# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2f
_database_code_depnum_ccdc_archive 'CCDC 1880502'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-03-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 N2 O4 S'
_chemical_formula_sum            'C26 H24 N2 O4 S'
_chemical_formula_weight         460.53
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H24 N2 O4 S1'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.27000(10)
_cell_length_b                   11.16340(10)
_cell_length_c                   14.17310(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.9580(10)
_cell_angle_gamma                90
_cell_volume                     1141.79(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17885
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6810
_cell_measurement_theta_min      3.9560
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    1.556
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             484
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -9 0.0517
-1 -7 0 0.0925
0 5 -6 0.0861
3 -6 2 0.0674
0 7 -4 0.0963
-5 1 2 0.0701
-1 6 5 0.0794
-1 0 9 0.0744
1 -5 -6 0.0701
0 -7 -1 0.0796
1 -1 8 0.0637
2 5 6 0.0783
2 -4 5 0.0622
4 1 4 0.0836
5 1 -2 0.0855
3 3 -7 0.0863
2 -6 -2 0.0691
3 -1 -7 0.0865
0 1 -9 0.0547
0 -3 -8 0.0570
0 6 5 0.0773
0 0 9 0.0626

_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 0.0000 -9.0000 -0.3509 0.8742 0.4248
-1.0000 -7.0000 -0.0000 -0.2184 0.4165 -0.8703
-0.0000 5.0000 -6.0000 -0.0881 0.2852 0.9048
3.0000 -6.0000 2.0000 0.6667 0.1774 -0.8377
-0.0000 7.0000 -4.0000 -0.0562 -0.0302 1.0587
-5.0000 1.0000 2.0000 -1.0360 -0.2754 0.0261
-1.0000 6.0000 5.0000 -0.1329 -0.8524 0.5082
-1.0000 -0.0000 9.0000 -0.0760 -0.8823 -0.4262
1.0000 -5.0000 -6.0000 0.1183 0.8899 -0.3367
-0.0000 -7.0000 -1.0000 -0.0202 0.5181 -0.8223
1.0000 -1.0000 8.0000 0.3349 -0.7166 -0.5018
2.0000 5.0000 6.0000 0.5220 -0.8778 0.3389
2.0000 -4.0000 5.0000 0.5005 -0.2396 -0.7319
4.0000 1.0000 4.0000 0.9156 -0.4343 -0.0620
5.0000 1.0000 -2.0000 1.0374 0.1553 0.2224
3.0000 3.0000 -7.0000 0.5356 0.5150 0.7058
2.0000 -6.0000 -2.0000 0.3922 0.5637 -0.6493
3.0000 -1.0000 -7.0000 0.5328 0.7553 0.2089
-0.0000 1.0000 -9.0000 -0.1367 0.8182 0.5497
-0.0000 -3.0000 -8.0000 -0.1243 0.9609 0.0056
0.0000 6.0000 5.0000 0.0805 -0.8484 0.5089
0.0000 -0.0000 9.0000 0.1374 -0.8783 -0.4255

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21276
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.109
_diffrn_reflns_theta_min         6.132
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00  34.00   1.00    1.00    --  -42.02  77.00  60.00  109
  2  ω   -114.00 -14.00   1.00    1.00    --  -42.02 -57.00 150.00  100
  3  ω   -114.00 -14.00   1.00    1.00    --  -42.02 -57.00-120.00  100
  4  ω     17.00 116.00   1.00    1.00    --   42.02  38.00-120.00   99
  5  ω     23.00  98.00   1.00    1.00    --   42.02-125.00-150.00   75
  6  ω     94.00 178.00   1.00    1.00    --  105.92 125.00  60.00   84
  7  ω     94.00 178.00   1.00    1.00    --  105.92 125.00 150.00   84
  8  ω     73.00 178.00   1.00    1.00    --  105.92  77.00 -60.00  105
  9  ω     77.00 178.00   1.00    1.00    --  105.92  61.00-120.00  101
 10  ω     77.00 178.00   1.00    1.00    --  105.92  61.00 -90.00  101
 11  ω     80.00 178.00   1.00    1.00    --  105.92  45.00 -30.00   98
 12  ω     73.00 178.00   1.00    1.00    --  105.92  77.00-180.00  105
 13  ω     77.00 178.00   1.00    1.00    --  105.92  61.00 -60.00  101
 14  ω     73.00 178.00   1.00    1.00    --  105.92  77.00-120.00  105
 15  ω     73.00 178.00   1.00    1.00    --  105.92  77.00 -90.00  105
 16  ω     80.00 178.00   1.00    1.00    --  105.92  45.00 -90.00   98
 17  ω     77.00 178.00   1.00    1.00    --  105.92  61.00-150.00  101
 18  ω     80.00 178.00   1.00    1.00    --  105.92  45.00   0.00   98
 19  ω     94.00 178.00   1.00    1.00    --  105.92 125.00-150.00   84
 20  ω     80.00 178.00   1.00    1.00    --  105.92  45.00-120.00   98
 21  ω     73.00 178.00   1.00    1.00    --  105.92  77.00-150.00  105
 22  ω     34.00 135.00   1.00    1.00    --  105.92 -61.00 150.00  101
 23  ω     77.00 178.00   1.00    1.00    --  105.92  61.00 -92.78  101
 24  ω    -67.00  32.00   1.00    1.00    --  -42.02  38.00 -30.00   99
 25  ω   -114.00 -14.00   1.00    1.00    --  -42.02 -57.00  30.00  100
 26  ω   -118.00  -9.00   1.00    1.00    --  -42.02 -77.00 120.00  109
 27  ω   -118.00  -9.00   1.00    1.00    --  -42.02 -77.00   0.00  109
 28  ω      9.00 118.00   1.00    1.00    --   42.02  77.00 -60.00  109
 29  ω     80.00 146.00   1.00    1.00    --  105.92  45.00  60.00   66
 30  ω     77.00 178.00   1.00    1.00    --  105.92  61.00 120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2134570000
_diffrn_orient_matrix_UB_12      0.0006994000
_diffrn_orient_matrix_UB_13      0.0152691000
_diffrn_orient_matrix_UB_21      0.0040377000
_diffrn_orient_matrix_UB_22      -0.0600719000
_diffrn_orient_matrix_UB_23      -0.0975860000
_diffrn_orient_matrix_UB_31      0.0007177000
_diffrn_orient_matrix_UB_32      0.1242205000
_diffrn_orient_matrix_UB_33      -0.0472810000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                4322
_reflns_number_total             4388
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0227
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.1560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0582
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6-C7 = C6-C7'
 1.5 with sigma of 0.01
 C11'-C10'
 1.43 with sigma of 0.02
3. Rigid bond restraints
 C7, S8, C9, C10, C11, C7', S8'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C7 \\sim C7': within 2A with sigma of 0.004 and sigma for terminal atoms of
0.004
5. Others
 Sof(C7')=Sof(S8')=Sof(C9')=Sof(H9')=Sof(C10')=Sof(H10')=Sof(C11')=Sof(H11')=1-
 FVAR(1)
 Sof(C7)=Sof(S8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B), C23(H23A,H23B)
6.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C9'(H9'), C10'(H10'), C11'(H11'), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29)
6.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6067(2) 0.46779(15) 0.71307(10) 0.0178(3) Uani 1 1 d . . . . .
O1 O 0.75945(15) 0.50858(12) 0.70732(8) 0.0222(2) Uani 1 1 d . . . . .
N2 N 0.58412(19) 0.36654(13) 0.76656(9) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.4129(2) 0.31437(16) 0.77150(11) 0.0198(3) Uani 1 1 d . . . . .
O3 O 0.38867(17) 0.23779(12) 0.82856(8) 0.0271(3) Uani 1 1 d . . . . .
C4 C 0.2519(2) 0.35340(16) 0.69774(11) 0.0194(3) Uani 1 1 d . . . . .
O4 O 0.11250(16) 0.29204(12) 0.68944(8) 0.0244(3) Uani 1 1 d . . . . .
N5 N 0.27465(18) 0.45295(13) 0.64569(9) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.4314(2) 0.53540(15) 0.67111(11) 0.0175(3) Uani 1 1 d D . . . .
C7 C 0.385(3) 0.6163(19) 0.7536(15) 0.018(2) Uani 0.639(3) 1 d D U P A 1
S8 S 0.5363(3) 0.7242(2) 0.79904(17) 0.0276(4) Uani 0.639(3) 1 d . U P A 1
C9 C 0.3964(18) 0.7600(9) 0.8846(6) 0.0320(18) Uani 0.639(3) 1 d . U P A 1
H9 H 0.4256 0.8187 0.9306 0.038 Uiso 0.639(3) 1 calc R . P A 1
C10 C 0.240(2) 0.6941(14) 0.8779(13) 0.028(2) Uani 0.639(3) 1 d . U P A 1
H10 H 0.1479 0.7034 0.9175 0.034 Uiso 0.639(3) 1 calc R . P A 1
C11 C 0.2328(18) 0.6083(14) 0.8027(10) 0.042(4) Uani 0.639(3) 1 d . U P A 1
H11 H 0.1369 0.5535 0.7887 0.050 Uiso 0.639(3) 1 calc R . P A 1
C7' C 0.387(6) 0.623(4) 0.746(3) 0.020(3) Uani 0.361(3) 1 d D U P A 2
S8' S 0.2096(7) 0.5991(5) 0.8102(4) 0.0205(6) Uani 0.361(3) 1 d . U P A 2
C9' C 0.272(4) 0.716(3) 0.883(2) 0.026(4) Uani 0.361(3) 1 d . . P A 2
H9' H 0.2080 0.7377 0.9332 0.032 Uiso 0.361(3) 1 calc R . P A 2
C10' C 0.421(3) 0.7740(16) 0.8622(9) 0.026(3) Uani 0.361(3) 1 d D . P A 2
H10' H 0.4734 0.8398 0.8955 0.032 Uiso 0.361(3) 1 calc R . P A 2
C11' C 0.489(2) 0.723(2) 0.7832(13) 0.037(5) Uani 0.361(3) 1 d D . P A 2
H11' H 0.5928 0.7517 0.7579 0.044 Uiso 0.361(3) 1 calc R . P A 2
C12 C 0.4771(2) 0.60568(16) 0.58365(11) 0.0207(3) Uani 1 1 d . . . . .
H12A H 0.3680 0.6499 0.5572 0.025 Uiso 1 1 calc R . . . .
H12B H 0.5739 0.6634 0.6035 0.025 Uiso 1 1 calc R . . . .
C13 C 0.5405(2) 0.52539(17) 0.50648(11) 0.0213(3) Uani 1 1 d . . . . .
H13A H 0.6680 0.5015 0.5254 0.026 Uiso 1 1 calc R . . . .
H13B H 0.4652 0.4534 0.5011 0.026 Uiso 1 1 calc R . . . .
C14 C 0.5274(2) 0.58571(17) 0.41043(11) 0.0221(3) Uani 1 1 d . . . . .
O14 O 0.51367(19) 0.69409(12) 0.40237(8) 0.0301(3) Uani 1 1 d . . . . .
C15 C 0.5319(3) 0.50397(19) 0.32681(12) 0.0291(4) Uani 1 1 d . . . . .
H15A H 0.6223 0.4422 0.3425 0.044 Uiso 1 1 calc GR . . . .
H15B H 0.5642 0.5491 0.2735 0.044 Uiso 1 1 calc GR . . . .
H15C H 0.4120 0.4683 0.3108 0.044 Uiso 1 1 calc GR . . . .
C16 C 0.7503(2) 0.31271(17) 0.81956(11) 0.0221(3) Uani 1 1 d . . . . .
H16A H 0.8428 0.3007 0.7766 0.027 Uiso 1 1 calc R . . . .
H16B H 0.7182 0.2348 0.8430 0.027 Uiso 1 1 calc R . . . .
C17 C 0.8331(2) 0.38861(17) 0.90258(11) 0.0226(3) Uani 1 1 d . . . . .
C18 C 0.7309(3) 0.47234(18) 0.94623(12) 0.0281(4) Uani 1 1 d . . . . .
H18 H 0.6066 0.4842 0.9239 0.034 Uiso 1 1 calc R . . . .
C19 C 0.8129(3) 0.5390(2) 1.02344(13) 0.0364(5) Uani 1 1 d . . . . .
H19 H 0.7433 0.5949 1.0525 0.044 Uiso 1 1 calc R . . . .
C20 C 0.9975(3) 0.5219(2) 1.05657(13) 0.0398(5) Uani 1 1 d . . . . .
H20 H 1.0527 0.5665 1.1077 0.048 Uiso 1 1 calc R . . . .
C21 C 1.1002(3) 0.4380(2) 1.01348(14) 0.0387(5) Uani 1 1 d . . . . .
H21 H 1.2243 0.4262 1.0362 0.046 Uiso 1 1 calc R . . . .
C22 C 1.0196(3) 0.37157(19) 0.93679(13) 0.0295(4) Uani 1 1 d . . . . .
H22 H 1.0897 0.3156 0.9081 0.035 Uiso 1 1 calc R . . . .
C23 C 0.1075(2) 0.49815(16) 0.58656(11) 0.0204(3) Uani 1 1 d . . . . .
H23A H 0.1074 0.5849 0.5901 0.024 Uiso 1 1 calc R . . . .
H23B H -0.0010 0.4697 0.6134 0.024 Uiso 1 1 calc R . . . .
C24 C 0.0904(2) 0.46195(16) 0.48310(11) 0.0194(3) Uani 1 1 d . . . . .
C25 C 0.0373(2) 0.54684(17) 0.41337(12) 0.0231(3) Uani 1 1 d . . . . .
H25 H 0.0231 0.6264 0.4306 0.028 Uiso 1 1 calc R . . . .
C26 C 0.0049(2) 0.51388(18) 0.31766(12) 0.0264(4) Uani 1 1 d . . . . .
H26 H -0.0323 0.5712 0.2716 0.032 Uiso 1 1 calc R . . . .
C27 C 0.0284(2) 0.39586(18) 0.29137(12) 0.0246(4) Uani 1 1 d . . . . .
H27 H 0.0060 0.3736 0.2278 0.030 Uiso 1 1 calc R . . . .
C28 C 0.0855(2) 0.31082(17) 0.36040(11) 0.0226(3) Uani 1 1 d . . . . .
H28 H 0.1030 0.2318 0.3428 0.027 Uiso 1 1 calc R . . . .
C29 C 0.1168(2) 0.34355(16) 0.45583(11) 0.0212(3) Uani 1 1 d . . . . .
H29 H 0.1553 0.2863 0.5016 0.025 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
C1 O1 1.212(2) . ?
C1 N2 1.382(2) . ?
C1 C6 1.537(2) . ?
N2 C3 1.384(2) . ?
N2 C16 1.472(2) . ?
C3 O3 1.204(2) . ?
C3 C4 1.535(2) . ?
C4 O4 1.217(2) . ?
C4 N5 1.355(2) . ?
N5 C6 1.475(2) . ?
N5 C23 1.4786(19) . ?
C6 C7 1.547(7) . ?
C6 C7' 1.504(13) . ?
C6 C12 1.537(2) . ?
C7 S8 1.71(2) . ?
C7 C11 1.38(2) . ?
S8 C9 1.722(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.348(15) . ?
C10 H10 0.9300 . ?
C10 C11 1.43(2) . ?
C11 H11 0.9300 . ?
C7' S8' 1.69(4) . ?
C7' C11' 1.41(4) . ?
S8' C9' 1.69(3) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.32(3) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.40(2) . ?
C11' H11' 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.528(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.511(2) . ?
C14 O14 1.218(2) . ?
C14 C15 1.499(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.514(2) . ?
C17 C18 1.386(3) . ?
C17 C22 1.396(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.396(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.511(2) . ?
C24 C25 1.390(2) . ?
C24 C29 1.397(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.398(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.393(2) . ?
C29 H29 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
O1 C1 N2 120.97(14) . . ?
O1 C1 C6 120.84(15) . . ?
N2 C1 C6 117.79(13) . . ?
C1 N2 C3 122.63(14) . . ?
C1 N2 C16 118.01(13) . . ?
C3 N2 C16 119.36(14) . . ?
N2 C3 C4 117.54(14) . . ?
O3 C3 N2 122.56(15) . . ?
O3 C3 C4 119.84(15) . . ?
O4 C4 C3 117.60(15) . . ?
O4 C4 N5 124.34(16) . . ?
N5 C4 C3 118.06(14) . . ?
C4 N5 C6 121.35(13) . . ?
C4 N5 C23 116.26(14) . . ?
C6 N5 C23 118.88(13) . . ?
C1 C6 C7 104.0(10) . . ?
N5 C6 C1 111.57(13) . . ?
N5 C6 C7 108.3(9) . . ?
N5 C6 C7' 110.6(17) . . ?
N5 C6 C12 110.94(13) . . ?
C7' C6 C1 106.7(19) . . ?
C7' C6 C12 108.6(19) . . ?
C12 C6 C1 108.25(13) . . ?
C12 C6 C7 113.6(10) . . ?
C6 C7 S8 120.4(14) . . ?
C11 C7 C6 127.4(16) . . ?
C11 C7 S8 112.1(8) . . ?
C7 S8 C9 91.2(7) . . ?
S8 C9 H9 123.6 . . ?
C10 C9 S8 112.9(12) . . ?
C10 C9 H9 123.6 . . ?
C9 C10 H10 124.1 . . ?
C9 C10 C11 111.9(15) . . ?
C11 C10 H10 124.1 . . ?
C7 C11 C10 112.0(13) . . ?
C7 C11 H11 124.0 . . ?
C10 C11 H11 124.0 . . ?
C6 C7' S8' 121(3) . . ?
C11' C7' C6 129(3) . . ?
C11' C7' S8' 108.9(12) . . ?
C9' S8' C7' 92.3(14) . . ?
S8' C9' H9' 122.9 . . ?
C10' C9' S8' 114(2) . . ?
C10' C9' H9' 122.9 . . ?
C9' C10' H10' 124.6 . . ?
C9' C10' C11' 111(2) . . ?
C11' C10' H10' 124.6 . . ?
C7' C11' C10' 114(2) . . ?
C7' C11' H11' 123.1 . . ?
C10' C11' H11' 123.1 . . ?
C6 C12 H12A 109.0 . . ?
C6 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C6 113.03(14) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C12 113.06(14) . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
O14 C14 C13 121.50(15) . . ?
O14 C14 C15 122.67(15) . . ?
C15 C14 C13 115.83(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.0 . . ?
N2 C16 H16B 109.0 . . ?
N2 C16 C17 113.12(14) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C18 C17 C16 122.67(16) . . ?
C18 C17 C22 119.19(17) . . ?
C22 C17 C16 118.13(16) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.53(18) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.86(19) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 119.99(19) . . ?
C21 C22 H22 120.0 . . ?
N5 C23 H23A 108.5 . . ?
N5 C23 H23B 108.5 . . ?
N5 C23 C24 115.09(13) . . ?
H23A C23 H23B 107.5 . . ?
C24 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
C25 C24 C23 119.38(15) . . ?
C25 C24 C29 118.95(15) . . ?
C29 C24 C23 121.57(15) . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.68(17) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.98(17) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.75(16) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.26(17) . . ?
C29 C28 H28 119.9 . . ?
C24 C29 H29 119.8 . . ?
C28 C29 C24 120.35(16) . . ?
C28 C29 H29 119.8 . . ?

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
C1 N2 C3 O3 -168.53(15) . . . . ?
C1 N2 C3 C4 14.2(2) . . . . ?
C1 N2 C16 C17 69.96(18) . . . . ?
C1 C6 C7 S8 62.3(18) . . . . ?
C1 C6 C7 C11 -113(2) . . . . ?
C1 C6 C7' S8' -105(3) . . . . ?
C1 C6 C7' C11' 65(5) . . . . ?
C1 C6 C12 C13 59.65(17) . . . . ?
O1 C1 N2 C3 -177.12(14) . . . . ?
O1 C1 N2 C16 2.5(2) . . . . ?
O1 C1 C6 N5 153.81(14) . . . . ?
O1 C1 C6 C7 -89.6(10) . . . . ?
O1 C1 C6 C7' -85.3(19) . . . . ?
O1 C1 C6 C12 31.5(2) . . . . ?
N2 C1 C6 N5 -33.35(18) . . . . ?
N2 C1 C6 C7 83.2(10) . . . . ?
N2 C1 C6 C7' 87.6(19) . . . . ?
N2 C1 C6 C12 -155.69(13) . . . . ?
N2 C3 C4 O4 165.70(14) . . . . ?
N2 C3 C4 N5 -13.7(2) . . . . ?
N2 C16 C17 C18 23.2(2) . . . . ?
N2 C16 C17 C22 -157.69(15) . . . . ?
C3 N2 C16 C17 -110.37(17) . . . . ?
C3 C4 N5 C6 -12.1(2) . . . . ?
C3 C4 N5 C23 -170.76(13) . . . . ?
O3 C3 C4 O4 -11.7(2) . . . . ?
O3 C3 C4 N5 168.90(15) . . . . ?
C4 N5 C6 C1 34.48(19) . . . . ?
C4 N5 C6 C7 -79.4(11) . . . . ?
C4 N5 C6 C7' -84(2) . . . . ?
C4 N5 C6 C12 155.26(14) . . . . ?
C4 N5 C23 C24 -98.50(17) . . . . ?
O4 C4 N5 C6 168.45(15) . . . . ?
O4 C4 N5 C23 9.8(2) . . . . ?
N5 C6 C7 S8 -178.9(14) . . . . ?
N5 C6 C7 C11 6(3) . . . . ?
N5 C6 C7' S8' 16(4) . . . . ?
N5 C6 C7' C11' -174(4) . . . . ?
N5 C6 C12 C13 -63.08(17) . . . . ?
N5 C23 C24 C25 -135.84(16) . . . . ?
N5 C23 C24 C29 47.7(2) . . . . ?
C6 C1 N2 C3 10.1(2) . . . . ?
C6 C1 N2 C16 -170.29(13) . . . . ?
C6 N5 C23 C24 102.33(16) . . . . ?
C6 C7 S8 C9 -176.2(18) . . . . ?
C6 C7 C11 C10 177(2) . . . . ?
C6 C7' S8' C9' 172(4) . . . . ?
C6 C7' C11' C10' -170(4) . . . . ?
C6 C12 C13 C14 161.82(13) . . . . ?
C7 C6 C12 C13 174.6(11) . . . . ?
C7 S8 C9 C10 -0.9(15) . . . . ?
S8 C7 C11 C10 1(2) . . . . ?
S8 C9 C10 C11 1.7(18) . . . . ?
C9 C10 C11 C7 -2(2) . . . . ?
C11 C7 S8 C9 -0.2(18) . . . . ?
C7' C6 C12 C13 175.1(19) . . . . ?
C7' S8' C9' C10' 0(3) . . . . ?
S8' C7' C11' C10' 0(4) . . . . ?
S8' C9' C10' C11' 0(3) . . . . ?
C9' C10' C11' C7' 0(4) . . . . ?
C11' C7' S8' C9' 0(3) . . . . ?
C12 C6 C7 S8 -55(2) . . . . ?
C12 C6 C7 C11 129(2) . . . . ?
C12 C6 C7' S8' 138(3) . . . . ?
C12 C6 C7' C11' -52(5) . . . . ?
C12 C13 C14 O14 17.4(2) . . . . ?
C12 C13 C14 C15 -162.43(15) . . . . ?
C16 N2 C3 O3 11.8(2) . . . . ?
C16 N2 C3 C4 -165.46(13) . . . . ?
C16 C17 C18 C19 179.10(16) . . . . ?
C16 C17 C22 C21 -179.13(16) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C17 C22 C21 0.0(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C17 -0.2(3) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C23 N5 C6 C1 -167.45(12) . . . . ?
C23 N5 C6 C7 78.7(11) . . . . ?
C23 N5 C6 C7' 74(2) . . . . ?
C23 N5 C6 C12 -46.67(18) . . . . ?
C23 C24 C25 C26 -174.51(15) . . . . ?
C23 C24 C29 C28 174.81(14) . . . . ?
C24 C25 C26 C27 -0.9(3) . . . . ?
C25 C24 C29 C28 -1.6(2) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
C26 C27 C28 C29 0.9(2) . . . . ?
C27 C28 C29 C24 0.2(2) . . . . ?
C29 C24 C25 C26 2.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.114
_oxdiff_exptl_absorpt_empirical_full_min 0.951
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1880503'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-03-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 N2 O'
_chemical_formula_sum            'C26 H26 N2 O'
_chemical_formula_weight         382.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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                   9.9803(5)
_cell_length_b                   10.7055(5)
_cell_length_c                   11.0770(7)
_cell_angle_alpha                76.953(5)
_cell_angle_beta                 64.440(6)
_cell_angle_gamma                72.474(4)
_cell_volume                     1011.80(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4124
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1720
_cell_measurement_theta_min      4.1330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 13 0.0517
1 -7 -12 0.0440
1 14 0 0.1112
-1 10 11 0.0855
2 1 -13 0.0896
12 -3 7 0.0823
13 7 4 0.0989
0 -13 5 0.1150
-11 -11 -1 0.1302
-14 -3 -5 0.1091
-1 13 -5 0.1282
7 0 15 0.0788
8 13 10 0.1179
8 7 15 0.0994
-8 -8 -14 0.1044
-7 0 9 0.0705
-5 11 3 0.1144
-11 2 2 0.0945
11 0 -2 0.0848

_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.125
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 -0.0000 13.0000 0.7384 -0.5334 0.4199
1.0000 -7.0000 -12.0000 -0.7662 0.6068 0.0690
1.0000 14.0000 -0.0000 0.2222 -0.2107 -0.9133
-1.0000 10.0000 11.0000 0.7852 -0.6013 -0.2971
2.0000 1.0000 -13.0000 -0.7171 0.5202 -0.4851
12.0000 -3.0000 7.0000 -0.6689 -0.5892 0.4260
13.0000 7.0000 4.0000 -0.6671 -0.6121 -0.3233
0.0000 -13.0000 5.0000 -0.0524 -0.0539 1.0101
-11.0000 -11.0000 -1.0000 0.5634 0.4774 0.6820
-14.0000 -3.0000 -5.0000 0.7841 0.6305 0.0296
-1.0000 13.0000 -5.0000 0.1291 0.0800 -1.0104
7.0000 -0.0000 15.0000 0.1385 -0.8586 0.4874
8.0000 13.0000 10.0000 0.1143 -0.8308 -0.5224
8.0000 7.0000 15.0000 0.2113 -0.9770 0.0309
-8.0000 -8.0000 -14.0000 -0.1876 0.9451 0.0667
-7.0000 -0.0000 9.0000 0.9417 -0.2226 0.2889
-5.0000 11.0000 3.0000 0.7531 -0.1496 -0.6224
-11.0000 2.0000 2.0000 0.9759 0.1709 -0.0693
11.0000 0.0000 -2.0000 -0.9332 -0.1972 -0.0612

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8126
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_min         3.606
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  80.00   1.00    9.56    --   10.48  57.00-120.00   93
  2  ω     -9.00  71.00   1.00    9.56    --   10.48  77.00   0.00   80
  3  ω    -58.00  36.00   1.00    9.56    --   10.48 -57.00  90.00   94
  4  ω     15.00  40.00   1.00    9.56    --   10.48 -99.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0766569000
_diffrn_orient_matrix_UB_12      0.0213456000
_diffrn_orient_matrix_UB_13      0.0450088000
_diffrn_orient_matrix_UB_21      -0.0261211000
_diffrn_orient_matrix_UB_22      -0.0131833000
_diffrn_orient_matrix_UB_23      -0.0450490000
_diffrn_orient_matrix_UB_31      0.0003168000
_diffrn_orient_matrix_UB_32      -0.0652596000
_diffrn_orient_matrix_UB_33      0.0323458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3616
_reflns_number_total             4266
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²+0.6290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
C5 C 0.81492(17) 0.87755(14) 0.41320(14) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.92334(17) 0.84233(14) 0.26931(14) 0.0147(3) Uani 1 1 d . . . . .
C7 C 0.83542(18) 0.93449(15) 0.18308(15) 0.0182(3) Uani 1 1 d . . . . .
H7A H 0.8011 1.0243 0.2057 0.022 Uiso 1 1 calc R . . . .
H7B H 0.8984 0.9340 0.0876 0.022 Uiso 1 1 calc R . . . .
C8 C 0.69933(17) 0.87226(15) 0.22295(15) 0.0186(3) Uani 1 1 d . . . . .
H8A H 0.6028 0.9338 0.2632 0.022 Uiso 1 1 calc R . . . .
H8B H 0.7007 0.8423 0.1460 0.022 Uiso 1 1 calc R . . . .
C9 C 0.72777(17) 0.75564(15) 0.32623(14) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.64086(18) 0.65146(16) 0.35839(16) 0.0213(3) Uani 1 1 d . . . . .
H10A H 0.5333 0.6904 0.3939 0.032 Uiso 1 1 calc GR . . . .
H10B H 0.6657 0.5839 0.4239 0.032 Uiso 1 1 calc GR . . . .
H10C H 0.6681 0.6135 0.2779 0.032 Uiso 1 1 calc GR . . . .
C11 C 1.08885(17) 0.84564(14) 0.21724(15) 0.0158(3) Uani 1 1 d . . . . .
C12 C 1.18437(18) 0.81051(15) 0.08773(15) 0.0187(3) Uani 1 1 d . . . . .
H12 H 1.1453 0.7831 0.0382 0.022 Uiso 1 1 calc R . . . .
C13 C 1.33677(18) 0.81602(15) 0.03220(16) 0.0217(3) Uani 1 1 d . . . . .
H13 H 1.3993 0.7923 -0.0540 0.026 Uiso 1 1 calc R . . . .
C14 C 1.39564(18) 0.85705(16) 0.10561(17) 0.0238(4) Uani 1 1 d . . . . .
H14 H 1.4973 0.8621 0.0683 0.029 Uiso 1 1 calc R . . . .
C15 C 1.30237(19) 0.89046(16) 0.23461(17) 0.0244(4) Uani 1 1 d . . . . .
H15 H 1.3419 0.9173 0.2841 0.029 Uiso 1 1 calc R . . . .
C16 C 1.14969(18) 0.88410(15) 0.29062(15) 0.0193(3) Uani 1 1 d . . . . .
H16 H 1.0881 0.9057 0.3777 0.023 Uiso 1 1 calc R . . . .
C17 C 0.96351(17) 0.59886(14) 0.33801(14) 0.0164(3) Uani 1 1 d . . . . .
H17A H 0.8953 0.5924 0.4323 0.020 Uiso 1 1 calc R . . . .
H17B H 1.0588 0.6104 0.3324 0.020 Uiso 1 1 calc R . . . .
C18 C 0.99364(16) 0.47240(14) 0.28164(15) 0.0156(3) Uani 1 1 d . . . . .
C19 C 1.06659(17) 0.46611(15) 0.14307(15) 0.0190(3) Uani 1 1 d . . . . .
H19 H 1.0901 0.5415 0.0855 0.023 Uiso 1 1 calc R . . . .
C20 C 1.10446(19) 0.34876(16) 0.09023(16) 0.0231(4) Uani 1 1 d . . . . .
H20 H 1.1532 0.3461 -0.0024 0.028 Uiso 1 1 calc R . . . .
C21 C 1.07052(19) 0.23551(16) 0.17395(17) 0.0233(4) Uani 1 1 d . . . . .
H21 H 1.0970 0.1567 0.1381 0.028 Uiso 1 1 calc R . . . .
C22 C 0.99655(19) 0.24062(15) 0.31197(16) 0.0218(3) Uani 1 1 d . . . . .
H22 H 0.9731 0.1650 0.3690 0.026 Uiso 1 1 calc R . . . .
C23 C 0.95754(17) 0.35820(15) 0.36508(15) 0.0178(3) Uani 1 1 d . . . . .
H23 H 0.9066 0.3610 0.4576 0.021 Uiso 1 1 calc R . . . .
C24 C 0.55712(17) 0.84362(15) 0.56042(15) 0.0190(3) Uani 1 1 d . . . . .
H24A H 0.4772 0.8802 0.5261 0.023 Uiso 1 1 calc R . . . .
H24B H 0.5592 0.9107 0.6052 0.023 Uiso 1 1 calc R . . . .
C25 C 0.51783(17) 0.72651(15) 0.66258(14) 0.0174(3) Uani 1 1 d . . . . .
C26 C 0.37156(17) 0.70580(15) 0.71127(15) 0.0183(3) Uani 1 1 d . . . . .
H26 H 0.3005 0.7620 0.6783 0.022 Uiso 1 1 calc R . . . .
C27 C 0.33097(18) 0.60143(15) 0.80895(15) 0.0198(3) Uani 1 1 d . . . . .
H27 H 0.2323 0.5891 0.8425 0.024 Uiso 1 1 calc R . . . .
C28 C 0.43704(19) 0.51591(16) 0.85624(15) 0.0218(3) Uani 1 1 d . . . . .
H28 H 0.4103 0.4453 0.9206 0.026 Uiso 1 1 calc R . . . .
C29 C 0.58387(19) 0.53570(16) 0.80731(15) 0.0223(3) Uani 1 1 d . . . . .
H29 H 0.6555 0.4781 0.8387 0.027 Uiso 1 1 calc R . . . .
C30 C 0.62349(18) 0.64147(15) 0.71155(15) 0.0196(3) Uani 1 1 d . . . . .
H30 H 0.7212 0.6554 0.6801 0.023 Uiso 1 1 calc R . . . .
N1 N 0.89522(14) 0.71439(12) 0.26510(12) 0.0147(3) Uani 1 1 d . . . . .
N4 N 0.70290(14) 0.81290(12) 0.44745(12) 0.0168(3) Uani 1 1 d . . . . .
O5 O 0.81706(13) 0.95466(11) 0.47798(11) 0.0209(3) 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
C5 C6 1.546(2) . ?
C5 N4 1.3618(19) . ?
C5 O5 1.2199(18) . ?
C6 C7 1.560(2) . ?
C6 C11 1.505(2) . ?
C6 N1 1.4929(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.542(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.539(2) . ?
C9 C10 1.503(2) . ?
C9 N1 1.4699(19) . ?
C9 N4 1.4942(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.398(2) . ?
C11 C16 1.388(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(2) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.512(2) . ?
C17 N1 1.4706(19) . ?
C18 C19 1.394(2) . ?
C18 C23 1.395(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(2) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.510(2) . ?
C24 N4 1.4552(18) . ?
C25 C26 1.390(2) . ?
C25 C30 1.388(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.390(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.383(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.391(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.389(2) . ?
C30 H30 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
N4 C5 C6 103.44(12) . . ?
O5 C5 C6 129.63(13) . . ?
O5 C5 N4 126.55(13) . . ?
C5 C6 C7 102.11(12) . . ?
C11 C6 C5 119.57(12) . . ?
C11 C6 C7 114.69(12) . . ?
N1 C6 C5 103.54(11) . . ?
N1 C6 C7 98.98(11) . . ?
N1 C6 C11 115.14(12) . . ?
C6 C7 H7A 111.3 . . ?
C6 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C8 C7 C6 102.48(11) . . ?
C8 C7 H7A 111.3 . . ?
C8 C7 H7B 111.3 . . ?
C7 C8 H8A 111.4 . . ?
C7 C8 H8B 111.4 . . ?
H8A C8 H8B 109.2 . . ?
C9 C8 C7 101.97(12) . . ?
C9 C8 H8A 111.4 . . ?
C9 C8 H8B 111.4 . . ?
C10 C9 C8 115.92(13) . . ?
N1 C9 C8 100.28(11) . . ?
N1 C9 C10 116.88(13) . . ?
N1 C9 N4 101.56(11) . . ?
N4 C9 C8 106.88(12) . . ?
N4 C9 C10 113.51(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C6 118.05(13) . . ?
C16 C11 C6 123.10(13) . . ?
C16 C11 C12 118.84(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.80(15) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.83(14) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.78(15) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.36(15) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.37(14) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
N1 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
N1 C17 C18 112.02(12) . . ?
C19 C18 C17 119.83(13) . . ?
C19 C18 C23 118.26(14) . . ?
C23 C18 C17 121.83(13) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.67(14) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.64(15) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.32(15) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.17(14) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 120.93(14) . . ?
C22 C23 H23 119.5 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
N4 C24 H24A 108.8 . . ?
N4 C24 H24B 108.8 . . ?
N4 C24 C25 113.97(12) . . ?
C26 C25 C24 119.23(14) . . ?
C30 C25 C24 121.28(14) . . ?
C30 C25 C26 119.47(14) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.30(15) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.09(14) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.86(14) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.02(15) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 C29 120.26(14) . . ?
C25 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C9 N1 C6 95.81(11) . . ?
C9 N1 C17 115.10(11) . . ?
C17 N1 C6 115.36(11) . . ?
C5 N4 C9 108.26(11) . . ?
C5 N4 C24 122.24(13) . . ?
C24 N4 C9 124.96(12) . . ?

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
C5 C6 C7 C8 -70.73(13) . . . . ?
C5 C6 C11 C12 178.66(13) . . . . ?
C5 C6 C11 C16 -2.6(2) . . . . ?
C5 C6 N1 C9 46.06(13) . . . . ?
C5 C6 N1 C17 -75.29(14) . . . . ?
C6 C5 N4 C9 -7.12(15) . . . . ?
C6 C5 N4 C24 -164.27(13) . . . . ?
C6 C7 C8 C9 0.57(14) . . . . ?
C6 C11 C12 C13 177.72(13) . . . . ?
C6 C11 C16 C15 -177.25(14) . . . . ?
C7 C6 C11 C12 -59.58(17) . . . . ?
C7 C6 C11 C16 119.19(15) . . . . ?
C7 C6 N1 C9 -58.81(12) . . . . ?
C7 C6 N1 C17 179.85(11) . . . . ?
C7 C8 C9 C10 -163.90(13) . . . . ?
C7 C8 C9 N1 -37.10(13) . . . . ?
C7 C8 C9 N4 68.43(14) . . . . ?
C8 C9 N1 C6 60.08(12) . . . . ?
C8 C9 N1 C17 -178.38(11) . . . . ?
C8 C9 N4 C5 -67.09(15) . . . . ?
C8 C9 N4 C24 89.28(16) . . . . ?
C10 C9 N1 C6 -173.76(13) . . . . ?
C10 C9 N1 C17 -52.22(17) . . . . ?
C10 C9 N4 C5 163.84(13) . . . . ?
C10 C9 N4 C24 -39.79(19) . . . . ?
C11 C6 C7 C8 158.41(12) . . . . ?
C11 C6 N1 C9 178.41(12) . . . . ?
C11 C6 N1 C17 57.07(16) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C11 C16 C15 1.5(2) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C15 C16 C11 -0.7(2) . . . . ?
C16 C11 C12 C13 -1.1(2) . . . . ?
C17 C18 C19 C20 175.60(15) . . . . ?
C17 C18 C23 C22 -175.07(14) . . . . ?
C18 C17 N1 C6 -154.25(12) . . . . ?
C18 C17 N1 C9 95.52(14) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C18 C23 C22 1.6(2) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C21 C22 C23 C18 -1.0(2) . . . . ?
C23 C18 C19 C20 -1.1(2) . . . . ?
C24 C25 C26 C27 -177.67(14) . . . . ?
C24 C25 C30 C29 178.85(14) . . . . ?
C25 C24 N4 C5 -124.48(15) . . . . ?
C25 C24 N4 C9 82.27(18) . . . . ?
C25 C26 C27 C28 -1.3(2) . . . . ?
C26 C25 C30 C29 0.7(2) . . . . ?
C26 C27 C28 C29 1.0(2) . . . . ?
C27 C28 C29 C30 0.2(2) . . . . ?
C28 C29 C30 C25 -1.1(2) . . . . ?
C30 C25 C26 C27 0.5(2) . . . . ?
N1 C6 C7 C8 35.31(13) . . . . ?
N1 C6 C11 C12 54.35(17) . . . . ?
N1 C6 C11 C16 -126.88(15) . . . . ?
N1 C9 N4 C5 37.53(14) . . . . ?
N1 C9 N4 C24 -166.10(12) . . . . ?
N1 C17 C18 C19 47.73(18) . . . . ?
N1 C17 C18 C23 -135.66(14) . . . . ?
N4 C5 C6 C7 77.38(13) . . . . ?
N4 C5 C6 C11 -154.82(13) . . . . ?
N4 C5 C6 N1 -25.09(14) . . . . ?
N4 C9 N1 C6 -49.69(12) . . . . ?
N4 C9 N1 C17 71.85(14) . . . . ?
N4 C24 C25 C26 -134.36(15) . . . . ?
N4 C24 C25 C30 47.5(2) . . . . ?
O5 C5 C6 C7 -95.84(18) . . . . ?
O5 C5 C6 C11 32.0(2) . . . . ?
O5 C5 C6 N1 161.69(15) . . . . ?
O5 C5 N4 C9 166.38(15) . . . . ?
O5 C5 N4 C24 9.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.899
