# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 1427984'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
_audit_creation_date             2015-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H57 N2 O4 P Si, 0.5(H2 O)'
_chemical_formula_sum            'C42 H58 N2 O4.50 P Si'
_chemical_formula_weight         721.96
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.473(4)
_cell_length_b                   13.299(5)
_cell_length_c                   13.766(5)
_cell_angle_alpha                85.201(5)
_cell_angle_beta                 86.909(5)
_cell_angle_gamma                86.437(5)
_cell_volume                     2086.5(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1081
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.49
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9145
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0557 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.9145.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             778
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.189
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.1281
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12527
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.217
_diffrn_reflns_theta_min         2.052
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3645
_reflns_number_total             8916
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0045(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         8916
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1240P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1911
_refine_ls_wR_factor_ref         0.2528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
C29: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C28 \\sim C29 \\sim C30 \\sim C31: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
3. Others
 Fixed Sof: O5(0.5) H5A(0.5) H5B(0.5)
4.a Riding coordinates:
 N1(H1)
4.b Free rotating group:
 O5(H5A,H5B)
4.c Ternary CH refined with riding coordinates:
 C13(H13)
4.d Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C35(H35A,H35B)
4.e Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C16(H16), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26),
  C27(H27)
4.f Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,
 H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.80844(9) 0.28919(8) 0.45698(7) 0.0488(3) Uani 1 1 d . . . . .
Si1 Si 0.56312(11) 0.20596(9) 0.13104(8) 0.0537(4) Uani 1 1 d . . . . .
O1 O 0.8297(3) 0.3933(2) 0.4755(2) 0.0607(8) Uani 1 1 d . . . . .
O2 O 0.2191(5) 0.1554(5) 0.5636(3) 0.162(2) Uani 1 1 d . . . . .
O3 O 0.4103(2) 0.3608(2) 0.1791(2) 0.0657(9) Uani 1 1 d . . . . .
O4 O 0.6138(2) 0.2764(2) 0.21095(17) 0.0494(7) Uani 1 1 d . . . . .
N1 N 0.7102(3) 0.2800(2) 0.3769(2) 0.0499(9) Uani 1 1 d . . . . .
H1 H 0.6902 0.2185 0.3807 0.060 Uiso 1 1 d R . . . .
N2 N 0.4245(3) 0.5022(3) 0.2508(2) 0.0591(9) Uani 1 1 d . . . . .
C1 C 0.7163(6) 0.1152(4) 0.7475(4) 0.0871(17) Uani 1 1 d . . . . .
H1A H 0.6998 0.0793 0.8071 0.105 Uiso 1 1 calc R . . . .
C2 C 0.6581(5) 0.0971(4) 0.6672(4) 0.0880(17) Uani 1 1 d . . . . .
H2 H 0.6012 0.0498 0.6718 0.106 Uiso 1 1 calc R . . . .
C3 C 0.6852(4) 0.1503(4) 0.5788(3) 0.0716(13) Uani 1 1 d . . . . .
H3 H 0.6462 0.1378 0.5240 0.086 Uiso 1 1 calc R . . . .
C4 C 0.7680(4) 0.2208(3) 0.5702(3) 0.0484(10) Uani 1 1 d . . . . .
C5 C 0.8249(4) 0.2380(3) 0.6519(3) 0.0648(12) Uani 1 1 d . . . . .
H5 H 0.8816 0.2854 0.6476 0.078 Uiso 1 1 calc R . . . .
C6 C 0.7984(6) 0.1855(4) 0.7405(4) 0.0877(17) Uani 1 1 d . . . . .
H6 H 0.8369 0.1982 0.7956 0.105 Uiso 1 1 calc R . . . .
C7 C 0.9305(3) 0.2216(3) 0.4039(3) 0.0517(10) Uani 1 1 d . . . . .
C8 C 1.0174(4) 0.2749(4) 0.3549(4) 0.0775(15) Uani 1 1 d . . . . .
H8 H 1.0139 0.3451 0.3529 0.093 Uiso 1 1 calc R . . . .
C9 C 1.1105(5) 0.2234(5) 0.3083(4) 0.0926(17) Uani 1 1 d . . . . .
H9 H 1.1688 0.2600 0.2750 0.111 Uiso 1 1 calc R . . . .
C10 C 1.1185(5) 0.1207(5) 0.3104(4) 0.0875(16) Uani 1 1 d . . . . .
H10 H 1.1808 0.0876 0.2778 0.105 Uiso 1 1 calc R . . . .
C11 C 1.0343(6) 0.0667(5) 0.3609(5) 0.111(2) Uani 1 1 d . . . . .
H11 H 1.0405 -0.0036 0.3646 0.134 Uiso 1 1 calc R . . . .
C12 C 0.9393(5) 0.1162(4) 0.4068(4) 0.0853(16) Uani 1 1 d . . . . .
H12 H 0.8811 0.0790 0.4396 0.102 Uiso 1 1 calc R . . . .
C13 C 0.6042(3) 0.3454(3) 0.3642(3) 0.0481(10) Uani 1 1 d . . . . .
H13 H 0.6153 0.4088 0.3932 0.058 Uiso 1 1 calc R . . . .
C14 C 0.4967(4) 0.2995(4) 0.4145(3) 0.0563(11) Uani 1 1 d . . . . .
C15 C 0.4790(4) 0.1955(4) 0.4114(3) 0.0755(15) Uani 1 1 d . . . . .
H15 H 0.5320 0.1561 0.3751 0.091 Uiso 1 1 calc R . . . .
C16 C 0.3861(5) 0.1513(5) 0.4602(4) 0.099(2) Uani 1 1 d . . . . .
H16 H 0.3759 0.0827 0.4581 0.119 Uiso 1 1 calc R . . . .
C17 C 0.3067(5) 0.2122(8) 0.5136(4) 0.113(3) Uani 1 1 d . . . . .
C18 C 0.3211(5) 0.3126(6) 0.5171(4) 0.0939(19) Uani 1 1 d . . . . .
H18 H 0.2678 0.3523 0.5528 0.113 Uiso 1 1 calc R . . . .
C19 C 0.4164(4) 0.3546(4) 0.4666(3) 0.0735(14) Uani 1 1 d . . . . .
H19 H 0.4255 0.4234 0.4686 0.088 Uiso 1 1 calc R . . . .
C20 C 0.1436(7) 0.2080(8) 0.6203(6) 0.191(5) Uani 1 1 d . . . . .
H20A H 0.1178 0.2699 0.5847 0.287 Uiso 1 1 calc GR . . . .
H20B H 0.1814 0.2232 0.6774 0.287 Uiso 1 1 calc GR . . . .
H20C H 0.0775 0.1688 0.6393 0.287 Uiso 1 1 calc GR . . . .
C21 C 0.5924(3) 0.3702(3) 0.2515(3) 0.0440(9) Uani 1 1 d . . . . .
C22 C 0.6779(3) 0.4444(3) 0.2028(3) 0.0468(10) Uani 1 1 d . . . . .
C23 C 0.6666(4) 0.4770(3) 0.1053(3) 0.0547(11) Uani 1 1 d . . . . .
H23 H 0.6088 0.4510 0.0714 0.066 Uiso 1 1 calc R . . . .
C24 C 0.7367(4) 0.5453(3) 0.0575(3) 0.0608(12) Uani 1 1 d . . . . .
H24 H 0.7255 0.5650 -0.0079 0.073 Uiso 1 1 calc R . . . .
C25 C 0.8246(4) 0.5864(3) 0.1039(3) 0.0572(11) Uani 1 1 d . . . . .
C26 C 0.8383(4) 0.5517(3) 0.2010(3) 0.0634(12) Uani 1 1 d . . . . .
H26 H 0.8973 0.5762 0.2345 0.076 Uiso 1 1 calc R . . . .
C27 C 0.7667(4) 0.4816(3) 0.2492(3) 0.0552(11) Uani 1 1 d . . . . .
H27 H 0.7791 0.4595 0.3139 0.066 Uiso 1 1 calc R . . . .
C28 C 0.8981(5) 0.6698(4) 0.0520(4) 0.0745(14) Uani 1 1 d . U . . .
C29 C 0.9216(9) 0.6550(8) -0.0526(5) 0.204(5) Uani 1 1 d . U . . .
H29A H 0.9636 0.5911 -0.0591 0.306 Uiso 1 1 calc GR . . . .
H29B H 0.9676 0.7083 -0.0823 0.306 Uiso 1 1 calc GR . . . .
H29C H 0.8489 0.6562 -0.0842 0.306 Uiso 1 1 calc GR . . . .
C30 C 0.8342(9) 0.7694(5) 0.0633(9) 0.255(7) Uani 1 1 d . U . . .
H30A H 0.7706 0.7777 0.0202 0.383 Uiso 1 1 calc GR . . . .
H30B H 0.8866 0.8226 0.0475 0.383 Uiso 1 1 calc GR . . . .
H30C H 0.8041 0.7722 0.1295 0.383 Uiso 1 1 calc GR . . . .
C31 C 1.0101(8) 0.6746(8) 0.0958(6) 0.224(6) Uani 1 1 d . U . . .
H31A H 0.9972 0.6923 0.1618 0.336 Uiso 1 1 calc GR . . . .
H31B H 1.0548 0.7247 0.0591 0.336 Uiso 1 1 calc GR . . . .
H31C H 1.0521 0.6099 0.0953 0.336 Uiso 1 1 calc GR . . . .
C32 C 0.4667(4) 0.4117(3) 0.2267(3) 0.0508(10) Uani 1 1 d . . . . .
C33 C 0.4809(4) 0.5735(3) 0.3074(3) 0.0649(12) Uani 1 1 d . . . . .
H33A H 0.5493 0.5389 0.3360 0.078 Uiso 1 1 calc R . . . .
H33B H 0.4270 0.5922 0.3605 0.078 Uiso 1 1 calc R . . . .
C34 C 0.5179(5) 0.6684(4) 0.2498(4) 0.0800(15) Uani 1 1 d . . . . .
H34A H 0.5770 0.6514 0.2009 0.120 Uiso 1 1 calc GR . . . .
H34B H 0.5486 0.7123 0.2929 0.120 Uiso 1 1 calc GR . . . .
H34C H 0.4515 0.7022 0.2189 0.120 Uiso 1 1 calc GR . . . .
C35 C 0.3051(4) 0.5354(4) 0.2218(4) 0.0781(15) Uani 1 1 d . . . . .
H35A H 0.2933 0.5135 0.1578 0.094 Uiso 1 1 calc R . . . .
H35B H 0.2965 0.6086 0.2176 0.094 Uiso 1 1 calc R . . . .
C36 C 0.2150(5) 0.4935(5) 0.2927(5) 0.1031(19) Uani 1 1 d . . . . .
H36A H 0.1390 0.5082 0.2674 0.155 Uiso 1 1 calc GR . . . .
H36B H 0.2185 0.5236 0.3534 0.155 Uiso 1 1 calc GR . . . .
H36C H 0.2294 0.4216 0.3032 0.155 Uiso 1 1 calc GR . . . .
C37 C 0.5497(5) 0.2675(4) 0.0062(3) 0.0833(16) Uani 1 1 d . . . . .
H37A H 0.4884 0.3200 0.0067 0.125 Uiso 1 1 calc GR . . . .
H37B H 0.5315 0.2183 -0.0370 0.125 Uiso 1 1 calc GR . . . .
H37C H 0.6222 0.2961 -0.0158 0.125 Uiso 1 1 calc GR . . . .
C38 C 0.4288(4) 0.1403(4) 0.1683(4) 0.0768(14) Uani 1 1 d . . . . .
H38A H 0.4375 0.1047 0.2313 0.115 Uiso 1 1 calc GR . . . .
H38B H 0.4155 0.0932 0.1215 0.115 Uiso 1 1 calc GR . . . .
H38C H 0.3635 0.1889 0.1714 0.115 Uiso 1 1 calc GR . . . .
C39 C 0.6865(5) 0.1063(4) 0.1250(4) 0.0708(13) Uani 1 1 d . . . . .
C40 C 0.6960(6) 0.0440(4) 0.2223(4) 0.1000(19) Uani 1 1 d . . . . .
H40A H 0.7222 0.0852 0.2699 0.150 Uiso 1 1 calc GR . . . .
H40B H 0.7509 -0.0126 0.2149 0.150 Uiso 1 1 calc GR . . . .
H40C H 0.6208 0.0201 0.2435 0.150 Uiso 1 1 calc GR . . . .
C41 C 0.8010(5) 0.1540(5) 0.0985(5) 0.135(3) Uani 1 1 d . . . . .
H41A H 0.7999 0.1848 0.0329 0.202 Uiso 1 1 calc GR . . . .
H41B H 0.8639 0.1030 0.1031 0.202 Uiso 1 1 calc GR . . . .
H41C H 0.8120 0.2045 0.1425 0.202 Uiso 1 1 calc GR . . . .
C42 C 0.6628(7) 0.0366(5) 0.0462(4) 0.129(3) Uani 1 1 d . . . . .
H42A H 0.5838 0.0163 0.0550 0.194 Uiso 1 1 calc GR . . . .
H42B H 0.7158 -0.0222 0.0514 0.194 Uiso 1 1 calc GR . . . .
H42C H 0.6738 0.0718 -0.0170 0.194 Uiso 1 1 calc GR . . . .
O5 O 0.9630(6) 0.5617(6) 0.4251(5) 0.089(2) Uani 0.5 1 d . . P . .
H5A H 1.0029 0.5887 0.4651 0.133 Uiso 0.5 1 d G . P . .
H5B H 0.9373 0.5071 0.4520 0.133 Uiso 0.5 1 d G . P . .


_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
P1 O1 1.465(3) . ?
P1 N1 1.636(3) . ?
P1 C4 1.792(4) . ?
P1 C7 1.774(4) . ?
Si1 O4 1.654(3) . ?
Si1 C37 1.850(5) . ?
Si1 C38 1.846(5) . ?
Si1 C39 1.881(5) . ?
O2 C17 1.410(7) . ?
O2 C20 1.338(9) . ?
O3 C32 1.217(4) . ?
O4 C21 1.411(4) . ?
N1 H1 0.8600 . ?
N1 C13 1.460(5) . ?
N2 C32 1.330(5) . ?
N2 C33 1.476(5) . ?
N2 C35 1.479(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.368(7) . ?
C1 C6 1.363(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(6) . ?
C4 C5 1.372(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(6) . ?
C7 C12 1.396(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 C14 1.517(6) . ?
C13 C21 1.571(5) . ?
C14 C15 1.416(6) . ?
C14 C19 1.354(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.401(9) . ?
C17 C18 1.360(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(7) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.524(5) . ?
C21 C32 1.557(5) . ?
C22 C23 1.386(5) . ?
C22 C27 1.370(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.357(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(6) . ?
C25 C26 1.391(6) . ?
C25 C28 1.540(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.384(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.478(8) . ?
C28 C30 1.489(9) . ?
C28 C31 1.455(8) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.505(6) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.484(7) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.521(7) . ?
C39 C41 1.508(7) . ?
C39 C42 1.530(7) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8499 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N1 114.22(17) . . ?
O1 P1 C4 109.00(17) . . ?
O1 P1 C7 114.48(19) . . ?
N1 P1 C4 110.28(18) . . ?
N1 P1 C7 101.11(17) . . ?
C7 P1 C4 107.37(19) . . ?
O4 Si1 C37 115.44(19) . . ?
O4 Si1 C38 117.01(18) . . ?
O4 Si1 C39 99.70(18) . . ?
C37 Si1 C39 107.0(2) . . ?
C38 Si1 C37 109.3(2) . . ?
C38 Si1 C39 107.1(2) . . ?
C20 O2 C17 114.8(8) . . ?
C21 O4 Si1 141.8(2) . . ?
P1 N1 H1 108.5 . . ?
C13 N1 P1 126.1(3) . . ?
C13 N1 H1 107.5 . . ?
C32 N2 C33 127.8(4) . . ?
C32 N2 C35 117.4(4) . . ?
C33 N2 C35 114.8(4) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C6 C1 C2 120.2(5) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.9(5) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 P1 123.2(3) . . ?
C3 C4 C5 118.4(4) . . ?
C5 C4 P1 118.4(3) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.3(5) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 P1 118.8(4) . . ?
C8 C7 C12 118.8(4) . . ?
C12 C7 P1 122.4(3) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(5) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(5) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.3(5) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.3(6) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.4(5) . . ?
C11 C12 H12 119.8 . . ?
N1 C13 H13 108.0 . . ?
N1 C13 C14 112.7(3) . . ?
N1 C13 C21 107.1(3) . . ?
C14 C13 H13 108.0 . . ?
C14 C13 C21 113.0(3) . . ?
C21 C13 H13 108.0 . . ?
C15 C14 C13 120.7(4) . . ?
C19 C14 C13 122.0(4) . . ?
C19 C14 C15 117.3(4) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.8(5) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.1(6) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 O2 111.6(8) . . ?
C18 C17 O2 127.0(8) . . ?
C18 C17 C16 121.3(5) . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.9(6) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 C18 122.6(6) . . ?
C14 C19 H19 118.7 . . ?
C18 C19 H19 118.7 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C13 104.8(3) . . ?
O4 C21 C22 108.8(3) . . ?
O4 C21 C32 108.1(3) . . ?
C22 C21 C13 115.2(3) . . ?
C22 C21 C32 107.7(3) . . ?
C32 C21 C13 112.0(3) . . ?
C23 C22 C21 118.8(3) . . ?
C27 C22 C21 124.2(3) . . ?
C27 C22 C23 117.0(4) . . ?
C22 C23 H23 118.8 . . ?
C24 C23 C22 122.4(4) . . ?
C24 C23 H23 118.8 . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.5(4) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C26 116.2(4) . . ?
C24 C25 C28 121.5(4) . . ?
C26 C25 C28 122.2(4) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 C25 122.0(4) . . ?
C27 C26 H26 119.0 . . ?
C22 C27 C26 120.9(4) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C29 C28 C25 111.9(5) . . ?
C29 C28 C30 110.0(7) . . ?
C30 C28 C25 108.5(5) . . ?
C31 C28 C25 112.2(5) . . ?
C31 C28 C29 107.8(7) . . ?
C31 C28 C30 106.3(7) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O3 C32 N2 120.7(4) . . ?
O3 C32 C21 117.5(4) . . ?
N2 C32 C21 121.7(4) . . ?
N2 C33 H33A 108.5 . . ?
N2 C33 H33B 108.5 . . ?
N2 C33 C34 115.0(4) . . ?
H33A C33 H33B 107.5 . . ?
C34 C33 H33A 108.5 . . ?
C34 C33 H33B 108.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N2 C35 H35A 109.3 . . ?
N2 C35 H35B 109.3 . . ?
N2 C35 C36 111.5(4) . . ?
H35A C35 H35B 108.0 . . ?
C36 C35 H35A 109.3 . . ?
C36 C35 H35B 109.3 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Si1 C37 H37A 109.5 . . ?
Si1 C37 H37B 109.5 . . ?
Si1 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
Si1 C38 H38A 109.5 . . ?
Si1 C38 H38B 109.5 . . ?
Si1 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 Si1 110.8(3) . . ?
C40 C39 C42 109.1(4) . . ?
C41 C39 Si1 110.6(4) . . ?
C41 C39 C40 109.0(5) . . ?
C41 C39 C42 108.6(5) . . ?
C42 C39 Si1 108.6(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
H5A O5 H5B 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_123
_database_code_depnum_ccdc_archive 'CCDC 1427986'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
_audit_creation_date             2015-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H31 Br N2 O3 S'
_chemical_formula_sum            'C24 H31 Br N2 O3 S'
_chemical_formula_weight         507.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.891(13)
_cell_length_b                   16.14(2)
_cell_length_c                   16.21(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2588(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1277
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.88
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0747 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8412.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.136
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.1660
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15227
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.179
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2281
_reflns_number_total             5656
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5656
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1860
_refine_ls_R_factor_gt           0.0672
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1054P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.2260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.99(2) 0.01(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C13-C18 = C17-C16 = C15-C14
 1.4 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.14176(17) 0.89778(10) -0.34481(10) 0.1128(8) Uani 1 1 d . . . . .
S1 S -0.6544(3) 0.73782(16) -0.13512(16) 0.0565(7) Uani 1 1 d . . . . .
O1 O -0.6914(7) 0.7786(5) -0.0565(5) 0.071(2) Uani 1 1 d . . . . .
O2 O -0.5187(8) 0.5547(5) 0.0157(5) 0.078(2) Uani 1 1 d . . . . .
O3 O -0.2096(6) 0.5999(5) -0.0606(4) 0.0612(19) Uani 1 1 d . . . . .
H3 H -0.2099 0.6336 -0.0228 0.092 Uiso 1 1 calc GR . . . .
N1 N -0.5633(7) 0.6533(5) -0.1156(5) 0.055(2) Uani 1 1 d . . . . .
H1 H -0.5967 0.6042 -0.1177 0.066 Uiso 1 1 calc R . . . .
N2 N -0.3631(10) 0.4556(5) 0.0039(5) 0.065(2) Uani 1 1 d . . . . .
C1 C -0.9097(13) 0.7531(10) -0.1808(11) 0.120(6) Uani 1 1 d . . . . .
H1A H -0.9253 0.7817 -0.1297 0.179 Uiso 1 1 calc GR . . . .
H1B H -0.9933 0.7303 -0.2005 0.179 Uiso 1 1 calc GR . . . .
H1C H -0.8744 0.7912 -0.2208 0.179 Uiso 1 1 calc GR . . . .
C2 C -0.8604(13) 0.6275(8) -0.0985(8) 0.087(4) Uani 1 1 d . . . . .
H2A H -0.7926 0.5869 -0.0861 0.130 Uiso 1 1 calc GR . . . .
H2B H -0.9416 0.6002 -0.1162 0.130 Uiso 1 1 calc GR . . . .
H2C H -0.8790 0.6598 -0.0501 0.130 Uiso 1 1 calc GR . . . .
C3 C -0.8096(10) 0.6843(7) -0.1671(8) 0.073(3) Uani 1 1 d . . . . .
C4 C -0.7772(14) 0.6358(10) -0.2464(8) 0.106(5) Uani 1 1 d . . . . .
H4A H -0.7119 0.6660 -0.2783 0.158 Uiso 1 1 calc GR . . . .
H4B H -0.8583 0.6288 -0.2781 0.158 Uiso 1 1 calc GR . . . .
H4C H -0.7411 0.5825 -0.2321 0.158 Uiso 1 1 calc GR . . . .
C5 C -0.3706(11) 0.7133(7) -0.2406(7) 0.061(3) Uani 1 1 d . . . . .
H5 H -0.4256 0.6705 -0.2593 0.074 Uiso 1 1 calc R . . . .
C6 C -0.3100(11) 0.7641(8) -0.2960(7) 0.067(3) Uani 1 1 d . . . . .
H6 H -0.3232 0.7569 -0.3524 0.080 Uiso 1 1 calc R . . . .
C7 C -0.2281(11) 0.8268(8) -0.2665(9) 0.069(3) Uani 1 1 d . . . . .
C8 C -0.2083(11) 0.8417(7) -0.1863(8) 0.063(3) Uani 1 1 d . . . . .
H8 H -0.1555 0.8860 -0.1687 0.076 Uiso 1 1 calc R . . . .
C9 C -0.2688(10) 0.7890(7) -0.1305(7) 0.064(3) Uani 1 1 d . . . . .
H9 H -0.2540 0.7967 -0.0744 0.077 Uiso 1 1 calc R . . . .
C10 C -0.3519(9) 0.7243(6) -0.1564(6) 0.051(2) Uani 1 1 d . . . . .
C11 C -0.4184(9) 0.6697(6) -0.0941(6) 0.048(2) Uani 1 1 d . . . . .
H11 H -0.4156 0.6978 -0.0405 0.058 Uiso 1 1 calc R . . . .
C12 C -0.3461(9) 0.5821(6) -0.0849(6) 0.050(2) Uani 1 1 d . . . . .
C13 C -0.3407(10) 0.5357(5) -0.1656(6) 0.048(2) Uani 1 1 d D . . . .
C14 C -0.2284(11) 0.5308(7) -0.2102(8) 0.066(3) Uani 1 1 d D . . . .
H14 H -0.1500 0.5555 -0.1902 0.079 Uiso 1 1 calc R . . . .
C15 C -0.2239(13) 0.4905(8) -0.2853(8) 0.077(4) Uani 1 1 d D . . . .
H15 H -0.1445 0.4891 -0.3160 0.092 Uiso 1 1 calc R . . . .
C16 C -0.3361(16) 0.4533(8) -0.3131(8) 0.086(4) Uani 1 1 d D . . . .
H16 H -0.3348 0.4261 -0.3636 0.103 Uiso 1 1 calc R . . . .
C17 C -0.4514(13) 0.4551(7) -0.2680(8) 0.074(3) Uani 1 1 d D . . . .
H17 H -0.5286 0.4288 -0.2877 0.089 Uiso 1 1 calc R . . . .
C18 C -0.4552(11) 0.4950(6) -0.1943(7) 0.062(3) Uani 1 1 d D . . . .
H18 H -0.5341 0.4951 -0.1631 0.075 Uiso 1 1 calc R . . . .
C19 C -0.4153(11) 0.5305(7) -0.0164(6) 0.055(3) Uani 1 1 d . . . . .
C20 C -0.4383(13) 0.4009(8) 0.0563(8) 0.085(4) Uani 1 1 d . . . . .
H20A H -0.5179 0.4290 0.0772 0.102 Uiso 1 1 calc R . . . .
H20B H -0.3831 0.3844 0.1030 0.102 Uiso 1 1 calc R . . . .
C21 C -0.4808(17) 0.3236(9) 0.0063(9) 0.102(5) Uani 1 1 d . . . . .
H21A H -0.5289 0.2854 0.0420 0.122 Uiso 1 1 calc R . . . .
H21B H -0.5417 0.3401 -0.0377 0.122 Uiso 1 1 calc R . . . .
C22 C -0.3572(19) 0.2797(9) -0.0309(10) 0.109(5) Uani 1 1 d . . . . .
H22A H -0.3024 0.2562 0.0129 0.130 Uiso 1 1 calc R . . . .
H22B H -0.3867 0.2349 -0.0665 0.130 Uiso 1 1 calc R . . . .
C23 C -0.2752(16) 0.3398(9) -0.0794(9) 0.098(4) Uani 1 1 d . . . . .
H23A H -0.3255 0.3559 -0.1282 0.118 Uiso 1 1 calc R . . . .
H23B H -0.1927 0.3129 -0.0975 0.118 Uiso 1 1 calc R . . . .
C24 C -0.2385(13) 0.4177(7) -0.0301(8) 0.084(4) Uani 1 1 d . . . . .
H24A H -0.1776 0.4032 0.0145 0.100 Uiso 1 1 calc R . . . .
H24B H -0.1929 0.4571 -0.0657 0.100 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.911(11) . ?
S1 O1 1.480(7) . ?
S1 N1 1.665(8) . ?
S1 C3 1.836(11) . ?
O2 C19 1.212(12) . ?
O3 H3 0.8200 . ?
O3 C12 1.436(11) . ?
N1 H1 0.8600 . ?
N1 C11 1.498(12) . ?
N2 C19 1.355(13) . ?
N2 C20 1.434(14) . ?
N2 C24 1.482(15) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C3 1.504(16) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C3 1.526(18) . ?
C3 C4 1.538(17) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.355(15) . ?
C5 C10 1.388(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(16) . ?
C7 C8 1.337(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(14) . ?
C10 C11 1.494(13) . ?
C11 H11 0.9800 . ?
C11 C12 1.591(13) . ?
C12 C13 1.509(13) . ?
C12 C19 1.548(14) . ?
C13 C14 1.327(13) . ?
C13 C18 1.389(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(14) . ?
C15 H15 0.9300 . ?
C15 C16 1.340(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.355(14) . ?
C17 H17 0.9300 . ?
C17 C18 1.359(15) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.547(18) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.54(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.49(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.533(17) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 109.6(4) . . ?
O1 S1 C3 104.2(5) . . ?
N1 S1 C3 97.0(4) . . ?
C12 O3 H3 109.5 . . ?
S1 N1 H1 122.7 . . ?
C11 N1 S1 114.7(6) . . ?
C11 N1 H1 122.7 . . ?
C19 N2 C20 119.7(10) . . ?
C19 N2 C24 126.5(9) . . ?
C20 N2 C24 113.4(9) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
C1 C3 S1 104.2(9) . . ?
C1 C3 C2 109.5(11) . . ?
C1 C3 C4 112.9(12) . . ?
C2 C3 S1 110.6(8) . . ?
C2 C3 C4 111.8(11) . . ?
C4 C3 S1 107.5(8) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C10 121.0(11) . . ?
C10 C5 H5 119.5 . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.2(11) . . ?
C7 C6 H6 120.9 . . ?
C6 C7 Br1 118.1(11) . . ?
C8 C7 Br1 118.2(11) . . ?
C8 C7 C6 123.7(11) . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.6(11) . . ?
C9 C8 H8 121.2 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(11) . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C9 118.1(10) . . ?
C5 C10 C11 122.1(9) . . ?
C9 C10 C11 119.9(9) . . ?
N1 C11 H11 108.3 . . ?
N1 C11 C12 107.2(7) . . ?
C10 C11 N1 111.6(8) . . ?
C10 C11 H11 108.3 . . ?
C10 C11 C12 112.9(8) . . ?
C12 C11 H11 108.3 . . ?
O3 C12 C11 105.7(7) . . ?
O3 C12 C13 107.6(7) . . ?
O3 C12 C19 109.1(7) . . ?
C13 C12 C11 112.0(7) . . ?
C13 C12 C19 111.8(8) . . ?
C19 C12 C11 110.3(8) . . ?
C14 C13 C12 122.1(9) . . ?
C14 C13 C18 118.2(10) . . ?
C18 C13 C12 119.7(9) . . ?
C13 C14 H14 118.8 . . ?
C13 C14 C15 122.3(11) . . ?
C15 C14 H14 118.8 . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.8(11) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(11) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(12) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.7(11) . . ?
C17 C18 H18 120.1 . . ?
O2 C19 N2 120.3(10) . . ?
O2 C19 C12 120.5(9) . . ?
N2 C19 C12 119.1(9) . . ?
N2 C20 H20A 109.9 . . ?
N2 C20 H20B 109.9 . . ?
N2 C20 C21 109.1(10) . . ?
H20A C20 H20B 108.3 . . ?
C21 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 C20 111.2(11) . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C23 C22 C21 109.9(11) . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C22 C23 C24 112.9(12) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
N2 C24 C23 109.6(10) . . ?
N2 C24 H24A 109.7 . . ?
N2 C24 H24B 109.7 . . ?
C23 C24 H24A 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C7 C8 C9 -178.7(7) . . . . ?
S1 N1 C11 C10 -51.4(9) . . . . ?
S1 N1 C11 C12 -175.5(6) . . . . ?
O1 S1 N1 C11 -77.8(7) . . . . ?
O1 S1 C3 C1 63.2(11) . . . . ?
O1 S1 C3 C2 -54.4(9) . . . . ?
O1 S1 C3 C4 -176.8(9) . . . . ?
O3 C12 C13 C14 -12.7(12) . . . . ?
O3 C12 C13 C18 165.9(9) . . . . ?
O3 C12 C19 O2 123.3(10) . . . . ?
O3 C12 C19 N2 -60.6(11) . . . . ?
N1 S1 C3 C1 175.4(10) . . . . ?
N1 S1 C3 C2 57.8(9) . . . . ?
N1 S1 C3 C4 -64.5(9) . . . . ?
N1 C11 C12 O3 -177.4(7) . . . . ?
N1 C11 C12 C13 65.6(10) . . . . ?
N1 C11 C12 C19 -59.6(9) . . . . ?
N2 C20 C21 C22 57.0(14) . . . . ?
C3 S1 N1 C11 174.5(7) . . . . ?
C5 C6 C7 Br1 179.6(8) . . . . ?
C5 C6 C7 C8 -2.0(16) . . . . ?
C5 C10 C11 N1 -43.2(12) . . . . ?
C5 C10 C11 C12 77.6(11) . . . . ?
C6 C5 C10 C9 0.0(15) . . . . ?
C6 C5 C10 C11 179.5(9) . . . . ?
C6 C7 C8 C9 2.9(16) . . . . ?
C7 C8 C9 C10 -2.4(15) . . . . ?
C8 C9 C10 C5 1.0(15) . . . . ?
C8 C9 C10 C11 -178.5(9) . . . . ?
C9 C10 C11 N1 136.3(9) . . . . ?
C9 C10 C11 C12 -102.9(10) . . . . ?
C10 C5 C6 C7 0.5(15) . . . . ?
C10 C11 C12 O3 59.3(10) . . . . ?
C10 C11 C12 C13 -57.7(10) . . . . ?
C10 C11 C12 C19 177.1(8) . . . . ?
C11 C12 C13 C14 103.1(11) . . . . ?
C11 C12 C13 C18 -78.3(11) . . . . ?
C11 C12 C19 O2 7.5(13) . . . . ?
C11 C12 C19 N2 -176.3(8) . . . . ?
C12 C13 C14 C15 -178.1(10) . . . . ?
C12 C13 C18 C17 178.3(9) . . . . ?
C13 C12 C19 O2 -117.8(10) . . . . ?
C13 C12 C19 N2 58.3(11) . . . . ?
C13 C14 C15 C16 -1.6(19) . . . . ?
C14 C13 C18 C17 -3.1(16) . . . . ?
C14 C15 C16 C17 0(2) . . . . ?
C15 C16 C17 C18 0(2) . . . . ?
C16 C17 C18 C13 1.3(18) . . . . ?
C18 C13 C14 C15 3.3(17) . . . . ?
C19 N2 C20 C21 113.4(12) . . . . ?
C19 N2 C24 C23 -114.6(12) . . . . ?
C19 C12 C13 C14 -132.5(10) . . . . ?
C19 C12 C13 C18 46.1(12) . . . . ?
C20 N2 C19 O2 7.1(15) . . . . ?
C20 N2 C19 C12 -169.1(9) . . . . ?
C20 N2 C24 C23 58.3(12) . . . . ?
C20 C21 C22 C23 -53.6(16) . . . . ?
C21 C22 C23 C24 52.6(16) . . . . ?
C22 C23 C24 N2 -53.9(14) . . . . ?
C24 N2 C19 O2 179.7(10) . . . . ?
C24 N2 C19 C12 3.5(14) . . . . ?
C24 N2 C20 C21 -60.0(13) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.99(2)
2 0.01(2)

