1 1 d . . . . .
H16 H 0.618259 0.563872 0.885271 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8627(2) 0.6720(2) 0.92781(7) 0.0176(3) Uani 1 1 d . . . . .
H17 H 0.820395 0.673708 0.967266 0.021 Uiso 1 1 calc R U . . .
C18 C 1.1079(2) 0.7331(2) 0.86594(7) 0.0156(3) Uani 1 1 d . . . . .
H18 H 1.234416 0.776042 0.862050 0.019 Uiso 1 1 calc R U . . .
C19 C 1.1678(2) 0.8105(2) 0.97504(7) 0.0193(3) Uani 1 1 d . . . . .
H19A H 1.107643 0.777965 1.012291 0.023 Uiso 1 1 calc R U . . .
H19B H 1.176275 0.945612 0.972420 0.023 Uiso 1 1 calc R U . . .
C20 C 1.3660(2) 0.7394(2) 0.98068(8) 0.0252(4) Uani 1 1 d . . . . .
H20A H 1.434464 0.789312 0.947681 0.038 Uiso 1 1 calc R U . . .
H20B H 1.358408 0.605492 0.977860 0.038 Uiso 1 1 calc R U . . .
H20C H 1.433607 0.777139 1.020174 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7453(2) 0.0429(2) 0.73903(7) 0.0148(3) Uani 1 1 d . . . . .
C22 C 0.7111(2) 0.0755(2) 0.79862(7) 0.0161(3) Uani 1 1 d . . . . .
H22 H 0.588187 0.053312 0.811239 0.019 Uiso 1 1 calc R U . . .
C23 C 0.8614(2) 0.1414(2) 0.83946(7) 0.0154(3) Uani 1 1 d . . . . .
H23 H 0.842145 0.164449 0.880743 0.018 Uiso 1 1 calc R U . . .
C24 C 1.0402(2) 0.1739(2) 0.82023(7) 0.0138(3) Uani 1 1 d . . . . .
C25 C 1.0701(2) 0.1411(2) 0.75975(7) 0.0154(3) Uani 1 1 d . . . . .
H25 H 1.192371 0.164527 0.746833 0.018 Uiso 1 1 calc R U . . .
C26 C 0.9218(2) 0.0744(2) 0.71845(7) 0.0157(3) Uani 1 1 d . . . . .
H26 H 0.940555 0.050879 0.677148 0.019 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
S001 O3 1.4506(12) . ?
S001 O2 1.4521(12) . ?
S001 O4 1.4541(12) . ?
S001 C24 1.7911(16) . ?
N1 C18 1.323(2) . ?
N1 C17 1.378(2) . ?
N1 C19 1.5003(19) . ?
O1 C2 1.3621(18) . ?
O1 C1 1.435(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 O6 1.2222(17) . ?
N2 O5 1.2295(18) . ?
N2 C21 1.4719(19) . ?
C2 C7 1.387(2) . ?
C2 C3 1.401(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C5 C8 1.466(2) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.339(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.467(2) . ?
C9 H9 0.9500 . ?
C10 C15 1.381(2) . ?
C10 C11 1.426(2) . ?
C11 C12 1.365(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.414(2) . ?
C12 H12 0.9500 . ?
C13 C18 1.404(2) . ?
C13 C14 1.418(2) . ?
C14 C15 1.413(2) . ?
C14 C16 1.416(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.360(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.510(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.383(2) . ?
C21 C26 1.387(2) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(2) . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
O3 S001 O2 113.59(7) . . ?
O3 S001 O4 113.07(7) . . ?
O2 S001 O4 113.35(7) . . ?
O3 S001 C24 105.75(7) . . ?
O2 S001 C24 105.41(7) . . ?
O4 S001 C24 104.62(7) . . ?
C18 N1 C17 121.00(13) . . ?
C18 N1 C19 120.73(13) . . ?
C17 N1 C19 118.26(12) . . ?
C2 O1 C1 117.50(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6 N2 O5 123.48(13) . . ?
O6 N2 C21 118.40(13) . . ?
O5 N2 C21 118.13(13) . . ?
O1 C2 C7 125.11(14) . . ?
O1 C2 C3 115.51(13) . . ?
C7 C2 C3 119.38(14) . . ?
C4 C3 C2 120.24(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.52(14) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 117.08(14) . . ?
C6 C5 C8 119.59(14) . . ?
C4 C5 C8 123.27(14) . . ?
C7 C6 C5 122.20(14) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C2 C7 C6 119.47(14) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C5 126.22(14) . . ?
C9 C8 H8 116.9 . . ?
C5 C8 H8 116.9 . . ?
C8 C9 C10 126.62(14) . . ?
C8 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
C15 C10 C11 118.89(14) . . ?
C15 C10 C9 123.20(14) . . ?
C11 C10 C9 117.90(13) . . ?
C12 C11 C10 121.94(14) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 119.44(14) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C18 C13 C12 121.40(14) . . ?
C18 C13 C14 119.00(14) . . ?
C12 C13 C14 119.60(14) . . ?
C15 C14 C16 122.76(14) . . ?
C15 C14 C13 119.68(14) . . ?
C16 C14 C13 117.56(14) . . ?
C10 C15 C14 120.43(14) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C14 120.44(15) . . ?
C17 C16 H16 119.8 . . ?
C14 C16 H16 119.8 . . ?
C16 C17 N1 120.69(14) . . ?
C16 C17 H17 119.7 . . ?
N1 C17 H17 119.7 . . ?
N1 C18 C13 121.30(14) . . ?
N1 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
N1 C19 C20 112.95(13) . . ?
N1 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
N1 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 123.00(14) . . ?
C22 C21 N2 118.97(13) . . ?
C26 C21 N2 118.03(13) . . ?
C21 C22 C23 118.07(14) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?
C22 C23 C24 120.27(14) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 120.39(14) . . ?
C23 C24 S001 120.87(12) . . ?
C25 C24 S001 118.69(11) . . ?
C26 C25 C24 120.11(14) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 118.16(14) . . ?
C25 C26 H26 120.9 . . ?
C21 C26 H26 120.9 . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_18162_a
_database_code_depnum_ccdc_archive 'CCDC 1960839'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 N O, C6 H4 N O5 S'
_chemical_formula_sum            'C23 H22 N2 O6 S'
_chemical_formula_weight         454.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   6.3747(2)
_cell_length_b                   38.0176(14)
_cell_length_c                   8.8064(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.289(2)
_cell_angle_gamma                90
_cell_volume                     2132.53(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9815
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      68.32

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.730
_shelx_estimated_absorpt_T_min   0.652
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4585
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48333
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.652
_diffrn_reflns_theta_max         68.377
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3912
_reflns_number_gt                3586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+1.5430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S001 S -0.21493(6) 0.80451(2) 0.43568(4) 0.01587(11) Uani 1 1 d . . . . .
N1 N -0.5027(2) 0.71892(3) 0.44795(16) 0.0165(3) Uani 1 1 d . . . . .
O1 O 1.0765(2) 0.50935(3) 0.20677(16) 0.0336(3) Uani 1 1 d . . . . .
C1 C 1.2274(3) 0.50609(5) 0.3305(2) 0.0339(5) Uani 1 1 d . . . . .
H1A H 1.331078 0.488115 0.306201 0.051 Uiso 1 1 calc R U . . .
H1B H 1.156224 0.499226 0.422503 0.051 Uiso 1 1 calc R U . . .
H1C H 1.298457 0.528690 0.347488 0.051 Uiso 1 1 calc R U . . .
O2 O -0.31334(18) 0.79374(3) 0.57428(13) 0.0210(3) Uani 1 1 d . . . . .
N2 N -0.1368(2) 0.93006(4) 0.21156(18) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.9158(3) 0.53265(5) 0.2234(2) 0.0271(4) Uani 1 1 d . . . . .
O3 O -0.28755(18) 0.78440(3) 0.30324(13) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.7551(3) 0.53144(5) 0.1116(2) 0.0304(4) Uani 1 1 d . . . . .
H3 H 0.761353 0.515105 0.030270 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5865(3) 0.55410(5) 0.1195(2) 0.0282(4) Uani 1 1 d . . . . .
H4 H 0.477087 0.553013 0.043166 0.034 Uiso 1 1 calc R U . . .
O4 O 0.01231(18) 0.80773(3) 0.45012(14) 0.0216(3) Uani 1 1 d . . . . .
C5 C 0.5728(3) 0.57872(4) 0.2378(2) 0.0234(4) Uani 1 1 d . . . . .
O5 O 0.0466(2) 0.92212(3) 0.19118(17) 0.0336(3) Uani 1 1 d . . . . .
C6 C 0.7364(3) 0.57943(5) 0.3478(2) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.731466 0.595913 0.428609 0.030 Uiso 1 1 calc R U . . .
O6 O -0.2161(2) 0.95767(4) 0.1678(2) 0.0440(4) Uani 1 1 d . . . . .
C7 C 0.9064(3) 0.55667(5) 0.3421(2) 0.0273(4) Uani 1 1 d . . . . .
H7 H 1.015372 0.557490 0.418812 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3876(3) 0.60119(4) 0.2437(2) 0.0239(4) Uani 1 1 d . . . . .
H8 H 0.294035 0.600663 0.157058 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3340(3) 0.62259(4) 0.3578(2) 0.0218(4) Uani 1 1 d . . . . .
H9 H 0.425315 0.624519 0.445340 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1419(3) 0.64263(4) 0.3508(2) 0.0208(4) Uani 1 1 d . . . . .
H10 H 0.061201 0.642241 0.257800 0.025 Uiso 1 1 calc R U . . .
C11 C 0.0676(3) 0.66183(4) 0.4651(2) 0.0205(4) Uani 1 1 d . . . . .
H11 H 0.148488 0.662607 0.558033 0.025 Uiso 1 1 calc R U . . .
C12 C -0.1286(3) 0.68153(4) 0.45611(19) 0.0179(3) Uani 1 1 d . . . . .
C13 C -0.2378(3) 0.68906(4) 0.3190(2) 0.0221(4) Uani 1 1 d . . . . .
H13 H -0.183401 0.681242 0.225965 0.027 Uiso 1 1 calc R U . . .
C14 C -0.4223(3) 0.70760(4) 0.31739(19) 0.0208(4) Uani 1 1 d . . . . .
H14 H -0.494334 0.712507 0.223255 0.025 Uiso 1 1 calc R U . . .
C15 C -0.4013(3) 0.71256(4) 0.58205(19) 0.0192(3) Uani 1 1 d . . . . .
H15 H -0.458790 0.720873 0.673253 0.023 Uiso 1 1 calc R U . . .
C16 C -0.2161(3) 0.69422(4) 0.5885(2) 0.0211(4) Uani 1 1 d . . . . .
H16 H -0.146232 0.690080 0.684150 0.025 Uiso 1 1 calc R U . . .
C17 C -0.6949(2) 0.74072(4) 0.4422(2) 0.0205(4) Uani 1 1 d . . . . .
H17A H -0.656387 0.765569 0.433105 0.031 Uiso 1 1 calc R U . . .
H17B H -0.771046 0.737233 0.535532 0.031 Uiso 1 1 calc R U . . .
H17C H -0.784558 0.733820 0.354280 0.031 Uiso 1 1 calc R U . . .
C18 C -0.3102(3) 0.84790(4) 0.39793(18) 0.0166(3) Uani 1 1 d . . . . .
C19 C -0.5146(3) 0.85694(4) 0.43371(19) 0.0204(4) Uani 1 1 d . . . . .
H19 H -0.601909 0.840132 0.479960 0.024 Uiso 1 1 calc R U . . .
C20 C -0.5903(3) 0.89045(5) 0.4018(2) 0.0271(4) Uani 1 1 d . . . . .
H20 H -0.727826 0.896722 0.429504 0.033 Uiso 1 1 calc R U . . .
C21 C -0.4666(3) 0.91488(5) 0.3297(2) 0.0270(4) Uani 1 1 d . . . . .
H21 H -0.517520 0.937863 0.307355 0.032 Uiso 1 1 calc R U . . .
C22 C -0.2673(3) 0.90476(4) 0.2915(2) 0.0211(4) Uani 1 1 d . . . . .
C23 C -0.1838(3) 0.87187(4) 0.32616(19) 0.0184(3) Uani 1 1 d . . . . .
H23 H -0.044455 0.865977 0.301410 0.022 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
S001 O2 1.4533(12) . ?
S001 O4 1.4543(12) . ?
S001 O3 1.4547(12) . ?
S001 C18 1.7845(16) . ?
N1 C15 1.345(2) . ?
N1 C14 1.348(2) . ?
N1 C17 1.478(2) . ?
O1 C2 1.367(2) . ?
O1 C1 1.430(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 O6 1.221(2) . ?
N2 O5 1.227(2) . ?
N2 C22 1.470(2) . ?
C2 C7 1.391(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(3) . ?
C5 C8 1.460(2) . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.348(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.441(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.345(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.457(2) . ?
C11 H11 0.9500 . ?
C12 C16 1.398(2) . ?
C12 C13 1.399(2) . ?
C13 C14 1.371(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.371(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.385(2) . ?
C18 C19 1.395(2) . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(2) . ?
C23 H23 0.9500 . ?

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
O2 S001 O4 114.34(7) . . ?
O2 S001 O3 113.02(7) . . ?
O4 S001 O3 113.47(7) . . ?
O2 S001 C18 105.18(7) . . ?
O4 S001 C18 105.61(7) . . ?
O3 S001 C18 103.97(7) . . ?
C15 N1 C14 120.39(14) . . ?
C15 N1 C17 119.93(14) . . ?
C14 N1 C17 119.52(14) . . ?
C2 O1 C1 117.34(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6 N2 O5 123.37(16) . . ?
O6 N2 C22 118.60(16) . . ?
O5 N2 C22 118.03(14) . . ?
O1 C2 C7 124.12(18) . . ?
O1 C2 C3 115.88(17) . . ?
C7 C2 C3 120.00(17) . . ?
C4 C3 C2 119.71(18) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.61(19) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 117.42(16) . . ?
C6 C5 C8 123.18(17) . . ?
C4 C5 C8 119.36(17) . . ?
C7 C6 C5 121.73(17) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 119.53(19) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
C9 C8 C5 127.56(18) . . ?
C9 C8 H8 116.2 . . ?
C5 C8 H8 116.2 . . ?
C8 C9 C10 121.85(17) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 125.38(17) . . ?
C11 C10 H10 117.3 . . ?
C9 C10 H10 117.3 . . ?
C10 C11 C12 124.44(16) . . ?
C10 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
C16 C12 C13 116.60(15) . . ?
C16 C12 C11 120.13(15) . . ?
C13 C12 C11 123.27(15) . . ?
C14 C13 C12 120.75(16) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N1 C14 C13 120.70(16) . . ?
N1 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N1 C15 C16 120.70(15) . . ?
N1 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C12 120.84(16) . . ?
C15 C16 H16 119.6 . . ?
C12 C16 H16 119.6 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 120.41(15) . . ?
C23 C18 S001 119.55(13) . . ?
C19 C18 S001 119.96(13) . . ?
C20 C19 C18 120.06(16) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.53(17) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 117.99(16) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
C21 C22 C23 123.05(16) . . ?
C21 C22 N2 118.57(15) . . ?
C23 C22 N2 118.37(16) . . ?
C18 C23 C22 117.89(16) . . ?
C18 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_19125_a
_database_code_depnum_ccdc_archive 'CCDC 1961452'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O6 S'
_chemical_formula_weight         454.48

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   6.6719(3)
_cell_length_b                   7.9424(4)
_cell_length_c                   39.7008(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2103.78(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8168
_cell_measurement_theta_min      4.45
_cell_measurement_theta_max      68.21

_exptl_crystal_description       Plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.753
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4075
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14778
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3848
_reflns_number_gt                3472
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1273 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.021(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3848
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.31142(13) 0.58468(12) 0.44197(2) 0.0267(2) Uani 1 1 d . . . . .
N1 N 0.3469(5) 0.4407(4) 0.53301(7) 0.0285(7) Uani 1 1 d . . . . .
O1 O 1.8339(4) 0.1577(4) 0.73858(6) 0.0332(6) Uani 1 1 d . . . . .
C1 C 1.8580(6) 0.0258(5) 0.76289(9) 0.0382(10) Uani 1 1 d . . . . .
H1A H 1.842205 -0.083585 0.751786 0.057 Uiso 1 1 calc R U . . .
H1B H 1.756477 0.037785 0.780557 0.057 Uiso 1 1 calc R U . . .
H1C H 1.991940 0.033061 0.772931 0.057 Uiso 1 1 calc R U . . .
O2 O -0.4577(4) 0.4630(3) 0.42957(6) 0.0307(6) Uani 1 1 d . . . . .
N2 N 0.2305(5) 0.7248(4) 0.32449(8) 0.0296(7) Uani 1 1 d . . . . .
C2 C 1.6581(6) 0.1635(5) 0.72114(8) 0.0264(8) Uani 1 1 d . . . . .
O3 O -0.1849(4) 0.5182(4) 0.46846(6) 0.0359(7) Uani 1 1 d . . . . .
C3 C 1.6470(6) 0.2910(5) 0.69680(9) 0.0284(8) Uani 1 1 d . . . . .
H3 H 1.757450 0.364860 0.693621 0.034 Uiso 1 1 calc R U . . .
C5 C 1.4781(6) 0.3100(5) 0.67758(9) 0.0279(8) Uani 1 1 d . . . . .
H5 H 1.473488 0.397180 0.661219 0.034 Uiso 1 1 calc R U . . .
O5 O 0.4055(4) 0.6760(4) 0.32561(7) 0.0406(8) Uani 1 1 d . . . . .
O4 O -0.4018(4) 0.7471(4) 0.44985(7) 0.0345(7) Uani 1 1 d . . . . .
C6 C 1.3118(6) 0.2038(5) 0.68146(8) 0.0261(8) Uani 1 1 d . . . . .
O6 O 0.1613(4) 0.8038(3) 0.30057(6) 0.0340(7) Uani 1 1 d . . . . .
C7 C 1.3266(6) 0.0778(5) 0.70604(8) 0.0279(8) Uani 1 1 d . . . . .
H7 H 1.216045 0.004308 0.709372 0.033 Uiso 1 1 calc R U . . .
C8 C 1.4965(5) 0.0565(5) 0.72570(8) 0.0268(8) Uani 1 1 d . . . . .
H8 H 1.501975 -0.030476 0.742100 0.032 Uiso 1 1 calc R U . . .
C9 C 1.1297(6) 0.2208(5) 0.66144(9) 0.0286(8) Uani 1 1 d . . . . .
H9 H 1.030987 0.135857 0.664412 0.034 Uiso 1 1 calc R U . . .
C10 C 1.0857(6) 0.3435(5) 0.63920(9) 0.0281(8) Uani 1 1 d . . . . .
H10 H 1.179432 0.432091 0.635968 0.034 Uiso 1 1 calc R U . . .
C11 C 0.9020(6) 0.3453(5) 0.62013(9) 0.0282(8) Uani 1 1 d . . . . .
H11 H 0.807310 0.258736 0.624517 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8547(5) 0.4594(5) 0.59677(9) 0.0277(8) Uani 1 1 d . . . . .
H12 H 0.946202 0.549403 0.593277 0.033 Uiso 1 1 calc R U . . .
C13 C 0.6732(6) 0.4570(5) 0.57613(8) 0.0266(8) Uani 1 1 d . . . . .
C14 C 0.5086(6) 0.3516(5) 0.58285(9) 0.0297(9) Uani 1 1 d . . . . .
H14 H 0.508175 0.283993 0.602589 0.036 Uiso 1 1 calc R U . . .
C15 C 0.3497(6) 0.3456(5) 0.56131(9) 0.0304(8) Uani 1 1 d . . . . .
H15 H 0.239581 0.273799 0.566212 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4963(5) 0.5483(5) 0.52657(9) 0.0312(9) Uani 1 1 d . . . . .
H16 H 0.488940 0.618518 0.507232 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6607(5) 0.5593(5) 0.54749(8) 0.0289(8) Uani 1 1 d . . . . .
H17 H 0.765546 0.636292 0.542464 0.035 Uiso 1 1 calc R U . . .
C18 C 0.1784(6) 0.4236(6) 0.50915(9) 0.0386(9) Uani 1 1 d . . . . .
H18A H 0.122476 0.535041 0.504291 0.058 Uiso 1 1 calc R U . . .
H18B H 0.074451 0.352057 0.519111 0.058 Uiso 1 1 calc R U . . .
H18C H 0.226526 0.372276 0.488202 0.058 Uiso 1 1 calc R U . . .
C19 C -0.1470(6) 0.6239(5) 0.40718(8) 0.0260(8) Uani 1 1 d . . . . .
C20 C 0.0566(6) 0.5822(5) 0.40891(8) 0.0274(8) Uani 1 1 d . . . . .
H20 H 0.109886 0.533310 0.428821 0.033 Uiso 1 1 calc R U . . .
C21 C 0.1798(6) 0.6123(5) 0.38162(8) 0.0284(8) Uani 1 1 d . . . . .
H21 H 0.317589 0.582305 0.382332 0.034 Uiso 1 1 calc R U . . .
C22 C 0.0992(6) 0.6867(5) 0.35330(9) 0.0255(8) Uani 1 1 d . . . . .
C23 C -0.1029(6) 0.7297(5) 0.35093(9) 0.0280(8) Uani 1 1 d . . . . .
H23 H -0.154773 0.779722 0.331018 0.034 Uiso 1 1 calc R U . . .
C24 C -0.2257(5) 0.6980(5) 0.37805(9) 0.0271(8) Uani 1 1 d . . . . .
H24 H -0.363825 0.726385 0.377006 0.032 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
S1 O3 1.448(3) . ?
S1 O4 1.458(3) . ?
S1 O2 1.459(3) . ?
S1 C19 1.791(4) . ?
N1 C16 1.338(5) . ?
N1 C15 1.354(5) . ?
N1 C18 1.476(4) . ?
O1 C2 1.363(4) . ?
O1 C1 1.433(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 O6 1.228(4) . ?
N2 O5 1.231(4) . ?
N2 C22 1.472(4) . ?
C2 C8 1.385(5) . ?
C2 C3 1.402(5) . ?
C3 C5 1.369(5) . ?
C3 H3 0.9500 . ?
C5 C6 1.402(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(5) . ?
C6 C9 1.458(5) . ?
C7 C8 1.387(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.347(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.441(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.334(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.462(5) . ?
C12 H12 0.9500 . ?
C13 C17 1.400(5) . ?
C13 C14 1.407(5) . ?
C14 C15 1.363(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.399(5) . ?
C19 C24 1.400(5) . ?
C20 C21 1.381(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(5) . ?
C23 C24 1.376(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
O3 S1 O4 114.08(17) . . ?
O3 S1 O2 113.17(17) . . ?
O4 S1 O2 112.44(16) . . ?
O3 S1 C19 105.43(16) . . ?
O4 S1 C19 105.37(17) . . ?
O2 S1 C19 105.34(15) . . ?
C16 N1 C15 120.3(3) . . ?
C16 N1 C18 120.2(3) . . ?
C15 N1 C18 119.4(3) . . ?
C2 O1 C1 117.6(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6 N2 O5 123.0(3) . . ?
O6 N2 C22 118.8(3) . . ?
O5 N2 C22 118.1(3) . . ?
O1 C2 C8 125.7(3) . . ?
O1 C2 C3 114.9(3) . . ?
C8 C2 C3 119.5(3) . . ?
C5 C3 C2 120.5(4) . . ?
C5 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C5 C6 121.6(4) . . ?
C3 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 116.8(3) . . ?
C7 C6 C9 120.3(4) . . ?
C5 C6 C9 122.9(3) . . ?
C8 C7 C6 122.5(4) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C2 C8 C7 119.2(3) . . ?
C2 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C6 127.3(4) . . ?
C10 C9 H9 116.4 . . ?
C6 C9 H9 116.4 . . ?
C9 C10 C11 122.5(4) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C10 125.0(4) . . ?
C12 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
C11 C12 C13 125.2(4) . . ?
C11 C12 H12 117.4 . . ?
C13 C12 H12 117.4 . . ?
C17 C13 C14 116.9(4) . . ?
C17 C13 C12 119.8(3) . . ?
C14 C13 C12 123.2(3) . . ?
C15 C14 C13 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N1 C15 C14 120.8(4) . . ?
N1 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N1 C16 C17 121.2(3) . . ?
N1 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C13 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
C13 C17 H17 120.0 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 120.2(3) . . ?
C20 C19 S1 121.0(3) . . ?
C24 C19 S1 118.7(3) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 118.8(4) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 122.5(3) . . ?
C21 C22 N2 119.3(3) . . ?
C23 C22 N2 118.2(3) . . ?
C24 C23 C22 118.6(3) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C19 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_19152_a
_database_code_depnum_ccdc_archive 'CCDC 1973403'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 N2 O7 S'
_chemical_formula_weight         496.52

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   10.5725(6)
_cell_length_b                   6.6821(4)
_cell_length_c                   32.4379(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.284(3)
_cell_angle_gamma                90
_cell_volume                     2281.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8143
_cell_measurement_theta_min      4.30
_cell_measurement_theta_max      68.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.702
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4545
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23631
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.736
_diffrn_reflns_theta_max         68.297
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4167
_reflns_number_gt                3703
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+1.3760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4167
_refine_ls_number_parameters     324
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.17962(4) 0.85123(6) 0.43263(2) 0.02045(13) Uani 1 1 d . . . . .
N1 N 0.46015(13) 0.7755(2) 0.58012(4) 0.0202(3) Uani 1 1 d . . . . .
O1 O 0.16423(11) 0.79039(19) 0.95982(4) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.27775(17) 0.7977(3) 0.98798(5) 0.0273(4) Uani 1 1 d . . . . .
H1A H 0.328547 0.677176 0.984541 0.041 Uiso 1 1 calc R U . . .
H1B H 0.254496 0.804514 1.016499 0.041 Uiso 1 1 calc R U . . .
H1C H 0.327439 0.916367 0.982046 0.041 Uiso 1 1 calc R U . . .
C2 C 0.18074(16) 0.7811(2) 0.91853(5) 0.0177(3) Uani 1 1 d . . . . .
O2 O 0.13894(14) 1.0499(2) 0.41881(4) 0.0345(3) Uani 1 1 d . . . . .
N2 N 0.13179(13) 0.3484(2) 0.27901(5) 0.0246(3) Uani 1 1 d . . . . .
O3 O 0.31258(12) 0.8397(2) 0.44690(4) 0.0381(4) Uani 1 1 d . . . . .
C3 C 0.06970(16) 0.7738(2) 0.89158(5) 0.0192(3) Uani 1 1 d . . . . .
H3 H -0.011052 0.772375 0.902223 0.023 Uiso 1 1 calc R U . . .
O4 O 0.09614(13) 0.7628(2) 0.46068(4) 0.0304(3) Uani 1 1 d . . . . .
C4 C 0.07837(16) 0.7687(2) 0.84940(5) 0.0186(3) Uani 1 1 d . . . . .
H4 H 0.002622 0.764479 0.831232 0.022 Uiso 1 1 calc R U . . .
C5 C 0.19628(16) 0.7695(2) 0.83260(5) 0.0178(3) Uani 1 1 d . . . . .
O5 O 0.14365(13) 0.4306(2) 0.24566(4) 0.0332(3) Uani 1 1 d . . . . .
C6 C 0.30574(16) 0.7744(3) 0.86053(5) 0.0195(4) Uani 1 1 d . . . . .
H6 H 0.386647 0.773667 0.849995 0.023 Uiso 1 1 calc R U . . .
O6 O 0.11270(13) 0.1680(2) 0.28231(4) 0.0344(3) Uani 1 1 d . . . . .
O7 O 0.07677(13) 0.7758(2) 0.54656(4) 0.0340(3) Uani 1 1 d D . . . .
HO71 H 0.0119(18) 0.844(3) 0.5506(7) 0.041 Uiso 1 1 d D U . . .
HO72 H 0.074(2) 0.781(4) 0.5201(5) 0.041 Uiso 1 1 d D U . . .
C7 C 0.29963(15) 0.7802(3) 0.90296(5) 0.0186(3) Uani 1 1 d . . . . .
H7 H 0.375184 0.783516 0.921224 0.022 Uiso 1 1 calc R U . . .
C8 C 0.20091(16) 0.7676(2) 0.78775(5) 0.0189(4) Uani 1 1 d . . . . .
H8 H 0.122039 0.772826 0.771192 0.023 Uiso 1 1 calc R U . . .
C9 C 0.30655(17) 0.7593(3) 0.76780(5) 0.0207(4) Uani 1 1 d . . . . .
H9 H 0.385021 0.750243 0.784494 0.025 Uiso 1 1 calc R U . . .
C10 C 0.31306(16) 0.7626(2) 0.72298(5) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.20290(16) 0.7727(3) 0.69395(5) 0.0199(4) Uani 1 1 d . . . . .
H11 H 0.121216 0.777678 0.703907 0.024 Uiso 1 1 calc R U . . .
C12 C 0.21237(16) 0.7754(3) 0.65250(5) 0.0201(4) Uani 1 1 d . . . . .
H12 H 0.137794 0.779521 0.633792 0.024 Uiso 1 1 calc R U . . .
C13 C 0.33337(16) 0.7720(2) 0.63719(5) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.44481(16) 0.7651(2) 0.66524(5) 0.0186(3) Uani 1 1 d . . . . .
C15 C 0.43148(16) 0.7575(2) 0.70805(5) 0.0194(4) Uani 1 1 d . . . . .
H15 H 0.505262 0.748809 0.727029 0.023 Uiso 1 1 calc R U . . .
C16 C 0.56356(16) 0.7678(3) 0.64831(5) 0.0219(4) Uani 1 1 d . . . . .
H16 H 0.639878 0.765465 0.666228 0.026 Uiso 1 1 calc R U . . .
C17 C 0.56922(16) 0.7736(3) 0.60664(6) 0.0228(4) Uani 1 1 d . . . . .
H17 H 0.649553 0.776434 0.595726 0.027 Uiso 1 1 calc R U . . .
C18 C 0.34611(16) 0.7760(2) 0.59442(5) 0.0189(4) Uani 1 1 d . . . . .
H18 H 0.272150 0.779078 0.575428 0.023 Uiso 1 1 calc R U . . .
C19 C 0.47266(18) 0.7747(3) 0.53503(5) 0.0269(4) Uani 1 1 d . . . . .
H19A H 0.389564 0.800514 0.520001 0.040 Uiso 1 1 calc R U . . .
H19B H 0.504064 0.643865 0.526872 0.040 Uiso 1 1 calc R U . . .
H19C H 0.532613 0.879078 0.528379 0.040 Uiso 1 1 calc R U . . .
C20 C 0.16197(15) 0.6998(3) 0.38701(5) 0.0182(3) Uani 1 1 d . . . . .
C21 C 0.19342(17) 0.7810(3) 0.34965(5) 0.0243(4) Uani 1 1 d . . . . .
H21 H 0.222383 0.915396 0.348750 0.029 Uiso 1 1 calc R U . . .
C22 C 0.18267(16) 0.6670(3) 0.31396(5) 0.0243(4) Uani 1 1 d . . . . .
H22 H 0.203246 0.721197 0.288341 0.029 Uiso 1 1 calc R U . . .
C23 C 0.14107(15) 0.4717(3) 0.31666(5) 0.0205(4) Uani 1 1 d . . . . .
C24 C 0.11038(15) 0.3866(3) 0.35350(5) 0.0201(4) Uani 1 1 d . . . . .
H24 H 0.083354 0.251200 0.354384 0.024 Uiso 1 1 calc R U . . .
C25 C 0.12004(15) 0.5037(3) 0.38903(5) 0.0189(3) Uani 1 1 d . . . . .
H25 H 0.098096 0.449911 0.414524 0.023 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
S1 O3 1.4410(13) . ?
S1 O4 1.4505(13) . ?
S1 O2 1.4536(14) . ?
S1 C20 1.7881(17) . ?
N1 C18 1.331(2) . ?
N1 C17 1.374(2) . ?
N1 C19 1.481(2) . ?
O1 C2 1.368(2) . ?
O1 C1 1.441(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.397(2) . ?
C2 C3 1.399(2) . ?
N2 O6 1.229(2) . ?
N2 O5 1.230(2) . ?
N2 C23 1.469(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(2) . ?
C5 C8 1.460(2) . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
O7 HO71 0.844(16) . ?
O7 HO72 0.858(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.343(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.462(2) . ?
C9 H9 0.9500 . ?
C10 C15 1.384(2) . ?
C10 C11 1.430(2) . ?
C11 C12 1.358(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.414(2) . ?
C12 H12 0.9500 . ?
C13 C18 1.407(2) . ?
C13 C14 1.421(2) . ?
C14 C15 1.410(2) . ?
C14 C16 1.416(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.359(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.387(2) . ?
C20 C21 1.396(2) . ?
C21 C22 1.382(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(2) . ?
C24 C25 1.389(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
O3 S1 O4 114.11(9) . . ?
O3 S1 O2 113.60(9) . . ?
O4 S1 O2 112.68(8) . . ?
O3 S1 C20 105.06(8) . . ?
O4 S1 C20 105.40(8) . . ?
O2 S1 C20 104.84(8) . . ?
C18 N1 C17 121.13(15) . . ?
C18 N1 C19 120.68(15) . . ?
C17 N1 C19 118.19(14) . . ?
C2 O1 C1 116.63(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 123.67(15) . . ?
O1 C2 C3 115.98(15) . . ?
C7 C2 C3 120.34(15) . . ?
O6 N2 O5 123.05(16) . . ?
O6 N2 C23 118.48(15) . . ?
O5 N2 C23 118.46(16) . . ?
C4 C3 C2 119.48(15) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.76(15) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 117.25(15) . . ?
C6 C5 C8 122.84(15) . . ?
C4 C5 C8 119.90(15) . . ?
C7 C6 C5 122.11(15) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
HO71 O7 HO72 101(2) . . ?
C6 C7 C2 119.05(15) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
C9 C8 C5 125.90(16) . . ?
C9 C8 H8 117.0 . . ?
C5 C8 H8 117.1 . . ?
C8 C9 C10 126.60(16) . . ?
C8 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
C15 C10 C11 118.61(15) . . ?
C15 C10 C9 118.34(15) . . ?
C11 C10 C9 123.05(15) . . ?
C12 C11 C10 121.52(16) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 119.94(16) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C18 C13 C12 121.19(15) . . ?
C18 C13 C14 118.88(15) . . ?
C12 C13 C14 119.93(16) . . ?
C15 C14 C16 123.71(16) . . ?
C15 C14 C13 118.66(15) . . ?
C16 C14 C13 117.63(16) . . ?
C10 C15 C14 121.31(16) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C14 120.51(16) . . ?
C17 C16 H16 119.7 . . ?
C14 C16 H16 119.7 . . ?
C16 C17 N1 120.78(16) . . ?
C16 C17 H17 119.6 . . ?
N1 C17 H17 119.6 . . ?
N1 C18 C13 121.04(15) . . ?
N1 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 120.74(16) . . ?
C25 C20 S1 120.33(13) . . ?
C21 C20 S1 118.92(13) . . ?
C22 C21 C20 120.35(17) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 118.01(16) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?
C22 C23 C24 122.82(16) . . ?
C22 C23 N2 118.30(16) . . ?
C24 C23 N2 118.86(16) . . ?
C23 C24 C25 118.55(16) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C20 C25 C24 119.51(16) . . ?
C20 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_18141_a
_database_code_depnum_ccdc_archive 'CCDC 1960849'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N O, C7 H4 F3 O3 S'
_chemical_formula_sum            'C26 H22 F3 N O4 S'
_chemical_formula_weight         501.50

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   7.8208(3)
_cell_length_b                   7.1973(3)
_cell_length_c                   19.9675(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.700(2)
_cell_angle_gamma                90
_cell_volume                     1116.27(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9247
_cell_measurement_theta_min      4.46
_cell_measurement_theta_max      68.32

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    1.828
_shelx_estimated_absorpt_T_min   0.556
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4673
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35178
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.459
_diffrn_reflns_theta_max         68.360
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4014
_reflns_number_gt                3964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.955

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.3207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1877 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.026(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4014
_refine_ls_number_parameters     318
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.16691(7) 0.60181(8) 0.35145(3) 0.01888(15) Uani 1 1 d . . . . .
F1 F 0.4735(2) 0.0567(3) 0.35426(12) 0.0424(5) Uani 1 1 d . . . . .
O1 O -0.3075(3) -0.1114(3) 0.63841(9) 0.0253(4) Uani 1 1 d . . . . .
N1 N 0.4700(3) 1.4361(3) 0.53793(12) 0.0212(5) Uani 1 1 d . . . . .
C1 C -0.3275(4) -0.1415(4) 0.70818(14) 0.0279(6) Uani 1 1 d . . . . .
H1A H -0.380184 -0.031579 0.726241 0.042 Uiso 1 1 calc R U . . .
H1B H -0.214504 -0.163750 0.733616 0.042 Uiso 1 1 calc R U . . .
H1C H -0.401627 -0.249768 0.712274 0.042 Uiso 1 1 calc R U . . .
F2 F 0.6659(2) -0.1252(3) 0.40353(9) 0.0328(4) Uani 1 1 d . . . . .
O2 O 1.1598(2) 0.7058(3) 0.41348(10) 0.0249(4) Uani 1 1 d . . . . .
C2 C -0.2194(3) 0.0449(4) 0.62400(13) 0.0201(5) Uani 1 1 d . . . . .
F3 F 0.6299(2) -0.1101(3) 0.29606(9) 0.0349(4) Uani 1 1 d . . . . .
O3 O 1.1090(3) 0.7081(3) 0.29146(10) 0.0260(4) Uani 1 1 d . . . . .
C3 C -0.2020(4) 0.0682(4) 0.55452(13) 0.0219(6) Uani 1 1 d . . . . .
H3 H -0.245960 -0.023260 0.522782 0.026 Uiso 1 1 calc R U . . .
C5 C -0.0549(3) 0.3608(4) 0.57961(13) 0.0188(5) Uani 1 1 d . . . . .
C4 C -0.1219(3) 0.2229(4) 0.53345(13) 0.0205(5) Uani 1 1 d . . . . .
H4 H -0.111128 0.237856 0.486860 0.025 Uiso 1 1 calc R U . . .
O4 O 1.3305(2) 0.5075(3) 0.34873(10) 0.0253(4) Uani 1 1 d . . . . .
C6 C -0.0709(3) 0.3345(4) 0.64909(13) 0.0176(5) Uani 1 1 d . . . . .
C7 C -0.1552(3) 0.1737(4) 0.67053(13) 0.0202(5) Uani 1 1 d . . . . .
H7 H -0.166788 0.156043 0.716936 0.024 Uiso 1 1 calc R U . . .
C8 C 0.0261(3) 0.5223(4) 0.55886(13) 0.0198(5) Uani 1 1 d . . . . .
H8 H 0.035288 0.540512 0.512293 0.024 Uiso 1 1 calc R U . . .
C9 C 0.0927(3) 0.6551(4) 0.60489(13) 0.0206(6) Uani 1 1 d . . . . .
C10 C 0.0760(4) 0.6264(4) 0.67463(14) 0.0223(6) Uani 1 1 d . . . . .
H10 H 0.120998 0.716282 0.706810 0.027 Uiso 1 1 calc R U . . .
C11 C -0.0034(3) 0.4723(4) 0.69575(13) 0.0219(6) Uani 1 1 d . . . . .
H11 H -0.013803 0.456808 0.742347 0.026 Uiso 1 1 calc R U . . .
C12 C 0.1738(3) 0.8186(4) 0.58008(13) 0.0207(5) Uani 1 1 d . . . . .
H12 H 0.172930 0.827973 0.532579 0.025 Uiso 1 1 calc R U . . .
C13 C 0.2500(3) 0.9581(4) 0.61699(13) 0.0219(6) Uani 1 1 d . . . . .
H13 H 0.254482 0.950170 0.664652 0.026 Uiso 1 1 calc R U . . .
C14 C 0.3261(3) 1.1204(4) 0.58883(13) 0.0199(6) Uani 1 1 d . . . . .
C15 C 0.3247(3) 1.1496(4) 0.51898(13) 0.0213(6) Uani 1 1 d . . . . .
H15 H 0.273866 1.059540 0.488040 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3956(3) 1.3062(4) 0.49544(13) 0.0212(5) Uani 1 1 d . . . . .
H16 H 0.392624 1.324103 0.448178 0.025 Uiso 1 1 calc R U . . .
C17 C 0.4766(4) 1.4114(4) 0.60524(14) 0.0229(6) Uani 1 1 d . . . . .
H17 H 0.531323 1.502229 0.634904 0.028 Uiso 1 1 calc R U . . .
C18 C 0.4054(4) 1.2571(4) 0.63152(14) 0.0231(6) Uani 1 1 d . . . . .
H18 H 0.410099 1.243094 0.679005 0.028 Uiso 1 1 calc R U . . .
C19 C 0.5438(4) 1.6033(4) 0.50994(16) 0.0265(6) Uani 1 1 d . . . . .
H19A H 0.649709 1.569936 0.490949 0.040 Uiso 1 1 calc R U . . .
H19B H 0.570194 1.695345 0.545826 0.040 Uiso 1 1 calc R U . . .
H19C H 0.460749 1.655818 0.474432 0.040 Uiso 1 1 calc R U . . .
C20 C 1.0118(3) 0.4205(4) 0.35353(12) 0.0179(5) Uani 1 1 d . . . . .
C21 C 1.0598(3) 0.2346(4) 0.35625(13) 0.0198(5) Uani 1 1 d . . . . .
H21 H 1.178031 0.202205 0.358057 0.024 Uiso 1 1 calc R U . . .
C22 C 0.9368(4) 0.0961(4) 0.35634(13) 0.0206(6) Uani 1 1 d . . . . .
H22 H 0.970011 -0.030963 0.358238 0.025 Uiso 1 1 calc R U . . .
C23 C 0.7636(3) 0.1456(4) 0.35360(12) 0.0191(5) Uani 1 1 d . . . . .
C24 C 0.7139(3) 0.3314(4) 0.35164(13) 0.0201(6) Uani 1 1 d . . . . .
H24 H 0.595882 0.363858 0.350494 0.024 Uiso 1 1 calc R U . . .
C25 C 0.8379(3) 0.4683(4) 0.35139(13) 0.0205(6) Uani 1 1 d . . . . .
H25 H 0.804854 0.595344 0.349750 0.025 Uiso 1 1 calc R U . . .
C26 C 0.6336(4) -0.0057(4) 0.35219(15) 0.0224(6) Uani 1 1 d . . . . .


_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 O3 1.449(2) . ?
S1 O2 1.454(2) . ?
S1 O4 1.4548(19) . ?
S1 C20 1.785(3) . ?
F1 C26 1.336(3) . ?
O1 C2 1.368(3) . ?
O1 C1 1.436(3) . ?
N1 C16 1.348(4) . ?
N1 C17 1.351(4) . ?
N1 C19 1.473(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
F2 C26 1.339(3) . ?
C2 C7 1.366(4) . ?
C2 C3 1.419(4) . ?
F3 C26 1.347(3) . ?
C3 C4 1.367(4) . ?
C3 H3 0.9500 . ?
C5 C8 1.409(4) . ?
C5 C4 1.413(4) . ?
C5 C6 1.420(3) . ?
C4 H4 0.9500 . ?
C6 C11 1.420(4) . ?
C6 C7 1.422(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.429(4) . ?
C9 C12 1.451(4) . ?
C10 C11 1.362(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.343(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.453(4) . ?
C13 H13 0.9500 . ?
C14 C18 1.398(4) . ?
C14 C15 1.409(4) . ?
C15 C16 1.364(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.374(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.389(4) . ?
C20 C25 1.398(4) . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.396(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(4) . ?
C23 C26 1.488(4) . ?
C24 C25 1.383(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
O3 S1 O2 113.14(11) . . ?
O3 S1 O4 114.03(11) . . ?
O2 S1 O4 113.15(12) . . ?
O3 S1 C20 104.92(12) . . ?
O2 S1 C20 105.24(11) . . ?
O4 S1 C20 105.24(13) . . ?
C2 O1 C1 116.3(2) . . ?
C16 N1 C17 119.9(2) . . ?
C16 N1 C19 119.2(2) . . ?
C17 N1 C19 120.9(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 124.7(2) . . ?
C7 C2 C3 121.0(3) . . ?
O1 C2 C3 114.3(2) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C8 C5 C4 122.2(2) . . ?
C8 C5 C6 119.4(2) . . ?
C4 C5 C6 118.3(2) . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C11 C6 C5 118.6(2) . . ?
C11 C6 C7 121.4(2) . . ?
C5 C6 C7 120.0(2) . . ?
C2 C7 C6 119.6(2) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C5 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C5 C8 H8 119.3 . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 C12 118.6(2) . . ?
C10 C9 C12 122.9(2) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 120.9(2) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 C9 127.0(2) . . ?
C13 C12 H12 116.5 . . ?
C9 C12 H12 116.5 . . ?
C12 C13 C14 124.3(2) . . ?
C12 C13 H13 117.8 . . ?
C14 C13 H13 117.8 . . ?
C18 C14 C15 116.7(2) . . ?
C18 C14 C13 120.1(2) . . ?
C15 C14 C13 123.1(2) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
N1 C16 C15 121.3(2) . . ?
N1 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
N1 C17 C18 121.1(2) . . ?
N1 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C14 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C14 C18 H18 119.8 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 119.7(3) . . ?
C21 C20 S1 121.6(2) . . ?
C25 C20 S1 118.7(2) . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.2(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 C26 121.0(2) . . ?
C22 C23 C26 118.2(2) . . ?
C25 C24 C23 119.4(2) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C20 120.3(2) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
F1 C26 F2 106.6(2) . . ?
F1 C26 F3 106.5(2) . . ?
F2 C26 F3 105.2(2) . . ?
F1 C26 C23 113.2(2) . . ?
F2 C26 C23 112.8(2) . . ?
F3 C26 C23 111.9(2) . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_19131_a
_database_code_depnum_ccdc_archive 'CCDC 1963594'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H30 N2 O4 S'
_chemical_formula_weight         454.57

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7592(5)
_cell_length_b                   10.6361(5)
_cell_length_c                   13.0359(6)
_cell_angle_alpha                109.272(3)
_cell_angle_beta                 99.244(3)
_cell_angle_gamma                108.409(3)
_cell_volume                     1157.73(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9668
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      68.20

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    1.520
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4509
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50075
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.760
_diffrn_reflns_theta_max         68.301
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4213
_reflns_number_gt                3709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.7228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4213
_refine_ls_number_parameters     330
_refine_ls_number_restraints     632
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.70268(8) 0.88626(12) 0.60258(8) 0.0228(2) Uani 0.904(3) 1 d D U P A 1
O1 O 0.55431(18) 0.8422(2) 0.52380(15) 0.0309(4) Uani 0.904(3) 1 d D U P A 1
O2 O 0.80773(17) 0.84782(19) 0.54577(14) 0.0350(5) Uani 0.904(3) 1 d D U P A 1
O3 O 0.76385(17) 1.03820(15) 0.68336(13) 0.0330(4) Uani 0.904(3) 1 d D U P A 1
S1A S 0.6844(8) 0.8219(12) 0.5666(8) 0.0336(18) Uani 0.096(3) 1 d D U P A 2
O1A O 0.569(2) 0.882(2) 0.5626(17) 0.0309(4) Uani 0.096(3) 1 d D U P A 2
O2A O 0.710(2) 0.723(2) 0.4785(15) 0.062(5) Uani 0.096(3) 1 d D U P A 2
O3A O 0.8253(13) 0.9558(17) 0.6271(14) 0.050(5) Uani 0.096(3) 1 d D U P A 2
C1 C 0.0241(3) -0.3143(2) 0.9723(2) 0.0426(5) Uani 1 1 d . U . . .
H1A H -0.056728 -0.371663 0.899980 0.064 Uiso 1 1 calc R U . . .
H1B H -0.002033 -0.238940 1.021413 0.064 Uiso 1 1 calc R U . . .
H1C H 0.036171 -0.377758 1.009918 0.064 Uiso 1 1 calc R U . . .
N1 N 0.16430(19) -0.24712(19) 0.95091(16) 0.0391(4) Uani 1 1 d . U . . .
C2 C 0.2863(2) -0.2911(2) 0.97895(19) 0.0400(5) Uani 1 1 d . U . . .
H2A H 0.302873 -0.346292 0.908796 0.060 Uiso 1 1 calc R U . . .
H2B H 0.259759 -0.351898 1.021039 0.060 Uiso 1 1 calc R U . . .
H2C H 0.378818 -0.204878 1.025998 0.060 Uiso 1 1 calc R U . . .
N2 N 0.16003(15) 0.75852(14) 0.57645(11) 0.0187(3) Uani 1 1 d . U . . .
C4 C 0.31260(19) -0.08585(17) 0.87731(14) 0.0227(4) Uani 1 1 d . U . . .
H4 H 0.392983 -0.116507 0.889441 0.027 Uiso 1 1 calc R U . . .
C3 C 0.1806(2) -0.14494(17) 0.90611(14) 0.0231(4) Uani 1 1 d . U . . .
C5 C 0.32590(19) 0.01624(17) 0.83163(14) 0.0216(3) Uani 1 1 d . U . . .
H5 H 0.415281 0.053032 0.811947 0.026 Uiso 1 1 calc R U . . .
C6 C 0.21201(19) 0.06744(17) 0.81331(13) 0.0210(3) Uani 1 1 d . U . . .
C8 C 0.0640(2) -0.09684(17) 0.88499(14) 0.0228(4) Uani 1 1 d . U . . .
H8 H -0.027180 -0.136087 0.901819 0.027 Uiso 1 1 calc R U . . .
C7 C 0.07993(19) 0.00622(17) 0.84030(14) 0.0219(3) Uani 1 1 d . U . . .
H7 H -0.000552 0.036552 0.827464 0.026 Uiso 1 1 calc R U . . .
C9 C 0.23434(19) 0.17831(17) 0.76852(14) 0.0223(4) Uani 1 1 d . U . . .
H9 H 0.324426 0.207107 0.747659 0.027 Uiso 1 1 calc R U . . .
C10 C 0.1400(2) 0.24462(18) 0.75353(14) 0.0234(4) Uani 1 1 d . U . . .
H10 H 0.047788 0.216630 0.771903 0.028 Uiso 1 1 calc R U . . .
C11 C 0.17380(19) 0.35574(17) 0.71091(14) 0.0215(3) Uani 1 1 d . U . . .
H11 H 0.263083 0.378628 0.688202 0.026 Uiso 1 1 calc R U . . .
C12 C 0.08582(19) 0.42972(17) 0.70123(13) 0.0208(3) Uani 1 1 d . U . . .
H12 H -0.003314 0.405097 0.723905 0.025 Uiso 1 1 calc R U . . .
C13 C 0.11515(18) 0.54299(16) 0.65945(13) 0.0178(3) Uani 1 1 d . U . . .
C14 C 0.24742(18) 0.59845(17) 0.62989(13) 0.0200(3) Uani 1 1 d . U . . .
H14 H 0.323863 0.562091 0.638422 0.024 Uiso 1 1 calc R U . . .
C15 C 0.26678(18) 0.70410(17) 0.58904(13) 0.0204(3) Uani 1 1 d . U . . .
H15 H 0.356362 0.739758 0.569243 0.024 Uiso 1 1 calc R U . . .
C16 C 0.03345(18) 0.71074(17) 0.60551(13) 0.0193(3) Uani 1 1 d . U . . .
H16 H -0.040028 0.750634 0.597504 0.023 Uiso 1 1 calc R U . . .
C17 C 0.00949(18) 0.60458(17) 0.64673(13) 0.0188(3) Uani 1 1 d . U . . .
H17 H -0.080509 0.572385 0.666974 0.023 Uiso 1 1 calc R U . . .
C18 C 0.1853(2) 0.87259(18) 0.53139(15) 0.0263(4) Uani 1 1 d . U . . .
H18A H 0.184386 0.831583 0.451899 0.039 Uiso 1 1 calc R U . . .
H18B H 0.283291 0.952608 0.576601 0.039 Uiso 1 1 calc R U . . .
H18C H 0.104775 0.908841 0.535922 0.039 Uiso 1 1 calc R U . . .
C19 C 0.5933(2) 0.5382(2) 0.89307(16) 0.0306(4) Uani 1 1 d . U . . .
H19A H 0.489221 0.512978 0.897167 0.046 Uiso 1 1 calc R U . . .
H19B H 0.663855 0.597530 0.969779 0.046 Uiso 1 1 calc R U . . .
H19C H 0.610136 0.449236 0.859825 0.046 Uiso 1 1 calc R U . . .
C20 C 0.61872(17) 0.62247(18) 0.81984(14) 0.0206(3) Uani 1 1 d . U . . .
O1S O 0.4166(3) 0.7974(2) 0.30032(14) 0.0610(5) Uani 1 1 d D . . . .
HO1S H 0.323(2) 0.802(3) 0.288(3) 0.073 Uiso 1 1 d D U . . .
HO2S H 0.466(3) 0.824(3) 0.3710(17) 0.073 Uiso 1 1 d D U . . .
C21 C 0.64296(18) 0.76898(18) 0.86268(14) 0.0225(4) Uani 1 1 d . U . . .
H21 H 0.642751 0.815464 0.938613 0.027 Uiso 1 1 calc R U . . .
C22 C 0.66736(18) 0.84818(18) 0.79666(15) 0.0230(4) Uani 1 1 d . U . . .
H22 H 0.683002 0.947702 0.827180 0.028 Uiso 1 1 calc R U . . .
C23 C 0.66882(17) 0.78161(18) 0.68609(14) 0.0208(3) Uani 1 1 d . U . . .
C24 C 0.64427(18) 0.63548(19) 0.64143(14) 0.0236(4) Uani 1 1 d . U . . .
H24 H 0.644705 0.589531 0.565477 0.028 Uiso 1 1 calc R U . . .
C25 C 0.61909(18) 0.55664(18) 0.70793(15) 0.0227(4) Uani 1 1 d . U . . .
H25 H 0.601940 0.456763 0.676815 0.027 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
S1 O2 1.4406(16) . ?
S1 O3 1.4636(19) . ?
S1 O1 1.4653(17) . ?
S1 C23 1.7933(17) . ?
S1A O2A 1.396(14) . ?
S1A O1A 1.462(15) . ?
S1A O3A 1.488(13) . ?
S1A C23 1.763(7) . ?
C1 N1 1.448(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N1 C3 1.374(2) . ?
N1 C2 1.447(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C16 1.345(2) . ?
N2 C15 1.355(2) . ?
N2 C18 1.485(2) . ?
C4 C5 1.383(2) . ?
C4 C3 1.413(3) . ?
C4 H4 0.9500 . ?
C3 C8 1.411(2) . ?
C5 C6 1.404(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(2) . ?
C6 C9 1.453(2) . ?
C8 C7 1.381(2) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.352(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.435(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.353(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.448(2) . ?
C12 H12 0.9500 . ?
C13 C17 1.401(2) . ?
C13 C14 1.411(2) . ?
C14 C15 1.369(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.376(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.509(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.395(2) . ?
C20 C25 1.396(2) . ?
O1S HO1S 0.923(18) . ?
O1S HO2S 0.872(18) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(2) . ?
C24 C25 1.390(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
O2 S1 O3 113.47(11) . . ?
O2 S1 O1 112.97(13) . . ?
O3 S1 O1 112.52(12) . . ?
O2 S1 C23 106.09(9) . . ?
O3 S1 C23 105.78(9) . . ?
O1 S1 C23 105.15(10) . . ?
O2A S1A O1A 129.5(13) . . ?
O2A S1A O3A 109.2(12) . . ?
O1A S1A O3A 101.8(13) . . ?
O2A S1A C23 116.6(9) . . ?
O1A S1A C23 97.9(10) . . ?
O3A S1A C23 96.2(7) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N1 C2 121.44(17) . . ?
C3 N1 C1 120.99(16) . . ?
C2 N1 C1 117.58(16) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C16 N2 C15 120.32(14) . . ?
C16 N2 C18 120.45(14) . . ?
C15 N2 C18 119.22(14) . . ?
C5 C4 C3 120.60(16) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N1 C3 C8 121.00(16) . . ?
N1 C3 C4 121.68(16) . . ?
C8 C3 C4 117.31(15) . . ?
C4 C5 C6 122.35(16) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C7 116.66(15) . . ?
C5 C6 C9 119.92(16) . . ?
C7 C6 C9 123.42(15) . . ?
C7 C8 C3 121.24(16) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
C8 C7 C6 121.80(16) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C10 C9 C6 126.63(16) . . ?
C10 C9 H9 116.7 . . ?
C6 C9 H9 116.7 . . ?
C9 C10 C11 122.48(16) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C10 123.75(16) . . ?
C12 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C11 C12 C13 125.92(16) . . ?
C11 C12 H12 117.0 . . ?
C13 C12 H12 117.0 . . ?
C17 C13 C14 116.09(15) . . ?
C17 C13 C12 120.15(15) . . ?
C14 C13 C12 123.76(15) . . ?
C15 C14 C13 120.72(15) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N2 C15 C14 120.97(15) . . ?
N2 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
N2 C16 C17 120.55(15) . . ?
N2 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C13 121.32(15) . . ?
C16 C17 H17 119.3 . . ?
C13 C17 H17 119.3 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 118.20(15) . . ?
C21 C20 C19 120.65(15) . . ?
C25 C20 C19 121.15(15) . . ?
HO1S O1S HO2S 116(3) . . ?
C22 C21 C20 121.35(15) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C21 119.76(16) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 119.88(15) . . ?
C22 C23 S1A 139.4(4) . . ?
C24 C23 S1A 100.6(4) . . ?
C22 C23 S1 119.12(13) . . ?
C24 C23 S1 121.00(13) . . ?
C25 C24 C23 120.02(15) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 120.79(15) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?

_refine_diff_density_max         0.722
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_19133_a
_database_code_depnum_ccdc_archive 'CCDC 1964071'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 N3 O5 S'
_chemical_formula_weight         467.53

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5802(6)
_cell_length_b                   17.0433(13)
_cell_length_c                   17.5161(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.416(6)
_cell_angle_gamma                90
_cell_volume                     2262.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3179
_cell_measurement_theta_min      5.05
_cell_measurement_theta_max      66.70

_exptl_crystal_description       Needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    1.624
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4581
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23400
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.619
_diffrn_reflns_theta_max         68.334
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4137
_reflns_number_gt                3107
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+0.6232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.00079(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4137
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.04403(8) 0.46647(3) 0.80595(3) 0.02474(18) Uani 1 1 d . . . . .
O1 O -0.0669(2) 0.53580(9) 0.80195(11) 0.0352(4) Uani 1 1 d . . . . .
N1 N 0.3649(3) 0.66110(13) 1.04256(12) 0.0336(5) Uani 1 1 d . . . . .
C1 C 0.3343(4) 0.57845(16) 1.05704(17) 0.0437(7) Uani 1 1 d . . . . .
H1A H 0.257796 0.556765 1.016337 0.066 Uiso 1 1 calc R U . . .
H1B H 0.277047 0.572338 1.106255 0.066 Uiso 1 1 calc R U . . .
H1C H 0.447176 0.550426 1.058321 0.066 Uiso 1 1 calc R U . . .
O2 O -0.0436(2) 0.39724(9) 0.77509(10) 0.0308(4) Uani 1 1 d . . . . .
N2 N 1.0644(2) 0.76485(11) 0.37058(10) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.3329(3) 0.71634(17) 1.10359(15) 0.0371(6) Uani 1 1 d . . . . .
H2A H 0.445859 0.735492 1.124663 0.056 Uiso 1 1 calc R U . . .
H2B H 0.267436 0.690204 1.143902 0.056 Uiso 1 1 calc R U . . .
H2C H 0.263728 0.760653 1.083480 0.056 Uiso 1 1 calc R U . . .
N3 N 0.6207(3) 0.52474(11) 0.58472(12) 0.0266(5) Uani 1 1 d . . . . .
O3 O 0.1294(2) 0.45337(12) 0.87975(10) 0.0408(5) Uani 1 1 d . . . . .
C3 C 0.4470(3) 0.68394(14) 0.97738(13) 0.0259(5) Uani 1 1 d . . . . .
C4 C 0.4829(3) 0.76310(14) 0.96127(14) 0.0268(5) Uani 1 1 d . . . . .
H4 H 0.452281 0.802522 0.996930 0.032 Uiso 1 1 calc R U . . .
O4 O 0.5897(2) 0.56822(10) 0.53005(10) 0.0312(4) Uani 1 1 d . . . . .
O5 O 0.7633(2) 0.49092(10) 0.59519(10) 0.0345(4) Uani 1 1 d . . . . .
C5 C 0.5619(3) 0.78402(14) 0.89433(14) 0.0250(5) Uani 1 1 d . . . . .
H5 H 0.583411 0.838031 0.884898 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6119(3) 0.72903(13) 0.83962(13) 0.0216(5) Uani 1 1 d . . . . .
C7 C 0.5794(3) 0.65016(14) 0.85684(14) 0.0271(6) Uani 1 1 d . . . . .
H7 H 0.615403 0.610751 0.822169 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4973(3) 0.62827(15) 0.92229(14) 0.0301(6) Uani 1 1 d . . . . .
H8 H 0.473538 0.574288 0.930847 0.036 Uiso 1 1 calc R U . . .
C9 C 0.6902(3) 0.75472(14) 0.76908(13) 0.0245(5) Uani 1 1 d . . . . .
H9 H 0.702304 0.809782 0.762579 0.029 Uiso 1 1 calc R U . . .
C10 C 0.7478(3) 0.70941(14) 0.71172(13) 0.0236(5) Uani 1 1 d . . . . .
H10 H 0.742211 0.654055 0.717556 0.028 Uiso 1 1 calc R U . . .
C11 C 0.8171(3) 0.74026(14) 0.64228(13) 0.0238(5) Uani 1 1 d . . . . .
H11 H 0.822939 0.795605 0.636444 0.029 Uiso 1 1 calc R U . . .
C12 C 0.8743(3) 0.69486(14) 0.58497(13) 0.0246(5) Uani 1 1 d . . . . .
H12 H 0.872616 0.639781 0.593250 0.029 Uiso 1 1 calc R U . . .
C13 C 0.9382(3) 0.72140(14) 0.51183(13) 0.0233(5) Uani 1 1 d . . . . .
C14 C 0.9505(3) 0.80077(14) 0.49059(13) 0.0247(5) Uani 1 1 d . . . . .
H14 H 0.915140 0.840584 0.524965 0.030 Uiso 1 1 calc R U . . .
C15 C 1.0131(3) 0.82093(14) 0.42058(13) 0.0245(5) Uani 1 1 d . . . . .
H15 H 1.020725 0.874705 0.406788 0.029 Uiso 1 1 calc R U . . .
C16 C 1.0524(3) 0.68813(14) 0.38884(14) 0.0260(5) Uani 1 1 d . . . . .
H16 H 1.087608 0.649441 0.353276 0.031 Uiso 1 1 calc R U . . .
C17 C 0.9901(3) 0.66562(15) 0.45800(14) 0.0273(6) Uani 1 1 d . . . . .
H17 H 0.981800 0.611360 0.469797 0.033 Uiso 1 1 calc R U . . .
C18 C 1.1414(3) 0.78785(15) 0.29714(13) 0.0281(6) Uani 1 1 d . . . . .
H18A H 1.117318 0.746905 0.259009 0.042 Uiso 1 1 calc R U . . .
H18B H 1.269194 0.794499 0.304056 0.042 Uiso 1 1 calc R U . . .
H18C H 1.088651 0.837402 0.279677 0.042 Uiso 1 1 calc R U . . .
C19 C 0.4816(3) 0.51205(13) 0.64026(14) 0.0231(5) Uani 1 1 d . . . . .
C20 C 0.3096(3) 0.53213(14) 0.61911(14) 0.0290(6) Uani 1 1 d . . . . .
H20 H 0.283160 0.554833 0.570628 0.035 Uiso 1 1 calc R U . . .
C21 C 0.1786(3) 0.51819(14) 0.67041(14) 0.0286(6) Uani 1 1 d . . . . .
H21 H 0.059618 0.530664 0.657068 0.034 Uiso 1 1 calc R U . . .
C22 C 0.2190(3) 0.48604(13) 0.74145(13) 0.0223(5) Uani 1 1 d . . . . .
C23 C 0.3923(3) 0.46767(14) 0.76194(14) 0.0260(5) Uani 1 1 d . . . . .
H23 H 0.419259 0.446590 0.811066 0.031 Uiso 1 1 calc R U . . .
C24 C 0.5265(3) 0.48011(13) 0.71055(14) 0.0258(5) Uani 1 1 d . . . . .
H24 H 0.645346 0.467040 0.723411 0.031 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
S1 O3 1.4485(19) . ?
S1 O1 1.4511(17) . ?
S1 O2 1.4519(17) . ?
S1 C22 1.795(2) . ?
N1 C3 1.370(3) . ?
N1 C2 1.450(3) . ?
N1 C1 1.451(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C16 1.350(3) . ?
N2 C15 1.360(3) . ?
N2 C18 1.479(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 O4 1.229(3) . ?
N3 O5 1.235(2) . ?
N3 C19 1.468(3) . ?
C3 C4 1.406(3) . ?
C3 C8 1.412(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 C9 1.452(3) . ?
C7 C8 1.370(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.348(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.437(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.347(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.453(3) . ?
C12 H12 0.9500 . ?
C13 C17 1.402(3) . ?
C13 C14 1.407(3) . ?
C14 C15 1.370(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.381(3) . ?
C19 C20 1.389(3) . ?
C20 C21 1.376(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C23 C24 1.391(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
O3 S1 O1 114.47(12) . . ?
O3 S1 O2 113.39(11) . . ?
O1 S1 O2 112.61(11) . . ?
O3 S1 C22 105.65(11) . . ?
O1 S1 C22 104.77(10) . . ?
O2 S1 C22 104.78(10) . . ?
C3 N1 C2 121.2(2) . . ?
C3 N1 C1 120.0(2) . . ?
C2 N1 C1 118.1(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C16 N2 C15 120.4(2) . . ?
C16 N2 C18 119.6(2) . . ?
C15 N2 C18 120.0(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 N3 O5 123.2(2) . . ?
O4 N3 C19 118.58(19) . . ?
O5 N3 C19 118.3(2) . . ?
N1 C3 C4 122.3(2) . . ?
N1 C3 C8 120.9(2) . . ?
C4 C3 C8 116.8(2) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 122.7(2) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C7 116.3(2) . . ?
C5 C6 C9 120.3(2) . . ?
C7 C6 C9 123.4(2) . . ?
C8 C7 C6 121.8(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C3 121.7(2) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
C10 C9 C6 127.5(2) . . ?
C10 C9 H9 116.3 . . ?
C6 C9 H9 116.3 . . ?
C9 C10 C11 123.6(2) . . ?
C9 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C12 C11 C10 123.5(2) . . ?
C12 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C11 C12 C13 126.8(2) . . ?
C11 C12 H12 116.6 . . ?
C13 C12 H12 116.6 . . ?
C17 C13 C14 116.9(2) . . ?
C17 C13 C12 119.2(2) . . ?
C14 C13 C12 123.9(2) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N2 C15 C14 120.8(2) . . ?
N2 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N2 C16 C17 120.6(2) . . ?
N2 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C13 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C13 C17 H17 119.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 122.9(2) . . ?
C24 C19 N3 118.9(2) . . ?
C20 C19 N3 118.1(2) . . ?
C21 C20 C19 118.1(2) . . ?
C21 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
C20 C21 C22 120.4(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 S1 119.18(18) . . ?
C23 C22 S1 120.29(18) . . ?
C22 C23 C24 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 118.0(2) . . ?
C19 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_20039_a
_database_code_depnum_ccdc_archive 'CCDC 2006490'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N O4 S'
_chemical_formula_weight         447.53

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.0739(2)
_cell_length_b                   8.1024(2)
_cell_length_c                   10.0726(2)
_cell_angle_alpha                103.7790(10)
_cell_angle_beta                 98.2090(10)
_cell_angle_gamma                91.3380(10)
_cell_volume                     553.97(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9752
_cell_measurement_theta_min      4.57
_cell_measurement_theta_max      74.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.573
_shelx_estimated_absorpt_T_min   0.765
_shelx_estimated_absorpt_T_max   0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4276
_exptl_absorpt_correction_T_max  0.5871
_exptl_absorpt_process_details   'SADABS-2016/2 (Krause, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker D8 Venture Cu/Mo dual source'
_diffrn_measurement_device_type  'kappa goniometer + Photon-III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30421
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.573
_diffrn_reflns_theta_max         74.655
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4366
_reflns_number_gt                4217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.955

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 853)'
_computing_publication_material  'Bruker APEX3'
_refine_special_details          
; 
Bruker D8 Venture with dual Cu and Mo diamond microfocus X-ray sources, 
kappa goniometer, Bruker Photon-III detector, Oxford 800+ low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1164P)²+0.1051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4366
_refine_ls_number_parameters     292
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.20433(15) 0.19254(13) 0.19671(11) 0.0508(3) Uani 1 1 d . . . . .
N1 N 1.1586(5) 0.0754(5) 0.5935(4) 0.0494(8) Uani 1 1 d . . . . .
O1 O -0.3395(5) 0.9332(5) 0.7873(3) 0.0573(8) Uani 1 1 d . . . . .
C1 C -0.3372(8) 1.0241(8) 0.9271(5) 0.0643(12) Uani 1 1 d . . . . .
H1A H -0.222002 1.096230 0.958191 0.096 Uiso 1 1 calc R U . . .
H1B H -0.342027 0.944948 0.984036 0.096 Uiso 1 1 calc R U . . .
H1C H -0.446107 1.092534 0.933324 0.096 Uiso 1 1 calc R U . . .
O2 O 1.2860(6) 0.1861(5) 0.0725(4) 0.0709(10) Uani 1 1 d . . . . .
C2 C -0.1903(6) 0.8356(5) 0.7586(4) 0.0445(8) Uani 1 1 d . . . . .
C3 C -0.1960(6) 0.7518(6) 0.6180(4) 0.0494(9) Uani 1 1 d . . . . .
H3 H -0.299873 0.763718 0.553789 0.059 Uiso 1 1 calc R U . . .
O3 O 1.3414(6) 0.2476(5) 0.3228(4) 0.0666(9) Uani 1 1 d . . . . .
C4 C -0.0535(6) 0.6546(5) 0.5750(4) 0.0482(9) Uani 1 1 d . . . . .
H4 H -0.059880 0.601438 0.481680 0.058 Uiso 1 1 calc R U . . .
O4 O 1.0915(6) 0.0383(4) 0.1925(4) 0.0639(9) Uani 1 1 d . . . . .
C5 C 0.1063(5) 0.6328(5) 0.6710(4) 0.0405(8) Uani 1 1 d . . . . .
C6 C 0.1111(6) 0.7155(5) 0.8124(4) 0.0407(8) Uani 1 1 d . . . . .
C7 C -0.0378(6) 0.8174(5) 0.8549(4) 0.0436(8) Uani 1 1 d . . . . .
H7 H -0.033621 0.872340 0.947665 0.052 Uiso 1 1 calc R U . . .
C9 C 0.4135(6) 0.5924(6) 0.8668(4) 0.0537(10) Uani 1 1 d . . . . .
H9 H 0.514483 0.577220 0.931956 0.064 Uiso 1 1 calc R U . . .
C8 C 0.2702(6) 0.6922(6) 0.9082(4) 0.0515(9) Uani 1 1 d . . . . .
H8 H 0.276568 0.746286 1.001329 0.062 Uiso 1 1 calc R U . . .
C10 C 0.4101(6) 0.5112(5) 0.7244(4) 0.0436(8) Uani 1 1 d . . . . .
C11 C 0.2583(6) 0.5334(5) 0.6297(4) 0.0435(8) Uani 1 1 d . . . . .
H11 H 0.255925 0.481776 0.536484 0.052 Uiso 1 1 calc R U . . .
C12 C 0.5621(6) 0.4063(5) 0.6753(4) 0.0459(8) Uani 1 1 d . . . . .
H12 H 0.549036 0.360145 0.580362 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7179(6) 0.3689(6) 0.7512(4) 0.0488(9) Uani 1 1 d . . . . .
H13 H 0.732544 0.411182 0.846619 0.059 Uiso 1 1 calc R U . . .
C14 C 0.8666(6) 0.2662(5) 0.6940(4) 0.0440(8) Uani 1 1 d . . . . .
C15 C 0.8638(6) 0.1982(6) 0.5527(4) 0.0478(9) Uani 1 1 d . . . . .
H15 H 0.760862 0.216107 0.490155 0.057 Uiso 1 1 calc R U . . .
C16 C 1.0093(6) 0.1062(6) 0.5049(4) 0.0494(9) Uani 1 1 d . . . . .
H16 H 1.005801 0.064079 0.410195 0.059 Uiso 1 1 calc R U . . .
C17 C 1.1657(6) 0.1368(7) 0.7298(5) 0.0548(10) Uani 1 1 d . . . . .
H17 H 1.268548 0.113758 0.789899 0.066 Uiso 1 1 calc R U . . .
C18 C 1.0246(6) 0.2328(6) 0.7829(5) 0.0522(10) Uani 1 1 d . . . . .
H18 H 1.033684 0.276005 0.877948 0.063 Uiso 1 1 calc R U . . .
C19 C 1.3124(7) -0.0250(7) 0.5364(6) 0.0650(13) Uani 1 1 d . . . . .
H19A H 1.262534 -0.138801 0.491228 0.098 Uiso 1 1 calc R U . . .
H19B H 1.413646 -0.028175 0.610062 0.098 Uiso 1 1 calc R U . . .
H19C H 1.361318 0.026736 0.470859 0.098 Uiso 1 1 calc R U . . .
C20 C 0.6523(10) 0.7624(8) 0.2336(6) 0.0744(15) Uani 1 1 d . . . . .
H20A H 0.691920 0.842966 0.185467 0.112 Uiso 1 1 calc R U . . .
H20B H 0.657847 0.817357 0.329847 0.112 Uiso 1 1 calc R U . . .
H20C H 0.523573 0.719199 0.195179 0.112 Uiso 1 1 calc R U . . .
C21 C 0.7840(7) 0.6168(6) 0.2186(4) 0.0551(11) Uani 1 1 d . . . . .
C22 C 0.7238(7) 0.4551(7) 0.2266(5) 0.0570(11) Uani 1 1 d . . . . .
H22 H 0.597493 0.433541 0.236452 0.068 Uiso 1 1 calc R U . . .
C23 C 0.8490(7) 0.3265(6) 0.2200(4) 0.0516(10) Uani 1 1 d . . . . .
H23 H 0.806425 0.219793 0.226835 0.062 Uiso 1 1 calc R U . . .
C24 C 1.0367(6) 0.3539(6) 0.2035(4) 0.0477(9) Uani 1 1 d . . . . .
C25 C 1.0973(8) 0.5142(6) 0.1921(6) 0.0600(11) Uani 1 1 d . . . . .
H25 H 1.222535 0.534229 0.179093 0.072 Uiso 1 1 calc R U . . .
C26 C 0.9724(8) 0.6435(6) 0.2001(5) 0.0627(12) Uani 1 1 d . . . . .
H26 H 1.014867 0.750047 0.192916 0.075 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
S1 O2 1.442(3) . ?
S1 O3 1.453(4) . ?
S1 O4 1.456(3) . ?
S1 C24 1.781(5) . ?
N1 C17 1.338(7) . ?
N1 C16 1.351(6) . ?
N1 C19 1.474(6) . ?
O1 C2 1.357(5) . ?
O1 C1 1.422(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.379(6) . ?
C2 C3 1.412(6) . ?
C3 C4 1.350(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.423(5) . ?
C4 H4 0.9300 . ?
C5 C11 1.409(5) . ?
C5 C6 1.417(5) . ?
C6 C7 1.406(6) . ?
C6 C8 1.422(6) . ?
C7 H7 0.9300 . ?
C9 C8 1.361(6) . ?
C9 C10 1.425(6) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.376(6) . ?
C10 C12 1.455(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.333(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.455(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(6) . ?
C14 C18 1.403(6) . ?
C15 C16 1.361(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.370(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.513(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.390(8) . ?
C21 C22 1.392(7) . ?
C22 C23 1.379(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.394(6) . ?
C25 C26 1.381(8) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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
O2 S1 O3 113.6(2) . . ?
O2 S1 O4 113.6(2) . . ?
O3 S1 O4 112.7(2) . . ?
O2 S1 C24 105.5(2) . . ?
O3 S1 C24 105.6(2) . . ?
O4 S1 C24 104.9(2) . . ?
C17 N1 C16 120.0(4) . . ?
C17 N1 C19 121.4(4) . . ?
C16 N1 C19 118.6(4) . . ?
C2 O1 C1 117.3(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 124.8(4) . . ?
O1 C2 C3 115.3(4) . . ?
C7 C2 C3 119.9(4) . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C11 C5 C6 119.7(3) . . ?
C11 C5 C4 122.2(3) . . ?
C6 C5 C4 118.1(4) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 C8 121.7(3) . . ?
C5 C6 C8 118.0(4) . . ?
C2 C7 C6 119.8(4) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C8 C6 121.5(4) . . ?
C9 C8 H8 119.3 . . ?
C6 C8 H8 119.3 . . ?
C11 C10 C9 118.9(4) . . ?
C11 C10 C12 118.7(3) . . ?
C9 C10 C12 122.4(4) . . ?
C10 C11 C5 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C5 C11 H11 119.3 . . ?
C13 C12 C10 127.2(4) . . ?
C13 C12 H12 116.4 . . ?
C10 C12 H12 116.4 . . ?
C12 C13 C14 124.0(4) . . ?
C12 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C15 C14 C18 116.7(4) . . ?
C15 C14 C13 123.6(4) . . ?
C18 C14 C13 119.7(4) . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
N1 C16 C15 120.7(4) . . ?
N1 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N1 C17 C18 121.4(4) . . ?
N1 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C14 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C14 C18 H18 120.0 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 118.1(5) . . ?
C26 C21 C20 120.1(5) . . ?
C22 C21 C20 121.7(5) . . ?
C23 C22 C21 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 121.0(4) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C25 118.7(5) . . ?
C23 C24 S1 122.5(3) . . ?
C25 C24 S1 118.8(4) . . ?
C26 C25 C24 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 121.0(4) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?

_refine_diff_density_max         0.129
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_20026_a
_database_code_depnum_ccdc_archive 'CCDC 1990758'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2020-03-16 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 N O5 S'
_chemical_formula_weight         465.54

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2355(5)
_cell_length_b                   11.1247(7)
_cell_length_c                   12.4991(6)
_cell_angle_alpha                86.568(4)
_cell_angle_beta                 75.984(4)
_cell_angle_gamma                88.350(4)
_cell_volume                     1108.93(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3934
_cell_measurement_theta_min      3.98
_cell_measurement_theta_max      67.93

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.626
_shelx_estimated_absorpt_T_min   0.641
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4761
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14426
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.650
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3884
_reflns_number_gt                2974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.3749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3884
_refine_ls_number_parameters     309
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.96499(8) 0.18842(5) 0.20878(5) 0.01616(18) Uani 1 1 d . . . . .
N1 N 0.7069(3) 0.61273(19) 0.15538(17) 0.0166(5) Uani 1 1 d . . . . .
O1 O -0.4611(2) 0.30740(16) 1.01935(14) 0.0210(4) Uani 1 1 d . . . . .
C1 C -0.5110(3) 0.1912(3) 1.0722(2) 0.0243(6) Uani 1 1 d . . . . .
H1A H -0.534483 0.138369 1.017939 0.036 Uiso 1 1 calc R U . . .
H1B H -0.611938 0.200366 1.131820 0.036 Uiso 1 1 calc R U . . .
H1C H -0.420617 0.155666 1.102893 0.036 Uiso 1 1 calc R U . . .
C2 C -0.3256(3) 0.3107(2) 0.9316(2) 0.0152(5) Uani 1 1 d . . . . .
O2 O 0.8249(2) 0.24657(19) 0.17418(16) 0.0298(5) Uani 1 1 d . . . . .
O3 O 1.0897(2) 0.27195(16) 0.22082(15) 0.0255(5) Uani 1 1 d . . . . .
C3 C -0.2296(3) 0.2110(2) 0.8920(2) 0.0161(5) Uani 1 1 d . . . . .
H3 H -0.253518 0.133626 0.928056 0.019 Uiso 1 1 calc R U . . .
O4 O 1.0359(2) 0.08797(16) 0.14208(15) 0.0243(4) Uani 1 1 d . . . . .
C4 C -0.0981(3) 0.2258(2) 0.7988(2) 0.0160(5) Uani 1 1 d . . . . .
H4 H -0.033093 0.157313 0.771540 0.019 Uiso 1 1 calc R U . . .
C5 C -0.0584(3) 0.3384(2) 0.7440(2) 0.0160(5) Uani 1 1 d . . . . .
O5 O 1.2109(3) 0.05070(18) -0.07493(16) 0.0254(5) Uani 1 1 d D . . . .
HO51 H 1.163(4) 0.068(3) -0.0114(19) 0.044(11) Uiso 1 1 d D . . . .
HO52 H 1.143(4) 0.006(3) -0.092(4) 0.071(15) Uiso 1 1 d D . . . .
C6 C -0.1540(3) 0.4383(2) 0.7883(2) 0.0165(5) Uani 1 1 d . . . . .
H6 H -0.127766 0.516284 0.754209 0.020 Uiso 1 1 calc R U . . .
C7 C -0.2850(3) 0.4252(2) 0.8802(2) 0.0156(5) Uani 1 1 d . . . . .
H7 H -0.348210 0.493838 0.908991 0.019 Uiso 1 1 calc R U . . .
C9 C 0.1358(3) 0.4492(2) 0.5865(2) 0.0181(6) Uani 1 1 d . . . . .
H9 H 0.084206 0.522230 0.614105 0.022 Uiso 1 1 calc R U . . .
C8 C 0.0776(3) 0.3471(2) 0.6437(2) 0.0156(5) Uani 1 1 d . . . . .
H8 H 0.129248 0.273820 0.616730 0.019 Uiso 1 1 calc R U . . .
C10 C 0.2708(3) 0.4597(2) 0.4858(2) 0.0155(5) Uani 1 1 d . . . . .
C11 C 0.3472(3) 0.3587(2) 0.4275(2) 0.0184(6) Uani 1 1 d . . . . .
H11 H 0.307765 0.280387 0.453701 0.022 Uiso 1 1 calc R U . . .
C12 C 0.4748(3) 0.3705(2) 0.3354(2) 0.0196(6) Uani 1 1 d . . . . .
H12 H 0.524989 0.301201 0.299233 0.024 Uiso 1 1 calc R U . . .
C13 C 0.5319(3) 0.4863(2) 0.2940(2) 0.0163(5) Uani 1 1 d . . . . .
C14 C 0.4568(3) 0.5893(2) 0.3477(2) 0.0164(5) Uani 1 1 d . . . . .
C15 C 0.3265(3) 0.5739(2) 0.4453(2) 0.0171(5) Uani 1 1 d . . . . .
H15 H 0.277087 0.642407 0.483153 0.021 Uiso 1 1 calc R U . . .
C16 C 0.5141(3) 0.7039(2) 0.3018(2) 0.0186(6) Uani 1 1 d . . . . .
H16 H 0.467005 0.774257 0.337541 0.022 Uiso 1 1 calc R U . . .
C17 C 0.6363(3) 0.7143(2) 0.2065(2) 0.0180(6) Uani 1 1 d . . . . .
H17 H 0.672785 0.791752 0.175280 0.022 Uiso 1 1 calc R U . . .
C18 C 0.6601(3) 0.5030(2) 0.1962(2) 0.0178(6) Uani 1 1 d . . . . .
H18 H 0.713234 0.434894 0.159434 0.021 Uiso 1 1 calc R U . . .
C19 C 0.8371(3) 0.6305(2) 0.0507(2) 0.0188(6) Uani 1 1 d . . . . .
H19A H 0.878388 0.551895 0.023203 0.028 Uiso 1 1 calc R U . . .
H19B H 0.929962 0.675699 0.064061 0.028 Uiso 1 1 calc R U . . .
H19C H 0.788774 0.675519 -0.004209 0.028 Uiso 1 1 calc R U . . .
C20 C 0.6666(3) -0.0400(3) 0.6667(2) 0.0226(6) Uani 1 1 d . . . . .
H20A H 0.550648 -0.062739 0.672250 0.034 Uiso 1 1 calc R U . . .
H20B H 0.669083 0.017752 0.722459 0.034 Uiso 1 1 calc R U . . .
H20C H 0.732558 -0.111942 0.679145 0.034 Uiso 1 1 calc R U . . .
C21 C 0.7399(3) 0.0168(2) 0.5530(2) 0.0171(6) Uani 1 1 d . . . . .
C22 C 0.7039(3) -0.0267(2) 0.4595(2) 0.0173(6) Uani 1 1 d . . . . .
H22 H 0.630349 -0.092625 0.467294 0.021 Uiso 1 1 calc R U . . .
C23 C 0.7735(3) 0.0243(2) 0.3550(2) 0.0163(5) Uani 1 1 d . . . . .
H23 H 0.747931 -0.006880 0.291985 0.020 Uiso 1 1 calc R U . . .
C24 C 0.8805(3) 0.1210(2) 0.3427(2) 0.0148(5) Uani 1 1 d . . . . .
C25 C 0.9185(3) 0.1648(2) 0.4346(2) 0.0167(5) Uani 1 1 d . . . . .
H25 H 0.992681 0.230393 0.426519 0.020 Uiso 1 1 calc R U . . .
C26 C 0.8483(3) 0.1129(2) 0.5391(2) 0.0184(6) Uani 1 1 d . . . . .
H26 H 0.874969 0.143732 0.601882 0.022 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
S1 O3 1.445(2) . ?
S1 O2 1.450(2) . ?
S1 O4 1.4570(19) . ?
S1 C24 1.779(3) . ?
N1 C18 1.325(3) . ?
N1 C17 1.376(3) . ?
N1 C19 1.483(3) . ?
O1 C2 1.361(3) . ?
O1 C1 1.440(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.388(4) . ?
C2 C7 1.403(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(4) . ?
C5 C8 1.466(3) . ?
O5 HO51 0.830(19) . ?
O5 HO52 0.837(19) . ?
C6 C7 1.376(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C8 1.341(4) . ?
C9 C10 1.465(4) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 C15 1.387(4) . ?
C10 C11 1.423(4) . ?
C11 C12 1.360(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.409(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.413(4) . ?
C13 C18 1.415(4) . ?
C14 C16 1.413(4) . ?
C14 C15 1.421(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.362(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.510(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.388(4) . ?
C21 C22 1.390(4) . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(4) . ?
C25 C26 1.391(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
O3 S1 O2 113.30(12) . . ?
O3 S1 O4 113.04(12) . . ?
O2 S1 O4 112.82(12) . . ?
O3 S1 C24 106.35(12) . . ?
O2 S1 C24 105.86(11) . . ?
O4 S1 C24 104.55(11) . . ?
C18 N1 C17 122.0(2) . . ?
C18 N1 C19 120.8(2) . . ?
C17 N1 C19 117.3(2) . . ?
C2 O1 C1 117.3(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.8(2) . . ?
O1 C2 C7 115.3(2) . . ?
C3 C2 C7 119.9(2) . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 122.1(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 C8 119.4(2) . . ?
C6 C5 C8 123.1(2) . . ?
HO51 O5 HO52 103(4) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C8 C9 C10 126.7(2) . . ?
C8 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
C9 C8 C5 125.9(2) . . ?
C9 C8 H8 117.0 . . ?
C5 C8 H8 117.0 . . ?
C15 C10 C11 118.5(2) . . ?
C15 C10 C9 118.2(2) . . ?
C11 C10 C9 123.3(2) . . ?
C12 C11 C10 122.2(2) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 C18 121.4(2) . . ?
C14 C13 C18 118.4(2) . . ?
C16 C14 C13 118.5(2) . . ?
C16 C14 C15 122.5(2) . . ?
C13 C14 C15 119.0(2) . . ?
C10 C15 C14 120.6(2) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C14 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C14 C16 H16 119.8 . . ?
C16 C17 N1 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
N1 C17 H17 120.0 . . ?
N1 C18 C13 120.7(2) . . ?
N1 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 118.1(2) . . ?
C26 C21 C20 120.6(2) . . ?
C22 C21 C20 121.3(2) . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.9(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 119.7(2) . . ?
C25 C24 S1 120.68(19) . . ?
C23 C24 S1 119.63(19) . . ?
C24 C25 C26 120.0(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 121.1(2) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.061

