# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_2
#==============================================================================

_audit_creation_date             2014-08-03
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 007pck14
_chemical_name_systematic        
'methyl 2-((2-benzamido-6-(2,5-dimethoxybenzamido)phenyl)ethynyl)benzoate'
_chemical_melting_point          'not measured'


_cell_length_a                   13.35240(10)
_cell_length_b                   9.24480(10)
_cell_length_c                   21.2654(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.8315(8)
_cell_angle_gamma                90
_cell_volume                     2623.67(4)

_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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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

# Given Formula = C32 H26 N2 O6 
# Dc =      1.35 Fooo =   1120.00 Mu =      7.72 M =    534.57
# Found Formula = C32 H26 N2 O6 
# Dc =      1.35 FOOO =   1120.00 Mu =      7.72 M =    534.57

_chemical_formula_sum            'C32 H26 N2 O6'
_chemical_formula_moiety         'C32 H26 N2 O6'
_chemical_compound_source        synthesis
_chemical_formula_weight         534.57


_cell_measurement_reflns_used    38091
_cell_measurement_theta_min      3
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.180
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_max          0.360

_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.772

# Sheldrick geometric approximatio 0.83 0.87 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_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      150
_diffrn_reflns_number            63238
_reflns_number_total             5483
_diffrn_reflns_av_R_equivalents  0.024
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5483 
# Theoretical number of reflections is about 10976 


_diffrn_reflns_theta_min         3.854
_diffrn_reflns_theta_max         76.137
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        76.137
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              26

_oxford_diffrn_Wilson_B_factor   2.32
_oxford_diffrn_Wilson_scale      0.06

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

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.22


# 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         5461
_refine_ls_number_restraints     0
_refine_ls_number_parameters     361
_oxford_refine_ls_R_factor_ref   0.0389
_refine_ls_wR_factor_ref         0.0496
_refine_ls_goodness_of_fit_ref   1.2313
_refine_ls_shift/su_max          0.0016289
_refine_ls_shift/su_mean         0.0003347


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5461
_refine_ls_R_factor_all          0.0389
_refine_ls_wR_factor_all         0.0496

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5202
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_gt          0.0490

# 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 .


_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: 
 255. 354. 112. 
;

# 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
O1 O 0.84274(7) 0.92643(10) 0.55302(4) 0.0322 1.0000 Uani . . . . . .
C2 C 0.90317(8) 1.04622(13) 0.56068(5) 0.0227 1.0000 Uani . . . . . .
C3 C 0.90415(8) 1.14794(13) 0.51132(5) 0.0216 1.0000 Uani . . . . . .
C4 C 0.96252(8) 1.27161(13) 0.51931(5) 0.0224 1.0000 Uani . . . . . .
C5 C 1.01964(8) 1.29473(13) 0.57425(5) 0.0235 1.0000 Uani . . . . . .
O6 O 1.07242(6) 1.42198(10) 0.57682(4) 0.0315 1.0000 Uani . . . . . .
C7 C 1.13228(10) 1.44805(15) 0.63274(6) 0.0336 1.0000 Uani . . . . . .
C8 C 1.02046(8) 1.19199(13) 0.62130(5) 0.0237 1.0000 Uani . . . . . .
C9 C 0.96222(8) 1.06801(13) 0.61458(5) 0.0243 1.0000 Uani . . . . . .
C10 C 0.85278(9) 1.13264(13) 0.44726(5) 0.0236 1.0000 Uani . . . . . .
O11 O 0.87398(7) 1.21441(10) 0.40453(4) 0.0325 1.0000 Uani . . . . . .
N12 N 0.78439(7) 1.02430(11) 0.44057(4) 0.0247 1.0000 Uani . . . . . .
C13 C 0.74082(8) 0.97137(13) 0.38398(5) 0.0216 1.0000 Uani . . . . . .
C14 C 0.65728(8) 0.87993(13) 0.38919(5) 0.0216 1.0000 Uani . . . . . .
C15 C 0.61453(8) 0.81342(13) 0.33482(5) 0.0231 1.0000 Uani . . . . . .
N16 N 0.52723(7) 0.72996(11) 0.34198(4) 0.0261 1.0000 Uani . . . . . .
C17 C 0.48269(9) 0.64191(14) 0.29797(6) 0.0278 1.0000 Uani . . . . . .
O18 O 0.52317(7) 0.60432(13) 0.25003(4) 0.0494 1.0000 Uani . . . . . .
C19 C 0.37786(8) 0.59542(14) 0.31017(5) 0.0235 1.0000 Uani . . . . . .
C20 C 0.34350(10) 0.46634(14) 0.28343(6) 0.0307 1.0000 Uani . . . . . .
C21 C 0.24503(10) 0.42410(17) 0.29061(6) 0.0372 1.0000 Uani . . . . . .
C22 C 0.18026(10) 0.50999(17) 0.32300(6) 0.0369 1.0000 Uani . . . . . .
C23 C 0.21340(10) 0.63883(16) 0.34880(6) 0.0366 1.0000 Uani . . . . . .
C24 C 0.31230(9) 0.68140(14) 0.34274(6) 0.0292 1.0000 Uani . . . . . .
C25 C 0.65588(9) 0.83929(14) 0.27656(5) 0.0264 1.0000 Uani . . . . . .
C26 C 0.73727(9) 0.93148(14) 0.27309(5) 0.0255 1.0000 Uani . . . . . .
C27 C 0.78024(8) 0.99868(13) 0.32542(5) 0.0237 1.0000 Uani . . . . . .
C28 C 0.61399(8) 0.85756(13) 0.44976(5) 0.0233 1.0000 Uani . . . . . .
C29 C 0.57713(9) 0.83935(13) 0.49833(5) 0.0249 1.0000 Uani . . . . . .
C30 C 0.53712(9) 0.82358(14) 0.56052(5) 0.0256 1.0000 Uani . . . . . .
C31 C 0.45569(9) 0.73341(15) 0.57339(6) 0.0286 1.0000 Uani . . . . . .
C32 C 0.40538(10) 0.64813(17) 0.52223(6) 0.0343 1.0000 Uani . . . . . .
O33 O 0.33634(7) 0.55939(11) 0.54336(4) 0.0389 1.0000 Uani . . . . . .
C34 C 0.27965(10) 0.47814(16) 0.49619(7) 0.0403 1.0000 Uani . . . . . .
O35 O 0.42393(9) 0.65691(15) 0.46767(4) 0.0679 1.0000 Uani . . . . . .
C36 C 0.42098(10) 0.72610(16) 0.63450(6) 0.0363 1.0000 Uani . . . . . .
C37 C 0.46612(11) 0.80614(17) 0.68226(6) 0.0414 1.0000 Uani . . . . . .
C38 C 0.54694(11) 0.89372(17) 0.66998(6) 0.0391 1.0000 Uani . . . . . .
C39 C 0.58269(10) 0.90269(15) 0.60967(6) 0.0324 1.0000 Uani . . . . . .
C40 C 0.85073(11) 0.81549(15) 0.60013(6) 0.0376 1.0000 Uani . . . . . .
H41 H 0.9638 1.3407 0.4864 0.0266 1.0000 Uiso R . . . . .
H72 H 1.1668 1.5447 0.6263 0.0495 1.0000 Uiso R . . . . .
H71 H 1.0893 1.4496 0.6711 0.0473 1.0000 Uiso R . . . . .
H73 H 1.1823 1.3706 0.6384 0.0491 1.0000 Uiso R . . . . .
H81 H 1.0610 1.2081 0.6587 0.0297 1.0000 Uiso R . . . . .
H91 H 0.9629 0.9964 0.6484 0.0276 1.0000 Uiso R . . . . .
H201 H 0.3877 0.4072 0.2612 0.0372 1.0000 Uiso R . . . . .
H211 H 0.2227 0.3368 0.2736 0.0462 1.0000 Uiso R . . . . .
H221 H 0.1112 0.4796 0.3287 0.0447 1.0000 Uiso R . . . . .
H231 H 0.1662 0.6979 0.3702 0.0466 1.0000 Uiso R . . . . .
H241 H 0.3355 0.7743 0.3603 0.0352 1.0000 Uiso R . . . . .
H251 H 0.6274 0.7951 0.2401 0.0331 1.0000 Uiso R . . . . .
H261 H 0.7650 0.9491 0.2314 0.0290 1.0000 Uiso R . . . . .
H271 H 0.8367 1.0609 0.3222 0.0296 1.0000 Uiso R . . . . .
H341 H 0.2480 0.3949 0.5186 0.0604 1.0000 Uiso R . . . . .
H342 H 0.2295 0.5416 0.4777 0.0620 1.0000 Uiso R . . . . .
H343 H 0.3245 0.4440 0.4623 0.0595 1.0000 Uiso R . . . . .
H361 H 0.3630 0.6597 0.6428 0.0453 1.0000 Uiso R . . . . .
H371 H 0.4375 0.8023 0.7243 0.0511 1.0000 Uiso R . . . . .
H381 H 0.5823 0.9479 0.7025 0.0477 1.0000 Uiso R . . . . .
H391 H 0.6413 0.9659 0.6001 0.0378 1.0000 Uiso R . . . . .
H401 H 0.8035 0.7367 0.5867 0.0548 1.0000 Uiso R . . . . .
H403 H 0.8309 0.8543 0.6415 0.0553 1.0000 Uiso R . . . . .
H402 H 0.9229 0.7789 0.6042 0.0549 1.0000 Uiso R . . . . .
H121 H 0.7726 0.9720 0.4737 0.0312 1.0000 Uiso R . . . . .
H161 H 0.5004 0.7296 0.3786 0.0322 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.23(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
O1 . C2 . 1.3768(14) yes
O1 . C40 . 1.4354(14) yes
C2 . C3 . 1.4096(15) yes
C2 . C9 . 1.3850(15) yes
C3 . C4 . 1.3911(16) yes
C3 . C10 . 1.5120(15) yes
C4 . C5 . 1.3913(15) yes
C4 . H41 . 0.947 no
C5 . O6 . 1.3715(14) yes
C5 . C8 . 1.3793(16) yes
O6 . C7 . 1.4318(14) yes
C7 . H72 . 1.017 no
C7 . H71 . 1.012 no
C7 . H73 . 0.984 no
C8 . C9 . 1.3899(16) yes
C8 . H81 . 0.959 no
C9 . H91 . 0.978 no
C10 . O11 . 1.2222(14) yes
C10 . N12 . 1.3598(15) yes
N12 . C13 . 1.4076(14) yes
N12 . H121 . 0.873 no
C13 . C14 . 1.4068(15) yes
C13 . C27 . 1.3904(15) yes
C14 . C15 . 1.4137(16) yes
C14 . C28 . 1.4434(15) yes
C15 . N16 . 1.4102(14) yes
C15 . C25 . 1.3930(15) yes
N16 . C17 . 1.3625(15) yes
N16 . H161 . 0.869 no
C17 . O18 . 1.2196(14) yes
C17 . C19 . 1.4949(16) yes
C19 . C20 . 1.3932(17) yes
C19 . C24 . 1.3845(16) yes
C20 . C21 . 1.3847(17) yes
C20 . H201 . 0.943 no
C21 . C22 . 1.375(2) yes
C21 . H211 . 0.930 no
C22 . C23 . 1.378(2) yes
C22 . H221 . 0.975 no
C23 . C24 . 1.3879(17) yes
C23 . H231 . 0.960 no
C24 . H241 . 0.982 no
C25 . C26 . 1.3849(17) yes
C25 . H251 . 0.946 no
C26 . C27 . 1.3830(16) yes
C26 . H261 . 0.985 no
C27 . H271 . 0.952 no
C28 . C29 . 1.1704(16) yes
C29 . C30 . 1.4494(16) yes
C30 . C31 . 1.4040(17) yes
C30 . C39 . 1.3990(17) yes
C31 . C32 . 1.4865(18) yes
C31 . C36 . 1.3951(16) yes
C32 . O33 . 1.3233(15) yes
C32 . O35 . 1.1969(15) yes
O33 . C34 . 1.4473(16) yes
C34 . H341 . 1.006 no
C34 . H342 . 0.964 no
C34 . H343 . 1.002 no
C36 . C37 . 1.380(2) yes
C36 . H361 . 1.008 no
C37 . C38 . 1.381(2) yes
C37 . H371 . 0.984 no
C38 . C39 . 1.3851(17) yes
C38 . H381 . 0.966 no
C39 . H391 . 1.002 no
C40 . H401 . 0.999 no
C40 . H403 . 0.994 no
C40 . H402 . 1.023 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 . O1 . C40 . 117.51(9) yes
O1 . C2 . C3 . 117.90(10) yes
O1 . C2 . C9 . 122.06(10) yes
C3 . C2 . C9 . 120.04(11) yes
C2 . C3 . C4 . 118.41(10) yes
C2 . C3 . C10 . 126.42(11) yes
C4 . C3 . C10 . 115.03(10) yes
C3 . C4 . C5 . 121.25(11) yes
C3 . C4 . H41 . 119.2 no
C5 . C4 . H41 . 119.6 no
C4 . C5 . O6 . 115.62(10) yes
C4 . C5 . C8 . 119.66(11) yes
O6 . C5 . C8 . 124.72(10) yes
C5 . O6 . C7 . 116.74(9) yes
O6 . C7 . H72 . 106.2 no
O6 . C7 . H71 . 110.9 no
H72 . C7 . H71 . 111.5 no
O6 . C7 . H73 . 109.7 no
H72 . C7 . H73 . 110.3 no
H71 . C7 . H73 . 108.2 no
C5 . C8 . C9 . 120.12(11) yes
C5 . C8 . H81 . 119.0 no
C9 . C8 . H81 . 120.9 no
C8 . C9 . C2 . 120.46(11) yes
C8 . C9 . H91 . 119.4 no
C2 . C9 . H91 . 120.2 no
C3 . C10 . O11 . 120.19(11) yes
C3 . C10 . N12 . 116.54(10) yes
O11 . C10 . N12 . 123.27(11) yes
C10 . N12 . C13 . 127.10(10) yes
C10 . N12 . H121 . 117.5 no
C13 . N12 . H121 . 114.6 no
N12 . C13 . C14 . 116.65(10) yes
N12 . C13 . C27 . 123.00(10) yes
C14 . C13 . C27 . 120.23(10) yes
C13 . C14 . C15 . 119.83(10) yes
C13 . C14 . C28 . 119.84(10) yes
C15 . C14 . C28 . 120.32(10) yes
C14 . C15 . N16 . 117.60(10) yes
C14 . C15 . C25 . 119.44(11) yes
N16 . C15 . C25 . 122.85(10) yes
C15 . N16 . C17 . 126.64(10) yes
C15 . N16 . H161 . 117.8 no
C17 . N16 . H161 . 115.5 no
N16 . C17 . O18 . 123.30(11) yes
N16 . C17 . C19 . 116.31(10) yes
O18 . C17 . C19 . 120.36(11) yes
C17 . C19 . C20 . 118.26(11) yes
C17 . C19 . C24 . 122.16(11) yes
C20 . C19 . C24 . 119.39(11) yes
C19 . C20 . C21 . 119.87(12) yes
C19 . C20 . H201 . 119.9 no
C21 . C20 . H201 . 120.2 no
C20 . C21 . C22 . 120.47(13) yes
C20 . C21 . H211 . 119.7 no
C22 . C21 . H211 . 119.8 no
C21 . C22 . C23 . 119.95(12) yes
C21 . C22 . H221 . 120.5 no
C23 . C22 . H221 . 119.5 no
C22 . C23 . C24 . 120.16(13) yes
C22 . C23 . H231 . 118.3 no
C24 . C23 . H231 . 121.6 no
C23 . C24 . C19 . 120.15(12) yes
C23 . C24 . H241 . 120.2 no
C19 . C24 . H241 . 119.6 no
C15 . C25 . C26 . 119.15(11) yes
C15 . C25 . H251 . 119.7 no
C26 . C25 . H251 . 121.1 no
C25 . C26 . C27 . 122.65(11) yes
C25 . C26 . H261 . 117.9 no
C27 . C26 . H261 . 119.5 no
C13 . C27 . C26 . 118.68(11) yes
C13 . C27 . H271 . 119.8 no
C26 . C27 . H271 . 121.5 no
C14 . C28 . C29 . 178.73(12) yes
C28 . C29 . C30 . 175.79(13) yes
C29 . C30 . C31 . 123.23(11) yes
C29 . C30 . C39 . 117.72(11) yes
C31 . C30 . C39 . 119.06(11) yes
C30 . C31 . C32 . 120.45(11) yes
C30 . C31 . C36 . 119.52(12) yes
C32 . C31 . C36 . 120.01(12) yes
C31 . C32 . O33 . 112.56(11) yes
C31 . C32 . O35 . 124.81(13) yes
O33 . C32 . O35 . 122.62(13) yes
C32 . O33 . C34 . 116.17(10) yes
O33 . C34 . H341 . 106.7 no
O33 . C34 . H342 . 107.9 no
H341 . C34 . H342 . 111.3 no
O33 . C34 . H343 . 110.5 no
H341 . C34 . H343 . 111.6 no
H342 . C34 . H343 . 108.7 no
C31 . C36 . C37 . 120.62(13) yes
C31 . C36 . H361 . 118.1 no
C37 . C36 . H361 . 121.2 no
C36 . C37 . C38 . 120.06(12) yes
C36 . C37 . H371 . 118.5 no
C38 . C37 . H371 . 121.4 no
C37 . C38 . C39 . 120.32(13) yes
C37 . C38 . H381 . 122.4 no
C39 . C38 . H381 . 117.2 no
C30 . C39 . C38 . 120.40(13) yes
C30 . C39 . H391 . 118.5 no
C38 . C39 . H391 . 121.1 no
O1 . C40 . H401 . 106.8 no
O1 . C40 . H403 . 110.1 no
H401 . C40 . H403 . 109.4 no
O1 . C40 . H402 . 110.1 no
H401 . C40 . H402 . 111.6 no
H403 . C40 . H402 . 108.7 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
C7 . H72 . O11 2_786 139.35 1.017 2.380 3.2200(18) yes
C9 . H91 . O18 3_565 153.70 0.978 2.464 3.3687(18) yes
C27 . H271 . O18 4_655 138.91 0.952 2.491 3.2692(18) yes
N12 . H121 . O1 . 136.37 0.873 1.949 2.6504(18) yes
N16 . H161 . O35 . 162.76 0.869 2.280 3.1206(18) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 03/08/14 at 15:00:44
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  72,X'S) H   (  71,X'S) H   (  73,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE N   (  12,X'S) H   ( 121,X'S) 
RIDE N   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,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   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) H   ( 343,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,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) H   ( 403,X'S) H   ( 402,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 03/08/14 at 15:00:44
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_common            2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
_database_code_depnum_ccdc_archive 'CCDC 1017646'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3
#==============================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'methyl 2-((2-benzamido-6-(2-hydroxy-5-methoxybenzamido)phenyl)ethynyl)benzoate'
_chemical_name_common            'Compound 3'
_chemical_formula_moiety         'C31 H24 N2 O6'
_chemical_formula_sum            'C31 H24 N2 O6'
_chemical_compound_source        'chemical synthesis'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_chemical_melting_point          402

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      93(2)
_diffrn_ambient_pressure         100
_chemical_formula_weight         520.52

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2591(7)
_cell_length_b                   24.5888(4)
_cell_length_c                   9.35660(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.437(8)
_cell_angle_gamma                90.00
_cell_volume                     2457.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    64821
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      65.9
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8549
_exptl_absorpt_correction_T_max  0.9234
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'

_exptl_special_details           
; 
 'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD' 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   'microfocus rotating anode'
_diffrn_radiation_monochromator  conical
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            74314
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         65.91
_reflns_number_total             4255
_reflns_number_gt                4147
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM 2.0 r12 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM 2.0 r12 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    .
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+1.0305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4255
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.05018(11) 0.19503(5) 0.11862(13) 0.0186(2) Uani 1 1 d . . .
C7 C -0.00972(11) 0.24017(5) 0.02803(13) 0.0198(3) Uani 1 1 d . . .
C8 C -0.05874(11) 0.28008(5) -0.04013(13) 0.0209(3) Uani 1 1 d . . .
C9 C -0.12237(11) 0.32651(5) -0.12192(14) 0.0216(3) Uani 1 1 d . . .
C10 C -0.20859(11) 0.31871(5) -0.26579(14) 0.0239(3) Uani 1 1 d . . .
H10 H -0.2207 0.2833 -0.3083 0.029 Uiso 1 1 calc R . .
C11 C -0.27635(12) 0.36181(5) -0.34690(14) 0.0257(3) Uani 1 1 d . . .
H11 H -0.3350 0.3558 -0.4439 0.031 Uiso 1 1 calc R . .
C12 C -0.25864(12) 0.41384(5) -0.28671(15) 0.0276(3) Uani 1 1 d . . .
H12 H -0.3050 0.4435 -0.3424 0.033 Uiso 1 1 calc R . .
C13 C -0.17346(12) 0.42255(5) -0.14562(15) 0.0255(3) Uani 1 1 d . . .
H13 H -0.1619 0.4583 -0.1049 0.031 Uiso 1 1 calc R . .
C14 C -0.10434(11) 0.37977(5) -0.06216(14) 0.0224(3) Uani 1 1 d . . .
C15 C -0.01119(12) 0.39025(5) 0.08831(14) 0.0234(3) Uani 1 1 d . . .
O1 O 0.05736(10) 0.35667(4) 0.16526(11) 0.0373(3) Uani 1 1 d . . .
O2 O -0.00967(8) 0.44216(4) 0.13223(10) 0.0279(2) Uani 1 1 d . . .
C16 C 0.08555(13) 0.45466(5) 0.27410(15) 0.0289(3) Uani 1 1 d . . .
H16A H 0.0765 0.4301 0.3526 0.043 Uiso 1 1 calc R . .
H16B H 0.0758 0.4924 0.3023 0.043 Uiso 1 1 calc R . .
H16C H 0.1687 0.4499 0.2632 0.043 Uiso 1 1 calc R . .
C2 C 0.14712(11) 0.20366(5) 0.25538(13) 0.0190(2) Uani 1 1 d . . .
N1 N 0.18739(10) 0.25743(4) 0.28998(12) 0.0200(2) Uani 1 1 d . . .
H1N H 0.1580(14) 0.2805(6) 0.2220(17) 0.024 Uiso 1 1 d . . .
C17 C 0.26960(11) 0.27690(5) 0.42044(13) 0.0198(3) Uani 1 1 d . . .
O3 O 0.30566(8) 0.25095(4) 0.53798(9) 0.0252(2) Uani 1 1 d . . .
C18 C 0.31838(11) 0.33302(5) 0.41007(13) 0.0203(3) Uani 1 1 d . . .
C19 C 0.35134(12) 0.34892(5) 0.28485(14) 0.0234(3) Uani 1 1 d . . .
H19 H 0.3356 0.3254 0.2004 0.028 Uiso 1 1 calc R . .
C20 C 0.40715(12) 0.39910(5) 0.28330(15) 0.0267(3) Uani 1 1 d . . .
H20 H 0.4309 0.4096 0.1985 0.032 Uiso 1 1 calc R . .
C21 C 0.42821(12) 0.43386(5) 0.40525(15) 0.0270(3) Uani 1 1 d . . .
H21 H 0.4665 0.4682 0.4040 0.032 Uiso 1 1 calc R . .
C22 C 0.39345(12) 0.41860(5) 0.52947(14) 0.0257(3) Uani 1 1 d . . .
H22 H 0.4064 0.4428 0.6121 0.031 Uiso 1 1 calc R . .
C23 C 0.33995(11) 0.36805(5) 0.53265(14) 0.0225(3) Uani 1 1 d . . .
H23 H 0.3180 0.3573 0.6185 0.027 Uiso 1 1 calc R . .
C3 C 0.20033(11) 0.15919(5) 0.34533(13) 0.0209(3) Uani 1 1 d . . .
H3 H 0.2644 0.1645 0.4387 0.025 Uiso 1 1 calc R . .
C4 C 0.15905(11) 0.10713(5) 0.29760(14) 0.0222(3) Uani 1 1 d . . .
H4 H 0.1962 0.0771 0.3595 0.027 Uiso 1 1 calc R . .
C5 C 0.06527(11) 0.09740(5) 0.16235(14) 0.0215(3) Uani 1 1 d . . .
H5 H 0.0395 0.0613 0.1313 0.026 Uiso 1 1 calc R . .
C6 C 0.01001(11) 0.14148(5) 0.07359(13) 0.0198(3) Uani 1 1 d . . .
N2 N -0.08628(10) 0.13731(4) -0.06500(12) 0.0217(2) Uani 1 1 d . . .
H2N H -0.1023(14) 0.1672(7) -0.1105(17) 0.026 Uiso 1 1 d . . .
C24 C -0.16110(11) 0.09484(5) -0.12771(14) 0.0214(3) Uani 1 1 d . . .
O4 O -0.14829(8) 0.04912(3) -0.06921(10) 0.0269(2) Uani 1 1 d . . .
C25 C -0.25957(11) 0.10620(5) -0.27381(14) 0.0217(3) Uani 1 1 d . . .
C26 C -0.33359(12) 0.06309(5) -0.35260(14) 0.0241(3) Uani 1 1 d . . .
O5 O -0.32199(10) 0.01143(4) -0.29791(11) 0.0337(2) Uani 1 1 d . . .
H5O H -0.2569(18) 0.0148(7) -0.203(2) 0.051 Uiso 1 1 d . . .
C27 C -0.42319(12) 0.07312(6) -0.49135(15) 0.0275(3) Uani 1 1 d . . .
H27 H -0.4726 0.0439 -0.5450 0.033 Uiso 1 1 calc R . .
C28 C -0.44183(12) 0.12467(5) -0.55279(14) 0.0260(3) Uani 1 1 d . . .
H28 H -0.5041 0.1307 -0.6472 0.031 Uiso 1 1 calc R . .
C29 C -0.36918(12) 0.16774(5) -0.47614(15) 0.0262(3) Uani 1 1 d . . .
O6 O -0.37739(9) 0.22015(4) -0.52772(11) 0.0353(2) Uani 1 1 d . . .
C31 C -0.46716(13) 0.23069(6) -0.67274(16) 0.0336(3) Uani 1 1 d . . .
H31A H -0.4471 0.2086 -0.7491 0.050 Uiso 1 1 calc R . .
H31B H -0.4644 0.2693 -0.6976 0.050 Uiso 1 1 calc R . .
H31C H -0.5512 0.2214 -0.6705 0.050 Uiso 1 1 calc R . .
C30 C -0.27983(12) 0.15812(5) -0.33843(15) 0.0269(3) Uani 1 1 d . . .
H30 H -0.2306 0.1876 -0.2860 0.032 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 C2 1.4108(17) . ?
C1 C6 1.4126(17) . ?
C1 C7 1.4296(17) . ?
C7 C8 1.2049(18) . ?
C8 C9 1.4337(17) . ?
C9 C10 1.4017(18) . ?
C9 C14 1.4131(18) . ?
C10 C11 1.3838(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3866(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3811(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3918(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.4881(18) . ?
C15 O1 1.2018(16) . ?
C15 O2 1.3394(15) . ?
O2 C16 1.4511(16) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C2 C3 1.3944(17) . ?
C2 N1 1.4019(15) . ?
N1 C17 1.3643(16) . ?
N1 H1N 0.838(16) . ?
C17 O3 1.2245(15) . ?
C17 C18 1.4996(16) . ?
C18 C19 1.3922(17) . ?
C18 C23 1.3930(17) . ?
C19 C20 1.3867(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.3848(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.3901(19) . ?
C21 H21 0.9500 . ?
C22 C23 1.3856(18) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C3 C4 1.3865(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3887(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3875(17) . ?
C5 H5 0.9500 . ?
C6 N2 1.4065(15) . ?
N2 C24 1.3535(16) . ?
N2 H2N 0.840(16) . ?
C24 O4 1.2388(15) . ?
C24 C25 1.4890(17) . ?
C25 C30 1.4001(18) . ?
C25 C26 1.4046(17) . ?
C26 O5 1.3603(16) . ?
C26 C27 1.3912(18) . ?
O5 H5O 0.96(2) . ?
C27 C28 1.3800(19) . ?
C27 H27 0.9500 . ?
C28 C29 1.3908(18) . ?
C28 H28 0.9500 . ?
C29 O6 1.3689(16) . ?
C29 C30 1.3814(18) . ?
O6 C31 1.4361(16) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C30 H30 0.9500 . ?

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
C2 C1 C6 119.58(11) . . ?
C2 C1 C7 120.37(11) . . ?
C6 C1 C7 120.02(11) . . ?
C8 C7 C1 175.89(12) . . ?
C7 C8 C9 177.47(13) . . ?
C10 C9 C14 118.43(11) . . ?
C10 C9 C8 118.75(11) . . ?
C14 C9 C8 122.80(11) . . ?
C11 C10 C9 121.07(12) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.02(12) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.89(12) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.01(12) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C9 119.56(12) . . ?
C13 C14 C15 120.11(11) . . ?
C9 C14 C15 120.32(11) . . ?
O1 C15 O2 121.83(12) . . ?
O1 C15 C14 125.09(12) . . ?
O2 C15 C14 113.08(10) . . ?
C15 O2 C16 114.62(10) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C2 N1 123.67(11) . . ?
C3 C2 C1 119.40(11) . . ?
N1 C2 C1 116.89(10) . . ?
C17 N1 C2 128.02(11) . . ?
C17 N1 H1N 115.8(10) . . ?
C2 N1 H1N 116.2(10) . . ?
O3 C17 N1 124.00(11) . . ?
O3 C17 C18 120.90(11) . . ?
N1 C17 C18 115.07(10) . . ?
C19 C18 C23 119.72(11) . . ?
C19 C18 C17 120.89(11) . . ?
C23 C18 C17 119.20(11) . . ?
C20 C19 C18 120.06(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.04(12) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.15(12) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 119.95(12) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C18 120.05(12) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C4 C3 C2 119.56(11) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 122.25(11) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 118.59(11) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 N2 124.33(11) . . ?
C5 C6 C1 120.60(11) . . ?
N2 C6 C1 115.07(11) . . ?
C24 N2 C6 130.43(11) . . ?
C24 N2 H2N 116.8(10) . . ?
C6 N2 H2N 112.5(10) . . ?
O4 C24 N2 122.63(11) . . ?
O4 C24 C25 121.65(11) . . ?
N2 C24 C25 115.72(11) . . ?
C30 C25 C26 118.22(11) . . ?
C30 C25 C24 122.67(11) . . ?
C26 C25 C24 119.10(11) . . ?
O5 C26 C27 118.14(11) . . ?
O5 C26 C25 122.47(11) . . ?
C27 C26 C25 119.39(12) . . ?
C26 O5 H5O 102.9(11) . . ?
C28 C27 C26 121.43(12) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C29 119.83(12) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
O6 C29 C30 115.99(11) . . ?
O6 C29 C28 124.89(12) . . ?
C30 C29 C28 119.11(12) . . ?
C29 O6 C31 116.86(11) . . ?
O6 C31 H31A 109.5 . . ?
O6 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O6 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C30 C25 122.02(12) . . ?
C29 C30 H30 119.0 . . ?
C25 C30 H30 119.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        65.91
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1017647'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_5
#==============================================================================

_audit_creation_date             2014-08-03
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 004pck14
_chemical_name_systematic        
'tetra-n-butylammonium 2-((3-benzamido-2-((2-(methoxycarbonyl)phenyl)ethynyl)phenyl)carbamoyl)-4-methoxyphenolate'
_chemical_melting_point          'not measured'

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
;
Examination of the structure during refinement revealed some disorder
in the methyl ether, which was modelled to ensure convergence
of the model.

H atoms were placed in calculated positions with
reference to Fourier difference maps and refined in a riding model.
;

_cell_length_a                   8.32320(10)
_cell_length_b                   15.9988(3)
_cell_length_c                   16.9150(3)
_cell_angle_alpha                106.3845(8)
_cell_angle_beta                 101.5498(8)
_cell_angle_gamma                101.9548(8)
_cell_volume                     2032.23(6)

_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            2

# Given Formula = C47 H59 N3 O6 
# Dc =      1.25 Fooo =    820.00 Mu =      0.82 M =    762.00
# Found Formula = C47 H59 N3 O6 
# Dc =      1.25 FOOO =    820.00 Mu =      0.82 M =    762.00

_chemical_formula_sum            'C47 H59 N3 O6'
_chemical_formula_moiety         'C47 H59 N3 O6'
_chemical_compound_source        synthesis
_chemical_formula_weight         762.00


_cell_measurement_reflns_used    8212
_cell_measurement_theta_min      5
_cell_measurement_theta_max      26
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_yellow
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_max          0.380

_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    0.082

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      150
_diffrn_ambient_pressure         100
_diffrn_reflns_number            44870
_reflns_number_total             8239
_diffrn_reflns_av_R_equivalents  0.032
# Number of reflections without Friedels Law is 15733 
# Number of reflections with Friedels Law is 8239 
# Theoretical number of reflections is about 8291 


_diffrn_reflns_theta_min         5.159
_diffrn_reflns_theta_max         26.347
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        25.821
_diffrn_measured_fraction_theta_full 0.992


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -19
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_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         -0.34
_refine_diff_density_max         0.36


# 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         8239
_refine_ls_number_restraints     0
_refine_ls_number_parameters     523
_oxford_refine_ls_R_factor_ref   0.0735
_refine_ls_wR_factor_ref         0.0856
_refine_ls_goodness_of_fit_ref   1.0039
_refine_ls_shift/su_max          0.0004128
_refine_ls_shift/su_mean         0.0000312


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        8239
_refine_ls_R_factor_all          0.0735
_refine_ls_wR_factor_all         0.0856

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5764
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_gt          0.0686

# 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 .


_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: 
 7.43 8.53 2.38 
;

# 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
C1 C 0.7479(3) 0.64799(14) 0.42645(14) 0.0364 1.0000 Uani . . . . . .
O2 O 0.76802(19) 0.55896(9) 0.42206(9) 0.0347 1.0000 Uani . . . . . .
C3 C 0.7441(2) 0.53267(13) 0.48834(12) 0.0285 1.0000 Uani . . . . . .
O4 O 0.7046(2) 0.57844(10) 0.54775(9) 0.0373 1.0000 Uani . . . . . .
C5 C 0.7723(2) 0.44202(13) 0.47909(12) 0.0262 1.0000 Uani . . . . . .
C6 C 0.8199(3) 0.39658(14) 0.40787(12) 0.0316 1.0000 Uani . . . . . .
C7 C 0.8461(3) 0.31188(14) 0.39787(13) 0.0342 1.0000 Uani . . . . . .
C8 C 0.8240(3) 0.27104(14) 0.45855(13) 0.0327 1.0000 Uani . . . . . .
C9 C 0.7783(2) 0.31526(13) 0.53011(12) 0.0292 1.0000 Uani . . . . . .
C10 C 0.7528(2) 0.40146(13) 0.54135(12) 0.0252 1.0000 Uani . . . . . .
C11 C 0.7065(2) 0.44310(13) 0.61777(12) 0.0258 1.0000 Uani . . . . . .
H11 H 0.7748 0.6597 0.3760 0.0555 1.0000 Uiso R . . . . .
C12 C 0.6655(2) 0.46952(12) 0.68214(12) 0.0244 1.0000 Uani . . . . . .
H12 H 0.6294 0.6504 0.4265 0.0546 1.0000 Uiso R . . . . .
C13 C 0.6179(2) 0.50662(12) 0.75844(11) 0.0230 1.0000 Uani . . . . . .
H13 H 0.8318 0.6953 0.4810 0.0543 1.0000 Uiso R . . . . .
C14 C 0.5657(2) 0.45149(12) 0.80672(11) 0.0238 1.0000 Uani . . . . . .
C15 C 0.5314(2) 0.49192(13) 0.88381(12) 0.0274 1.0000 Uani . . . . . .
C16 C 0.5381(2) 0.58327(13) 0.90922(12) 0.0278 1.0000 Uani . . . . . .
C17 C 0.5804(2) 0.63675(13) 0.86086(12) 0.0275 1.0000 Uani . . . . . .
C18 C 0.6232(2) 0.59927(13) 0.78589(12) 0.0246 1.0000 Uani . . . . . .
N19 N 0.6683(2) 0.65113(10) 0.73429(10) 0.0271 1.0000 Uani . . . . . .
C20 C 0.7434(2) 0.74297(13) 0.76418(12) 0.0266 1.0000 Uani . . . . . .
O21 O 0.79021(19) 0.78889(9) 0.84075(8) 0.0365 1.0000 Uani . . . . . .
C22 C 0.7662(2) 0.78699(12) 0.69891(12) 0.0259 1.0000 Uani . . . . . .
C23 C 0.9120(3) 0.85822(13) 0.71889(13) 0.0335 1.0000 Uani . . . . . .
C24 C 0.9319(3) 0.90595(14) 0.66298(15) 0.0385 1.0000 Uani . . . . . .
C25 C 0.8035(3) 0.88474(14) 0.58851(13) 0.0355 1.0000 Uani . . . . . .
C26 C 0.6567(3) 0.81455(13) 0.56842(13) 0.0333 1.0000 Uani . . . . . .
C27 C 0.6391(3) 0.76461(13) 0.62319(12) 0.0292 1.0000 Uani . . . . . .
N28 N 0.54705(19) 0.35830(10) 0.77217(10) 0.0251 1.0000 Uani . . . . . .
C29 C 0.5057(2) 0.29361(13) 0.80851(12) 0.0257 1.0000 Uani . . . . . .
O30 O 0.48635(19) 0.31062(10) 0.88208(9) 0.0370 1.0000 Uani . . . . . .
C31 C 0.4867(2) 0.19993(13) 0.75392(12) 0.0257 1.0000 Uani . . . . . .
C32 C 0.4501(2) 0.13085(14) 0.78931(14) 0.0311 1.0000 Uani . . . . . .
C33 C 0.4281(3) 0.04134(14) 0.74295(15) 0.0371 1.0000 Uani . . . . . .
C36 C 0.4407(3) 0.01815(15) 0.65924(15) 0.0396 1.0000 Uani . . . . . .
C37 C 0.4770(3) 0.08468(14) 0.62329(14) 0.0357 1.0000 Uani . . . . . .
C38 C 0.5052(2) 0.17825(13) 0.66928(13) 0.0285 1.0000 Uani . . . . . .
O39 O 0.54799(19) 0.23975(9) 0.63468(9) 0.0355 1.0000 Uani . . . . . .
C40 C -0.1772(3) 0.29443(17) 1.17048(14) 0.0465 1.0000 Uani . . . . . .
C41 C -0.2305(3) 0.26554(16) 1.07344(13) 0.0373 1.0000 Uani . . . . . .
C42 C -0.0782(3) 0.26632(15) 1.03622(13) 0.0348 1.0000 Uani . . . . . .
C43 C -0.1373(2) 0.22301(14) 0.93965(12) 0.0294 1.0000 Uani . . . . . .
N44 N 0.00177(19) 0.23154(11) 0.89381(10) 0.0261 1.0000 Uani . . . . . .
C45 C -0.0830(2) 0.17625(14) 0.79972(12) 0.0292 1.0000 Uani . . . . . .
C46 C 0.0302(3) 0.17602(14) 0.73987(13) 0.0327 1.0000 Uani . . . . . .
C47 C -0.0821(3) 0.13279(14) 0.64764(12) 0.0323 1.0000 Uani . . . . . .
C48 C 0.0214(3) 0.11717(15) 0.58305(14) 0.0392 1.0000 Uani . . . . . .
C49 C 0.0803(2) 0.33074(13) 0.90570(13) 0.0290 1.0000 Uani . . . . . .
C50 C -0.0441(3) 0.38054(15) 0.87649(16) 0.0395 1.0000 Uani . . . . . .
C51 C 0.0505(3) 0.46540(15) 0.86176(16) 0.0419 1.0000 Uani . . . . . .
C52 C 0.1035(3) 0.44363(18) 0.77919(16) 0.0506 1.0000 Uani . . . . . .
C53 C 0.1484(2) 0.19759(13) 0.93032(12) 0.0283 1.0000 Uani . . . . . .
C54 C 0.1078(3) 0.09638(13) 0.91505(13) 0.0322 1.0000 Uani . . . . . .
C55 C 0.2510(3) 0.07808(14) 0.97415(13) 0.0359 1.0000 Uani . . . . . .
C56 C 0.2327(3) -0.02264(15) 0.95655(15) 0.0434 1.0000 Uani . . . . . .
H61 H 0.8331 0.4244 0.3657 0.0382 1.0000 Uiso R . . . . .
H71 H 0.8803 0.2811 0.3486 0.0412 1.0000 Uiso R . . . . .
H81 H 0.8397 0.2118 0.4514 0.0395 1.0000 Uiso R . . . . .
H91 H 0.7612 0.2862 0.5706 0.0354 1.0000 Uiso R . . . . .
H151 H 0.5019 0.4564 0.9177 0.0317 1.0000 Uiso R . . . . .
H161 H 0.5129 0.6108 0.9626 0.0331 1.0000 Uiso R . . . . .
H171 H 0.5813 0.6989 0.8782 0.0332 1.0000 Uiso R . . . . .
H191 H 0.6663 0.6220 0.6819 0.0330 1.0000 Uiso R . . . . .
H231 H 0.9975 0.8729 0.7716 0.0405 1.0000 Uiso R . . . . .
H241 H 1.0327 0.9545 0.6764 0.0465 1.0000 Uiso R . . . . .
H251 H 0.8169 0.9200 0.5512 0.0432 1.0000 Uiso R . . . . .
H261 H 0.5669 0.7993 0.5158 0.0403 1.0000 Uiso R . . . . .
H271 H 0.5371 0.7161 0.6094 0.0353 1.0000 Uiso R . . . . .
H281 H 0.5549 0.3371 0.7189 0.0313 1.0000 Uiso R . . . . .
H321 H 0.4398 0.1466 0.8475 0.0372 1.0000 Uiso R . . . . .
O340 O 0.405(3) -0.0169(13) 0.7882(14) 0.0575 0.4863 Uani . . . 1 2 .
O341 O 0.376(2) -0.0287(13) 0.7767(14) 0.0520 0.5137 Uani . . . 1 1 .
C350 C 0.485(2) -0.0883(12) 0.7702(13) 0.0749 0.4863 Uani . . . 1 2 .
C351 C 0.4908(13) -0.0785(11) 0.7870(11) 0.0436 0.5137 Uani . . . 1 1 .
H361 H 0.4237 -0.0445 0.6276 0.0483 1.0000 Uiso R . . . . .
H371 H 0.4865 0.0685 0.5658 0.0428 1.0000 Uiso R . . . . .
H401 H -0.2727 0.2986 1.1949 0.0698 1.0000 Uiso R . . . . .
H402 H -0.1226 0.2496 1.1887 0.0698 1.0000 Uiso R . . . . .
H403 H -0.0904 0.3553 1.1948 0.0699 1.0000 Uiso R . . . . .
H411 H -0.2896 0.3075 1.0555 0.0456 1.0000 Uiso R . . . . .
H412 H -0.3094 0.2032 1.0495 0.0450 1.0000 Uiso R . . . . .
H421 H -0.0065 0.2333 1.0601 0.0425 1.0000 Uiso R . . . . .
H422 H -0.0105 0.3284 1.0508 0.0426 1.0000 Uiso R . . . . .
H431 H -0.2226 0.2502 0.9156 0.0341 1.0000 Uiso R . . . . .
H432 H -0.1875 0.1572 0.9250 0.0351 1.0000 Uiso R . . . . .
H451 H -0.1791 0.2010 0.7814 0.0353 1.0000 Uiso R . . . . .
H452 H -0.1290 0.1134 0.7980 0.0346 1.0000 Uiso R . . . . .
H461 H 0.1130 0.1412 0.7515 0.0392 1.0000 Uiso R . . . . .
H462 H 0.0932 0.2399 0.7505 0.0403 1.0000 Uiso R . . . . .
H471 H -0.1575 0.1714 0.6352 0.0398 1.0000 Uiso R . . . . .
H472 H -0.1573 0.0730 0.6420 0.0381 1.0000 Uiso R . . . . .
H481 H -0.0535 0.0891 0.5239 0.0591 1.0000 Uiso R . . . . .
H482 H 0.0993 0.1746 0.5867 0.0594 1.0000 Uiso R . . . . .
H483 H 0.0885 0.0741 0.5931 0.0593 1.0000 Uiso R . . . . .
H491 H 0.1646 0.3304 0.8726 0.0345 1.0000 Uiso R . . . . .
H492 H 0.1388 0.3607 0.9666 0.0339 1.0000 Uiso R . . . . .
H501 H -0.1038 0.3964 0.9207 0.0469 1.0000 Uiso R . . . . .
H502 H -0.1272 0.3407 0.8223 0.0475 1.0000 Uiso R . . . . .
H511 H -0.0220 0.5061 0.8608 0.0514 1.0000 Uiso R . . . . .
H512 H 0.1526 0.4976 0.9100 0.0497 1.0000 Uiso R . . . . .
H521 H 0.0037 0.4142 0.7305 0.0764 1.0000 Uiso R . . . . .
H522 H 0.1638 0.5005 0.7734 0.0761 1.0000 Uiso R . . . . .
H523 H 0.1776 0.4016 0.7800 0.0752 1.0000 Uiso R . . . . .
H531 H 0.2398 0.2157 0.9044 0.0328 1.0000 Uiso R . . . . .
H532 H 0.1862 0.2309 0.9915 0.0334 1.0000 Uiso R . . . . .
H541 H -0.0037 0.0764 0.9267 0.0392 1.0000 Uiso R . . . . .
H542 H 0.0991 0.0643 0.8550 0.0392 1.0000 Uiso R . . . . .
H551 H 0.3601 0.1061 0.9666 0.0432 1.0000 Uiso R . . . . .
H552 H 0.2518 0.1063 1.0330 0.0427 1.0000 Uiso R . . . . .
H561 H 0.3175 -0.0309 1.0020 0.0650 1.0000 Uiso R . . . . .
H562 H 0.2548 -0.0505 0.8992 0.0645 1.0000 Uiso R . . . . .
H563 H 0.1179 -0.0551 0.9564 0.0652 1.0000 Uiso R . . . . .
H3501 H 0.4154 -0.1354 0.7144 0.1119 0.4863 Uiso R . . 1 2 .
H3502 H 0.4883 -0.1147 0.8156 0.1119 0.4863 Uiso R . . 1 2 .
H3503 H 0.5997 -0.0665 0.7660 0.1121 0.4863 Uiso R . . 1 2 .
H3511 H 0.5108 -0.1081 0.7310 0.0653 0.5137 Uiso R . . 1 1 .
H3512 H 0.4449 -0.1241 0.8108 0.0648 0.5137 Uiso R . . 1 1 .
H3513 H 0.5970 -0.0375 0.8277 0.0651 0.5137 Uiso R . . 1 1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.5387(5)
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 . O2 . 1.451(2) yes
C1 . H11 . 0.981 no
C1 . H12 . 0.995 no
C1 . H13 . 1.020 no
O2 . C3 . 1.339(2) yes
C3 . O4 . 1.213(2) yes
C3 . C5 . 1.487(3) yes
C5 . C6 . 1.398(3) yes
C5 . C10 . 1.402(3) yes
C6 . C7 . 1.386(3) yes
C6 . H61 . 0.953 no
C7 . C8 . 1.385(3) yes
C7 . H71 . 0.970 no
C8 . C9 . 1.387(3) yes
C8 . H81 . 0.961 no
C9 . C10 . 1.405(3) yes
C9 . H91 . 0.947 no
C10 . C11 . 1.443(3) yes
C11 . C12 . 1.196(3) yes
C12 . C13 . 1.430(2) yes
C13 . C14 . 1.422(2) yes
C13 . C18 . 1.411(2) yes
C14 . C15 . 1.396(2) yes
C14 . N28 . 1.402(2) yes
C15 . C16 . 1.388(3) yes
C15 . H151 . 0.947 no
C16 . C17 . 1.382(3) yes
C16 . H161 . 0.971 no
C17 . C18 . 1.391(3) yes
C17 . H171 . 0.953 no
C18 . N19 . 1.415(2) yes
N19 . C20 . 1.371(2) yes
N19 . H191 . 0.872 no
C20 . O21 . 1.229(2) yes
C20 . C22 . 1.489(3) yes
C22 . C23 . 1.390(3) yes
C22 . C27 . 1.389(3) yes
C23 . C24 . 1.387(3) yes
C23 . H231 . 0.957 no
C24 . C25 . 1.383(3) yes
C24 . H241 . 0.956 no
C25 . C26 . 1.385(3) yes
C25 . H251 . 0.966 no
C26 . C27 . 1.393(3) yes
C26 . H261 . 0.973 no
C27 . H271 . 0.961 no
N28 . C29 . 1.365(2) yes
N28 . H281 . 0.890 no
C29 . O30 . 1.247(2) yes
C29 . C31 . 1.479(3) yes
C31 . C32 . 1.407(3) yes
C31 . C38 . 1.423(3) yes
C32 . C33 . 1.378(3) yes
C32 . H321 . 0.970 no
C33 . C36 . 1.390(3) yes
C33 . O341 . 1.42(2) yes
C33 . C36 . 1.390(3) yes
C33 . O340 . 1.37(2) yes
C36 . C37 . 1.378(3) yes
C36 . H361 . 0.959 no
C37 . C38 . 1.423(3) yes
C37 . H371 . 0.957 no
C38 . O39 . 1.304(2) yes
C40 . C41 . 1.517(3) yes
C40 . H401 . 0.972 no
C40 . H402 . 1.010 no
C40 . H403 . 1.002 no
C41 . C42 . 1.523(3) yes
C41 . H411 . 0.988 no
C41 . H412 . 0.992 no
C42 . C43 . 1.513(3) yes
C42 . H421 . 0.976 no
C42 . H422 . 0.970 no
C43 . N44 . 1.521(2) yes
C43 . H431 . 0.986 no
C43 . H432 . 0.986 no
N44 . C45 . 1.520(2) yes
N44 . C49 . 1.524(2) yes
N44 . C53 . 1.525(2) yes
C45 . C46 . 1.514(3) yes
C45 . H451 . 0.997 no
C45 . H452 . 0.989 no
C46 . C47 . 1.525(3) yes
C46 . H461 . 0.996 no
C46 . H462 . 0.994 no
C47 . C48 . 1.520(3) yes
C47 . H471 . 1.001 no
C47 . H472 . 0.996 no
C48 . H481 . 0.985 no
C48 . H482 . 0.987 no
C48 . H483 . 1.001 no
C49 . C50 . 1.520(3) yes
C49 . H491 . 0.981 no
C49 . H492 . 0.976 no
C50 . C51 . 1.534(3) yes
C50 . H501 . 0.982 no
C50 . H502 . 0.979 no
C51 . C52 . 1.517(3) yes
C51 . H511 . 0.976 no
C51 . H512 . 0.979 no
C52 . H521 . 0.967 no
C52 . H522 . 0.985 no
C52 . H523 . 1.003 no
C53 . C54 . 1.518(3) yes
C53 . H531 . 0.985 no
C53 . H532 . 0.971 no
C54 . C55 . 1.530(3) yes
C54 . H541 . 0.994 no
C54 . H542 . 0.981 no
C55 . C56 . 1.522(3) yes
C55 . H551 . 0.976 no
C55 . H552 . 0.968 no
C56 . H561 . 0.993 no
C56 . H562 . 1.018 no
C56 . H563 . 0.987 no
O340 . C350 . 1.43(2) yes
O341 . C351 . 1.38(2) yes
C350 . H3501 . 0.996 no
C350 . H3502 . 0.975 no
C350 . H3503 . 0.974 no
C351 . H3511 . 0.997 no
C351 . H3512 . 0.976 no
C351 . H3513 . 0.973 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
O2 . C1 . H11 . 106.9 no
O2 . C1 . H12 . 111.4 no
H11 . C1 . H12 . 110.2 no
O2 . C1 . H13 . 109.1 no
H11 . C1 . H13 . 109.9 no
H12 . C1 . H13 . 109.4 no
C1 . O2 . C3 . 115.58(15) yes
O2 . C3 . O4 . 123.11(18) yes
O2 . C3 . C5 . 111.48(16) yes
O4 . C3 . C5 . 125.41(18) yes
C3 . C5 . C6 . 119.86(17) yes
C3 . C5 . C10 . 120.81(17) yes
C6 . C5 . C10 . 119.32(18) yes
C5 . C6 . C7 . 120.76(19) yes
C5 . C6 . H61 . 119.0 no
C7 . C6 . H61 . 120.2 no
C6 . C7 . C8 . 119.99(18) yes
C6 . C7 . H71 . 120.2 no
C8 . C7 . H71 . 119.8 no
C7 . C8 . C9 . 120.22(19) yes
C7 . C8 . H81 . 120.4 no
C9 . C8 . H81 . 119.3 no
C8 . C9 . C10 . 120.33(18) yes
C8 . C9 . H91 . 119.5 no
C10 . C9 . H91 . 120.1 no
C9 . C10 . C5 . 119.36(17) yes
C9 . C10 . C11 . 116.89(17) yes
C5 . C10 . C11 . 123.75(17) yes
C10 . C11 . C12 . 173.6(2) yes
C11 . C12 . C13 . 176.4(2) yes
C12 . C13 . C14 . 120.91(17) yes
C12 . C13 . C18 . 119.25(16) yes
C14 . C13 . C18 . 119.84(16) yes
C13 . C14 . C15 . 118.90(17) yes
C13 . C14 . N28 . 117.32(16) yes
C15 . C14 . N28 . 123.75(17) yes
C14 . C15 . C16 . 119.80(18) yes
C14 . C15 . H151 . 119.5 no
C16 . C15 . H151 . 120.7 no
C15 . C16 . C17 . 121.93(18) yes
C15 . C16 . H161 . 119.4 no
C17 . C16 . H161 . 118.7 no
C16 . C17 . C18 . 119.45(18) yes
C16 . C17 . H171 . 121.1 no
C18 . C17 . H171 . 119.4 no
C13 . C18 . C17 . 119.92(17) yes
C13 . C18 . N19 . 118.33(16) yes
C17 . C18 . N19 . 121.73(17) yes
C18 . N19 . C20 . 124.76(16) yes
C18 . N19 . H191 . 117.9 no
C20 . N19 . H191 . 116.4 no
N19 . C20 . O21 . 123.11(18) yes
N19 . C20 . C22 . 116.86(16) yes
O21 . C20 . C22 . 120.03(17) yes
C20 . C22 . C23 . 118.29(17) yes
C20 . C22 . C27 . 121.73(17) yes
C23 . C22 . C27 . 119.69(18) yes
C22 . C23 . C24 . 120.23(19) yes
C22 . C23 . H231 . 118.4 no
C24 . C23 . H231 . 121.4 no
C23 . C24 . C25 . 119.9(2) yes
C23 . C24 . H241 . 120.3 no
C25 . C24 . H241 . 119.8 no
C24 . C25 . C26 . 120.33(19) yes
C24 . C25 . H251 . 119.1 no
C26 . C25 . H251 . 120.5 no
C25 . C26 . C27 . 119.77(19) yes
C25 . C26 . H261 . 120.3 no
C27 . C26 . H261 . 119.9 no
C26 . C27 . C22 . 120.02(19) yes
C26 . C27 . H271 . 119.8 no
C22 . C27 . H271 . 120.1 no
C14 . N28 . C29 . 127.48(16) yes
C14 . N28 . H281 . 117.5 no
C29 . N28 . H281 . 114.9 no
N28 . C29 . O30 . 123.72(18) yes
N28 . C29 . C31 . 114.70(16) yes
O30 . C29 . C31 . 121.58(17) yes
C29 . C31 . C32 . 117.14(17) yes
C29 . C31 . C38 . 122.86(17) yes
C32 . C31 . C38 . 120.00(18) yes
C31 . C32 . C33 . 121.34(19) yes
C31 . C32 . H321 . 119.2 no
C33 . C32 . H321 . 119.5 no
C32 . C33 . C36 . 119.72(19) yes
C32 . C33 . O341 . 120.7(7) yes
C36 . C33 . O341 . 119.3(8) yes
C32 . C33 . C36 . 119.72(19) yes
C32 . C33 . O340 . 114.3(8) yes
C36 . C33 . O340 . 125.8(7) yes
C33 . C36 . C37 . 120.0(2) yes
C33 . C36 . H361 . 118.7 no
C37 . C36 . H361 . 121.3 no
C36 . C37 . C38 . 122.4(2) yes
C36 . C37 . H371 . 119.7 no
C38 . C37 . H371 . 117.8 no
C37 . C38 . C31 . 116.50(18) yes
C37 . C38 . O39 . 120.66(18) yes
C31 . C38 . O39 . 122.83(18) yes
C41 . C40 . H401 . 112.6 no
C41 . C40 . H402 . 109.6 no
H401 . C40 . H402 . 108.9 no
C41 . C40 . H403 . 109.5 no
H401 . C40 . H403 . 108.2 no
H402 . C40 . H403 . 108.0 no
C40 . C41 . C42 . 112.18(18) yes
C40 . C41 . H411 . 109.6 no
C42 . C41 . H411 . 107.9 no
C40 . C41 . H412 . 109.3 no
C42 . C41 . H412 . 108.6 no
H411 . C41 . H412 . 109.1 no
C41 . C42 . C43 . 110.71(17) yes
C41 . C42 . H421 . 110.1 no
C43 . C42 . H421 . 109.2 no
C41 . C42 . H422 . 109.5 no
C43 . C42 . H422 . 108.7 no
H421 . C42 . H422 . 108.6 no
C42 . C43 . N44 . 115.67(16) yes
C42 . C43 . H431 . 109.7 no
N44 . C43 . H431 . 107.0 no
C42 . C43 . H432 . 108.7 no
N44 . C43 . H432 . 105.4 no
H431 . C43 . H432 . 110.3 no
C43 . N44 . C45 . 106.48(14) yes
C43 . N44 . C49 . 110.51(14) yes
C45 . N44 . C49 . 111.10(15) yes
C43 . N44 . C53 . 111.71(15) yes
C45 . N44 . C53 . 111.05(14) yes
C49 . N44 . C53 . 106.07(14) yes
N44 . C45 . C46 . 116.43(16) yes
N44 . C45 . H451 . 106.1 no
C46 . C45 . H451 . 109.8 no
N44 . C45 . H452 . 105.6 no
C46 . C45 . H452 . 109.1 no
H451 . C45 . H452 . 109.6 no
C45 . C46 . C47 . 108.74(16) yes
C45 . C46 . H461 . 109.5 no
C47 . C46 . H461 . 110.4 no
C45 . C46 . H462 . 108.3 no
C47 . C46 . H462 . 110.2 no
H461 . C46 . H462 . 109.6 no
C46 . C47 . C48 . 112.56(17) yes
C46 . C47 . H471 . 109.6 no
C48 . C47 . H471 . 110.6 no
C46 . C47 . H472 . 107.9 no
C48 . C47 . H472 . 108.5 no
H471 . C47 . H472 . 107.6 no
C47 . C48 . H481 . 111.3 no
C47 . C48 . H482 . 111.5 no
H481 . C48 . H482 . 107.7 no
C47 . C48 . H483 . 109.6 no
H481 . C48 . H483 . 106.8 no
H482 . C48 . H483 . 109.9 no
N44 . C49 . C50 . 115.66(16) yes
N44 . C49 . H491 . 105.7 no
C50 . C49 . H491 . 109.3 no
N44 . C49 . H492 . 106.4 no
C50 . C49 . H492 . 110.2 no
H491 . C49 . H492 . 109.5 no
C49 . C50 . C51 . 110.65(17) yes
C49 . C50 . H501 . 107.8 no
C51 . C50 . H501 . 111.3 no
C49 . C50 . H502 . 109.5 no
C51 . C50 . H502 . 108.2 no
H501 . C50 . H502 . 109.4 no
C50 . C51 . C52 . 113.0(2) yes
C50 . C51 . H511 . 109.6 no
C52 . C51 . H511 . 109.1 no
C50 . C51 . H512 . 108.6 no
C52 . C51 . H512 . 108.9 no
H511 . C51 . H512 . 107.5 no
C51 . C52 . H521 . 110.1 no
C51 . C52 . H522 . 109.2 no
H521 . C52 . H522 . 108.0 no
C51 . C52 . H523 . 109.3 no
H521 . C52 . H523 . 108.8 no
H522 . C52 . H523 . 111.4 no
N44 . C53 . C54 . 116.31(16) yes
N44 . C53 . H531 . 105.8 no
C54 . C53 . H531 . 109.8 no
N44 . C53 . H532 . 106.0 no
C54 . C53 . H532 . 109.6 no
H531 . C53 . H532 . 109.0 no
C53 . C54 . C55 . 109.03(16) yes
C53 . C54 . H541 . 108.5 no
C55 . C54 . H541 . 111.1 no
C53 . C54 . H542 . 109.0 no
C55 . C54 . H542 . 109.9 no
H541 . C54 . H542 . 109.3 no
C54 . C55 . C56 . 113.06(18) yes
C54 . C55 . H551 . 108.7 no
C56 . C55 . H551 . 108.7 no
C54 . C55 . H552 . 108.7 no
C56 . C55 . H552 . 109.3 no
H551 . C55 . H552 . 108.2 no
C55 . C56 . H561 . 109.8 no
C55 . C56 . H562 . 110.0 no
H561 . C56 . H562 . 108.3 no
C55 . C56 . H563 . 111.3 no
H561 . C56 . H563 . 107.7 no
H562 . C56 . H563 . 109.6 no
C33 . O340 . C350 . 115.5(13) yes
C33 . O341 . C351 . 114.5(13) yes
O340 . C350 . H3501 . 108.7 no
O340 . C350 . H3502 . 108.8 no
H3501 . C350 . H3502 . 109.6 no
O340 . C350 . H3503 . 111.6 no
H3501 . C350 . H3503 . 108.4 no
H3502 . C350 . H3503 . 109.7 no
O341 . C351 . H3511 . 110.3 no
O341 . C351 . H3512 . 108.6 no
H3511 . C351 . H3512 . 110.4 no
O341 . C351 . H3513 . 108.2 no
H3511 . C351 . H3513 . 110.5 no
H3512 . C351 . H3513 . 108.7 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
C9 . H91 . O39 . 139.90 0.947 2.357 3.141(4) yes
C15 . H151 . O30 . 123.23 0.947 2.206 2.838(4) yes
C16 . H161 . O30 2_667 167.90 0.971 2.571 3.526(4) yes
N19 . H191 . O4 . 166.11 0.872 2.287 3.140(4) yes
C26 . H261 . O39 2_666 155.40 0.973 2.380 3.289(4) yes
N28 . H281 . O39 . 145.59 0.890 1.771 2.556(4) yes
C42 . H421 . O21 2_667 157.23 0.976 2.360 3.282(4) yes
C53 . H531 . O30 . 159.60 0.985 2.450 3.390(4) yes
C55 . H552 . O21 2_667 160.30 0.968 2.453 3.380(4) yes
C56 . H562 . O340 . 144.5 1.018 2.571 3.451(4) yes
C56 . H562 . O341 . 148.9 1.018 2.555 3.467(4) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 03/08/14 at 15:43:02
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) H   (  13,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE N   (  19,X'S) H   ( 191,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   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE N   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 403,X'S) H   ( 402,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) 
RIDE C   (  42,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) H   ( 432,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) H   ( 452,X'S) 
RIDE C   (  46,X'S) H   ( 462,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) H   ( 472,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) H   ( 482,X'S) H   ( 483,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 492,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) H   ( 502,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 512,X'S) 
RIDE C   (  52,X'S) H   ( 522,X'S) H   ( 521,X'S) H   ( 523,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) 
RIDE C   (  54,X'S) H   ( 542,X'S) H   ( 541,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) H   ( 562,X'S) H   ( 563,X'S) 
RIDE C   ( 350,X'S) H   (3502,X'S) H   (3501,X'S) H   (3503,X'S) 
RIDE C   ( 351,X'S) H   (3512,X'S) H   (3511,X'S) H   (3513,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 03/08/14 at 15:43:02
#
#LIST     16                                                                    
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   SHIFTLIMIT   START (DO NOT REMOVE THIS LINE) 
REM   SHIFTLIMIT   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

_chemical_name_common            'Compound 5'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_database_code_depnum_ccdc_archive 'CCDC 1017648'
