# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_cyg219m
_database_code_depnum_ccdc_archive 'CCDC 1854098'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Br N O7 P S'
_chemical_formula_iupac          ?
_chemical_formula_weight         542.33
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   8.8385(5)
_cell_length_b                   14.3341(9)
_cell_length_c                   17.8495(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2261.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5297
_cell_measurement_theta_min      2.5715
_cell_measurement_theta_max      28.8741
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104

_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            24245
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         29.58
_diffrn_reflns_theta_full        29.58
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             6347
_reflns_number_gt                4609
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0981
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_refine_ls_number_reflns         6347
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.670
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1561 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 1.18925(5) 0.74568(4) 0.05949(3) 0.03148(15) Uani d . . . 1 . .
C C1 0.4101(5) 0.6641(3) 0.3203(3) 0.0139(9) Uani d . . . 1 . .
C C2 0.5040(5) 0.6788(3) 0.2484(3) 0.0163(9) Uani d . . . 1 . .
H H2A 0.43717 0.669796 0.204488 0.02 Uiso calc U . R 1 . .
H H2B 0.540418 0.74408 0.247377 0.02 Uiso calc U . R 1 . .
C C3 0.6379(5) 0.6147(3) 0.2409(3) 0.0169(10) Uani d . . . 1 . .
C C4 0.6298(5) 0.5299(3) 0.2717(3) 0.0189(10) Uani d . . . 1 . .
H H4 0.716312 0.490733 0.26915 0.023 Uiso calc U . R 1 . .
C C5 0.4952(5) 0.4946(3) 0.3088(3) 0.0178(10) Uani d . . . 1 . .
C C6 0.7678(5) 0.6462(3) 0.1959(3) 0.0164(10) Uani d . . . 1 . .
C C7 0.9060(5) 0.5975(3) 0.1992(3) 0.0202(11) Uani d . . . 1 . .
H H7 0.913947 0.543938 0.230359 0.024 Uiso calc U . R 1 . .
C C8 1.0297(5) 0.6257(3) 0.1582(3) 0.0230(11) Uani d . . . 1 . .
H H8 1.122592 0.592547 0.161233 0.028 Uiso calc U . R 1 . .
C C9 1.0164(5) 0.7030(3) 0.1127(3) 0.0208(10) Uani d . . . 1 . .
C C10 0.8837(4) 0.7527(4) 0.1073(3) 0.0193(9) Uani d . . . 1 . .
H H10 0.877307 0.805823 0.075639 0.023 Uiso calc U . R 1 . .
C C11 0.7587(5) 0.7238(3) 0.1491(3) 0.0174(10) Uani d . . . 1 . .
H H11 0.66629 0.757402 0.145502 0.021 Uiso calc U . R 1 . .
C C12 0.2578(5) 0.7123(3) 0.3125(3) 0.0176(10) Uani d . . . 1 . .
C C13 0.1365(5) 0.6822(3) 0.3547(3) 0.0161(10) Uani d . . . 1 . .
C C14 -0.0059(5) 0.7224(3) 0.3529(3) 0.0201(10) Uani d . . . 1 . .
H H14 -0.086225 0.699018 0.382931 0.024 Uiso calc U . R 1 . .
C C15 -0.0268(5) 0.7978(3) 0.3057(3) 0.0221(11) Uani d . . . 1 . .
H H15 -0.123047 0.827118 0.302921 0.026 Uiso calc U . R 1 . .
C C16 0.0919(5) 0.8311(3) 0.2623(3) 0.0205(11) Uani d . . . 1 . .
H H16 0.076295 0.882805 0.229967 0.025 Uiso calc U . R 1 . .
C C17 0.2344(5) 0.7889(3) 0.2660(3) 0.0178(10) Uani d . . . 1 . .
H H17 0.31538 0.812613 0.236626 0.021 Uiso calc U . R 1 . .
C C18 0.6310(6) 0.8742(3) 0.4221(3) 0.0228(12) Uani d . . . 1 . .
H H18A 0.73524 0.861732 0.439746 0.027 Uiso calc U . R 1 . .
H H18B 0.563835 0.877791 0.466447 0.027 Uiso calc U . R 1 . .
C C19 0.6264(6) 0.9641(4) 0.3801(3) 0.0289(12) Uani d . . . 1 . .
H H19A 0.690279 0.959349 0.335407 0.043 Uiso calc U . R 1 . .
H H19B 0.664007 1.014491 0.412272 0.043 Uiso calc U . R 1 . .
H H19C 0.522053 0.977655 0.365129 0.043 Uiso calc U . R 1 . .
C C20 0.6473(6) 0.5942(4) 0.4981(3) 0.0290(13) Uani d . . . 1 . .
H H20A 0.709695 0.633418 0.531765 0.035 Uiso calc U . R 1 . .
H H20B 0.546227 0.586343 0.521141 0.035 Uiso calc U . R 1 . .
C C21 0.7193(8) 0.5029(5) 0.4876(4) 0.055(2) Uani d . . . 1 . .
H H21A 0.65982 0.465918 0.451997 0.082 Uiso calc U . R 1 . .
H H21B 0.724253 0.47021 0.535714 0.082 Uiso calc U . R 1 . .
H H21C 0.821863 0.511616 0.467916 0.082 Uiso calc U . R 1 . .
N N1 0.3862(4) 0.5604(3) 0.3309(2) 0.0170(9) Uani d . . . 1 . .
O O1 0.4720(4) 0.4117(2) 0.3198(2) 0.0221(8) Uani d . . . 1 . .
O O2 0.1602(3) 0.6069(2) 0.40431(19) 0.0200(7) Uani d . . . 1 . .
O O3 0.2718(3) 0.4629(2) 0.4368(2) 0.0238(8) Uani d . . . 1 . .
O O4 0.1387(3) 0.4766(2) 0.3158(2) 0.0223(8) Uani d . . . 1 . .
O O5 0.3984(3) 0.7268(2) 0.46855(18) 0.0207(8) Uani d . . . 1 . .
O O6 0.5810(4) 0.7989(2) 0.37276(19) 0.0209(7) Uani d . . . 1 . .
O O7 0.6328(3) 0.6392(2) 0.42426(19) 0.0213(8) Uani d . . . 1 . .
P P1 0.50284(13) 0.71035(8) 0.40636(7) 0.0153(2) Uani d . . . 1 . .
S S1 0.23311(12) 0.51548(8) 0.37245(7) 0.0174(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.900(4) ?
C1 N1 . 1.514(6) ?
C1 C12 . 1.519(6) ?
C1 C2 . 1.542(6) ?
C1 P1 . 1.864(5) ?
C2 C3 . 1.504(6) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.336(6) ?
C3 C6 . 1.472(6) ?
C4 C5 . 1.452(7) ?
C4 H4 . 0.95 ?
C5 O1 . 1.221(5) ?
C5 N1 . 1.405(6) ?
C6 C11 . 1.394(6) ?
C6 C7 . 1.408(6) ?
C7 C8 . 1.377(6) ?
C7 H7 . 0.95 ?
C8 C9 . 1.379(7) ?
C8 H8 . 0.95 ?
C9 C10 . 1.375(6) ?
C10 C11 . 1.396(6) ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?
C12 C13 . 1.379(6) ?
C12 C17 . 1.393(6) ?
C13 C14 . 1.385(6) ?
C13 O2 . 1.412(6) ?
C14 C15 . 1.384(7) ?
C14 H14 . 0.95 ?
C15 C16 . 1.388(7) ?
C15 H15 . 0.95 ?
C16 C17 . 1.398(6) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 O6 . 1.461(6) ?
C18 C19 . 1.492(7) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C21 . 1.467(8) ?
C20 O7 . 1.473(6) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
N1 S1 . 1.671(4) ?
O2 S1 . 1.567(3) ?
O3 S1 . 1.416(4) ?
O4 S1 . 1.424(3) ?
O5 P1 . 1.463(3) ?
O6 P1 . 1.564(3) ?
O7 P1 . 1.569(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C12 . . 109.5(3) ?
N1 C1 C2 . . 108.3(4) ?
C12 C1 C2 . . 109.8(4) ?
N1 C1 P1 . . 107.9(3) ?
C12 C1 P1 . . 107.6(3) ?
C2 C1 P1 . . 113.6(3) ?
C3 C2 C1 . . 114.5(4) ?
C3 C2 H2A . . 108.6 ?
C1 C2 H2A . . 108.6 ?
C3 C2 H2B . . 108.6 ?
C1 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.6 ?
C4 C3 C6 . . 123.0(4) ?
C4 C3 C2 . . 118.5(4) ?
C6 C3 C2 . . 118.4(4) ?
C3 C4 C5 . . 123.3(4) ?
C3 C4 H4 . . 118.4 ?
C5 C4 H4 . . 118.4 ?
O1 C5 N1 . . 119.5(4) ?
O1 C5 C4 . . 123.4(4) ?
N1 C5 C4 . . 117.1(4) ?
C11 C6 C7 . . 118.1(4) ?
C11 C6 C3 . . 121.8(4) ?
C7 C6 C3 . . 120.1(4) ?
C8 C7 C6 . . 121.4(5) ?
C8 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C7 C8 C9 . . 118.8(4) ?
C7 C8 H8 . . 120.6 ?
C9 C8 H8 . . 120.6 ?
C10 C9 C8 . . 122.0(4) ?
C10 C9 Br1 . . 118.9(4) ?
C8 C9 Br1 . . 119.0(4) ?
C9 C10 C11 . . 118.9(5) ?
C9 C10 H10 . . 120.5 ?
C11 C10 H10 . . 120.5 ?
C6 C11 C10 . . 120.8(4) ?
C6 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C13 C12 C17 . . 117.2(4) ?
C13 C12 C1 . . 119.8(4) ?
C17 C12 C1 . . 123.0(4) ?
C12 C13 C14 . . 124.4(4) ?
C12 C13 O2 . . 117.8(4) ?
C14 C13 O2 . . 117.8(4) ?
C15 C14 C13 . . 117.4(4) ?
C15 C14 H14 . . 121.3 ?
C13 C14 H14 . . 121.3 ?
C14 C15 C16 . . 120.5(4) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C17 . . 120.4(5) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C12 C17 C16 . . 120.2(4) ?
C12 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
O6 C18 C19 . . 109.1(4) ?
O6 C18 H18A . . 109.9 ?
C19 C18 H18A . . 109.9 ?
O6 C18 H18B . . 109.9 ?
C19 C18 H18B . . 109.9 ?
H18A C18 H18B . . 108.3 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C21 C20 O7 . . 108.3(5) ?
C21 C20 H20A . . 110.0 ?
O7 C20 H20A . . 110.0 ?
C21 C20 H20B . . 110.0 ?
O7 C20 H20B . . 110.0 ?
H20A C20 H20B . . 108.4 ?
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 ?
C5 N1 C1 . . 121.9(4) ?
C5 N1 S1 . . 114.9(3) ?
C1 N1 S1 . . 123.1(3) ?
C13 O2 S1 . . 118.2(3) ?
C18 O6 P1 . . 120.1(3) ?
C20 O7 P1 . . 122.0(3) ?
O5 P1 O6 . . 116.1(2) ?
O5 P1 O7 . . 114.34(19) ?
O6 P1 O7 . . 106.36(18) ?
O5 P1 C1 . . 113.90(19) ?
O6 P1 C1 . . 99.6(2) ?
O7 P1 C1 . . 105.00(19) ?
O3 S1 O4 . . 120.6(2) ?
O3 S1 O2 . . 104.5(2) ?
O4 S1 O2 . . 110.08(19) ?
O3 S1 N1 . . 111.7(2) ?
O4 S1 N1 . . 108.1(2) ?
O2 S1 N1 . . 99.91(19) ?



