# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1
_database_code_depnum_ccdc_archive 'CCDC 1476585'
_audit_update_record             
;
2016-06-29 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;

_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          ', SQUEEZE'
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   16.6624(17)
_cell_length_b                   15.2623(14)
_cell_length_c                   19.0219(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.390(10)
_cell_angle_gamma                90
_cell_volume                     4685.6(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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'
Cu -1.9646 0.5888 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 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

# Given Formula = C100 H100 Br2 Cu2 N2 O16 
# Dc =      1.33 Fooo =   1799.99 Mu =     20.83 M =    936.40
# Found Formula = C94 H115.99 Br2 Cu2 N4 O8 
# Dc =      1.22 FOOO =   1799.99 Mu =     19.72 M =    858.43

_chemical_formula_sum            'C47 H58 Br Cu N2 O4'
_chemical_formula_moiety         'C47 H58 Br Cu N2 O4'
_chemical_compound_source        ?
_chemical_formula_weight         858.40


_cell_measurement_reflns_used    8255
_cell_measurement_theta_min      3.8590
_cell_measurement_theta_max      67.7250
_cell_measurement_temperature    150.00(10)

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.047
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_max          0.421

_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1799.987

# Sheldrick geometric approximatio 0.62 0.91 
_exptl_absorpt_coefficient_mu    1.973
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.583
_oxdiff_exptl_absorpt_empirical_full_max 2.102
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_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_reflns_number            31760
_reflns_number_total             8407
_diffrn_reflns_av_R_equivalents  0.065
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 8407 
# Theoretical number of reflections is about 17070 


_diffrn_reflns_theta_min         3.761
_diffrn_reflns_theta_max         67.994
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        66.359
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -20
_reflns_limit_h_max              19
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   3.89
_oxford_diffrn_Wilson_scale      0.39

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

_refine_diff_density_min         -1.80
_refine_diff_density_max         1.49


# 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         8364
_refine_ls_number_restraints     0
_refine_ls_number_parameters     496
_oxford_refine_ls_R_factor_ref   0.0903
_refine_ls_wR_factor_ref         0.1740
_refine_ls_goodness_of_fit_ref   1.0181
_refine_ls_shift/su_max          0.0005681
_refine_ls_shift/su_mean         0.0000409


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        8369
_refine_ls_R_factor_all          0.0905
_refine_ls_wR_factor_all         0.1745

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6458
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_gt          0.1491

# 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: 
 835. 0.129E+04 659. 165. 
;

# 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
Br1 Br 0.28890(6) 0.71066(6) 0.43005(4) 0.0858 1.0000 Uani . . . . . .
Cu2 Cu 0.31604(4) 0.75464(4) 0.54317(3) 0.0409 1.0000 Uani . . . . . .
C3 C 0.3428(2) 0.7885(3) 0.6411(2) 0.0318 1.0000 Uani . . . . . .
N4 N 0.3007(2) 0.7721(2) 0.6920(2) 0.0368 1.0000 Uani . . . . . .
C5 C 0.2202(3) 0.7284(3) 0.6769(3) 0.0423 1.0000 Uani . . . . . .
C6 C 0.1517(4) 0.7870(4) 0.6372(3) 0.0643 1.0000 Uani . . . . . .
C7 C 0.1406(3) 0.8712(4) 0.6737(3) 0.0595 1.0000 Uani . . . . . .
C8 C 0.1150(5) 0.8656(6) 0.7419(4) 0.0953 1.0000 Uani . . . . . .
H82 H 0.1034 0.9243 0.7557 0.1439 1.0000 Uiso R . . . . .
H83 H 0.0660 0.8303 0.7343 0.1438 1.0000 Uiso R . . . . .
H81 H 0.1583 0.8399 0.7783 0.1440 1.0000 Uiso R . . . . .
H71 H 0.1006 0.9062 0.6406 0.0709 1.0000 Uiso R . . . . .
H72 H 0.1932 0.9011 0.6840 0.0710 1.0000 Uiso R . . . . .
H62 H 0.1603 0.8003 0.5884 0.0771 1.0000 Uiso R . . . . .
H61 H 0.1006 0.7536 0.6322 0.0771 1.0000 Uiso R . . . . .
H51 H 0.2232 0.6750 0.6503 0.0512 1.0000 Uiso R . . . . .
H52 H 0.2074 0.7134 0.7222 0.0514 1.0000 Uiso R . . . . .
C9 C 0.3429(3) 0.8030(3) 0.7589(2) 0.0424 1.0000 Uani . . . . . .
C10 C 0.4134(3) 0.8393(3) 0.7507(2) 0.0423 1.0000 Uani . . . . . .
N11 N 0.4122(2) 0.8305(2) 0.67800(18) 0.0332 1.0000 Uani . . . . . .
C12 C 0.4768(2) 0.8608(3) 0.6471(2) 0.0326 1.0000 Uani . . . . . .
C13 C 0.5051(2) 0.8091(3) 0.5988(2) 0.0322 1.0000 Uani . . . . . .
C14 C 0.5680(2) 0.8390(3) 0.5687(2) 0.0314 1.0000 Uani . . . . . .
C15 C 0.5998(3) 0.7782(3) 0.5189(2) 0.0346 1.0000 Uani . . . . . .
C16 C 0.6253(3) 0.6900(3) 0.5534(2) 0.0345 1.0000 Uani . . . . . .
C17 C 0.6890(3) 0.6839(3) 0.6166(2) 0.0354 1.0000 Uani . . . . . .
O18 O 0.73162(19) 0.75948(19) 0.64285(16) 0.0380 1.0000 Uani . . . . . .
C19 C 0.8162(4) 0.7652(4) 0.6377(4) 0.0632 1.0000 Uani . . . . . .
C20 C 0.8255(4) 0.8033(5) 0.5712(4) 0.0736 1.0000 Uani . . . . . .
C21 C 0.9177(4) 0.8226(7) 0.5752(4) 0.0949 1.0000 Uani . . . . . .
H211 H 0.9218 0.8510 0.5313 0.1448 1.0000 Uiso R . . . . .
H213 H 0.9453 0.7659 0.5806 0.1445 1.0000 Uiso R . . . . .
H212 H 0.9396 0.8584 0.6167 0.1449 1.0000 Uiso R . . . . .
H202 H 0.8044 0.7615 0.5320 0.0889 1.0000 Uiso R . . . . .
H201 H 0.7944 0.8585 0.5632 0.0890 1.0000 Uiso R . . . . .
H191 H 0.8424 0.7069 0.6390 0.0758 1.0000 Uiso R . . . . .
H192 H 0.8473 0.8033 0.6775 0.0762 1.0000 Uiso R . . . . .
C22 C 0.7052(3) 0.6060(3) 0.6560(2) 0.0405 1.0000 Uani . . . . . .
C23 C 0.7608(3) 0.6071(3) 0.7328(3) 0.0470 1.0000 Uani . . . . . .
C24 C 0.7235(3) 0.6660(3) 0.7804(2) 0.0397 1.0000 Uani . . . . . .
C25 C 0.6433(3) 0.6507(3) 0.7865(2) 0.0453 1.0000 Uani . . . . . .
C26 C 0.6062(3) 0.7069(3) 0.8255(3) 0.0480 1.0000 Uani . . . . . .
C27 C 0.6481(3) 0.7809(3) 0.8575(2) 0.0443 1.0000 Uani . . . . . .
C28 C 0.7285(3) 0.7986(3) 0.8535(2) 0.0396 1.0000 Uani . . . . . .
C29 C 0.7657(3) 0.7392(3) 0.8154(2) 0.0399 1.0000 Uani . . . . . .
O30 O 0.8460(2) 0.7551(2) 0.81078(17) 0.0449 1.0000 Uani . . . . . .
C31 C 0.9061(3) 0.7165(4) 0.8694(3) 0.0590 1.0000 Uani . . . . . .
C32 C 0.9895(4) 0.7398(5) 0.8617(4) 0.0669 1.0000 Uani . . . . . .
C33 C 1.0571(4) 0.6950(6) 0.9199(4) 0.0930 1.0000 Uani . . . . . .
H333 H 1.1101 0.7074 0.9120 0.1378 1.0000 Uiso R . . . . .
H331 H 1.0483 0.6329 0.9173 0.1378 1.0000 Uiso R . . . . .
H332 H 1.0549 0.7150 0.9670 0.1378 1.0000 Uiso R . . . . .
H322 H 0.9953 0.7215 0.8144 0.0798 1.0000 Uiso R . . . . .
H321 H 0.9965 0.8030 0.8660 0.0798 1.0000 Uiso R . . . . .
H312 H 0.8994 0.6527 0.8667 0.0708 1.0000 Uiso R . . . . .
H311 H 0.8988 0.7376 0.9158 0.0713 1.0000 Uiso R . . . . .
C34 C 0.7713(3) 0.8823(3) 0.8849(2) 0.0463 1.0000 Uani . . . . . .
C35 C 0.7185(3) 0.9605(3) 0.8566(2) 0.0407 1.0000 Uani . . . . . .
C36 C 0.7063(3) 0.9868(3) 0.7842(2) 0.0372 1.0000 Uani . . . . . .
O37 O 0.75094(19) 0.9445(2) 0.74244(16) 0.0382 1.0000 Uani . . . . . .
C38 C 0.8136(3) 0.9978(4) 0.7233(3) 0.0482 1.0000 Uani . . . . . .
C39 C 0.8916(4) 1.0012(5) 0.7817(4) 0.0695 1.0000 Uani . . . . . .
C40 C 0.9542(4) 1.0609(6) 0.7589(5) 0.1001 1.0000 Uani . . . . . .
H401 H 1.0037 1.0643 0.7967 0.1478 1.0000 Uiso R . . . . .
H403 H 0.9309 1.1180 0.7494 0.1479 1.0000 Uiso R . . . . .
H402 H 0.9668 1.0388 0.7161 0.1478 1.0000 Uiso R . . . . .
H391 H 0.8803 1.0240 0.8256 0.0828 1.0000 Uiso R . . . . .
H392 H 0.9139 0.9423 0.7903 0.0829 1.0000 Uiso R . . . . .
H381 H 0.7939 1.0578 0.7128 0.0576 1.0000 Uiso R . . . . .
H382 H 0.8264 0.9717 0.6807 0.0584 1.0000 Uiso R . . . . .
C41 C 0.6456(3) 1.0483(3) 0.7524(2) 0.0367 1.0000 Uani . . . . . .
C42 C 0.6191(3) 1.0571(3) 0.6700(2) 0.0391 1.0000 Uani . . . . . .
C43 C 0.5765(3) 0.9725(3) 0.6396(2) 0.0343 1.0000 Uani . . . . . .
C44 C 0.6013(2) 0.9211(3) 0.5886(2) 0.0302 1.0000 Uani . . . . . .
O45 O 0.66609(18) 0.9501(2) 0.56114(15) 0.0353 1.0000 Uani . . . . . .
C46 C 0.6391(3) 0.9938(3) 0.4916(2) 0.0435 1.0000 Uani . . . . . .
C47 C 0.7084(3) 0.9923(4) 0.4545(3) 0.0500 1.0000 Uani . . . . . .
C48 C 0.7863(4) 1.0371(4) 0.4967(3) 0.0618 1.0000 Uani . . . . . .
H481 H 0.8271 1.0362 0.4687 0.0928 1.0000 Uiso R . . . . .
H482 H 0.7733 1.0972 0.5057 0.0932 1.0000 Uiso R . . . . .
H483 H 0.8079 1.0075 0.5418 0.0929 1.0000 Uiso R . . . . .
H472 H 0.6887 1.0213 0.4079 0.0598 1.0000 Uiso R . . . . .
H471 H 0.7213 0.9315 0.4462 0.0598 1.0000 Uiso R . . . . .
H461 H 0.5911 0.9637 0.4631 0.0521 1.0000 Uiso R . . . . .
H462 H 0.6254 1.0538 0.4997 0.0521 1.0000 Uiso R . . . . .
C49 C 0.5117(3) 0.9416(3) 0.6672(2) 0.0344 1.0000 Uani . . . . . .
H491 H 0.4926 0.9754 0.6999 0.0409 1.0000 Uiso R . . . . .
H421 H 0.5823 1.1067 0.6567 0.0467 1.0000 Uiso R . . . . .
H422 H 0.6668 1.0667 0.6512 0.0466 1.0000 Uiso R . . . . .
C50 C 0.6010(3) 1.0877(3) 0.7959(3) 0.0436 1.0000 Uani . . . . . .
C51 C 0.6152(3) 1.0674(3) 0.8688(3) 0.0512 1.0000 Uani . . . . . .
C52 C 0.6719(3) 1.0031(3) 0.8980(3) 0.0500 1.0000 Uani . . . . . .
H521 H 0.6797 0.9883 0.9465 0.0587 1.0000 Uiso R . . . . .
H511 H 0.5864 1.0955 0.8975 0.0613 1.0000 Uiso R . . . . .
H501 H 0.5612 1.1288 0.7758 0.0522 1.0000 Uiso R . . . . .
H341 H 0.8232 0.8857 0.8715 0.0548 1.0000 Uiso R . . . . .
H342 H 0.7819 0.8809 0.9372 0.0551 1.0000 Uiso R . . . . .
H271 H 0.6217 0.8199 0.8813 0.0532 1.0000 Uiso R . . . . .
H261 H 0.5528 0.6962 0.8296 0.0567 1.0000 Uiso R . . . . .
H251 H 0.6141 0.6022 0.7639 0.0538 1.0000 Uiso R . . . . .
H232 H 0.8149 0.6267 0.7331 0.0557 1.0000 Uiso R . . . . .
H231 H 0.7645 0.5483 0.7514 0.0556 1.0000 Uiso R . . . . .
C53 C 0.6621(4) 0.5309(3) 0.6270(3) 0.0509 1.0000 Uani . . . . . .
C54 C 0.6031(4) 0.5340(3) 0.5626(3) 0.0525 1.0000 Uani . . . . . .
C55 C 0.5828(3) 0.6137(3) 0.5271(2) 0.0453 1.0000 Uani . . . . . .
H551 H 0.5412 0.6166 0.4846 0.0538 1.0000 Uiso R . . . . .
H541 H 0.5774 0.4827 0.5431 0.0628 1.0000 Uiso R . . . . .
H531 H 0.6741 0.4784 0.6518 0.0612 1.0000 Uiso R . . . . .
H152 H 0.5578 0.7703 0.4742 0.0412 1.0000 Uiso R . . . . .
H151 H 0.6475 0.8049 0.5080 0.0411 1.0000 Uiso R . . . . .
H131 H 0.4834 0.7541 0.5875 0.0383 1.0000 Uiso R . . . . .
H101 H 0.4541 0.8657 0.7857 0.0499 1.0000 Uiso R . . . . .
H91 H 0.3257 0.7991 0.8015 0.0511 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.808(10)
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 . Cu2 . 2.1912(9) yes
Cu2 . C3 . 1.877(4) yes
C3 . N4 . 1.350(5) yes
C3 . N11 . 1.357(5) yes
N4 . C5 . 1.462(6) yes
N4 . C9 . 1.376(6) yes
C5 . C6 . 1.499(8) yes
C5 . H51 . 0.967 no
C5 . H52 . 0.965 no
C6 . C7 . 1.494(8) yes
C6 . H62 . 0.994 no
C6 . H61 . 0.976 no
C7 . C8 . 1.466(9) yes
C7 . H71 . 0.958 no
C7 . H72 . 0.965 no
C8 . H82 . 0.967 no
C8 . H83 . 0.959 no
C8 . H81 . 0.952 no
C9 . C10 . 1.343(7) yes
C9 . H91 . 0.926 no
C10 . N11 . 1.384(5) yes
C10 . H101 . 0.918 no
N11 . C12 . 1.426(5) yes
C12 . C13 . 1.379(6) yes
C12 . C49 . 1.376(6) yes
C13 . C14 . 1.389(6) yes
C13 . H131 . 0.919 no
C14 . C15 . 1.513(6) yes
C14 . C44 . 1.385(6) yes
C15 . C16 . 1.512(6) yes
C15 . H152 . 0.964 no
C15 . H151 . 0.961 no
C16 . C17 . 1.395(6) yes
C16 . C55 . 1.390(6) yes
C17 . O18 . 1.382(5) yes
C17 . C22 . 1.396(6) yes
O18 . C19 . 1.439(7) yes
C19 . C20 . 1.435(9) yes
C19 . H191 . 0.989 no
C19 . H192 . 0.992 no
C20 . C21 . 1.547(9) yes
C20 . H202 . 0.978 no
C20 . H201 . 0.981 no
C21 . H211 . 0.960 no
C21 . H213 . 0.972 no
C21 . H212 . 0.954 no
C22 . C23 . 1.523(6) yes
C22 . C53 . 1.391(7) yes
C23 . C24 . 1.514(7) yes
C23 . H232 . 0.948 no
C23 . H231 . 0.961 no
C24 . C25 . 1.389(7) yes
C24 . C29 . 1.398(6) yes
C25 . C26 . 1.377(7) yes
C25 . H251 . 0.930 no
C26 . C27 . 1.387(7) yes
C26 . H261 . 0.927 no
C27 . C28 . 1.386(7) yes
C27 . H271 . 0.924 no
C28 . C29 . 1.398(7) yes
C28 . C34 . 1.511(6) yes
C29 . O30 . 1.385(6) yes
O30 . C31 . 1.427(6) yes
C31 . C32 . 1.478(8) yes
C31 . H312 . 0.981 no
C31 . H311 . 0.974 no
C32 . C33 . 1.530(9) yes
C32 . H322 . 0.970 no
C32 . H321 . 0.971 no
C33 . H333 . 0.950 no
C33 . H331 . 0.960 no
C33 . H332 . 0.956 no
C34 . C35 . 1.501(7) yes
C34 . H341 . 0.963 no
C34 . H342 . 0.966 no
C35 . C36 . 1.399(6) yes
C35 . C52 . 1.397(7) yes
C36 . O37 . 1.376(5) yes
C36 . C41 . 1.401(6) yes
O37 . C38 . 1.439(6) yes
C38 . C39 . 1.487(8) yes
C38 . H381 . 0.976 no
C38 . H382 . 0.974 no
C39 . C40 . 1.527(9) yes
C39 . H391 . 0.966 no
C39 . H392 . 0.970 no
C40 . H401 . 0.951 no
C40 . H403 . 0.954 no
C40 . H402 . 0.953 no
C41 . C42 . 1.524(6) yes
C41 . C50 . 1.382(6) yes
C42 . C43 . 1.518(6) yes
C42 . H421 . 0.967 no
C42 . H422 . 0.962 no
C43 . C44 . 1.388(6) yes
C43 . C49 . 1.394(6) yes
C44 . O45 . 1.384(5) yes
O45 . C46 . 1.449(5) yes
C46 . C47 . 1.497(7) yes
C46 . H461 . 0.964 no
C46 . H462 . 0.965 no
C47 . C48 . 1.510(7) yes
C47 . H472 . 0.971 no
C47 . H471 . 0.974 no
C48 . H481 . 0.962 no
C48 . H482 . 0.966 no
C48 . H483 . 0.957 no
C49 . H491 . 0.923 no
C50 . C51 . 1.382(7) yes
C50 . H501 . 0.923 no
C51 . C52 . 1.379(8) yes
C51 . H511 . 0.918 no
C52 . H521 . 0.927 no
C53 . C54 . 1.367(8) yes
C53 . H531 . 0.927 no
C54 . C55 . 1.393(7) yes
C54 . H541 . 0.924 no
C55 . H551 . 0.925 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
Br1 . Cu2 . C3 . 177.51(13) yes
Cu2 . C3 . N4 . 128.5(3) yes
Cu2 . C3 . N11 . 127.2(3) yes
N4 . C3 . N11 . 104.2(4) yes
C3 . N4 . C5 . 123.9(4) yes
C3 . N4 . C9 . 111.3(4) yes
C5 . N4 . C9 . 124.8(4) yes
N4 . C5 . C6 . 111.9(4) yes
N4 . C5 . H51 . 108.9 no
C6 . C5 . H51 . 111.8 no
N4 . C5 . H52 . 109.2 no
C6 . C5 . H52 . 106.4 no
H51 . C5 . H52 . 108.6 no
C5 . C6 . C7 . 116.5(5) yes
C5 . C6 . H62 . 108.9 no
C7 . C6 . H62 . 108.8 no
C5 . C6 . H61 . 105.8 no
C7 . C6 . H61 . 106.8 no
H62 . C6 . H61 . 109.8 no
C6 . C7 . C8 . 117.3(6) yes
C6 . C7 . H71 . 108.7 no
C8 . C7 . H71 . 107.9 no
C6 . C7 . H72 . 106.9 no
C8 . C7 . H72 . 107.3 no
H71 . C7 . H72 . 108.6 no
C7 . C8 . H82 . 107.9 no
C7 . C8 . H83 . 108.8 no
H82 . C8 . H83 . 110.0 no
C7 . C8 . H81 . 109.4 no
H82 . C8 . H81 . 110.5 no
H83 . C8 . H81 . 110.0 no
N4 . C9 . C10 . 107.1(4) yes
N4 . C9 . H91 . 126.2 no
C10 . C9 . H91 . 126.7 no
C9 . C10 . N11 . 106.3(4) yes
C9 . C10 . H101 . 127.3 no
N11 . C10 . H101 . 126.3 no
C10 . N11 . C3 . 111.1(4) yes
C10 . N11 . C12 . 123.8(4) yes
C3 . N11 . C12 . 125.1(3) yes
N11 . C12 . C13 . 120.5(4) yes
N11 . C12 . C49 . 119.1(4) yes
C13 . C12 . C49 . 120.5(4) yes
C12 . C13 . C14 . 120.3(4) yes
C12 . C13 . H131 . 120.0 no
C14 . C13 . H131 . 119.7 no
C13 . C14 . C15 . 118.4(4) yes
C13 . C14 . C44 . 118.5(4) yes
C15 . C14 . C44 . 123.1(4) yes
C14 . C15 . C16 . 112.2(3) yes
C14 . C15 . H152 . 109.8 no
C16 . C15 . H152 . 109.6 no
C14 . C15 . H151 . 108.2 no
C16 . C15 . H151 . 108.3 no
H152 . C15 . H151 . 108.7 no
C15 . C16 . C17 . 120.4(4) yes
C15 . C16 . C55 . 121.7(4) yes
C17 . C16 . C55 . 117.7(4) yes
C16 . C17 . O18 . 117.9(4) yes
C16 . C17 . C22 . 121.6(4) yes
O18 . C17 . C22 . 120.3(4) yes
C17 . O18 . C19 . 116.8(4) yes
O18 . C19 . C20 . 114.0(5) yes
O18 . C19 . H191 . 112.2 no
C20 . C19 . H191 . 104.0 no
O18 . C19 . H192 . 108.5 no
C20 . C19 . H192 . 106.6 no
H191 . C19 . H192 . 111.4 no
C19 . C20 . C21 . 110.9(6) yes
C19 . C20 . H202 . 108.1 no
C21 . C20 . H202 . 109.0 no
C19 . C20 . H201 . 108.5 no
C21 . C20 . H201 . 108.9 no
H202 . C20 . H201 . 111.4 no
C20 . C21 . H211 . 109.1 no
C20 . C21 . H213 . 105.9 no
H211 . C21 . H213 . 111.1 no
C20 . C21 . H212 . 108.7 no
H211 . C21 . H212 . 111.4 no
H213 . C21 . H212 . 110.4 no
C17 . C22 . C23 . 119.7(4) yes
C17 . C22 . C53 . 118.5(4) yes
C23 . C22 . C53 . 121.4(4) yes
C22 . C23 . C24 . 109.8(4) yes
C22 . C23 . H232 . 111.2 no
C24 . C23 . H232 . 109.9 no
C22 . C23 . H231 . 108.0 no
C24 . C23 . H231 . 109.4 no
H232 . C23 . H231 . 108.5 no
C23 . C24 . C25 . 119.8(4) yes
C23 . C24 . C29 . 121.7(4) yes
C25 . C24 . C29 . 118.4(4) yes
C24 . C25 . C26 . 120.7(5) yes
C24 . C25 . H251 . 120.0 no
C26 . C25 . H251 . 119.4 no
C25 . C26 . C27 . 120.0(5) yes
C25 . C26 . H261 . 120.3 no
C27 . C26 . H261 . 119.7 no
C26 . C27 . C28 . 121.5(5) yes
C26 . C27 . H271 . 119.4 no
C28 . C27 . H271 . 119.1 no
C27 . C28 . C29 . 117.4(4) yes
C27 . C28 . C34 . 120.7(4) yes
C29 . C28 . C34 . 121.8(4) yes
C28 . C29 . C24 . 122.0(5) yes
C28 . C29 . O30 . 118.6(4) yes
C24 . C29 . O30 . 119.4(4) yes
C29 . O30 . C31 . 112.2(4) yes
O30 . C31 . C32 . 108.5(5) yes
O30 . C31 . H312 . 108.7 no
C32 . C31 . H312 . 109.4 no
O30 . C31 . H311 . 110.5 no
C32 . C31 . H311 . 110.0 no
H312 . C31 . H311 . 109.7 no
C31 . C32 . C33 . 111.2(6) yes
C31 . C32 . H322 . 109.6 no
C33 . C32 . H322 . 108.5 no
C31 . C32 . H321 . 109.1 no
C33 . C32 . H321 . 109.4 no
H322 . C32 . H321 . 109.1 no
C32 . C33 . H333 . 110.0 no
C32 . C33 . H331 . 109.2 no
H333 . C33 . H331 . 108.9 no
C32 . C33 . H332 . 110.0 no
H333 . C33 . H332 . 109.8 no
H331 . C33 . H332 . 108.8 no
C28 . C34 . C35 . 110.7(4) yes
C28 . C34 . H341 . 107.9 no
C35 . C34 . H341 . 110.3 no
C28 . C34 . H342 . 109.7 no
C35 . C34 . H342 . 109.2 no
H341 . C34 . H342 . 109.0 no
C34 . C35 . C36 . 120.7(4) yes
C34 . C35 . C52 . 121.7(4) yes
C36 . C35 . C52 . 117.1(5) yes
C35 . C36 . O37 . 117.7(4) yes
C35 . C36 . C41 . 122.0(4) yes
O37 . C36 . C41 . 120.0(4) yes
C36 . O37 . C38 . 114.3(3) yes
O37 . C38 . C39 . 112.7(4) yes
O37 . C38 . H381 . 110.8 no
C39 . C38 . H381 . 107.9 no
O37 . C38 . H382 . 107.6 no
C39 . C38 . H382 . 107.7 no
H381 . C38 . H382 . 110.2 no
C38 . C39 . C40 . 109.9(5) yes
C38 . C39 . H391 . 109.6 no
C40 . C39 . H391 . 109.0 no
C38 . C39 . H392 . 108.7 no
C40 . C39 . H392 . 109.9 no
H391 . C39 . H392 . 109.8 no
C39 . C40 . H401 . 110.0 no
C39 . C40 . H403 . 109.0 no
H401 . C40 . H403 . 109.2 no
C39 . C40 . H402 . 110.1 no
H401 . C40 . H402 . 109.4 no
H403 . C40 . H402 . 109.1 no
C36 . C41 . C42 . 119.8(4) yes
C36 . C41 . C50 . 118.1(4) yes
C42 . C41 . C50 . 121.0(4) yes
C41 . C42 . C43 . 107.8(3) yes
C41 . C42 . H421 . 110.1 no
C43 . C42 . H421 . 111.0 no
C41 . C42 . H422 . 110.0 no
C43 . C42 . H422 . 109.8 no
H421 . C42 . H422 . 108.2 no
C42 . C43 . C44 . 123.7(4) yes
C42 . C43 . C49 . 118.5(4) yes
C44 . C43 . C49 . 117.7(4) yes
C43 . C44 . C14 . 122.2(4) yes
C43 . C44 . O45 . 118.6(4) yes
C14 . C44 . O45 . 119.0(4) yes
C44 . O45 . C46 . 113.4(3) yes
O45 . C46 . C47 . 108.8(4) yes
O45 . C46 . H461 . 108.7 no
C47 . C46 . H461 . 110.9 no
O45 . C46 . H462 . 108.8 no
C47 . C46 . H462 . 109.3 no
H461 . C46 . H462 . 110.3 no
C46 . C47 . C48 . 113.8(4) yes
C46 . C47 . H472 . 107.3 no
C48 . C47 . H472 . 109.3 no
C46 . C47 . H471 . 108.6 no
C48 . C47 . H471 . 108.8 no
H472 . C47 . H471 . 108.9 no
C47 . C48 . H481 . 109.3 no
C47 . C48 . H482 . 108.9 no
H481 . C48 . H482 . 109.3 no
C47 . C48 . H483 . 110.2 no
H481 . C48 . H483 . 109.2 no
H482 . C48 . H483 . 109.9 no
C43 . C49 . C12 . 120.7(4) yes
C43 . C49 . H491 . 119.6 no
C12 . C49 . H491 . 119.7 no
C41 . C50 . C51 . 121.3(5) yes
C41 . C50 . H501 . 119.0 no
C51 . C50 . H501 . 119.7 no
C50 . C51 . C52 . 119.5(4) yes
C50 . C51 . H511 . 120.4 no
C52 . C51 . H511 . 120.1 no
C35 . C52 . C51 . 121.7(5) yes
C35 . C52 . H521 . 119.2 no
C51 . C52 . H521 . 119.1 no
C22 . C53 . C54 . 120.8(5) yes
C22 . C53 . H531 . 119.0 no
C54 . C53 . H531 . 120.2 no
C53 . C54 . C55 . 119.9(5) yes
C53 . C54 . H541 . 119.2 no
C55 . C54 . H541 . 120.9 no
C54 . C55 . C16 . 121.1(5) yes
C54 . C55 . H551 . 120.2 no
C16 . C55 . H551 . 118.7 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
C20 . H201 . O45 . 152.00 0.981 2.547 3.445(8) yes


_iucr_refine_instructions_constraints 
;
#
# Punched on 26/04/16 at 11:38: 9
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  82,X'S) H   (  83,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 213,X'S) H   ( 212,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,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   (  31,X'S) H   ( 312,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 322,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 333,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 392,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 403,X'S) H   ( 402,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 462,X'S) 
RIDE C   (  47,X'S) H   ( 472,X'S) H   ( 471,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) 
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) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
END                                                                             
;
_iucr_refine_instructions_restraints 
;
#
# Punched on 26/04/16 at 11:38: 9
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 0.000 0.000 0.000 209 43 ' '
2 0.000 0.000 0.500 27 0 ' '
3 1.000 0.500 0.500 209 43 ' '
4 1.000 0.500 1.000 27 0 ' '
_platon_squeeze_details          
;
;
