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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MU_10_FINAL_5H_ace
_database_code_depnum_ccdc_archive 'CCDC 1035702'
_audit_update_record             
;
2014-11-24 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             14-05-06
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'mu_10f in Pcca'
_chemical_name_systematic        ?
_chemical_melting_point          ?
#end of refcif 
_cell_length_a                   26.7092(14)
_cell_length_b                   9.0357(4)
_cell_length_c                   17.2708(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4168.1(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c c a '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y,z+1/2
-x,y,-z+1/2
-x+1/2,-y,z
x+1/2,y,-z
x+1/2,-y,-z+1/2
-x+1/2,y,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'
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'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 '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'


_cell_formula_units_Z            4

# Given Formula = C46.75 H42.50 B4.25 N4.25 O8.50 
# Dc =      1.35 Fooo =   1648.00 Mu =      0.91 M =    422.91
# Found Formula = C53 H46 B2 N2 O3 
# Dc =      1.24 FOOO =   1648.00 Mu =      0.76 M =    390.29

_chemical_formula_sum            'C53 H46 B2 N2 O3'
_chemical_formula_moiety         'C53 H46 B2 N2 O3'
_chemical_compound_source        ?
_chemical_formula_weight         780.58


_cell_measurement_reflns_used    15227
_cell_measurement_theta_min      2
_cell_measurement_theta_max      32
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_max          0.560

_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    0.076

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            98328
_reflns_number_total             6363
_diffrn_reflns_av_R_equivalents  0.100
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 6363 
# Theoretical number of reflections is about 12725 


_diffrn_reflns_theta_min         2.254
_diffrn_reflns_theta_max         30.508
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        30.508
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              0
_reflns_limit_h_max              38
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.55
_refine_diff_density_max         0.85


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         6344
_refine_ls_number_restraints     0
_refine_ls_number_parameters     285
_oxford_refine_ls_R_factor_ref   0.0929
_refine_ls_wR_factor_ref         0.1694
_refine_ls_goodness_of_fit_ref   0.9995
_refine_ls_shift/su_max          0.0003500
_refine_ls_shift/su_mean         0.0000429


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6346
_refine_ls_R_factor_all          0.0930
_refine_ls_wR_factor_all         0.1695

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4657
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_gt          0.1490

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 10.9 14.3 3.96 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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
H291 H 0.5576 0.6753 0.6700 0.0483 0.5000 Uiso R . . . . .
H292 H 0.5073 0.6325 0.6313 0.0483 0.5000 Uiso R . . . . .
H293 H 0.5385 0.5134 0.6743 0.0483 0.5000 Uiso R . . . . .
H1 H 0.5723 0.9023 0.2885 0.0278 1.0000 Uiso R . . . . .
H4 H 0.4714 0.6253 0.5096 0.0301 1.0000 Uiso R . . . . .
H5 H 0.4174 0.8340 0.5089 0.0330 1.0000 Uiso R . . . . .
H6 H 0.4334 1.0386 0.4268 0.0343 1.0000 Uiso R . . . . .
H7 H 0.5005 1.0413 0.3470 0.0302 1.0000 Uiso R . . . . .
H9 H 0.5909 0.7348 0.1866 0.0329 1.0000 Uiso R . . . . .
H10 H 0.6501 0.7020 0.0867 0.0343 1.0000 Uiso R . . . . .
H11 H 0.7331 0.6681 0.1132 0.0373 1.0000 Uiso R . . . . .
H12 H 0.7623 0.6620 0.2430 0.0366 1.0000 Uiso R . . . . .
H13 H 0.7025 0.6916 0.3449 0.0325 1.0000 Uiso R . . . . .
H15 H 0.6958 0.5108 0.4748 0.0490 1.0000 Uiso R . . . . .
H16 H 0.7344 0.2738 0.4534 0.0635 1.0000 Uiso R . . . . .
H17 H 0.6976 0.1080 0.3663 0.0673 1.0000 Uiso R . . . . .
H18 H 0.6246 0.1612 0.3067 0.0681 1.0000 Uiso R . . . . .
H19 H 0.5858 0.3981 0.3284 0.0502 1.0000 Uiso R . . . . .
H21 H 0.6605 0.9103 0.4260 0.0335 1.0000 Uiso R . . . . .
H22 H 0.6941 1.0373 0.5316 0.0398 1.0000 Uiso R . . . . .
H23 H 0.6888 0.9368 0.6564 0.0475 1.0000 Uiso R . . . . .
H24 H 0.6499 0.7035 0.6727 0.0532 1.0000 Uiso R . . . . .
H25 H 0.6173 0.5758 0.5691 0.0396 1.0000 Uiso R . . . . .
H261 H 0.5043 0.4375 0.7253 0.0834 0.5000 Uiso R . . . . .
H262 H 0.5196 0.5409 0.6576 0.0834 0.5000 Uiso R . . . . .
H263 H 0.5559 0.5164 0.7266 0.0834 0.5000 Uiso R . . . . .
N1 N 0.60665(5) 0.73266(17) 0.33716(9) 0.0220 1.0000 Uani . . . . . .
B1 B 0.60830(7) 0.6344(2) 0.41658(12) 0.0227 1.0000 Uani . . . . . .
C20 C 0.63307(6) 0.7312(2) 0.48503(11) 0.0233 1.0000 Uani . . . . . .
C21 C 0.65808(7) 0.8659(2) 0.47629(12) 0.0278 1.0000 Uani . . . . . .
C22 C 0.67935(7) 0.9414(2) 0.53880(13) 0.0325 1.0000 Uani . . . . . .
C23 C 0.67607(8) 0.8822(3) 0.61263(14) 0.0381 1.0000 Uani . . . . . .
C24 C 0.65152(9) 0.7490(3) 0.62348(14) 0.0409 1.0000 Uani . . . . . .
C25 C 0.63034(8) 0.6750(3) 0.56064(12) 0.0328 1.0000 Uani . . . . . .
O2 O 0.51499(15) 0.7792(4) 0.7448(3) 0.0506 0.5000 Uani . . . . . .
C26 C 0.5217(2) 0.5255(8) 0.7119(4) 0.0646 0.5000 Uani . . . . . .
C28 C 0.5000 0.6518(4) 0.7500 0.0478 1.0000 Uani S T . . . .
C29 C 0.52874(19) 0.6145(6) 0.6741(3) 0.0416 0.5000 Uani . . . . . .
C1 C 0.57115(6) 0.8315(2) 0.33020(11) 0.0230 1.0000 Uani . . . . . .
C2 C 0.53011(6) 0.8404(2) 0.38376(10) 0.0218 1.0000 Uani . . . . . .
C3 C 0.52189(6) 0.71904(19) 0.43336(10) 0.0216 1.0000 Uani . . . . . .
C4 C 0.47793(7) 0.7147(2) 0.47837(11) 0.0248 1.0000 Uani . . . . . .
C5 C 0.44527(6) 0.8337(2) 0.47556(11) 0.0262 1.0000 Uani . . . . . .
C6 C 0.45363(7) 0.9559(2) 0.42754(11) 0.0276 1.0000 Uani . . . . . .
C7 C 0.49555(7) 0.9583(2) 0.38057(11) 0.0252 1.0000 Uani . . . . . .
C8 C 0.64198(6) 0.7172(2) 0.27495(10) 0.0226 1.0000 Uani . . . . . .
C9 C 0.62557(7) 0.7195(2) 0.19830(11) 0.0251 1.0000 Uani . . . . . .
C10 C 0.66012(7) 0.7025(2) 0.13847(11) 0.0278 1.0000 Uani . . . . . .
C11 C 0.71066(7) 0.6844(2) 0.15524(11) 0.0287 1.0000 Uani . . . . . .
C12 C 0.72698(7) 0.6822(2) 0.23155(11) 0.0289 1.0000 Uani . . . . . .
C13 C 0.69273(7) 0.6985(2) 0.29205(11) 0.0259 1.0000 Uani . . . . . .
C14 C 0.63550(7) 0.4771(2) 0.40276(12) 0.0293 1.0000 Uani . . . . . .
C15 C 0.68122(8) 0.4386(3) 0.43895(14) 0.0376 1.0000 Uani . . . . . .
C16 C 0.70457(11) 0.3023(3) 0.42521(16) 0.0505 1.0000 Uani . . . . . .
C17 C 0.68349(12) 0.2030(3) 0.37527(18) 0.0555 1.0000 Uani . . . . . .
C18 C 0.63833(13) 0.2352(3) 0.33924(18) 0.0544 1.0000 Uani . . . . . .
C19 C 0.61486(10) 0.3724(3) 0.35406(15) 0.0409 1.0000 Uani . . . . . .
O1 O 0.55391(5) 0.60409(14) 0.43424(8) 0.0237 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2559(2)
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
H291 . C29 . 0.950 no
H292 . C29 . 0.950 no
H293 . H262 . 0.632 no
H293 . C26 . 0.797 no
H293 . C29 . 0.950 no
H1 . C1 . 0.964 no
H4 . C4 . 0.987 no
H5 . C5 . 0.941 no
H6 . C6 . 0.923 no
H7 . C7 . 0.957 no
H9 . C9 . 0.958 no
H10 . C10 . 0.933 no
H11 . C11 . 0.954 no
H12 . C12 . 0.981 no
H13 . C13 . 0.951 no
H15 . C15 . 0.980 no
H16 . C16 . 0.969 no
H17 . C17 . 0.951 no
H18 . C18 . 0.947 no
H19 . C19 . 0.925 no
H21 . C21 . 0.959 no
H22 . C22 . 0.960 no
H23 . C23 . 0.964 no
H24 . C24 . 0.945 no
H25 . C25 . 0.973 no
H261 . C26 . 0.950 no
H262 . C26 . 0.950 no
H262 . C29 . 0.764 no
H263 . C26 . 0.950 no
N1 . B1 . 1.634(2) yes
N1 . C1 . 1.308(2) yes
N1 . C8 . 1.437(2) yes
B1 . C20 . 1.613(3) yes
B1 . C14 . 1.614(3) yes
B1 . O1 . 1.509(2) yes
C20 . C21 . 1.396(3) yes
C20 . C25 . 1.403(3) yes
C21 . C22 . 1.398(3) yes
C22 . C23 . 1.385(3) yes
C23 . C24 . 1.384(4) yes
C24 . C25 . 1.394(3) yes
O2 . O2 4_656 0.821(7) yes
O2 . C28 . 1.222(5) yes
C26 . C26 4_656 1.754(14) yes
C26 . C28 . 1.439(6) yes
C26 . C29 . 1.053(9) yes
C28 . C29 4_656 1.556(5) yes
C28 . C29 . 1.556(5) yes
C1 . C2 . 1.437(2) yes
C2 . C3 . 1.408(2) yes
C2 . C7 . 1.411(2) yes
C3 . C4 . 1.409(2) yes
C3 . O1 . 1.345(2) yes
C4 . C5 . 1.386(3) yes
C5 . C6 . 1.399(3) yes
C6 . C7 . 1.383(3) yes
C8 . C9 . 1.395(3) yes
C8 . C13 . 1.397(2) yes
C9 . C10 . 1.394(3) yes
C10 . C11 . 1.390(3) yes
C11 . C12 . 1.388(3) yes
C12 . C13 . 1.397(2) yes
C14 . C15 . 1.415(3) yes
C14 . C19 . 1.381(3) yes
C15 . C16 . 1.401(3) yes
C16 . C17 . 1.366(5) yes
C17 . C18 . 1.388(5) yes
C18 . C19 . 1.412(3) yes
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
H262 . H293 . C26 . 82.4 no
H262 . H293 . C29 . 53.2 no
C26 . H293 . C29 . 73.6 no
H293 . H262 . C26 . 56.3 no
H293 . H262 . C29 . 85.2 no
C26 . H262 . C29 . 75.0 no
B1 . N1 . C1 . 117.86(14) yes
B1 . N1 . C8 . 123.86(14) yes
C1 . N1 . C8 . 118.27(15) yes
N1 . B1 . C20 . 109.38(14) yes
N1 . B1 . C14 . 111.48(14) yes
C20 . B1 . C14 . 113.66(16) yes
N1 . B1 . O1 . 104.02(14) yes
C20 . B1 . O1 . 110.20(14) yes
C14 . B1 . O1 . 107.65(15) yes
B1 . C20 . C21 . 126.13(16) yes
B1 . C20 . C25 . 117.70(17) yes
C21 . C20 . C25 . 116.16(19) yes
H21 . C21 . C20 . 119.7 no
H21 . C21 . C22 . 117.9 no
C20 . C21 . C22 . 122.42(19) yes
H22 . C22 . C21 . 120.5 no
H22 . C22 . C23 . 119.6 no
C21 . C22 . C23 . 119.8(2) yes
H23 . C23 . C22 . 120.1 no
H23 . C23 . C24 . 120.4 no
C22 . C23 . C24 . 119.4(2) yes
H24 . C24 . C23 . 121.5 no
H24 . C24 . C25 . 118.2 no
C23 . C24 . C25 . 120.2(2) yes
H25 . C25 . C20 . 119.5 no
H25 . C25 . C24 . 118.0 no
C20 . C25 . C24 . 122.0(2) yes
O2 4_656 O2 . C28 . 70.38(19) yes
H262 . C26 . H261 . 109.5 no
H262 . C26 . H263 . 109.5 no
H261 . C26 . H263 . 109.5 no
H262 . C26 . C26 4_656 134.5 no
H261 . C26 . C26 4_656 59.6 no
H263 . C26 . C26 4_656 115.8 no
H262 . C26 . H293 . 41.3 no
H261 . C26 . H293 . 111.1 no
H263 . C26 . H293 . 70.5 no
C26 4_656 C26 . H293 . 169.6 no
H262 . C26 . C28 . 108.1 no
H261 . C26 . C28 . 110.8 no
H263 . C26 . C28 . 109.5 no
C26 4_656 C26 . C28 . 52.5(4) yes
H293 . C26 . C28 . 135.0 no
H262 . C26 . C29 . 44.4 no
H261 . C26 . C29 . 151.3 no
H263 . C26 . C29 . 93.5 no
C26 4_656 C26 . C29 . 125.7(5) yes
H293 . C26 . C29 . 59.9 no
C28 . C26 . C29 . 75.5(5) yes
C29 4_656 C28 . C26 4_656 40.9(4) yes
C29 4_656 C28 . C26 . 114.3(5) yes
C26 4_656 C28 . C26 . 75.1(7) yes
C29 4_656 C28 . O2 4_656 88.9(3) yes
C26 4_656 C28 . O2 4_656 125.5(4) yes
C26 . C28 . O2 4_656 155.9(4) yes
C29 4_656 C28 . O2 . 115.3(3) yes
C26 4_656 C28 . O2 . 155.9(4) yes
C26 . C28 . O2 . 125.5(4) yes
O2 4_656 C28 . O2 . 39.2(4) yes
C29 4_656 C28 . C29 . 155.0(5) yes
C26 4_656 C28 . C29 . 114.3(5) yes
C26 . C28 . C29 . 40.9(4) yes
O2 4_656 C28 . C29 . 115.3(3) yes
O2 . C28 . C29 . 88.9(3) yes
C28 . C29 . H292 . 108.7 no
C28 . C29 . H293 . 109.9 no
H292 . C29 . H293 . 109.5 no
C28 . C29 . H291 . 109.8 no
H292 . C29 . H291 . 109.5 no
H293 . C29 . H291 . 109.5 no
C28 . C29 . H262 . 110.1 no
H292 . C29 . H262 . 70.5 no
H293 . C29 . H262 . 41.6 no
H291 . C29 . H262 . 137.4 no
C28 . C29 . C26 . 63.6(4) yes
H292 . C29 . C26 . 120.4 no
H293 . C29 . C26 . 46.5 no
H291 . C29 . C26 . 129.2 no
H262 . C29 . C26 . 60.6 no
H1 . C1 . N1 . 120.0 no
H1 . C1 . C2 . 117.9 no
N1 . C1 . C2 . 122.15(16) yes
C1 . C2 . C3 . 117.84(16) yes
C1 . C2 . C7 . 121.08(16) yes
C3 . C2 . C7 . 120.65(16) yes
C2 . C3 . C4 . 119.15(16) yes
C2 . C3 . O1 . 120.57(15) yes
C4 . C3 . O1 . 120.15(16) yes
H4 . C4 . C3 . 118.2 no
H4 . C4 . C5 . 122.9 no
C3 . C4 . C5 . 118.94(18) yes
H5 . C5 . C4 . 118.6 no
H5 . C5 . C6 . 119.2 no
C4 . C5 . C6 . 122.19(17) yes
C5 . C6 . H6 . 123.6 no
C5 . C6 . C7 . 119.32(17) yes
H6 . C6 . C7 . 117.0 no
C2 . C7 . H7 . 121.6 no
C2 . C7 . C6 . 119.66(18) yes
H7 . C7 . C6 . 118.7 no
N1 . C8 . C9 . 120.13(16) yes
N1 . C8 . C13 . 119.38(16) yes
C9 . C8 . C13 . 120.49(16) yes
H9 . C9 . C8 . 120.4 no
H9 . C9 . C10 . 119.9 no
C8 . C9 . C10 . 119.59(17) yes
C9 . C10 . H10 . 121.4 no
C9 . C10 . C11 . 120.09(18) yes
H10 . C10 . C11 . 118.5 no
H11 . C11 . C10 . 118.0 no
H11 . C11 . C12 . 121.6 no
C10 . C11 . C12 . 120.30(18) yes
H12 . C12 . C11 . 119.8 no
H12 . C12 . C13 . 119.9 no
C11 . C12 . C13 . 120.19(18) yes
H13 . C13 . C8 . 118.5 no
H13 . C13 . C12 . 122.1 no
C8 . C13 . C12 . 119.35(17) yes
B1 . C14 . C15 . 122.7(2) yes
B1 . C14 . C19 . 120.94(19) yes
C15 . C14 . C19 . 116.4(2) yes
H15 . C15 . C14 . 117.3 no
H15 . C15 . C16 . 121.0 no
C14 . C15 . C16 . 121.7(3) yes
H16 . C16 . C15 . 121.0 no
H16 . C16 . C17 . 118.9 no
C15 . C16 . C17 . 120.0(3) yes
H17 . C17 . C16 . 122.1 no
H17 . C17 . C18 . 117.5 no
C16 . C17 . C18 . 120.3(2) yes
H18 . C18 . C17 . 117.0 no
H18 . C18 . C19 . 123.7 no
C17 . C18 . C19 . 119.2(3) yes
C18 . C19 . C14 . 122.3(3) yes
C18 . C19 . H19 . 120.4 no
C14 . C19 . H19 . 117.1 no
B1 . O1 . C3 . 117.99(14) yes
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
C4 . H4 . O1 2_666 169.48(6) 0.987 2.386 3.361(3) yes
C7 . H7 . O2 2_676 160.51(11) 0.957 2.306 3.224(3) yes
C7 . H7 . O2 3_574 170.36(10) 0.957 2.429 3.376(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 06/05/14 at 16:03:13
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (  21,X'S) H   (  21,X'S) 
RIDE C   (  22,X'S) H   (  22,X'S) 
RIDE C   (  23,X'S) H   (  23,X'S) 
RIDE C   (  24,X'S) H   (  24,X'S) 
RIDE C   (  25,X'S) H   (  25,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) H   ( 263,X'S) 
RIDE C   (  29,X'S) H   ( 292,X'S) H   ( 293,X'S) H   ( 291,X'S) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   4,X'S) H   (   4,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   6,X'S) H   (   6,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) 
RIDE C   (   9,X'S) H   (   9,X'S) 
RIDE C   (  10,X'S) H   (  10,X'S) 
RIDE C   (  11,X'S) H   (  11,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  15,X'S) H   (  15,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE C   (  18,X'S) H   (  18,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 06/05/14 at 16:03:13
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
#end of refcif 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration unk

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: aceton'
_exptl_crystal_preparation       Luminescent
_refine_special_details          'disordered solvent position'
