# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_S27_4b
_database_code_depnum_ccdc_archive 'CCDC 1433186'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-03-06 downloaded from the CCDC.
;
_chemical_name_systematic        
3-[(5-Bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)methyl]-5-[(5-bromo-3,3-dimethyl-3H-indol-2-yl)methylene]-4-hydroxy-3-cyclopentene-1,2-dione'
_diffrn_radiation_source         'Sealed X-ray tube'
_cell_length_a                   10.8186(2)
_cell_length_b                   10.0198(2)
_cell_length_c                   23.1493(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.0900(10)
_cell_angle_gamma                90
_cell_volume                     2444.18(9)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4
_chemical_formula_sum            'C27 H22 Br2 N2 O3'
_chemical_formula_moiety         'C27 H22 Br2 N2 O3'
_chemical_compound_source        ?
_chemical_formula_weight         582.29


_cell_measurement_reflns_used    9024
_cell_measurement_theta_min      2
_cell_measurement_theta_max      35
_cell_measurement_temperature    293

_exptl_crystal_description       platly
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.070
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.375

_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    3.349

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

_computing_data_collection       'Apex2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  CRYSTALS
_computing_molecular_graphics    'Mecrury (Macrae et al., 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            27449
_reflns_number_total             3509
_diffrn_reflns_av_R_equivalents  0.068


_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_max         23.279
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        23.279
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -12
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   4.05
_oxford_diffrn_Wilson_scale      45.05

_atom_sites_solution_primary     iterative
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.63
_refine_diff_density_max         0.60



_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_number_parameters     307
_oxford_refine_ls_R_factor_ref   0.0647
_refine_ls_wR_factor_ref         0.0914
_refine_ls_goodness_of_fit_ref   0.9696
_refine_ls_shift/su_max          0.0004246
_refine_ls_shift/su_mean         0.0000159



_oxford_reflns_number_all        3491
_refine_ls_R_factor_all          0.0647
_refine_ls_wR_factor_all         0.0914


_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2536
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_gt          0.0854



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 6.75P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br -0.15246(6) -0.36759(6) 0.72857(3) 0.0740 1.0000 Uani . . . . . .
Br2 Br 0.79168(6) 0.51009(6) 0.24798(3) 0.0680 1.0000 Uani . . . . . .
N1 N 0.0492(3) 0.0321(3) 0.58038(16) 0.0372 1.0000 Uani . . . . . .
N2 N 0.4439(4) 0.4478(4) 0.41352(17) 0.0431 1.0000 Uani . . . . . .
O1 O 0.1119(3) 0.5417(3) 0.55130(16) 0.0519 1.0000 Uani . . . . . .
O2 O 0.2822(3) 0.5470(3) 0.47311(17) 0.0568 1.0000 Uani . . . . . .
O3 O 0.2128(3) 0.0963(3) 0.51655(15) 0.0467 1.0000 Uani . . . . . .
C1 C 0.1537(4) 0.4421(4) 0.5321(2) 0.0355 1.0000 Uani . . . . . .
C2 C 0.2454(4) 0.4429(4) 0.4933(2) 0.0379 1.0000 Uani . . . . . .
C3 C 0.2809(4) 0.3057(4) 0.48612(19) 0.0331 1.0000 Uani . . . . . .
C4 C 0.2058(4) 0.2214(4) 0.51612(19) 0.0337 1.0000 Uani . . . . . .
C5 C 0.1255(4) 0.3029(4) 0.54352(19) 0.0341 1.0000 Uani . . . . . .
C6 C 0.0369(4) 0.2724(4) 0.5761(2) 0.0376 1.0000 Uani . . . . . .
C7 C 0.0047(4) 0.1479(4) 0.5942(2) 0.0359 1.0000 Uani . . . . . .
C8 C -0.0852(4) 0.1232(4) 0.63517(19) 0.0347 1.0000 Uani . . . . . .
C9 C -0.0685(4) -0.0256(4) 0.64602(19) 0.0319 1.0000 Uani . . . . . .
C10 C 0.0072(4) -0.0761(4) 0.6101(2) 0.0326 1.0000 Uani . . . . . .
C11 C 0.0338(4) -0.2093(5) 0.6063(2) 0.0390 1.0000 Uani . . . . . .
C12 C -0.0178(4) -0.2959(5) 0.6423(2) 0.0417 1.0000 Uani . . . . . .
C13 C -0.0888(4) -0.2455(5) 0.6793(2) 0.0430 1.0000 Uani . . . . . .
C14 C -0.1176(4) -0.1112(5) 0.6813(2) 0.0395 1.0000 Uani . . . . . .
C15 C -0.2225(4) 0.1520(5) 0.6014(2) 0.0532 1.0000 Uani . . . . . .
C16 C -0.0504(5) 0.2072(5) 0.6914(2) 0.0518 1.0000 Uani . . . . . .
C17 C 0.3678(4) 0.2516(4) 0.4564(2) 0.0385 1.0000 Uani . . . . . .
C18 C 0.4416(4) 0.3163(4) 0.4236(2) 0.0368 1.0000 Uani . . . . . .
C19 C 0.5325(4) 0.2480(4) 0.3912(2) 0.0345 1.0000 Uani . . . . . .
C20 C 0.5801(4) 0.3671(5) 0.36141(19) 0.0357 1.0000 Uani . . . . . .
C21 C 0.5241(4) 0.4817(5) 0.3767(2) 0.0392 1.0000 Uani . . . . . .
C22 C 0.5477(5) 0.6067(5) 0.3561(2) 0.0527 1.0000 Uani . . . . . .
C23 C 0.6297(5) 0.6135(5) 0.3180(2) 0.0520 1.0000 Uani . . . . . .
C24 C 0.6851(4) 0.4988(5) 0.3026(2) 0.0433 1.0000 Uani . . . . . .
C25 C 0.6632(4) 0.3754(5) 0.3247(2) 0.0399 1.0000 Uani . . . . . .
C26 C 0.6407(5) 0.1794(5) 0.4350(2) 0.0491 1.0000 Uani . . . . . .
C27 C 0.4634(5) 0.1486(5) 0.3451(2) 0.0490 1.0000 Uani . . . . . .
H61 H -0.0055 0.3443 0.5872 0.0451 1.0000 Uiso R . . . . .
H111 H 0.0816 -0.2407 0.5809 0.0471 1.0000 Uiso R . . . . .
H121 H -0.0033 -0.3863 0.6414 0.0502 1.0000 Uiso R . . . . .
H141 H -0.1663 -0.0805 0.7067 0.0469 1.0000 Uiso R . . . . .
H151 H -0.2796 0.1341 0.6269 0.0798 1.0000 Uiso R . . . . .
H153 H -0.2285 0.2437 0.5904 0.0794 1.0000 Uiso R . . . . .
H152 H -0.2441 0.0981 0.5667 0.0799 1.0000 Uiso R . . . . .
H162 H -0.0993 0.1795 0.7186 0.0778 1.0000 Uiso R . . . . .
H161 H 0.0374 0.1978 0.7098 0.0777 1.0000 Uiso R . . . . .
H163 H -0.0681 0.2999 0.6816 0.0777 1.0000 Uiso R . . . . .
H171 H 0.3776 0.1597 0.4594 0.0454 1.0000 Uiso R . . . . .
H221 H 0.5115 0.6835 0.3678 0.0627 1.0000 Uiso R . . . . .
H231 H 0.6467 0.6944 0.3024 0.0618 1.0000 Uiso R . . . . .
H251 H 0.7013 0.2989 0.3147 0.0479 1.0000 Uiso R . . . . .
H261 H 0.6973 0.1411 0.4131 0.0737 1.0000 Uiso R . . . . .
H262 H 0.6873 0.2406 0.4637 0.0739 1.0000 Uiso R . . . . .
H263 H 0.6070 0.1092 0.4553 0.0736 1.0000 Uiso R . . . . .
H272 H 0.5205 0.1108 0.3235 0.0737 1.0000 Uiso R . . . . .
H273 H 0.4278 0.0777 0.3642 0.0736 1.0000 Uiso R . . . . .
H271 H 0.3964 0.1921 0.3179 0.0738 1.0000 Uiso R . . . . .
H21 H 0.3973 0.5040 0.4276 0.0521 1.0000 Uiso R . . . . .
H11 H 0.0991 0.0248 0.5568 0.0455 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.16233(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C13 . 1.905(4) yes
Br2 . C24 . 1.899(4) yes
N1 . C7 . 1.322(5) yes
N1 . C10 . 1.414(5) yes
N1 . H11 . 0.854 no
N2 . C18 . 1.340(6) yes
N2 . C21 . 1.390(5) yes
N2 . H21 . 0.867 no
O1 . C1 . 1.220(5) yes
O2 . C2 . 1.245(5) yes
O3 . C4 . 1.256(5) yes
C1 . C2 . 1.482(6) yes
C1 . C5 . 1.465(6) yes
C2 . C3 . 1.446(6) yes
C3 . C4 . 1.453(6) yes
C3 . C17 . 1.395(6) yes
C4 . C5 . 1.440(6) yes
C5 . C6 . 1.380(6) yes
C6 . C7 . 1.386(6) yes
C6 . H61 . 0.922 no
C7 . C8 . 1.525(6) yes
C8 . C9 . 1.516(6) yes
C8 . C15 . 1.540(6) yes
C8 . C16 . 1.523(6) yes
C9 . C10 . 1.388(6) yes
C9 . C14 . 1.372(6) yes
C10 . C11 . 1.372(6) yes
C11 . C12 . 1.403(6) yes
C11 . H111 . 0.922 no
C12 . C13 . 1.370(6) yes
C12 . H121 . 0.921 no
C13 . C14 . 1.385(6) yes
C14 . H141 . 0.926 no
C15 . H151 . 0.963 no
C15 . H153 . 0.952 no
C15 . H152 . 0.952 no
C16 . H162 . 0.952 no
C16 . H161 . 0.953 no
C16 . H163 . 0.964 no
C17 . C18 . 1.381(6) yes
C17 . H171 . 0.929 no
C18 . C19 . 1.526(6) yes
C19 . C20 . 1.525(6) yes
C19 . C26 . 1.527(6) yes
C19 . C27 . 1.526(6) yes
C20 . C21 . 1.381(6) yes
C20 . C25 . 1.372(6) yes
C21 . C22 . 1.383(7) yes
C22 . C23 . 1.387(7) yes
C22 . H221 . 0.932 no
C23 . C24 . 1.380(7) yes
C23 . H231 . 0.923 no
C24 . C25 . 1.379(6) yes
C25 . H251 . 0.924 no
C26 . H261 . 0.959 no
C26 . H262 . 0.960 no
C26 . H263 . 0.962 no
C27 . H272 . 0.957 no
C27 . H273 . 0.962 no
C27 . H271 . 0.952 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . N1 . C10 . 112.4(3) yes
C7 . N1 . H11 . 123.2 no
C10 . N1 . H11 . 124.4 no
C18 . N2 . C21 . 112.6(4) yes
C18 . N2 . H21 . 122.5 no
C21 . N2 . H21 . 124.8 no
O1 . C1 . C2 . 124.8(4) yes
O1 . C1 . C5 . 127.2(4) yes
C2 . C1 . C5 . 108.1(4) yes
C1 . C2 . O2 . 123.2(4) yes
C1 . C2 . C3 . 107.2(4) yes
O2 . C2 . C3 . 129.6(4) yes
C2 . C3 . C4 . 107.8(4) yes
C2 . C3 . C17 . 130.7(4) yes
C4 . C3 . C17 . 121.5(4) yes
C3 . C4 . O3 . 123.0(4) yes
C3 . C4 . C5 . 109.8(4) yes
O3 . C4 . C5 . 127.1(4) yes
C1 . C5 . C4 . 106.8(4) yes
C1 . C5 . C6 . 120.5(4) yes
C4 . C5 . C6 . 132.7(4) yes
C5 . C6 . C7 . 128.1(4) yes
C5 . C6 . H61 . 115.6 no
C7 . C6 . H61 . 116.3 no
C6 . C7 . N1 . 125.9(4) yes
C6 . C7 . C8 . 125.0(4) yes
N1 . C7 . C8 . 109.1(4) yes
C7 . C8 . C9 . 101.1(3) yes
C7 . C8 . C15 . 109.4(4) yes
C9 . C8 . C15 . 109.4(4) yes
C7 . C8 . C16 . 111.8(4) yes
C9 . C8 . C16 . 113.9(4) yes
C15 . C8 . C16 . 110.7(4) yes
C8 . C9 . C10 . 108.9(4) yes
C8 . C9 . C14 . 131.7(4) yes
C10 . C9 . C14 . 119.3(4) yes
N1 . C10 . C9 . 108.1(4) yes
N1 . C10 . C11 . 128.3(4) yes
C9 . C10 . C11 . 123.6(4) yes
C10 . C11 . C12 . 116.5(4) yes
C10 . C11 . H111 . 121.9 no
C12 . C11 . H111 . 121.6 no
C11 . C12 . C13 . 119.9(4) yes
C11 . C12 . H121 . 120.2 no
C13 . C12 . H121 . 120.0 no
Br1 . C13 . C12 . 117.9(4) yes
Br1 . C13 . C14 . 119.3(4) yes
C12 . C13 . C14 . 122.8(4) yes
C13 . C14 . C9 . 117.8(4) yes
C13 . C14 . H141 . 120.6 no
C9 . C14 . H141 . 121.6 no
C8 . C15 . H151 . 109.4 no
C8 . C15 . H153 . 108.4 no
H151 . C15 . H153 . 109.2 no
C8 . C15 . H152 . 110.3 no
H151 . C15 . H152 . 110.0 no
H153 . C15 . H152 . 109.5 no
C8 . C16 . H162 . 109.7 no
C8 . C16 . H161 . 110.9 no
H162 . C16 . H161 . 108.8 no
C8 . C16 . H163 . 109.5 no
H162 . C16 . H163 . 109.0 no
H161 . C16 . H163 . 109.0 no
C3 . C17 . C18 . 128.9(4) yes
C3 . C17 . H171 . 115.1 no
C18 . C17 . H171 . 116.0 no
C17 . C18 . N2 . 126.3(4) yes
C17 . C18 . C19 . 125.2(4) yes
N2 . C18 . C19 . 108.5(4) yes
C18 . C19 . C20 . 101.1(3) yes
C18 . C19 . C26 . 111.0(4) yes
C20 . C19 . C26 . 111.5(4) yes
C18 . C19 . C27 . 111.5(4) yes
C20 . C19 . C27 . 110.9(4) yes
C26 . C19 . C27 . 110.5(4) yes
C19 . C20 . C21 . 108.8(4) yes
C19 . C20 . C25 . 131.5(4) yes
C21 . C20 . C25 . 119.7(4) yes
N2 . C21 . C20 . 109.0(4) yes
N2 . C21 . C22 . 128.4(4) yes
C20 . C21 . C22 . 122.6(4) yes
C21 . C22 . C23 . 117.2(5) yes
C21 . C22 . H221 . 121.7 no
C23 . C22 . H221 . 121.1 no
C22 . C23 . C24 . 120.1(4) yes
C22 . C23 . H231 . 120.3 no
C24 . C23 . H231 . 119.6 no
Br2 . C24 . C23 . 119.2(4) yes
Br2 . C24 . C25 . 118.8(4) yes
C23 . C24 . C25 . 122.0(4) yes
C24 . C25 . C20 . 118.4(5) yes
C24 . C25 . H251 . 121.8 no
C20 . C25 . H251 . 119.8 no
C19 . C26 . H261 . 108.4 no
C19 . C26 . H262 . 112.0 no
H261 . C26 . H262 . 108.9 no
C19 . C26 . H263 . 109.6 no
H261 . C26 . H263 . 108.9 no
H262 . C26 . H263 . 109.0 no
C19 . C27 . H272 . 110.6 no
C19 . C27 . H273 . 110.1 no
H272 . C27 . H273 . 108.8 no
C19 . C27 . H271 . 110.0 no
H272 . C27 . H271 . 108.6 no
H273 . C27 . H271 . 108.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag

N1 . H11 . O3 . 151.54(14) 0.854 1.847 2.630(7) yes
N2 . H21 . O2 . 152.55(15) 0.867 1.854 2.654(7) yes
N2 . H21 . C2 . 125.21(13) 0.867 2.552 3.133(7) no
N1 . H11 . C4 . 124.81(12) 0.854 2.567 3.134(7) no
C11 . H111 . O1 1_545 130.03(13) 0.922 2.331 3.008(7) yes
C15 . H153 . O2 2_566 160.10(15) 0.952 2.552 3.462(7) yes
C26 . H262 . O2 2_666 155.08(13) 0.960 2.560 3.454(7) yes



_iucr_refine_instruction_details_constraints 
;
#
# Punched on 29/06/15 at 10:13:53
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE N   (   2,X'S) H   (  21,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 153,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 161,X'S) H   ( 163,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) H   ( 263,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 273,X'S) H   ( 271,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 29/06/15 at 10:13:53
#
#LIST     16                                                                    
NO 
END                                                                             
;
_refine_special_details          SQUEEZE
####################################################################### 
# 
# 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_S41_4a
_database_code_depnum_ccdc_archive 'CCDC 1433187'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-03-06 downloaded from the CCDC.
;
_cell_length_a                   11.0823(3)
_cell_length_b                   14.6505(5)
_cell_length_c                   18.1033(6)
_cell_angle_alpha                66.188(2)
_cell_angle_beta                 81.891(2)
_cell_angle_gamma                72.294(2)
_cell_volume                     2561.12(15)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C27 H24 N2 O3'
_chemical_formula_moiety         'C27 H24 N2 O3'
_chemical_compound_source        ?
_chemical_formula_weight         424.50


_cell_measurement_reflns_used    4509
_cell_measurement_theta_min      2
_cell_measurement_theta_max      32
_cell_measurement_temperature    293

_exptl_crystal_description       platly
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.130
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_max          0.480

_exptl_crystal_density_diffrn    1.101
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.072


_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

_computing_data_collection       'Apex2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  CRYSTALS
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            5370
_reflns_number_total             5370
_diffrn_reflns_av_R_equivalents  0.054

_diffrn_reflns_theta_min         1.579
_diffrn_reflns_theta_max         20.882
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        20.464
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -10
_reflns_limit_h_max              11
_reflns_limit_k_min              -13
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   3.08
_oxford_diffrn_Wilson_scale      12.04

_atom_sites_solution_primary     iterative
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.31

_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         5331
_refine_ls_number_restraints     14
_refine_ls_number_parameters     577
_oxford_refine_ls_R_factor_ref   0.1105
_refine_ls_wR_factor_ref         0.1601
_refine_ls_goodness_of_fit_ref   0.9025
_refine_ls_shift/su_max          0.0001964
_refine_ls_shift/su_mean         0.0000176



_oxford_reflns_number_all        5331
_refine_ls_R_factor_all          0.1105
_refine_ls_wR_factor_all         0.1601


_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3300
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_gt          0.1514


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 1.34P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.7035(4) 0.6107(4) 0.5818(3) 0.0573 1.0000 Uani . . . . . .
C2 C 0.6028(4) 0.5596(4) 0.5857(3) 0.0520 1.0000 Uani . . . . . .
C3 C 0.4941(4) 0.6385(3) 0.5476(3) 0.0498 1.0000 Uani . . . . . .
C4 C 0.5287(4) 0.7378(4) 0.5117(3) 0.0524 1.0000 Uani . . . . . .
C5 C 0.6561(4) 0.7212(3) 0.5326(3) 0.0504 1.0000 Uani . . . . . .
C6 C 0.7288(4) 0.7885(4) 0.5150(3) 0.0596 1.0000 Uani . . . . . .
C7 C 0.7019(4) 0.8943(4) 0.4669(3) 0.0547 1.0000 Uani . . . . . .
C8 C 0.7906(4) 0.9625(4) 0.4512(3) 0.0587 1.0000 Uani . . . . . .
C9 C 0.7113(4) 1.0642(3) 0.3974(3) 0.0562 1.0000 Uani . . . . . .
C10 C 0.5958(4) 1.0559(4) 0.3862(3) 0.0545 1.0000 Uani . . . . . .
C11 C 0.5039(5) 1.1353(4) 0.3390(3) 0.0663 1.0000 Uani . . . . . .
C12 C 0.5282(5) 1.2325(4) 0.3025(3) 0.0796 1.0000 Uani . . . . . .
C13 C 0.6451(6) 1.2430(4) 0.3133(3) 0.0784 1.0000 Uani . . . . . .
C14 C 0.7356(5) 1.1597(4) 0.3601(3) 0.0715 1.0000 Uani . . . . . .
C15 C 0.9123(4) 0.9237(4) 0.4088(3) 0.0841 1.0000 Uani . . . . . .
C16 C 0.8187(5) 0.9660(4) 0.5319(3) 0.0875 1.0000 Uani . . . . . .
C17 C 0.3700(4) 0.6364(3) 0.5440(3) 0.0534 1.0000 Uani . . . . . .
C18 C 0.3215(4) 0.5517(4) 0.5742(3) 0.0510 1.0000 Uani . . . . . .
C19 C 0.1806(4) 0.5573(3) 0.5789(3) 0.0527 1.0000 Uani . . . . . .
C20 C 0.1868(4) 0.4428(3) 0.6157(3) 0.0549 1.0000 Uani . . . . . .
C21 C 0.3118(4) 0.3843(4) 0.6298(3) 0.0536 1.0000 Uani . . . . . .
C22 C 0.3472(5) 0.2769(4) 0.6634(3) 0.0637 1.0000 Uani . . . . . .
C23 C 0.2508(5) 0.2295(4) 0.6815(3) 0.0688 1.0000 Uani . . . . . .
C24 C 0.1258(5) 0.2861(4) 0.6679(3) 0.0719 1.0000 Uani . . . . . .
C25 C 0.0920(4) 0.3942(4) 0.6349(3) 0.0653 1.0000 Uani . . . . . .
C26 C 0.1113(4) 0.6121(4) 0.6356(3) 0.0700 1.0000 Uani . . . . . .
C27 C 0.1203(4) 0.6130(4) 0.4963(3) 0.0665 1.0000 Uani . . . . . .
C28 C 0.2996(5) 0.8030(4) 1.0683(3) 0.0713 1.0000 Uani . . . . . .
C29 C 0.3979(4) 0.8464(4) 1.0750(3) 0.0596 1.0000 Uani . . . . . .
C30 C 0.5097(4) 0.8099(3) 1.0336(3) 0.0524 1.0000 Uani . . . . . .
C31 C 0.4772(4) 0.7484(3) 0.9953(3) 0.0560 1.0000 Uani . . . . . .
C32 C 0.3494(4) 0.7444(3) 1.0160(3) 0.0582 1.0000 Uani . . . . . .
C33 C 0.2743(4) 0.6964(4) 0.9963(3) 0.0676 1.0000 Uani . . . . . .
C34 C 0.3063(5) 0.6347(4) 0.9521(3) 0.0622 1.0000 Uani . . . . . .
C35 C 0.2185(5) 0.5864(4) 0.9340(3) 0.0732 1.0000 Uani . . . . . .
C36 C 0.3044(5) 0.5291(4) 0.8849(3) 0.0740 1.0000 Uani D . . . . .
C37 C 0.4241(5) 0.5438(4) 0.8789(3) 0.0644 1.0000 Uani . . . . . .
C38 C 0.5242(5) 0.5006(4) 0.8382(3) 0.0774 1.0000 Uani . . . . . .
C39 C 0.5034(7) 0.4393(4) 0.8020(3) 0.0953 1.0000 Uani . . . . . .
C40 C 0.3816(8) 0.4256(5) 0.8070(4) 0.0995 1.0000 Uani . . . . . .
C41 C 0.2818(6) 0.4706(4) 0.8480(3) 0.0855 1.0000 Uani D . . . . .
C42 C 0.1062(5) 0.6700(5) 0.8859(4) 0.1112 1.0000 Uani . . . . . .
C43 C 0.1741(5) 0.5107(4) 1.0123(3) 0.0950 1.0000 Uani . . . . . .
C44 C 0.6316(4) 0.8166(3) 1.0297(3) 0.0611 1.0000 Uani . . . . . .
C45 C 0.6793(4) 0.8684(3) 1.0629(3) 0.0531 1.0000 Uani . . . . . .
C46 C 0.8196(4) 0.8584(3) 1.0680(3) 0.0561 1.0000 Uani . . . . . .
C47 C 0.8121(4) 0.9301(3) 1.1100(3) 0.0571 1.0000 Uani D . . . . .
C48 C 0.6880(4) 0.9715(3) 1.1272(3) 0.0541 1.0000 Uani . . . . . .
C49 C 0.6493(5) 1.0397(4) 1.1657(3) 0.0626 1.0000 Uani . . . . . .
C50 C 0.7426(5) 1.0660(4) 1.1885(3) 0.0714 1.0000 Uani D . . . . .
C51 C 0.8689(5) 1.0253(4) 1.1740(3) 0.0749 1.0000 Uani D . . . . .
C52 C 0.9064(4) 0.9547(4) 1.1338(3) 0.0673 1.0000 Uani D . . . . .
C53 C 0.8905(4) 0.7461(4) 1.1169(3) 0.0706 1.0000 Uani . . . . . .
C54 C 0.8818(4) 0.8947(4) 0.9833(3) 0.0742 1.0000 Uani . . . . . .
N1 N 0.5948(3) 0.9513(3) 0.4293(2) 0.0587 1.0000 Uani . . . . . .
N2 N 0.3886(3) 0.4527(3) 0.6045(2) 0.0543 1.0000 Uani . . . . . .
N3 N 0.4209(4) 0.6079(3) 0.9191(2) 0.0641 1.0000 Uani . . . . . .
N4 N 0.6105(3) 0.9317(3) 1.0991(2) 0.0587 1.0000 Uani . . . . . .
O1 O 0.8068(3) 0.5673(2) 0.6145(2) 0.0806 1.0000 Uani . . . . . .
O2 O 0.6209(3) 0.4643(2) 0.61701(19) 0.0643 1.0000 Uani . . . . . .
O3 O 0.4534(3) 0.8220(2) 0.46993(19) 0.0636 1.0000 Uani . . . . . .
O4 O 0.1938(3) 0.8126(3) 1.1022(3) 0.1037 1.0000 Uani . . . . . .
O5 O 0.3803(3) 0.9062(3) 1.1109(2) 0.0828 1.0000 Uani . . . . . .
O6 O 0.5557(3) 0.7067(3) 0.9533(2) 0.0713 1.0000 Uani . . . . . .
H61 H 0.8074 0.7590 0.5394 0.0692 1.0000 Uiso R . . . . .
H111 H 0.4249 1.1268 0.3325 0.0787 1.0000 Uiso R . . . . .
H121 H 0.4657 1.2898 0.2710 0.0930 1.0000 Uiso R . . . . .
H131 H 0.6629 1.3076 0.2880 0.0933 1.0000 Uiso R . . . . .
H141 H 0.8144 1.1664 0.3668 0.0844 1.0000 Uiso R . . . . .
H151 H 0.9671 0.9689 0.3963 0.1239 1.0000 Uiso R . . . . .
H153 H 0.9575 0.8553 0.4431 0.1239 1.0000 Uiso R . . . . .
H152 H 0.8929 0.9220 0.3582 0.1237 1.0000 Uiso R . . . . .
H161 H 0.8696 1.0124 0.5216 0.1291 1.0000 Uiso R . . . . .
H163 H 0.7400 0.9883 0.5598 0.1289 1.0000 Uiso R . . . . .
H162 H 0.8646 0.8976 0.5678 0.1287 1.0000 Uiso R . . . . .
H171 H 0.3119 0.7009 0.5184 0.0621 1.0000 Uiso R . . . . .
H221 H 0.4325 0.2391 0.6724 0.0762 1.0000 Uiso R . . . . .
H231 H 0.2709 0.1574 0.7034 0.0816 1.0000 Uiso R . . . . .
H241 H 0.0620 0.2521 0.6800 0.0847 1.0000 Uiso R . . . . .
H251 H 0.0075 0.4326 0.6254 0.0777 1.0000 Uiso R . . . . .
H262 H 0.0250 0.6075 0.6424 0.1004 1.0000 Uiso R . . . . .
H261 H 0.1110 0.6834 0.6131 0.1008 1.0000 Uiso R . . . . .
H263 H 0.1520 0.5764 0.6881 0.1009 1.0000 Uiso R . . . . .
H272 H 0.0331 0.6135 0.5025 0.0967 1.0000 Uiso R . . . . .
H271 H 0.1255 0.6843 0.4735 0.0964 1.0000 Uiso R . . . . .
H273 H 0.1628 0.5772 0.4615 0.0965 1.0000 Uiso R . . . . .
H331 H 0.1899 0.7078 1.0157 0.0786 1.0000 Uiso R . . . . .
H381 H 0.6041 0.5118 0.8347 0.0910 1.0000 Uiso R . . . . .
H391 H 0.5707 0.4084 0.7753 0.1125 1.0000 Uiso R . . . . .
H401 H 0.3672 0.3862 0.7806 0.1178 1.0000 Uiso R . . . . .
H411 H 0.2001 0.4615 0.8507 0.1091 1.0000 Uiso R . . . . .
H423 H 0.0500 0.6399 0.8746 0.1639 1.0000 Uiso R . . . . .
H422 H 0.0589 0.7109 0.9152 0.1640 1.0000 Uiso R . . . . .
H421 H 0.1358 0.7142 0.8358 0.1638 1.0000 Uiso R . . . . .
H433 H 0.1313 0.4712 0.9997 0.1410 1.0000 Uiso R . . . . .
H432 H 0.1166 0.5484 1.0421 0.1408 1.0000 Uiso R . . . . .
H431 H 0.2464 0.4642 1.0447 0.1409 1.0000 Uiso R . . . . .
H441 H 0.6893 0.7826 0.9991 0.0726 1.0000 Uiso R . . . . .
H491 H 0.5644 1.0666 1.1753 0.0748 1.0000 Uiso R . . . . .
H501 H 0.7190 1.1118 1.2147 0.0840 1.0000 Uiso R . . . . .
H511 H 0.9323 1.0440 1.1894 0.0868 1.0000 Uiso R . . . . .
H521 H 0.9932 0.9256 1.1234 0.0807 1.0000 Uiso R . . . . .
H531 H 0.9764 0.7427 1.1252 0.1048 1.0000 Uiso R . . . . .
H533 H 0.8464 0.7225 1.1689 0.1047 1.0000 Uiso R . . . . .
H532 H 0.8916 0.7019 1.0890 0.1046 1.0000 Uiso R . . . . .
H541 H 0.9704 0.8864 0.9899 0.1096 1.0000 Uiso R . . . . .
H543 H 0.8394 0.9664 0.9520 0.1098 1.0000 Uiso R . . . . .
H542 H 0.8768 0.8522 0.9549 0.1097 1.0000 Uiso R . . . . .
H31 H 0.4817 0.6348 0.9172 0.0756 1.0000 Uiso R . . . . .
H11 H 0.5317 0.9270 0.4287 0.0690 1.0000 Uiso R . . . . .
H21 H 0.4700 0.4328 0.6038 0.0650 1.0000 Uiso R . . . . .
H41 H 0.5284 0.9510 1.1005 0.0690 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4039(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.501(6) yes
C1 . C5 . 1.463(6) yes
C1 . O1 . 1.229(5) yes
C2 . C3 . 1.417(6) yes
C2 . O2 . 1.238(5) yes
C3 . C4 . 1.481(6) yes
C3 . C17 . 1.397(5) yes
C4 . C5 . 1.436(6) yes
C4 . O3 . 1.260(5) yes
C5 . C6 . 1.371(6) yes
C6 . C7 . 1.397(6) yes
C6 . H61 . 0.930 no
C7 . C8 . 1.528(6) yes
C7 . N1 . 1.317(5) yes
C8 . C9 . 1.488(6) yes
C8 . C15 . 1.525(6) yes
C8 . C16 . 1.559(6) yes
C9 . C10 . 1.372(6) yes
C9 . C14 . 1.379(6) yes
C10 . C11 . 1.358(6) yes
C10 . N1 . 1.414(5) yes
C11 . C12 . 1.399(6) yes
C11 . H111 . 0.951 no
C12 . C13 . 1.400(7) yes
C12 . H121 . 0.938 no
C13 . C14 . 1.369(7) yes
C13 . H131 . 0.939 no
C14 . H141 . 0.936 no
C15 . H151 . 0.971 no
C15 . H153 . 0.959 no
C15 . H152 . 0.981 no
C16 . H161 . 0.958 no
C16 . H163 . 0.979 no
C16 . H162 . 0.971 no
C17 . C18 . 1.378(6) yes
C17 . H171 . 0.939 no
C18 . C19 . 1.531(5) yes
C18 . N2 . 1.333(5) yes
C19 . C20 . 1.517(6) yes
C19 . C26 . 1.536(6) yes
C19 . C27 . 1.521(6) yes
C20 . C21 . 1.386(6) yes
C20 . C25 . 1.373(6) yes
C21 . C22 . 1.386(6) yes
C21 . N2 . 1.406(5) yes
C22 . C23 . 1.377(6) yes
C22 . H221 . 0.938 no
C23 . C24 . 1.378(6) yes
C23 . H231 . 0.930 no
C24 . C25 . 1.394(6) yes
C24 . H241 . 0.938 no
C25 . H251 . 0.933 no
C26 . H262 . 0.966 no
C26 . H261 . 0.954 no
C26 . H263 . 0.978 no
C27 . H272 . 0.955 no
C27 . H271 . 0.973 no
C27 . H273 . 0.963 no
C28 . C29 . 1.458(6) yes
C28 . C32 . 1.470(6) yes
C28 . O4 . 1.240(5) yes
C29 . C30 . 1.430(6) yes
C29 . O5 . 1.244(5) yes
C30 . C31 . 1.480(6) yes
C30 . C44 . 1.374(6) yes
C31 . C32 . 1.426(6) yes
C31 . O6 . 1.254(5) yes
C32 . C33 . 1.399(6) yes
C33 . C34 . 1.376(6) yes
C33 . H331 . 0.942 no
C34 . C35 . 1.500(6) yes
C34 . N3 . 1.340(5) yes
C35 . C36 . 1.509(7) yes
C35 . C42 . 1.525(7) yes
C35 . C43 . 1.532(7) yes
C36 . C37 . 1.390(6) yes
C36 . C41 . 1.373(7) yes
C37 . C38 . 1.376(7) yes
C37 . N3 . 1.392(6) yes
C38 . C39 . 1.392(7) yes
C38 . H381 . 0.937 no
C39 . C40 . 1.410(8) yes
C39 . H391 . 0.930 no
C40 . C41 . 1.389(8) yes
C40 . H401 . 0.942 no
C41 . H411 . 0.946 no
C42 . H423 . 0.948 no
C42 . H422 . 0.950 no
C42 . H421 . 0.960 no
C43 . H433 . 0.956 no
C43 . H432 . 0.965 no
C43 . H431 . 0.964 no
C44 . C45 . 1.386(6) yes
C44 . H441 . 0.944 no
C45 . C46 . 1.530(6) yes
C45 . N4 . 1.339(5) yes
C46 . C47 . 1.505(6) yes
C46 . C53 . 1.531(6) yes
C46 . C54 . 1.541(6) yes
C47 . C48 . 1.370(6) yes
C47 . C52 . 1.374(6) yes
C48 . C49 . 1.374(6) yes
C48 . N4 . 1.414(5) yes
C49 . C50 . 1.371(6) yes
C49 . H491 . 0.924 no
C50 . C51 . 1.379(6) yes
C50 . H501 . 0.927 no
C51 . C52 . 1.426(6) yes
C51 . H511 . 0.939 no
C52 . H521 . 0.951 no
C53 . H531 . 0.968 no
C53 . H533 . 0.977 no
C53 . H532 . 0.966 no
C54 . H541 . 0.970 no
C54 . H543 . 0.970 no
C54 . H542 . 0.971 no
N1 . H11 . 0.880 no
N2 . H21 . 0.859 no
N3 . H31 . 0.868 no
N4 . H41 . 0.867 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C5 . 107.8(4) yes
C2 . C1 . O1 . 125.9(4) yes
C5 . C1 . O1 . 126.3(4) yes
C1 . C2 . C3 . 107.8(4) yes
C1 . C2 . O2 . 122.3(4) yes
C3 . C2 . O2 . 130.0(4) yes
C2 . C3 . C4 . 107.6(4) yes
C2 . C3 . C17 . 131.7(4) yes
C4 . C3 . C17 . 120.5(4) yes
C3 . C4 . C5 . 109.6(4) yes
C3 . C4 . O3 . 122.7(4) yes
C5 . C4 . O3 . 127.7(4) yes
C1 . C5 . C4 . 106.9(4) yes
C1 . C5 . C6 . 121.8(4) yes
C4 . C5 . C6 . 131.3(4) yes
C5 . C6 . C7 . 129.7(4) yes
C5 . C6 . H61 . 114.7 no
C7 . C6 . H61 . 115.6 no
C6 . C7 . C8 . 125.4(4) yes
C6 . C7 . N1 . 125.2(4) yes
C8 . C7 . N1 . 109.4(4) yes
C7 . C8 . C9 . 100.5(4) yes
C7 . C8 . C15 . 110.4(4) yes
C9 . C8 . C15 . 112.0(4) yes
C7 . C8 . C16 . 110.3(4) yes
C9 . C8 . C16 . 111.7(4) yes
C15 . C8 . C16 . 111.5(4) yes
C8 . C9 . C10 . 110.7(4) yes
C8 . C9 . C14 . 130.9(4) yes
C10 . C9 . C14 . 118.4(5) yes
C9 . C10 . C11 . 124.3(4) yes
C9 . C10 . N1 . 107.6(4) yes
C11 . C10 . N1 . 128.1(4) yes
C10 . C11 . C12 . 117.1(5) yes
C10 . C11 . H111 . 122.1 no
C12 . C11 . H111 . 120.8 no
C11 . C12 . C13 . 119.7(5) yes
C11 . C12 . H121 . 119.5 no
C13 . C12 . H121 . 120.9 no
C12 . C13 . C14 . 120.8(5) yes
C12 . C13 . H131 . 120.2 no
C14 . C13 . H131 . 118.9 no
C9 . C14 . C13 . 119.7(5) yes
C9 . C14 . H141 . 119.3 no
C13 . C14 . H141 . 121.0 no
C8 . C15 . H151 . 110.5 no
C8 . C15 . H153 . 110.1 no
H151 . C15 . H153 . 108.2 no
C8 . C15 . H152 . 110.4 no
H151 . C15 . H152 . 108.5 no
H153 . C15 . H152 . 109.1 no
C8 . C16 . H161 . 110.2 no
C8 . C16 . H163 . 111.0 no
H161 . C16 . H163 . 109.4 no
C8 . C16 . H162 . 110.3 no
H161 . C16 . H162 . 108.2 no
H163 . C16 . H162 . 107.6 no
C3 . C17 . C18 . 128.2(4) yes
C3 . C17 . H171 . 115.9 no
C18 . C17 . H171 . 115.9 no
C17 . C18 . C19 . 124.9(4) yes
C17 . C18 . N2 . 125.9(4) yes
C19 . C18 . N2 . 109.1(3) yes
C18 . C19 . C20 . 100.7(3) yes
C18 . C19 . C26 . 109.3(3) yes
C20 . C19 . C26 . 111.3(4) yes
C18 . C19 . C27 . 112.2(4) yes
C20 . C19 . C27 . 112.9(3) yes
C26 . C19 . C27 . 110.1(4) yes
C19 . C20 . C21 . 109.7(4) yes
C19 . C20 . C25 . 130.5(4) yes
C21 . C20 . C25 . 119.8(4) yes
C20 . C21 . C22 . 122.9(4) yes
C20 . C21 . N2 . 108.1(4) yes
C22 . C21 . N2 . 129.0(4) yes
C21 . C22 . C23 . 116.4(4) yes
C21 . C22 . H221 . 121.1 no
C23 . C22 . H221 . 122.4 no
C22 . C23 . C24 . 121.7(5) yes
C22 . C23 . H231 . 119.0 no
C24 . C23 . H231 . 119.3 no
C23 . C24 . C25 . 121.1(5) yes
C23 . C24 . H241 . 120.1 no
C25 . C24 . H241 . 118.8 no
C24 . C25 . C20 . 118.1(4) yes
C24 . C25 . H251 . 121.1 no
C20 . C25 . H251 . 120.8 no
C19 . C26 . H262 . 107.6 no
C19 . C26 . H261 . 110.9 no
H262 . C26 . H261 . 109.3 no
C19 . C26 . H263 . 109.2 no
H262 . C26 . H263 . 109.1 no
H261 . C26 . H263 . 110.8 no
C19 . C27 . H272 . 108.8 no
C19 . C27 . H271 . 109.5 no
H272 . C27 . H271 . 108.7 no
C19 . C27 . H273 . 109.6 no
H272 . C27 . H273 . 109.5 no
H271 . C27 . H273 . 110.7 no
C29 . C28 . C32 . 107.9(4) yes
C29 . C28 . O4 . 125.7(5) yes
C32 . C28 . O4 . 126.4(4) yes
C28 . C29 . C30 . 108.7(4) yes
C28 . C29 . O5 . 122.8(4) yes
C30 . C29 . O5 . 128.5(4) yes
C29 . C30 . C31 . 106.9(4) yes
C29 . C30 . C44 . 132.3(4) yes
C31 . C30 . C44 . 120.6(4) yes
C30 . C31 . C32 . 109.3(4) yes
C30 . C31 . O6 . 122.4(4) yes
C32 . C31 . O6 . 128.3(4) yes
C28 . C32 . C31 . 107.1(4) yes
C28 . C32 . C33 . 121.0(4) yes
C31 . C32 . C33 . 131.9(5) yes
C32 . C33 . C34 . 129.1(4) yes
C32 . C33 . H331 . 115.9 no
C34 . C33 . H331 . 115.0 no
C33 . C34 . C35 . 125.2(5) yes
C33 . C34 . N3 . 125.2(4) yes
C35 . C34 . N3 . 109.6(4) yes
C34 . C35 . C36 . 101.3(4) yes
C34 . C35 . C42 . 110.4(4) yes
C36 . C35 . C42 . 112.2(5) yes
C34 . C35 . C43 . 110.5(4) yes
C36 . C35 . C43 . 110.8(4) yes
C42 . C35 . C43 . 111.1(5) yes
C35 . C36 . C37 . 108.9(4) yes
C35 . C36 . C41 . 131.3(5) yes
C37 . C36 . C41 . 119.8(6) yes
C36 . C37 . C38 . 123.1(5) yes
C36 . C37 . N3 . 108.4(5) yes
C38 . C37 . N3 . 128.5(5) yes
C37 . C38 . C39 . 117.8(5) yes
C37 . C38 . H381 . 121.6 no
C39 . C38 . H381 . 120.6 no
C38 . C39 . C40 . 119.3(6) yes
C38 . C39 . H391 . 118.7 no
C40 . C39 . H391 . 122.0 no
C39 . C40 . C41 . 121.9(6) yes
C39 . C40 . H401 . 118.9 no
C41 . C40 . H401 . 119.3 no
C40 . C41 . C36 . 118.3(6) yes
C40 . C41 . H411 . 121.3 no
C36 . C41 . H411 . 120.4 no
C35 . C42 . H423 . 110.8 no
C35 . C42 . H422 . 111.3 no
H423 . C42 . H422 . 107.1 no
C35 . C42 . H421 . 109.8 no
H423 . C42 . H421 . 108.8 no
H422 . C42 . H421 . 109.0 no
C35 . C43 . H433 . 109.6 no
C35 . C43 . H432 . 110.0 no
H433 . C43 . H432 . 109.0 no
C35 . C43 . H431 . 109.4 no
H433 . C43 . H431 . 109.2 no
H432 . C43 . H431 . 109.6 no
C30 . C44 . C45 . 128.5(4) yes
C30 . C44 . H441 . 115.1 no
C45 . C44 . H441 . 116.4 no
C44 . C45 . C46 . 125.6(4) yes
C44 . C45 . N4 . 125.6(4) yes
C46 . C45 . N4 . 108.7(4) yes
C45 . C46 . C47 . 101.2(3) yes
C45 . C46 . C53 . 110.5(3) yes
C47 . C46 . C53 . 112.6(4) yes
C45 . C46 . C54 . 111.3(4) yes
C47 . C46 . C54 . 111.7(4) yes
C53 . C46 . C54 . 109.4(4) yes
C46 . C47 . C48 . 109.8(4) yes
C46 . C47 . C52 . 130.5(4) yes
C48 . C47 . C52 . 119.7(4) yes
C47 . C48 . C49 . 124.1(4) yes
C47 . C48 . N4 . 108.7(4) yes
C49 . C48 . N4 . 127.2(4) yes
C48 . C49 . C50 . 116.7(4) yes
C48 . C49 . H491 . 121.3 no
C50 . C49 . H491 . 122.0 no
C49 . C50 . C51 . 121.5(5) yes
C49 . C50 . H501 . 118.4 no
C51 . C50 . H501 . 120.0 no
C50 . C51 . C52 . 120.6(5) yes
C50 . C51 . H511 . 121.1 no
C52 . C51 . H511 . 118.3 no
C51 . C52 . C47 . 117.4(4) yes
C51 . C52 . H521 . 121.8 no
C47 . C52 . H521 . 120.9 no
C46 . C53 . H531 . 109.4 no
C46 . C53 . H533 . 108.5 no
H531 . C53 . H533 . 110.0 no
C46 . C53 . H532 . 110.5 no
H531 . C53 . H532 . 109.7 no
H533 . C53 . H532 . 108.7 no
C46 . C54 . H541 . 108.0 no
C46 . C54 . H543 . 110.5 no
H541 . C54 . H543 . 110.8 no
C46 . C54 . H542 . 110.2 no
H541 . C54 . H542 . 108.7 no
H543 . C54 . H542 . 108.7 no
C10 . N1 . C7 . 111.8(4) yes
C10 . N1 . H11 . 123.7 no
C7 . N1 . H11 . 124.4 no
C21 . N2 . C18 . 112.4(3) yes
C21 . N2 . H21 . 123.7 no
C18 . N2 . H21 . 123.6 no
C37 . N3 . C34 . 111.7(4) yes
C37 . N3 . H31 . 124.3 no
C34 . N3 . H31 . 123.4 no
C48 . N4 . C45 . 111.6(4) yes
C48 . N4 . H41 . 124.3 no
C45 . N4 . H41 . 123.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C25 . H251 . O1 1_455 162.5 0.933 2.453 3.355(8) no
C52 . H521 . O4 1_655 164.8 0.951 2.422 3.349(8) no
N3 . H31 . C31 . 123.9 0.868 2.570 3.138(8) no
N3 . H31 . O6 . 150.8 0.868 1.856 2.648(8) yes
N1 . H11 . C4 . 123.1 0.880 2.572 3.140(8) yes
N1 . H11 . O3 . 149.7 0.880 1.837 2.634(8) yes
N2 . H21 . O2 . 144.1 0.859 1.934 2.677(8) yes
N4 . H41 . O5 . 144.1 0.867 1.905 2.656(8) yes

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.202 0.103 0.251 266 54 ' '
2 -0.202 0.577 0.749 266 54 ' '
_platon_squeeze_details          
;
;

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/07/15 at 18:22:01
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 153,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 163,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) H   ( 263,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 271,X'S) H   ( 273,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 423,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 433,X'S) H   ( 432,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 533,X'S) H   ( 532,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 543,X'S) H   ( 542,X'S) 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE N   (   2,X'S) H   (  21,X'S) 
RIDE N   (   3,X'S) H   (  31,X'S) 
RIDE N   (   4,X'S) H   (  41,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/07/15 at 18:22:01
#
#LIST     16                                                                    
SIMU  C(51)  C(50)  AND C(61)  C(60) 
DELU  C(51)  C(50)  AND C(61)  C(60) 
SIMU  0.005 C(36)  C(41)  AND C(47)  C(52) 
DELU  0.005 C(36)  C(41)  AND C(47)  C(52) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 0 4 x .
-1 0 3 x .
1 0 3 x .
0 1 4 x .
2 1 2 x .
2 1 4 x .
-1 0 5 x .


_VRF_THETM01_ALERT_3_A           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
          Calculated sin(theta_max)/wavelength =    0.5015
RESPONSE:Even though crystal data was collected up to 0.65 \%A resolution,
 the crystal (the largest available) still diffracted quite weakly at 
high angle. 
 Several recrystallisations did not provide better crystals.
;
_VRF_PLAT027_ALERT_3_A           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
          Calculated sin(theta_max)/wavelength =    0.5015
RESPONSE:Even though crystal data was collected up to 0.65 \%A resolution,
 the crystal (the largest available) still diffracted quite weakly at 
high angle. 
 Several recrystallisations did not provide better crystals.
;

