# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1OxCl
_database_code_depnum_ccdc_archive 'CCDC 1531018'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
#==============================================================================
# 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 0.250 0.250 0.430 62 12 ' '
2 0.750 0.750 0.570 62 12 ' '
_platon_squeeze_details          
;
;

_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          
;The asymmetric unit cell contains one quarter of the tetra-cationic ligand,
an oxalate anion located about a special position, and two chloride anions.
The symmetry of the system means the the formula of the framework is 
[L.oxalate.2Cl].

A small amount of residual density remains, which could not be sensibly
modeled - this is located close to a four-fold rotation axis, and may
be due to a solvent water molecule located about this position. PLATON-SQUEEZE
was used to include this electron density in the refinement.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. N-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement., SQUEEZE
;

_cell_length_a                   11.86816(16)
_cell_length_b                   11.86816(16)
_cell_length_c                   11.6198(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1636.69(3)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 4/n '
_symmetry_space_group_name_Hall  '-P 4a'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
y,-x+1/2,z
-y,x+1/2,-z
-x+1/2,-y+1/2,z
x+1/2,y+1/2,-z
-y+1/2,x,z
y+1/2,-x,-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 0.0181 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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Na 0.1353 0.1239 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240
0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

_chemical_formula_sum            'C31 H32 Cl2 N8 O4'
_chemical_formula_moiety         'C29 H32 N8, C2 O4, 2(Cl)'
_chemical_compound_source        synthesized
_chemical_formula_weight         651.55

_cell_measurement_reflns_used    7517
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      72.33
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.16

_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.186

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            14714
_reflns_number_total             1466
_diffrn_reflns_av_R_equivalents  0.028

_diffrn_reflns_theta_min         3.804
_diffrn_reflns_theta_max         67.073
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        67.073
_diffrn_measured_fraction_theta_full 1.000

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -9
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.06
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.07
_refine_diff_density_max         0.79

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1458
_refine_ls_number_restraints     8
_refine_ls_number_parameters     120
_oxford_refine_ls_R_factor_ref   0.0713
_refine_ls_wR_factor_ref         0.1940
_refine_ls_goodness_of_fit_ref   1.0673
_refine_ls_shift/su_max          0.0000890
_refine_ls_shift/su_mean         0.0000123

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1458
_refine_ls_R_factor_all          0.0713
_refine_ls_wR_factor_all         0.1940

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1426
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_gt          0.1940

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.608E+04 0.992E+04 0.717E+04 0.341E+04 0.136E+04 
;

# 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
N1 N 0.4799(2) 0.4086(2) 0.1221(2) 0.0324 1.0000 Uani D . . . . .
N2 N 0.6311(2) 0.5199(3) 0.1650(3) 0.0372 1.0000 Uani D . . . . .
C3 C 0.5262(3) 0.4910(3) 0.1812(3) 0.0271 1.0000 Uani D . . . . .
C4 C 0.4578(2) 0.5522(2) 0.2668(3) 0.0248 1.0000 Uani . . . . . .
C5 C 0.3417(3) 0.5624(3) 0.2505(3) 0.0281 1.0000 Uani . . . . . .
C6 C 0.2787(2) 0.6245(3) 0.3259(3) 0.0272 1.0000 Uani . . . . . .
C7 C 0.3266(2) 0.6786(2) 0.4211(3) 0.0234 1.0000 Uani . . . . . .
C8 C 0.4418(3) 0.6652(3) 0.4387(3) 0.0262 1.0000 Uani . . . . . .
C9 C 0.5069(3) 0.6031(3) 0.3619(3) 0.0280 1.0000 Uani . . . . . .
C10 C 0.2500 0.7500 0.5000 0.0203 1.0000 Uani S T . . . .
O11 O 0.7688(2) 0.39372(19) 0.0196(2) 0.0408 1.0000 Uani . . . . . .
C12 C 0.8024(5) 0.2901(5) 0.0068(4) 0.0227 0.5000 Uani . . . . . .
Cl1 Cl 0.7500 0.7500 0.26371(17) 0.0391 1.0000 Uani S T . . . .
H51 H 0.3080 0.5283 0.1865 0.0332 1.0000 Uiso R . . . . .
H61 H 0.2009 0.6308 0.3138 0.0305 1.0000 Uiso R . . . . .
H81 H 0.4758 0.6999 0.5017 0.0313 1.0000 Uiso R . . . . .
H91 H 0.5831 0.5949 0.3742 0.0319 1.0000 Uiso R . . . . .
H22 H 0.672(2) 0.482(3) 0.118(3) 0.0437 1.0000 Uiso D . . . . .
H12 H 0.522(2) 0.376(3) 0.068(3) 0.0381 1.0000 Uiso D . . . . .
Cl2 Cl 0.2500 0.2500 0.17280(19) 0.0486 1.0000 Uani S T . . . .
H21 H 0.656(2) 0.581(2) 0.195(3) 0.0444 1.0000 Uiso D . . . . .
H11 H 0.413(2) 0.385(3) 0.139(3) 0.0388 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.9(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
N1 . C3 . 1.315(4) yes
N1 . H12 . 0.892(18) no
N1 . H11 . 0.869(18) no
N2 . C3 . 1.306(4) yes
N2 . H22 . 0.856(18) no
N2 . H21 . 0.859(18) no
C3 . C4 . 1.475(4) yes
C4 . C5 . 1.397(4) yes
C4 . C9 . 1.388(5) yes
C5 . C6 . 1.367(5) yes
C5 . H51 . 0.937 no
C6 . C7 . 1.400(4) yes
C6 . H61 . 0.937 no
C7 . C8 . 1.392(4) yes
C7 . C10 . 1.544(3) yes
C8 . C9 . 1.392(4) yes
C8 . H81 . 0.931 no
C9 . H91 . 0.921 no
O11 . C12 4_645 1.325(7) yes
O11 . C12 . 1.302(7) yes
C12 . C12 5_655 1.566(13) yes
C12 . C12 8_565 1.119(9) yes
C12 . C12 4_645 1.119(9) yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 . N1 . H12 . 117.0(16) no
C3 . N1 . H11 . 120.7(16) no
H12 . N1 . H11 . 122(2) no
C3 . N2 . H22 . 119.2(17) no
C3 . N2 . H21 . 119.2(16) no
H22 . N2 . H21 . 121(2) no
N1 . C3 . N2 . 121.3(3) yes
N1 . C3 . C4 . 119.2(3) yes
N2 . C3 . C4 . 119.5(3) yes
C3 . C4 . C5 . 119.6(3) yes
C3 . C4 . C9 . 121.4(3) yes
C5 . C4 . C9 . 119.0(3) yes
C4 . C5 . C6 . 120.0(3) yes
C4 . C5 . H51 . 119.4 no
C6 . C5 . H51 . 120.5 no
C5 . C6 . C7 . 122.1(3) yes
C5 . C6 . H61 . 119.1 no
C7 . C6 . H61 . 118.8 no
C6 . C7 . C8 . 117.6(3) yes
C6 . C7 . C10 . 118.8(2) yes
C8 . C7 . C10 . 123.6(2) yes
C7 . C8 . C9 . 120.8(3) yes
C7 . C8 . H81 . 119.3 no
C9 . C8 . H81 . 119.9 no
C8 . C9 . C4 . 120.5(3) yes
C8 . C9 . H91 . 120.1 no
C4 . C9 . H91 . 119.3 no
C7 4_656 C10 . C7 . 110.65(11) yes
C7 4_656 C10 . C7 5_565 110.65(11) yes
C7 . C10 . C7 5_565 107.1(2) yes
C7 4_656 C10 . C7 8_466 107.1(2) yes
C7 . C10 . C7 8_466 110.65(11) yes
C7 5_565 C10 . C7 8_466 110.65(11) yes
C12 4_645 O11 . C12 . 50.4(5) yes
C12 5_655 C12 . O11 8_565 109.3(6) yes
C12 5_655 C12 . O11 . 109.3(6) yes
O11 8_565 C12 . O11 . 140.8(5) yes
C12 5_655 C12 . C12 8_565 45.58(8) yes
O11 8_565 C12 . C12 8_565 63.7(6) yes
O11 . C12 . C12 8_565 154.6(6) yes
C12 5_655 C12 . C12 4_645 45.58(8) yes
O11 8_565 C12 . C12 4_645 147.0(7) yes
O11 . C12 . C12 4_645 65.9(6) yes
C12 8_565 C12 . C12 4_645 88.85(15) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C8 . H81 . C6 4_656 125.95(10) 0.931 2.511 3.149(4) yes
N2 . H22 . O11 . 177(4) 0.856 1.931 2.787(4) yes
N1 . H12 . O11 4_645 163(3) 0.892 1.912 2.778(4) yes
N1 . H12 . C12 4_645 152(3) 0.892 2.547 3.360(4) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 31/05/16 at 15:49:11
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL CL   (    1 ) 
CONT H    (   22 ,X'S)  UNTIL H    (   12 ) 
CONT CL   (    2 ,X'S,U'S) 
CONT H    (   21 ,X'S)  UNTIL H    (   11 ) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
END   
;

_iucr_refine_instructions_details_restraints 
;                                                                          
#
# Punched on 31/05/16 at 15:49:11
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(12) 
CONT N ( 1) TO H(11) 
REST 0.039, 0.002 = H(12,U[ISO]) 
REST 0.039, 0.002 = H(11,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 1) TO H(12) 
CONT C(3) TO N ( 1) TO H(11) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 2) TO H(22) 
CONT N ( 2) TO H(21) 
REST 0.045, 0.002 = H(22,U[ISO]) 
REST 0.045, 0.002 = H(21,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 2) TO H(22) 
CONT C(3) TO N ( 2) TO H(21) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_1NO3
_database_code_depnum_ccdc_archive 'CCDC 1531017'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-04-12 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          
; 
Several crystals were screened and all gave "split"-looking diffraction
patterns. In the end, the most single-looking crystal was used for data
collection, but data are still only of moderate quality. A twin law
was found using the ROTAX program within CRYSTALs, and the occupancies
of the two components was refined.

Due to the relatively low quality of the data, it was necessary to restrain
bond lengths to be the "same" as others in the same environment (e.g. all 
phenyl C-C bond lengths were restrained to be the same as one another, within 
error). It was also necessary to restrain C-O bond lengths and to apply 
thermal and vibrational restraints to the ellipsoids of two of the nitrate
anions. A small amount of residual electron density is visible near two 
of the nitrate anions.

C-H and N-H hydrogen atoms were generally visible in the Fourier difference 
map and were initially refined with restraints on bond lengths and angles, 
after which the positions were used as the basis for a riding model. 
O-H protons on water and methanol solvent molecules could not be sensibly 
refined, and so were inserted at idealised hydrogen bonding positions and then
these positions used as the basis for a riding model.
;

_cell_length_a                   11.6729(15)
_cell_length_b                   11.8954(9)
_cell_length_c                   26.963(2)
_cell_angle_alpha                101.982(7)
_cell_angle_beta                 91.167(8)
_cell_angle_gamma                90.664(8)
_cell_volume                     3661.1(3)

_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 0.0181 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            2

_chemical_formula_sum            'C61 H78 N24 O28'
_chemical_formula_moiety         '2(C29 H32 N8), 8(N O3), 3(C H4 O), H2 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         1595.44

_cell_measurement_reflns_used    4419
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      68.3
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.36

_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1671.990
_exptl_absorpt_coefficient_mu    0.994

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            22057
_reflns_number_total             12917
_diffrn_reflns_av_R_equivalents  0.041

_diffrn_reflns_theta_min         3.788
_diffrn_reflns_theta_max         68.252
_diffrn_measured_fraction_theta_max 0.963

_diffrn_reflns_theta_full        68.252
_diffrn_measured_fraction_theta_full 0.963

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       32
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              -14
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              32

_oxford_diffrn_Wilson_B_factor   3.74
_oxford_diffrn_Wilson_scale      0.14

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.88
_refine_diff_density_max         1.15

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         11000
_refine_ls_number_restraints     169
_refine_ls_number_parameters     1019
_oxford_refine_ls_R_factor_ref   0.1618
_refine_ls_wR_factor_ref         0.3474
_refine_ls_goodness_of_fit_ref   0.9703
_refine_ls_shift/su_max          0.0001955
_refine_ls_shift/su_mean         0.0000140

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        11000
_refine_ls_R_factor_all          0.1618
_refine_ls_wR_factor_all         0.3474

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7779
_refine_ls_R_factor_gt           0.1386
_refine_ls_wR_factor_gt          0.3309

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, 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: 
 0.341E+04 0.560E+04 0.338E+04 0.137E+04 325. 
;

# 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
N1 N 0.6255(7) 0.4161(6) 0.4458(3) 0.0569 1.0000 Uani D . . . . .
N2 N 0.5944(7) 0.3364(6) 0.5138(3) 0.0580 1.0000 Uani D . . . . .
C3 C 0.6405(7) 0.4175(6) 0.4940(3) 0.0455 1.0000 Uani D . . . . .
C4 C 0.7103(7) 0.5101(5) 0.5267(3) 0.0408 1.0000 Uani D . . . . .
C5 C 0.7121(7) 0.6222(5) 0.5191(3) 0.0412 1.0000 Uani D . . . . .
C6 C 0.7805(7) 0.7044(6) 0.5502(3) 0.0396 1.0000 Uani D . . . . .
C7 C 0.8464(7) 0.6816(5) 0.5908(3) 0.0405 1.0000 Uani D . . . . .
C8 C 0.8439(7) 0.5691(5) 0.5969(3) 0.0454 1.0000 Uani D . . . . .
C9 C 0.7782(7) 0.4844(6) 0.5659(3) 0.0460 1.0000 Uani D . . . . .
C10 C 0.9197(6) 0.7791(5) 0.6239(2) 0.0373 1.0000 Uani D . . . . .
N11 N 1.2114(8) 0.5765(7) 0.8012(3) 0.0674 1.0000 Uani D . . . . .
N12 N 1.2975(7) 0.4974(6) 0.7273(3) 0.0594 1.0000 Uani D . . . . .
C13 C 1.2217(8) 0.5662(7) 0.7519(3) 0.0534 1.0000 Uani D . . . . .
C14 C 1.1445(6) 0.6271(7) 0.7221(3) 0.0486 1.0000 Uani D . . . . .
C15 C 1.0288(6) 0.6376(7) 0.7314(3) 0.0496 1.0000 Uani D . . . . .
C16 C 0.9593(7) 0.6885(7) 0.6996(3) 0.0447 1.0000 Uani D . . . . .
C17 C 1.0034(6) 0.7300(6) 0.6590(3) 0.0386 1.0000 Uani D . . . . .
C18 C 1.1218(6) 0.7246(7) 0.6531(3) 0.0461 1.0000 Uani D . . . . .
C19 C 1.1927(7) 0.6729(7) 0.6837(3) 0.0466 1.0000 Uani D . . . . .
N21 N 1.2974(7) 1.0663(6) 0.5286(3) 0.0597 1.0000 Uani D . . . . .
N22 N 1.2632(7) 0.9328(7) 0.4560(3) 0.0621 1.0000 Uani D . . . . .
C23 C 1.2370(7) 0.9790(7) 0.5027(3) 0.0518 1.0000 Uani D . . . . .
C24 C 1.1447(6) 0.9291(6) 0.5283(3) 0.0449 1.0000 Uani D . . . . .
C25 C 1.0745(7) 1.0008(7) 0.5615(3) 0.0517 1.0000 Uani D . . . . .
C26 C 0.9994(7) 0.9530(6) 0.5909(3) 0.0461 1.0000 Uani D . . . . .
C27 C 0.9897(6) 0.8348(5) 0.5869(3) 0.0388 1.0000 Uani D . . . . .
C28 C 1.0509(7) 0.7662(6) 0.5490(3) 0.0449 1.0000 Uani D . . . . .
C29 C 1.1291(7) 0.8109(6) 0.5205(3) 0.0477 1.0000 Uani D . . . . .
N31 N 0.6081(7) 1.2079(6) 0.7286(3) 0.0581 1.0000 Uani D . . . . .
N32 N 0.6360(8) 1.1269(8) 0.7976(3) 0.0687 1.0000 Uani D . . . . .
C33 C 0.6519(7) 1.1302(6) 0.7501(3) 0.0468 1.0000 Uani D . . . . .
C34 C 0.7212(6) 1.0390(6) 0.7189(3) 0.0405 1.0000 Uani D . . . . .
C35 C 0.8372(6) 1.0313(6) 0.7273(3) 0.0470 1.0000 Uani D . . . . .
C36 C 0.9004(7) 0.9479(6) 0.6965(3) 0.0459 1.0000 Uani D . . . . .
C37 C 0.8458(6) 0.8677(6) 0.6580(2) 0.0381 1.0000 Uani D . . . . .
C38 C 0.7282(6) 0.8750(7) 0.6505(3) 0.0494 1.0000 Uani D . . . . .
C39 C 0.6674(7) 0.9605(7) 0.6804(3) 0.0480 1.0000 Uani D . . . . .
N51 N 0.6490(7) 0.5570(7) 0.7936(3) 0.0625 1.0000 Uani D . . . . .
N52 N 0.7195(9) 0.4616(8) 0.7183(3) 0.0773 1.0000 Uani D . . . . .
C53 C 0.7193(7) 0.4836(7) 0.7679(3) 0.0580 1.0000 Uani D . . . . .
C54 C 0.8064(7) 0.4257(7) 0.7947(3) 0.0512 1.0000 Uani D . . . . .
C55 C 0.7902(9) 0.4162(11) 0.8445(4) 0.0771 1.0000 Uani D . . . . .
C56 C 0.8691(7) 0.3621(9) 0.8706(4) 0.0628 1.0000 Uani D . . . . .
C57 C 0.9659(7) 0.3128(7) 0.8468(3) 0.0506 1.0000 Uani D . . . . .
C58 C 0.9799(8) 0.3170(7) 0.7966(3) 0.0527 1.0000 Uani D . . . . .
C59 C 0.9011(8) 0.3727(7) 0.7716(3) 0.0589 1.0000 Uani D . . . . .
C60 C 1.0532(6) 0.2567(6) 0.8775(3) 0.0455 1.0000 Uani D . . . . .
N61 N 1.3797(8) 0.6930(7) 0.9959(4) 0.0799 1.0000 Uani D . . . . .
N62 N 1.3944(8) 0.5655(9) 1.0486(3) 0.0779 1.0000 Uani D . . . . .
C63 C 1.3571(9) 0.5933(8) 1.0067(3) 0.0679 1.0000 Uani D . . . . .
C64 C 1.2823(7) 0.5078(6) 0.9721(3) 0.0576 1.0000 Uani D . . . . .
C65 C 1.3041(7) 0.3911(6) 0.9641(3) 0.0504 1.0000 Uani D . . . . .
C66 C 1.2301(7) 0.3128(7) 0.9336(3) 0.0468 1.0000 Uani D . . . . .
C67 C 1.1364(6) 0.3485(6) 0.9082(3) 0.0444 1.0000 Uani D . . . . .
C68 C 1.1169(8) 0.4657(6) 0.9149(3) 0.0511 1.0000 Uani D . . . . .
C69 C 1.1908(8) 0.5440(8) 0.9456(3) 0.0622 1.0000 Uani D . . . . .
N71 N 0.7917(8) 0.0475(8) 1.0554(3) 0.0715 1.0000 Uani D . . . . .
N72 N 0.6834(11) -0.0255(14) 0.9856(4) 0.1376 1.0000 Uani D . . . . .
C73 C 0.7720(8) 0.0342(9) 1.0066(3) 0.0671 1.0000 Uani D . . . . .
C74 C 0.8474(7) 0.0901(8) 0.9748(3) 0.0562 1.0000 Uani D . . . . .
C75 C 0.9421(8) 0.1538(9) 0.9953(3) 0.0679 1.0000 Uani D . . . . .
C76 C 1.0077(8) 0.2087(8) 0.9648(3) 0.0573 1.0000 Uani D . . . . .
C77 C 0.9854(7) 0.1956(7) 0.9133(3) 0.0484 1.0000 Uani D . . . . .
C78 C 0.8913(7) 0.1271(8) 0.8943(3) 0.0597 1.0000 Uani D . . . . .
C79 C 0.8234(8) 0.0717(9) 0.9238(3) 0.0609 1.0000 Uani D . . . . .
N81 N 1.3850(9) -0.1470(7) 0.7584(4) 0.0819 1.0000 Uani D . . . . .
N82 N 1.3474(8) -0.0546(7) 0.6937(3) 0.0678 1.0000 Uani D . . . . .
C83 C 1.3366(8) -0.0641(7) 0.7407(3) 0.0584 1.0000 Uani D . . . . .
C84 C 1.2626(7) 0.0159(6) 0.7748(3) 0.0525 1.0000 Uani D . . . . .
C85 C 1.2791(8) 0.1340(6) 0.7819(3) 0.0552 1.0000 Uani D . . . . .
C86 C 1.2132(7) 0.2074(7) 0.8161(3) 0.0463 1.0000 Uani D . . . . .
C87 C 1.1261(6) 0.1674(6) 0.8424(3) 0.0442 1.0000 Uani D . . . . .
C88 C 1.1103(8) 0.0497(6) 0.8343(3) 0.0559 1.0000 Uani D . . . . .
C89 C 1.1781(8) -0.0256(8) 0.8016(3) 0.0668 1.0000 Uani D . . . . .
N101 N 0.4832(6) 0.2874(7) 0.6234(2) 0.0577 1.0000 Uani D . . . . .
O102 O 0.5896(6) 0.2873(6) 0.6210(3) 0.0673 1.0000 Uani D . . . . .
O103 O 0.4195(6) 0.2776(6) 0.5852(2) 0.0627 1.0000 Uani D . . . . .
O104 O 0.4356(7) 0.2919(7) 0.6657(2) 0.0762 1.0000 Uani D . . . . .
N111 N 0.4501(6) 0.3916(6) 0.8293(2) 0.0529 1.0000 Uani D . . . . .
O112 O 0.5142(6) 0.3327(6) 0.8512(2) 0.0703 1.0000 Uani D . . . . .
O113 O 0.4391(6) 0.3631(5) 0.78213(19) 0.0509 1.0000 Uani D . . . . .
O114 O 0.3970(7) 0.4728(6) 0.8541(2) 0.0734 1.0000 Uani D . . . . .
N121 N 0.5265(7) 0.6513(6) 0.6728(2) 0.0558 1.0000 Uani D . . . . .
O122 O 0.5694(8) 0.5626(7) 0.6489(3) 0.0903 1.0000 Uani D . . . . .
O123 O 0.4727(5) 0.7164(5) 0.6503(2) 0.0539 1.0000 Uani D . . . . .
O124 O 0.5432(8) 0.6773(6) 0.7195(2) 0.0815 1.0000 Uani D . . . . .
N131 N 0.4644(7) 0.0997(7) 0.9120(3) 0.0612 1.0000 Uani D . . . . .
O132 O 0.5581(8) 0.1221(13) 0.8966(4) 0.1390 1.0000 Uani D . . . . .
O133 O 0.3937(8) 0.0331(7) 0.8867(3) 0.0858 1.0000 Uani D . . . . .
O134 O 0.4469(7) 0.1493(7) 0.9558(3) 0.0805 1.0000 Uani D . . . . .
N141 N 0.9889(9) 0.7420(8) 0.8722(3) 0.1555 1.0000 Uani D U . . . .
O142 O 1.0912(10) 0.7570(9) 0.8694(3) 0.1548 1.0000 Uani D U . . . .
O143 O 0.9455(10) 0.6475(8) 0.8511(3) 0.1462 1.0000 Uani D U . . . .
O144 O 0.9317(12) 0.8195(9) 0.8974(3) 0.1908 1.0000 Uani D U . . . .
N151 N 0.4855(6) 0.9155(5) 0.5704(2) 0.0470 1.0000 Uani D . . . . .
O152 O 0.5407(6) 0.8543(5) 0.5360(3) 0.0652 1.0000 Uani D . . . . .
O153 O 0.3977(6) 0.8730(6) 0.5854(2) 0.0651 1.0000 Uani D . . . . .
O154 O 0.5171(6) 1.0153(5) 0.5890(2) 0.0610 1.0000 Uani D . . . . .
N161 N 0.4555(8) 0.7729(7) 0.8822(3) 0.1210 1.0000 Uani D U . . . .
O162 O 0.4953(9) 0.7641(6) 0.8396(3) 0.1130 1.0000 Uani D U . . . .
O163 O 0.5188(10) 0.8043(7) 0.9204(3) 0.1345 1.0000 Uani D U . . . .
O164 O 0.3544(9) 0.7496(7) 0.8878(4) 0.1488 1.0000 Uani D U . . . .
N171 N 0.8751(7) 0.2692(5) 0.6333(2) 0.0467 1.0000 Uani D . . . . .
O172 O 0.9126(9) 0.2273(7) 0.5918(3) 0.0956 1.0000 Uani D . . . . .
O173 O 0.8197(10) 0.2076(9) 0.6565(4) 0.1175 1.0000 Uani D . . . . .
O174 O 0.9038(11) 0.3682(6) 0.6543(3) 0.1091 1.0000 Uani D . . . . .
O201 O 0.2564(6) 0.4376(6) 0.6126(3) 0.0675 1.0000 Uani D . . . . .
C202 C 0.1393(9) 0.4131(12) 0.5945(5) 0.0952 1.0000 Uani D . . . . .
O211 O 0.2574(8) 0.1334(7) 0.6521(3) 0.0826 1.0000 Uani D . . . . .
C212 C 0.1591(10) 0.1969(11) 0.6743(5) 0.0823 1.0000 Uani D . . . . .
O221 O 0.6859(9) 0.9156(7) 0.8268(3) 0.0976 1.0000 Uani D . . . . .
C222 C 0.7629(13) 0.8340(10) 0.7995(5) 0.1004 1.0000 Uani D . . . . .
O231 O 0.6694(15) 0.6408(9) 0.9096(4) 0.1623 1.0000 Uani . . . . . .
H51 H 0.6687 0.6412 0.4923 0.0554 1.0000 Uiso R . . . . .
H61 H 0.7805 0.7784 0.5445 0.0483 1.0000 Uiso R . . . . .
H81 H 0.8898 0.5495 0.6220 0.0542 1.0000 Uiso R . . . . .
H91 H 0.7782 0.4088 0.5715 0.0588 1.0000 Uiso R . . . . .
H151 H 0.9984 0.6121 0.7583 0.0580 1.0000 Uiso R . . . . .
H161 H 0.8805 0.6945 0.7050 0.0540 1.0000 Uiso R . . . . .
H181 H 1.1558 0.7565 0.6285 0.0570 1.0000 Uiso R . . . . .
H191 H 1.2713 0.6684 0.6780 0.0626 1.0000 Uiso R . . . . .
H251 H 1.0770 1.0799 0.5648 0.0608 1.0000 Uiso R . . . . .
H261 H 0.9541 1.0013 0.6137 0.0542 1.0000 Uiso R . . . . .
H281 H 1.0407 0.6865 0.5435 0.0503 1.0000 Uiso R . . . . .
H291 H 1.1710 0.7620 0.4962 0.0548 1.0000 Uiso R . . . . .
H351 H 0.8727 1.0826 0.7542 0.0558 1.0000 Uiso R . . . . .
H361 H 0.9794 0.9453 0.7018 0.0567 1.0000 Uiso R . . . . .
H381 H 0.6895 0.8220 0.6254 0.0579 1.0000 Uiso R . . . . .
H391 H 0.5891 0.9651 0.6745 0.0598 1.0000 Uiso R . . . . .
H551 H 0.7264 0.4495 0.8615 0.0888 1.0000 Uiso R . . . . .
H561 H 0.8566 0.3579 0.9040 0.0821 1.0000 Uiso R . . . . .
H581 H 1.0422 0.2804 0.7792 0.0640 1.0000 Uiso R . . . . .
H591 H 0.9136 0.3754 0.7379 0.0691 1.0000 Uiso R . . . . .
H651 H 1.3670 0.3646 0.9802 0.0641 1.0000 Uiso R . . . . .
H661 H 1.2454 0.2349 0.9281 0.0582 1.0000 Uiso R . . . . .
H681 H 1.0545 0.4922 0.8984 0.0631 1.0000 Uiso R . . . . .
H691 H 1.1781 0.6220 0.9486 0.0752 1.0000 Uiso R . . . . .
H751 H 0.9624 0.1622 1.0295 0.0818 1.0000 Uiso R . . . . .
H761 H 1.0697 0.2547 0.9790 0.0691 1.0000 Uiso R . . . . .
H781 H 0.8720 0.1172 0.8601 0.0791 1.0000 Uiso R . . . . .
H791 H 0.7630 0.0224 0.9094 0.0741 1.0000 Uiso R . . . . .
H851 H 1.3351 0.1646 0.7638 0.0678 1.0000 Uiso R . . . . .
H861 H 1.2262 0.2862 0.8209 0.0562 1.0000 Uiso R . . . . .
H881 H 1.0529 0.0198 0.8513 0.0670 1.0000 Uiso R . . . . .
H891 H 1.1676 -0.1043 0.7976 0.0739 1.0000 Uiso R . . . . .
H2221 H 0.8298 0.8741 0.7928 0.1209 1.0000 Uiso R . . . . .
H2222 H 0.7836 0.7779 0.8184 0.1209 1.0000 Uiso R . . . . .
H2223 H 0.7268 0.7972 0.7684 0.1209 1.0000 Uiso R . . . . .
H2021 H 0.1142 0.4765 0.5810 0.1082 1.0000 Uiso R . . . . .
H2022 H 0.0913 0.4038 0.6215 0.1082 1.0000 Uiso R . . . . .
H2023 H 0.1357 0.3453 0.5687 0.1082 1.0000 Uiso R . . . . .
H2121 H 0.0950 0.1456 0.6704 0.1039 1.0000 Uiso R . . . . .
H2122 H 0.1753 0.2253 0.7094 0.1039 1.0000 Uiso R . . . . .
H2123 H 0.1422 0.2593 0.6585 0.1039 1.0000 Uiso R . . . . .
H311 H 0.5585 1.2534 0.7447 0.0700 1.0000 Uiso R . . . . .
H312 H 0.5724 1.1861 0.6995 0.0700 1.0000 Uiso R . . . . .
H321 H 0.6055 1.1841 0.8175 0.0858 1.0000 Uiso R . . . . .
H322 H 0.6553 1.0672 0.8090 0.0858 1.0000 Uiso R . . . . .
H211 H 1.3699 1.0733 0.5241 0.0714 1.0000 Uiso R . . . . .
H212 H 1.2739 1.1010 0.5576 0.0714 1.0000 Uiso R . . . . .
H221 H 1.3106 0.9677 0.4395 0.0785 1.0000 Uiso R . . . . .
H222 H 1.2240 0.8743 0.4396 0.0785 1.0000 Uiso R . . . . .
H111 H 1.2571 0.5419 0.8182 0.0813 1.0000 Uiso R . . . . .
H112 H 1.1773 0.6352 0.8182 0.0813 1.0000 Uiso R . . . . .
H121 H 1.3543 0.4747 0.7432 0.0730 1.0000 Uiso R . . . . .
H122 H 1.2842 0.4672 0.6957 0.0730 1.0000 Uiso R . . . . .
H11 H 0.6629 0.4631 0.4318 0.0648 1.0000 Uiso R . . . . .
H12 H 0.6239 0.3536 0.4234 0.0648 1.0000 Uiso R . . . . .
H21 H 0.6174 0.3301 0.5436 0.0691 1.0000 Uiso R . . . . .
H22 H 0.5667 0.2739 0.4949 0.0691 1.0000 Uiso R . . . . .
H621 H 1.3962 0.6168 1.0762 0.0957 1.0000 Uiso R . . . . .
H622 H 1.3642 0.5073 1.0583 0.0957 1.0000 Uiso R . . . . .
H611 H 1.4346 0.7347 1.0120 0.0930 1.0000 Uiso R . . . . .
H612 H 1.3612 0.7043 0.9660 0.0930 1.0000 Uiso R . . . . .
H811 H 1.3720 -0.1525 0.7913 0.0949 1.0000 Uiso R . . . . .
H812 H 1.4182 -0.2015 0.7382 0.0949 1.0000 Uiso R . . . . .
H821 H 1.2995 -0.0146 0.6803 0.0815 1.0000 Uiso R . . . . .
H822 H 1.4008 -0.0924 0.6756 0.0815 1.0000 Uiso R . . . . .
H711 H 0.8441 0.0943 1.0711 0.0904 1.0000 Uiso R . . . . .
H712 H 0.7510 0.0947 1.0762 0.0904 1.0000 Uiso R . . . . .
H721 H 0.6285 -0.0447 1.0089 0.1641 1.0000 Uiso R . . . . .
H722 H 0.6523 -0.0129 0.9580 0.1641 1.0000 Uiso R . . . . .
H521 H 0.6965 0.5131 0.7026 0.0923 1.0000 Uiso R . . . . .
H522 H 0.7650 0.4128 0.7019 0.0923 1.0000 Uiso R . . . . .
H511 H 0.6583 0.5814 0.8261 0.0833 1.0000 Uiso R . . . . .
H512 H 0.5930 0.5834 0.7780 0.0833 1.0000 Uiso R . . . . .
H2311 H 0.6212 0.6947 0.9129 0.1966 1.0000 Uiso R . . . . .
H2312 H 0.7337 0.6424 0.8955 0.1966 1.0000 Uiso R . . . . .
H2011 H 0.3074 0.3873 0.6040 0.0811 1.0000 Uiso R . . . . .
H2111 H 0.3123 0.1823 0.6563 0.0981 1.0000 Uiso R . . . . .
H2211 H 0.6287 0.8704 0.8305 0.1179 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.54(9)

loop_
_oxford_twin_element_scale_factors
0.648(4)
0.352(4)

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
N1 . C3 . 1.305(7) yes
N1 . H11 . 0.856 no
N1 . H12 . 0.854 no
N2 . C3 . 1.310(7) yes
N2 . H21 . 0.860 no
N2 . H22 . 0.865 no
C3 . C4 . 1.484(7) yes
C4 . C5 . 1.391(7) yes
C4 . C9 . 1.394(7) yes
C5 . C6 . 1.382(7) yes
C5 . H51 . 0.940 no
C6 . C7 . 1.398(7) yes
C6 . H61 . 0.926 no
C7 . C8 . 1.381(7) yes
C7 . C10 . 1.546(7) yes
C8 . C9 . 1.383(7) yes
C8 . H81 . 0.925 no
C9 . H91 . 0.942 no
C10 . C17 . 1.548(7) yes
C10 . C27 . 1.548(7) yes
C10 . C37 . 1.535(7) yes
N11 . C13 . 1.317(8) yes
N11 . H111 . 0.858 no
N11 . H112 . 0.858 no
N12 . C13 . 1.306(8) yes
N12 . H121 . 0.859 no
N12 . H122 . 0.864 no
C13 . C14 . 1.487(7) yes
C14 . C15 . 1.380(8) yes
C14 . C19 . 1.393(8) yes
C15 . C16 . 1.399(8) yes
C15 . H151 . 0.919 no
C16 . C17 . 1.395(7) yes
C16 . H161 . 0.936 no
C17 . C18 . 1.395(8) yes
C18 . C19 . 1.393(7) yes
C18 . H181 . 0.923 no
C19 . H191 . 0.934 no
N21 . C23 . 1.314(7) yes
N21 . H211 . 0.862 no
N21 . H212 . 0.858 no
N22 . C23 . 1.307(7) yes
N22 . H221 . 0.872 no
N22 . H222 . 0.864 no
C23 . C24 . 1.475(8) yes
C24 . C25 . 1.388(8) yes
C24 . C29 . 1.387(7) yes
C25 . C26 . 1.388(8) yes
C25 . H251 . 0.927 no
C26 . C27 . 1.391(7) yes
C26 . H261 . 0.928 no
C27 . C28 . 1.385(7) yes
C28 . C29 . 1.376(8) yes
C28 . H281 . 0.934 no
C29 . H291 . 0.931 no
N31 . C33 . 1.294(7) yes
N31 . H311 . 0.858 no
N31 . H312 . 0.871 no
N32 . C33 . 1.307(7) yes
N32 . H321 . 0.861 no
N32 . H322 . 0.861 no
C33 . C34 . 1.486(7) yes
C34 . C35 . 1.374(8) yes
C34 . C39 . 1.378(8) yes
C35 . C36 . 1.385(8) yes
C35 . H351 . 0.934 no
C36 . C37 . 1.392(7) yes
C36 . H361 . 0.933 no
C37 . C38 . 1.390(8) yes
C38 . C39 . 1.374(8) yes
C38 . H381 . 0.929 no
C39 . H391 . 0.929 no
N51 . C53 . 1.305(8) yes
N51 . H511 . 0.869 no
N51 . H512 . 0.867 no
N52 . C53 . 1.308(8) yes
N52 . H521 . 0.857 no
N52 . H522 . 0.851 no
C53 . C54 . 1.492(8) yes
C54 . C55 . 1.386(8) yes
C54 . C59 . 1.375(8) yes
C55 . C56 . 1.391(8) yes
C55 . H551 . 0.931 no
C56 . C57 . 1.385(8) yes
C56 . H561 . 0.927 no
C57 . C58 . 1.378(8) yes
C57 . C60 . 1.541(7) yes
C58 . C59 . 1.385(8) yes
C58 . H581 . 0.936 no
C59 . H591 . 0.928 no
C60 . C67 . 1.546(7) yes
C60 . C77 . 1.548(7) yes
C60 . C87 . 1.543(8) yes
N61 . C63 . 1.305(8) yes
N61 . H611 . 0.859 no
N61 . H612 . 0.866 no
N62 . C63 . 1.310(8) yes
N62 . H621 . 0.858 no
N62 . H622 . 0.862 no
C63 . C64 . 1.490(8) yes
C64 . C65 . 1.388(8) yes
C64 . C69 . 1.394(8) yes
C65 . C66 . 1.387(8) yes
C65 . H651 . 0.937 no
C66 . C67 . 1.396(7) yes
C66 . H661 . 0.928 no
C67 . C68 . 1.390(7) yes
C68 . C69 . 1.388(8) yes
C68 . H681 . 0.938 no
C69 . H691 . 0.929 no
N71 . C73 . 1.306(8) yes
N71 . H711 . 0.864 no
N71 . H712 . 0.861 no
N72 . C73 . 1.299(8) yes
N72 . H721 . 0.964 no
N72 . H722 . 0.863 no
C73 . C74 . 1.487(8) yes
C74 . C75 . 1.374(8) yes
C74 . C79 . 1.368(8) yes
C75 . C76 . 1.388(8) yes
C75 . H751 . 0.932 no
C76 . C77 . 1.385(8) yes
C76 . H761 . 0.929 no
C77 . C78 . 1.384(8) yes
C78 . C79 . 1.389(8) yes
C78 . H781 . 0.928 no
C79 . H791 . 0.936 no
N81 . C83 . 1.310(8) yes
N81 . H811 . 0.918 no
N81 . H812 . 0.858 no
N82 . C83 . 1.303(8) yes
N82 . H821 . 0.860 no
N82 . H822 . 0.871 no
C83 . C84 . 1.479(8) yes
C84 . C85 . 1.388(8) yes
C84 . C89 . 1.381(8) yes
C85 . C86 . 1.383(8) yes
C85 . H851 . 0.936 no
C86 . C87 . 1.386(7) yes
C86 . H861 . 0.930 no
C87 . C88 . 1.382(8) yes
C88 . C89 . 1.386(8) yes
C88 . H881 . 0.928 no
C89 . H891 . 0.927 no
N101 . O102 . 1.245(7) yes
N101 . O103 . 1.241(7) yes
N101 . O104 . 1.272(7) yes
N111 . O112 . 1.251(7) yes
N111 . O113 . 1.250(7) yes
N111 . O114 . 1.235(7) yes
N121 . O122 . 1.234(7) yes
N121 . O123 . 1.246(7) yes
N121 . O124 . 1.244(7) yes
N131 . O132 . 1.224(8) yes
N131 . O133 . 1.229(7) yes
N131 . O134 . 1.227(7) yes
N141 . O142 . 1.212(9) yes
N141 . O143 . 1.246(8) yes
N141 . O144 . 1.237(8) yes
N151 . O152 . 1.248(7) yes
N151 . O153 . 1.248(7) yes
N151 . O154 . 1.237(7) yes
N161 . O162 . 1.235(8) yes
N161 . O163 . 1.245(8) yes
N161 . O164 . 1.227(8) yes
N171 . O172 . 1.219(7) yes
N171 . O173 . 1.241(8) yes
N171 . O174 . 1.235(7) yes
O201 . C202 . 1.447(8) yes
O201 . H2011 . 0.850 no
C202 . H2021 . 0.950 no
C202 . H2022 . 0.950 no
C202 . H2023 . 0.950 no
O211 . C212 . 1.452(8) yes
O211 . H2111 . 0.850 no
C212 . H2121 . 0.950 no
C212 . H2122 . 0.950 no
C212 . H2123 . 0.950 no
O221 . C222 . 1.430(9) yes
O221 . H2211 . 0.872 no
C222 . H2221 . 0.950 no
C222 . H2222 . 0.950 no
C222 . H2223 . 0.950 no
O231 . H2311 . 0.850 no
O231 . H2312 . 0.850 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
C3 . N1 . H11 . 120.3 no
C3 . N1 . H12 . 122.1 no
H11 . N1 . H12 . 104.0 no
C3 . N2 . H21 . 118.3 no
C3 . N2 . H22 . 121.3 no
H21 . N2 . H22 . 115.0 no
N2 . C3 . N1 . 120.1(7) yes
N2 . C3 . C4 . 119.5(6) yes
N1 . C3 . C4 . 120.4(6) yes
C3 . C4 . C5 . 122.2(6) yes
C3 . C4 . C9 . 119.4(6) yes
C5 . C4 . C9 . 118.4(6) yes
C4 . C5 . C6 . 119.5(6) yes
C4 . C5 . H51 . 120.0 no
C6 . C5 . H51 . 120.5 no
C5 . C6 . C7 . 123.1(6) yes
C5 . C6 . H61 . 118.1 no
C7 . C6 . H61 . 118.7 no
C6 . C7 . C8 . 115.9(6) yes
C6 . C7 . C10 . 119.6(5) yes
C8 . C7 . C10 . 124.5(6) yes
C7 . C8 . C9 . 122.5(7) yes
C7 . C8 . H81 . 118.6 no
C9 . C8 . H81 . 118.9 no
C4 . C9 . C8 . 120.5(6) yes
C4 . C9 . H91 . 119.6 no
C8 . C9 . H91 . 119.8 no
C7 . C10 . C17 . 110.6(5) yes
C7 . C10 . C27 . 106.5(5) yes
C17 . C10 . C27 . 109.1(5) yes
C7 . C10 . C37 . 112.0(6) yes
C17 . C10 . C37 . 107.1(5) yes
C27 . C10 . C37 . 111.5(5) yes
C13 . N11 . H111 . 120.9 no
C13 . N11 . H112 . 119.2 no
H111 . N11 . H112 . 116.1 no
C13 . N12 . H121 . 120.5 no
C13 . N12 . H122 . 118.8 no
H121 . N12 . H122 . 120.0 no
N11 . C13 . N12 . 120.5(7) yes
N11 . C13 . C14 . 121.6(7) yes
N12 . C13 . C14 . 117.8(7) yes
C13 . C14 . C15 . 122.0(7) yes
C13 . C14 . C19 . 117.6(7) yes
C15 . C14 . C19 . 120.5(7) yes
C14 . C15 . C16 . 119.1(7) yes
C14 . C15 . H151 . 120.1 no
C16 . C15 . H151 . 120.8 no
C15 . C16 . C17 . 122.1(7) yes
C15 . C16 . H161 . 119.8 no
C17 . C16 . H161 . 118.1 no
C10 . C17 . C16 . 118.8(6) yes
C10 . C17 . C18 . 124.3(6) yes
C16 . C17 . C18 . 116.9(6) yes
C17 . C18 . C19 . 122.1(7) yes
C17 . C18 . H181 . 120.2 no
C19 . C18 . H181 . 117.7 no
C14 . C19 . C18 . 119.1(7) yes
C14 . C19 . H191 . 120.9 no
C18 . C19 . H191 . 120.0 no
C23 . N21 . H211 . 121.5 no
C23 . N21 . H212 . 118.9 no
H211 . N21 . H212 . 115.1 no
C23 . N22 . H221 . 120.5 no
C23 . N22 . H222 . 119.7 no
H221 . N22 . H222 . 118.8 no
N21 . C23 . N22 . 120.4(8) yes
N21 . C23 . C24 . 118.8(7) yes
N22 . C23 . C24 . 120.7(7) yes
C23 . C24 . C25 . 119.8(6) yes
C23 . C24 . C29 . 120.5(7) yes
C25 . C24 . C29 . 119.6(7) yes
C24 . C25 . C26 . 119.3(7) yes
C24 . C25 . H251 . 121.8 no
C26 . C25 . H251 . 119.0 no
C25 . C26 . C27 . 121.8(7) yes
C25 . C26 . H261 . 119.0 no
C27 . C26 . H261 . 119.2 no
C10 . C27 . C26 . 123.2(6) yes
C10 . C27 . C28 . 119.8(5) yes
C26 . C27 . C28 . 116.9(6) yes
C27 . C28 . C29 . 122.3(7) yes
C27 . C28 . H281 . 118.6 no
C29 . C28 . H281 . 119.0 no
C24 . C29 . C28 . 119.4(7) yes
C24 . C29 . H291 . 120.6 no
C28 . C29 . H291 . 120.0 no
C33 . N31 . H311 . 118.8 no
C33 . N31 . H312 . 118.5 no
H311 . N31 . H312 . 100.2 no
C33 . N32 . H321 . 120.1 no
C33 . N32 . H322 . 120.3 no
H321 . N32 . H322 . 119.6 no
N32 . C33 . N31 . 123.0(7) yes
N32 . C33 . C34 . 118.6(6) yes
N31 . C33 . C34 . 118.4(6) yes
C33 . C34 . C35 . 121.8(6) yes
C33 . C34 . C39 . 118.8(7) yes
C35 . C34 . C39 . 119.4(7) yes
C34 . C35 . C36 . 120.6(7) yes
C34 . C35 . H351 . 119.1 no
C36 . C35 . H351 . 120.3 no
C35 . C36 . C37 . 120.0(7) yes
C35 . C36 . H361 . 119.7 no
C37 . C36 . H361 . 120.2 no
C10 . C37 . C36 . 118.2(6) yes
C10 . C37 . C38 . 122.9(6) yes
C36 . C37 . C38 . 118.9(7) yes
C37 . C38 . C39 . 120.3(7) yes
C37 . C38 . H381 . 120.6 no
C39 . C38 . H381 . 119.1 no
C34 . C39 . C38 . 120.8(7) yes
C34 . C39 . H391 . 120.0 no
C38 . C39 . H391 . 119.2 no
C53 . N51 . H511 . 121.1 no
C53 . N51 . H512 . 119.8 no
H511 . N51 . H512 . 119.0 no
C53 . N52 . H521 . 119.1 no
C53 . N52 . H522 . 121.0 no
H521 . N52 . H522 . 115.2 no
N52 . C53 . N51 . 121.8(8) yes
N52 . C53 . C54 . 117.7(8) yes
N51 . C53 . C54 . 120.4(7) yes
C53 . C54 . C55 . 120.2(7) yes
C53 . C54 . C59 . 123.2(7) yes
C55 . C54 . C59 . 116.4(7) yes
C54 . C55 . C56 . 121.8(9) yes
C54 . C55 . H551 . 119.5 no
C56 . C55 . H551 . 118.6 no
C55 . C56 . C57 . 120.5(8) yes
C55 . C56 . H561 . 120.0 no
C57 . C56 . H561 . 119.5 no
C56 . C57 . C58 . 118.1(7) yes
C56 . C57 . C60 . 119.0(6) yes
C58 . C57 . C60 . 122.9(7) yes
C57 . C58 . C59 . 120.5(8) yes
C57 . C58 . H581 . 119.7 no
C59 . C58 . H581 . 119.8 no
C58 . C59 . C54 . 122.6(8) yes
C58 . C59 . H591 . 118.5 no
C54 . C59 . H591 . 118.9 no
C57 . C60 . C67 . 110.5(6) yes
C57 . C60 . C77 . 107.8(6) yes
C67 . C60 . C77 . 110.6(6) yes
C57 . C60 . C87 . 111.5(6) yes
C67 . C60 . C87 . 107.5(6) yes
C77 . C60 . C87 . 109.0(6) yes
C63 . N61 . H611 . 119.1 no
C63 . N61 . H612 . 119.1 no
H611 . N61 . H612 . 117.1 no
C63 . N62 . H621 . 119.0 no
C63 . N62 . H622 . 119.6 no
H621 . N62 . H622 . 102.1 no
N62 . C63 . N61 . 122.4(9) yes
N62 . C63 . C64 . 117.3(8) yes
N61 . C63 . C64 . 120.3(8) yes
C63 . C64 . C65 . 121.1(7) yes
C63 . C64 . C69 . 120.5(7) yes
C65 . C64 . C69 . 118.4(7) yes
C64 . C65 . C66 . 120.0(7) yes
C64 . C65 . H651 . 120.3 no
C66 . C65 . H651 . 119.7 no
C65 . C66 . C67 . 121.6(7) yes
C65 . C66 . H661 . 119.7 no
C67 . C66 . H661 . 118.6 no
C60 . C67 . C66 . 118.9(6) yes
C60 . C67 . C68 . 122.7(6) yes
C66 . C67 . C68 . 118.3(7) yes
C67 . C68 . C69 . 120.1(7) yes
C67 . C68 . H681 . 120.2 no
C69 . C68 . H681 . 119.7 no
C64 . C69 . C68 . 121.4(8) yes
C64 . C69 . H691 . 119.7 no
C68 . C69 . H691 . 118.9 no
C73 . N71 . H711 . 122.0 no
C73 . N71 . H712 . 119.5 no
H711 . N71 . H712 . 79.0 no
C73 . N72 . H721 . 115.1 no
C73 . N72 . H722 . 121.0 no
H721 . N72 . H722 . 113.2 no
N71 . C73 . N72 . 120.0(9) yes
N71 . C73 . C74 . 121.0(8) yes
N72 . C73 . C74 . 119.0(9) yes
C73 . C74 . C75 . 121.0(7) yes
C73 . C74 . C79 . 118.3(7) yes
C75 . C74 . C79 . 120.7(7) yes
C74 . C75 . C76 . 119.3(8) yes
C74 . C75 . H751 . 121.3 no
C76 . C75 . H751 . 119.4 no
C75 . C76 . C77 . 122.3(8) yes
C75 . C76 . H761 . 119.5 no
C77 . C76 . H761 . 118.2 no
C60 . C77 . C76 . 124.8(7) yes
C60 . C77 . C78 . 119.3(6) yes
C76 . C77 . C78 . 115.8(7) yes
C77 . C78 . C79 . 123.4(8) yes
C77 . C78 . H781 . 118.9 no
C79 . C78 . H781 . 117.7 no
C78 . C79 . C74 . 118.3(8) yes
C78 . C79 . H791 . 121.3 no
C74 . C79 . H791 . 120.4 no
C83 . N81 . H811 . 118.9 no
C83 . N81 . H812 . 120.0 no
H811 . N81 . H812 . 120.3 no
C83 . N82 . H821 . 120.2 no
C83 . N82 . H822 . 119.4 no
H821 . N82 . H822 . 120.3 no
N81 . C83 . N82 . 121.9(9) yes
N81 . C83 . C84 . 118.1(8) yes
N82 . C83 . C84 . 119.9(8) yes
C83 . C84 . C85 . 120.8(7) yes
C83 . C84 . C89 . 120.5(7) yes
C85 . C84 . C89 . 118.7(8) yes
C84 . C85 . C86 . 120.0(8) yes
C84 . C85 . H851 . 120.5 no
C86 . C85 . H851 . 119.5 no
C85 . C86 . C87 . 122.1(8) yes
C85 . C86 . H861 . 119.1 no
C87 . C86 . H861 . 118.7 no
C60 . C87 . C86 . 118.1(6) yes
C60 . C87 . C88 . 125.1(6) yes
C86 . C87 . C88 . 116.8(7) yes
C87 . C88 . C89 . 122.0(8) yes
C87 . C88 . H881 . 119.2 no
C89 . C88 . H881 . 118.8 no
C88 . C89 . C84 . 120.3(8) yes
C88 . C89 . H891 . 120.5 no
C84 . C89 . H891 . 119.1 no
O102 . N101 . O103 . 122.6(7) yes
O102 . N101 . O104 . 120.0(7) yes
O103 . N101 . O104 . 117.3(7) yes
O112 . N111 . O113 . 117.8(6) yes
O112 . N111 . O114 . 120.5(7) yes
O113 . N111 . O114 . 121.7(6) yes
O122 . N121 . O123 . 120.6(7) yes
O122 . N121 . O124 . 118.6(7) yes
O123 . N121 . O124 . 120.7(7) yes
O132 . N131 . O133 . 124.0(9) yes
O132 . N131 . O134 . 113.7(9) yes
O133 . N131 . O134 . 122.3(8) yes
O142 . N141 . O143 . 118.9(7) yes
O142 . N141 . O144 . 118.8(7) yes
O143 . N141 . O144 . 122.2(7) yes
O152 . N151 . O153 . 118.0(7) yes
O152 . N151 . O154 . 120.9(7) yes
O153 . N151 . O154 . 121.1(7) yes
O162 . N161 . O163 . 119.7(7) yes
O162 . N161 . O164 . 121.1(7) yes
O163 . N161 . O164 . 119.2(7) yes
O172 . N171 . O173 . 119.4(8) yes
O172 . N171 . O174 . 119.6(8) yes
O173 . N171 . O174 . 120.4(8) yes
C202 . O201 . H2011 . 119.8 no
O201 . C202 . H2021 . 107.4 no
O201 . C202 . H2022 . 110.8 no
H2021 . C202 . H2022 . 109.5 no
O201 . C202 . H2023 . 110.2 no
H2021 . C202 . H2023 . 109.5 no
H2022 . C202 . H2023 . 109.5 no
C212 . O211 . H2111 . 105.1 no
O211 . C212 . H2121 . 108.2 no
O211 . C212 . H2122 . 108.5 no
H2121 . C212 . H2122 . 109.5 no
O211 . C212 . H2123 . 111.7 no
H2121 . C212 . H2123 . 109.5 no
H2122 . C212 . H2123 . 109.5 no
C222 . O221 . H2211 . 100.5 no
O221 . C222 . H2221 . 108.4 no
O221 . C222 . H2222 . 111.3 no
H2221 . C222 . H2222 . 109.5 no
O221 . C222 . H2223 . 108.7 no
H2221 . C222 . H2223 . 109.5 no
H2222 . C222 . H2223 . 109.5 no
H2311 . O231 . H2312 . 124.1 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
C8 . H81 . C16 . 124.1(2) 0.925 2.495 3.109(12) yes
C8 . H81 . O174 . 131.5(3) 0.925 2.494 3.183(12) yes
C15 . H151 . O143 . 150.4(3) 0.919 2.539 3.369(12) yes
C18 . H181 . C28 . 120.9(2) 0.923 2.472 3.050(12) yes
C19 . H191 . O123 1_655 160.55(19) 0.934 2.575 3.470(12) yes
C26 . H261 . C36 . 120.3(2) 0.928 2.532 3.106(12) yes
C38 . H381 . C6 . 124.7(2) 0.929 2.478 3.102(12) yes
C55 . H551 . O231 . 138.0(5) 0.931 2.480 3.233(12) yes
C58 . H581 . C86 . 127.1(2) 0.936 2.459 3.114(12) yes
C59 . H591 . O174 . 167.4(4) 0.928 2.238 3.150(12) yes
C75 . H751 . O144 2_767 161.8(4) 0.932 2.275 3.173(12) yes
C76 . H761 . C66 . 126.4(3) 0.929 2.427 3.070(12) yes
C79 . H791 . O221 1_545 141.7(3) 0.936 2.470 3.256(12) yes
C85 . H851 . O113 1_655 131.1(2) 0.936 2.593 3.285(12) yes
C88 . H881 . C78 . 125.9(3) 0.928 2.462 3.099(12) yes
C202 . H2022 . O174 1_455 151.4(4) 0.950 2.443 3.309(12) yes
N31 . H311 . O113 1_565 179.1(2) 0.858 2.054 2.911(12) yes
N31 . H312 . O104 1_565 125.5(3) 0.871 2.329 2.922(12) yes
N32 . H321 . O112 1_565 167.0(3) 0.861 2.121 2.966(12) yes
N32 . H322 . O221 . 171.4(4) 0.861 1.995 2.849(12) yes
N21 . H211 . O152 2_776 128.9(3) 0.862 2.256 2.876(12) yes
N21 . H212 . O211 1_665 154.7(3) 0.858 2.508 3.304(12) yes
N22 . H221 . O154 2_776 149.3(3) 0.872 2.190 2.973(12) yes
N22 . H222 . N171 2_766 161.4(2) 0.864 2.566 3.396(12) yes
N22 . H222 . O172 2_766 160.8(3) 0.864 2.047 2.877(12) yes
N11 . H111 . O114 1_655 168.6(3) 0.858 2.139 2.985(12) yes
N11 . H112 . O142 . 168.9(3) 0.858 2.068 2.915(12) yes
N12 . H121 . O113 1_655 154.9(3) 0.859 2.100 2.900(12) yes
N12 . H122 . O201 1_655 164.7(3) 0.864 2.213 3.055(12) yes
N1 . H11 . O201 2_666 171.1(3) 0.856 2.080 2.928(12) yes
N1 . H12 . O123 2_666 136.6(2) 0.854 2.261 2.940(12) yes
N2 . H21 . O102 . 152.7(3) 0.860 2.278 3.067(12) yes
N2 . H22 . O152 2_666 162.0(3) 0.865 1.994 2.830(12) yes
N2 . H22 . O153 2_666 142.5(2) 0.865 2.528 3.258(12) yes
N62 . H621 . O112 2_767 142.6(3) 0.858 2.169 2.898(12) yes
N62 . H622 . O231 2_767 165.7(5) 0.862 2.154 2.997(12) yes
N61 . H611 . O134 2_767 171.1(4) 0.859 1.995 2.846(12) yes
N61 . H612 . O164 1_655 166.9(4) 0.866 2.284 3.134(12) yes
N81 . H811 . O162 1_645 124.1(4) 0.918 2.291 2.906(12) yes
N81 . H812 . N121 1_645 173.9(3) 0.858 2.576 3.430(12) yes
N81 . H812 . O123 1_645 147.1(2) 0.858 2.468 3.222(12) yes
N81 . H812 . O124 1_645 153.6(3) 0.858 2.058 2.852(12) yes
N82 . H821 . O211 1_655 151.3(3) 0.860 2.116 2.899(12) yes
N82 . H822 . O123 1_645 141.0(3) 0.871 2.402 3.126(12) yes
N82 . H822 . O153 1_645 122.6(3) 0.871 2.381 2.943(12) yes
N71 . H711 . O142 2_767 154.2(4) 0.864 2.239 3.040(12) yes
N71 . H712 . O164 2_667 162.7(3) 0.861 2.290 3.122(12) yes
N72 . H721 . O134 2_657 153.4(6) 0.964 1.932 2.827(12) yes
N52 . H521 . O122 . 147.3(3) 0.857 2.221 2.978(12) yes
N52 . H522 . O173 . 153.2(3) 0.851 2.587 3.368(12) yes
N52 . H522 . O174 . 152.1(3) 0.851 2.091 2.872(12) yes
N51 . H511 . O231 . 176.1(5) 0.869 2.216 3.084(12) yes
N51 . H512 . O124 . 146.4(3) 0.867 2.186 2.948(12) yes
O231 . H2311 . N161 . 148.8(3) 0.850 2.363 3.122(12) yes
O231 . H2311 . O163 . 178.6(6) 0.850 1.761 2.611(12) yes
O201 . H2011 . N101 . 151.1(2) 0.850 2.483 3.253(12) yes
O201 . H2011 . O103 . 179.8(3) 0.850 1.861 2.711(12) yes
O211 . H2111 . O104 . 179.9(3) 0.850 1.908 2.758(12) yes
O221 . H2211 . O162 . 179.5(3) 0.872 2.045 2.917(12) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 24/10/16 at 14:40:58
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
SUMFIX ELEMENT SCALES 
RIDE N   (   1,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE N   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE N   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE N   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE N   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE N   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE N   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE N   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE N   (  51,X'S) H   ( 511,X'S) H   ( 512,X'S) 
RIDE N   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE N   (  61,X'S) H   ( 611,X'S) H   ( 612,X'S) 
RIDE N   (  62,X'S) H   ( 621,X'S) H   ( 622,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) 
RIDE N   (  71,X'S) H   ( 711,X'S) H   ( 712,X'S) 
RIDE N   (  72,X'S) H   ( 721,X'S) H   ( 722,X'S) 
RIDE C   (  75,X'S) H   ( 751,X'S) 
RIDE C   (  76,X'S) H   ( 761,X'S) 
RIDE C   (  78,X'S) H   ( 781,X'S) 
RIDE C   (  79,X'S) H   ( 791,X'S) 
RIDE N   (  81,X'S) H   ( 811,X'S) H   ( 812,X'S) 
RIDE N   (  82,X'S) H   ( 821,X'S) H   ( 822,X'S) 
RIDE C   (  85,X'S) H   ( 851,X'S) 
RIDE C   (  86,X'S) H   ( 861,X'S) 
RIDE C   (  88,X'S) H   ( 881,X'S) 
RIDE C   (  89,X'S) H   ( 891,X'S) 
RIDE O   ( 201,X'S) H   (2011,X'S) 
RIDE C   ( 202,X'S) H   (2021,X'S) H   (2022,X'S) H   (2023,X'S) 
RIDE O   ( 211,X'S) H   (2111,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) H   (2122,X'S) H   (2123,X'S) 
RIDE O   ( 221,X'S) H   (2211,X'S) 
RIDE C   ( 222,X'S) H   (2221,X'S) H   (2222,X'S) H   (2223,X'S) 
RIDE O   ( 231,X'S) H   (2311,X'S) H   (2312,X'S) 
END 
;

_iucr_refine_instructions_details_restraints 
;                                                                       
#
# Punched on 24/10/16 at 14:40:58
#
#LIST     16                                                                    
REM 
REM MEOHS 
REM 
DIST 1.45, 0.01 = O(201) TO C(202), O(211) TO C(212) 
CONT O(221) TO C(222) 
REM 
REM NITRATES REM 
DIST 0, 0.01 = MEAN N(101) TO O(102), N(101) TO O(103) 
CONT N(101) TO O(104) 
CONT N(111) TO O(112), N(111) TO O(113) 
CONT N(111) TO O(114) 
CONT N(121) TO O(122), N(121) TO O(123) 
CONT N(121) TO O(124) 
CONT N(131) TO O(132), N(131) TO O(133) 
CONT N(131) TO O(134) 
CONT N(141) TO O(142), N(141) TO O(143) 
CONT N(141) TO O(144) 
CONT N(151) TO O(152), N(151) TO O(153) 
CONT N(151) TO O(154) 
CONT N(161) TO O(162), N(161) TO O(163) 
CONT N(161) TO O(164) 
CONT N(171) TO O(172), N(171) TO O(173) 
CONT N(171) TO O(174) 
PLANAR N(141) O(142) O(143) O(144) 
PLANAR N(161) O(162) O(163) O(164) 
ANGL 120, 1 = O(142) TO N(141) TO O(143) 
CONT O(142) TO N(141) TO O(144) 
CONT O(143) TO N(141) TO O(144) 
CONT O(162) TO N(161) TO O(163) 
CONT O(162) TO N(161) TO O(164) 
CONT O(163) TO N(161) TO O(164) 
REM 
REM PHENYLS 
REM 
DIST 0, 0.01 = MEAN C(4) TO C(5), C(5) TO C(6) 
CONT C(6) TO C(7), C(7) TO C(8) 
CONT C(8) TO C(9), C(9) TO C(4) 
CONT C(14) TO C(15), C(15) TO C(16) 
CONT C(16) TO C(17), C(17) TO C(18) 
CONT C(18) TO C(19), C(19) TO C(14) 
CONT C(24) TO C(25), C(25) TO C(26) 
CONT C(26) TO C(27), C(27) TO C(28) 
CONT C(28) TO C(29), C(29) TO C(24) 
CONT C(34) TO C(35), C(35) TO C(36) 
CONT C(36) TO C(37), C(37) TO C(38) 
CONT C(38) TO C(39), C(39) TO C(34) 
CONT C(54) TO C(55), C(55) TO C(56) 
CONT C(56) TO C(57), C(57) TO C(58) 
CONT C(58) TO C(59), C(59) TO C(54) 
CONT C(64) TO C(65), C(65) TO C(66) 
CONT C(66) TO C(67), C(67) TO C(68) 
CONT C(68) TO C(69), C(69) TO C(64) 
CONT C(74) TO C(75), C(75) TO C(76) 
CONT C(76) TO C(77), C(77) TO C(78) 
CONT C(78) TO C(79), C(79) TO C(74) 
CONT C(84) TO C(85), C(85) TO C(86) 
CONT C(86) TO C(87), C(87) TO C(88) 
CONT C(88) TO C(89), C(89) TO C(84) 
REM 
REM OTHER 
REM 
DIST 0, 0.01 = MEAN N(1) TO C(3), N(2) TO C(3) 
CONT N(11) TO C(13), N(12) TO C(13) 
CONT N(21) TO C(23), N(22) TO C(23) 
CONT N(31) TO C(33), N(32) TO C(33) 
CONT N(51) TO C(53), N(52) TO C(53) 
CONT N(61) TO C(63), N(62) TO C(63) 
CONT N(71) TO C(73), N(72) TO C(73) 
CONT N(81) TO C(83), N(82) TO C(83) 
DIST 0, 0.01 = MEAN C(3) TO C(4), C(13) TO C(14) 
CONT C(23) TO C(24), C(33) TO C(34) 
CONT C(53) TO C(54), C(63) TO C(64) 
CONT C(73) TO C(74), C(83) TO C(84) 
DIST 0, 0.01 = MEAN C(7) TO C(10), C(17) TO C(10) 
CONT C(27) TO C(10), C(37) TO C(10) 
CONT C(57) TO C(60), C(67) TO C(60) 
CONT C(77) TO C(60), C(87) TO C(60) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00100 = N(141) TO O(142) 
VIBR .0, 0.00100 = N(141) TO O(143) 
VIBR .0, 0.00100 = N(141) TO O(144) 
VIBR .0, 0.00200 = O(143) TO O(142) 
VIBR .0, 0.00200 = O(144) TO O(142) 
VIBR .0, 0.00200 = O(144) TO O(143) 
VIBR .0, 0.00100 = N(161) TO O(162) 
VIBR .0, 0.00100 = N(161) TO O(163) 
VIBR .0, 0.00100 = N(161) TO O(164) 
VIBR .0, 0.00200 = O(163) TO O(162) 
VIBR .0, 0.00200 = O(164) TO O(162) 
VIBR .0, 0.00200 = O(164) TO O(163) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.01000 = N(141) TO O(142) 
U(IJ) .0, 0.01000 = N(141) TO O(143) 
U(IJ) .0, 0.01000 = N(141) TO O(144) 
U(IJ) .0, 0.01000 = N(161) TO O(162) 
U(IJ) .0, 0.01000 = N(161) TO O(163) 
U(IJ) .0, 0.01000 = N(161) TO O(164) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-2 -3 1 x .
3 0 4 x .
-2 0 7 x .
-2 -1 6 x .
1 -2 6 x .
-2 2 0 x .
2 2 0 x .
1 -2 9 x .
-1 -2 7 x .
-2 -1 7 x .
-2 -2 8 x .
3 -2 6 x .
1 -1 8 x .
-2 2 2 x .
-1 -2 6 x .
-3 -2 8 x .
1 -2 9 x .
2 3 1 x .
-2 3 0 x .
-3 2 0 x .
-4 -5 11 x .
2 -2 6 x .
-5 -2 7 x .
-3 -4 9 x .
3 1 4 x .
-5 -4 9 x .
-5 -5 11 x .
-3 -3 13 x .
-4 -4 12 x .
4 2 1 x .
1 -4 12 x .
1 -3 12 x .
-3 3 0 x .
3 1 2 x .
-2 0 4 x .
-3 -2 9 x .
1 -3 10 x .
3 -4 10 x .
-4 -2 8 x .
-2 1 4 x .
-2 1 2 x .
-3 0 4 x .
####################################################################### 
# 
# 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_1OxBr
_database_code_depnum_ccdc_archive 'CCDC 1531019'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
#==============================================================================
# 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 0.250 0.250 0.076 62 13 ' '
2 0.750 0.750 0.924 62 13 ' '
_platon_squeeze_details          
;
;

_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          
;The asymmetric unit cell contains one quarter of the tetra-cationic ligand,
an oxalate anion located about a special position, and two bromide anions.
The symmetry of the system means the the formula of the framework is 
[L.oxalate.2Br].

A small amount of residual density remains, which could not be sensibly
modeled - this is located close to a four-fold rotation axis, and may
be due to a solvent water molecule located about this position. Attempts to 
include this electron density in the refinement using PLATON-SQUEEZE gave
non-sensible ellipsoids for the disordered oxalate anion, and so this was not 
performed.

The carbon atom from the disordered oxalate group has a relatively 
non-spherical ellipsoid, leading to a level B alert in checkCIF. No restraints
have been added to this, and the refinement proceeded smoothly regardless. 

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. N-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement., SQUEEZE
;

_cell_length_a                   12.07173(18)
_cell_length_b                   12.07173(18)
_cell_length_c                   11.3545(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1654.66(4)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 4/n '
_symmetry_space_group_name_Hall  '-P 4a'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-y+1/2,x,z
y+1/2,-x,-z
-x+1/2,-y+1/2,z
x+1/2,y+1/2,-z
y,-x+1/2,z
-y,x+1/2,-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 0.0181 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'
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            2

_chemical_formula_sum            'C31 H32 Br2 N8 O4'
_chemical_formula_moiety         'C29 H32 N8, 2(Br), C2 O4'
_chemical_compound_source        synthesized
_chemical_formula_weight         740.45

_cell_measurement_temperature    150
_cell_measurement_reflns_used    7794
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      73.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_max          0.09

_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    3.506

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            15992
_reflns_number_total             1673
_diffrn_reflns_av_R_equivalents  0.033

_diffrn_reflns_theta_min         3.893
_diffrn_reflns_theta_max         73.764
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        72.289
_diffrn_measured_fraction_theta_full 1.000

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.55
_oxford_diffrn_Wilson_scale      0.05

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.62
_refine_diff_density_max         2.36

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1665
_refine_ls_number_restraints     8
_refine_ls_number_parameters     120
_oxford_refine_ls_R_factor_ref   0.0754
_refine_ls_wR_factor_ref         0.1880
_refine_ls_goodness_of_fit_ref   1.0299
_refine_ls_shift/su_max          0.0001049
_refine_ls_shift/su_mean         0.0000106

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1665
_refine_ls_R_factor_all          0.0754
_refine_ls_wR_factor_all         0.1880

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1591
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_gt          0.1877

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.449E+04 0.729E+04 0.477E+04 0.236E+04 571. 
;

# 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
N1 N 0.4831(4) 0.4087(4) 0.3800(4) 0.0266 1.0000 Uani D . . . . .
N2 N 0.6314(4) 0.5152(4) 0.3299(4) 0.0309 1.0000 Uani D . . . . .
C3 C 0.5273(4) 0.4896(4) 0.3166(4) 0.0246 1.0000 Uani D . . . . .
C4 C 0.4578(4) 0.5513(4) 0.2326(4) 0.0234 1.0000 Uani . . . . . .
C5 C 0.3447(4) 0.5639(4) 0.2546(4) 0.0246 1.0000 Uani . . . . . .
C6 C 0.2803(4) 0.6271(4) 0.1797(5) 0.0253 1.0000 Uani . . . . . .
C7 C 0.3264(4) 0.6795(4) 0.0802(4) 0.0208 1.0000 Uani . . . . . .
C8 C 0.4384(4) 0.6634(4) 0.0576(4) 0.0230 1.0000 Uani . . . . . .
C9 C 0.5031(4) 0.6002(4) 0.1332(4) 0.0245 1.0000 Uani . . . . . .
C10 C 0.2500 0.7500 0.0000 0.0184 1.0000 Uani S T . . . .
Br1 Br 0.7500 0.7500 0.22178(10) 0.0324 1.0000 Uani S T . . . .
Br2 Br 0.2500 0.2500 0.34315(12) 0.0377 1.0000 Uani S T . . . .
O11 O 0.3910(3) 0.7331(4) 0.4794(3) 0.0341 1.0000 Uani . . . . . .
C12 C 0.2901(8) 0.6985(8) 0.4949(7) 0.0181 0.5000 Uani . . . . . .
H51 H 0.3130 0.5300 0.3193 0.0290 1.0000 Uiso R . . . . .
H61 H 0.2050 0.6349 0.1948 0.0301 1.0000 Uiso R . . . . .
H81 H 0.4699 0.6951 -0.0088 0.0280 1.0000 Uiso R . . . . .
H91 H 0.5774 0.5909 0.1174 0.0289 1.0000 Uiso R . . . . .
H22 H 0.657(3) 0.574(3) 0.297(5) 0.0371 1.0000 Uiso D . . . . .
H12 H 0.520(3) 0.377(4) 0.435(4) 0.0312 1.0000 Uiso D . . . . .
H21 H 0.670(2) 0.478(4) 0.379(5) 0.0370 1.0000 Uiso D . . . . .
H11 H 0.421(3) 0.381(4) 0.358(4) 0.0311 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.56(19)

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
N1 . C3 . 1.326(7) yes
N1 . H12 . 0.854(19) no
N1 . H11 . 0.858(19) no
N2 . C3 . 1.303(7) yes
N2 . H22 . 0.855(19) no
N2 . H21 . 0.857(19) no
C3 . C4 . 1.473(7) yes
C4 . C5 . 1.398(7) yes
C4 . C9 . 1.386(7) yes
C5 . C6 . 1.382(7) yes
C5 . H51 . 0.924 no
C6 . C7 . 1.409(7) yes
C6 . H61 . 0.929 no
C7 . C8 . 1.389(7) yes
C7 . C10 . 1.551(5) yes
C8 . C9 . 1.389(7) yes
C8 . H81 . 0.928 no
C9 . H91 . 0.922 no
O11 . C12 8_656 1.314(9) yes
O11 . C12 . 1.300(10) yes
C12 . C12 5_565 1.58(2) yes
C12 . C12 4_466 1.120(14) yes
C12 . C12 8_656 1.120(14) yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 . N1 . H12 . 120.7(18) no
C3 . N1 . H11 . 118.8(18) no
H12 . N1 . H11 . 120(3) no
C3 . N2 . H22 . 119.5(18) no
C3 . N2 . H21 . 118.5(18) no
H22 . N2 . H21 . 121(3) no
N1 . C3 . N2 . 120.0(5) yes
N1 . C3 . C4 . 119.7(5) yes
N2 . C3 . C4 . 120.3(5) yes
C3 . C4 . C5 . 119.7(5) yes
C3 . C4 . C9 . 121.3(5) yes
C5 . C4 . C9 . 119.0(4) yes
C4 . C5 . C6 . 120.0(5) yes
C4 . C5 . H51 . 119.9 no
C6 . C5 . H51 . 120.1 no
C5 . C6 . C7 . 121.2(4) yes
C5 . C6 . H61 . 119.5 no
C7 . C6 . H61 . 119.2 no
C6 . C7 . C8 . 118.0(4) yes
C6 . C7 . C10 . 118.8(4) yes
C8 . C7 . C10 . 123.2(4) yes
C7 . C8 . C9 . 120.6(4) yes
C7 . C8 . H81 . 119.5 no
C9 . C8 . H81 . 119.9 no
C8 . C9 . C4 . 121.1(5) yes
C8 . C9 . H91 . 119.6 no
C4 . C9 . H91 . 119.3 no
C7 4_465 C10 . C7 8_655 108.1(3) yes
C7 4_465 C10 . C7 5_565 110.16(17) yes
C7 8_655 C10 . C7 5_565 110.16(17) yes
C7 4_465 C10 . C7 . 110.16(17) yes
C7 8_655 C10 . C7 . 110.16(17) yes
C7 5_565 C10 . C7 . 108.1(3) yes
C12 8_656 O11 . C12 . 50.8(8) yes
C12 5_565 C12 . O11 4_466 109.1(9) yes
C12 5_565 C12 . O11 . 108.8(9) yes
O11 4_466 C12 . O11 . 141.7(8) yes
C12 5_565 C12 . C12 4_466 45.31(8) yes
O11 4_466 C12 . C12 4_466 64.0(9) yes
O11 . C12 . C12 4_466 154.1(9) yes
C12 5_565 C12 . C12 8_656 45.31(8) yes
O11 4_466 C12 . C12 8_656 148.5(9) yes
O11 . C12 . C12 8_656 65.3(9) yes
C12 4_466 C12 . C12 8_656 89.38(16) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C8 . H81 . C6 8_655 127.65(16) 0.928 2.489 3.143(7) yes
N1 . H12 . O11 2_666 161(6) 0.854 1.970 2.791(7) yes
N1 . H12 . C12 2_666 147(4) 0.854 2.594 3.345(7) yes
N2 . H21 . O11 3_655 175(6) 0.857 1.939 2.794(7) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 02/06/16 at 12:38:56
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   12 ) 
CONT H    (   22 ,X'S)  UNTIL H    (   11 ) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
END  
;

_iucr_refine_instructions_details_restraints 
;                                                                         
#
# Punched on 02/06/16 at 12:38:56
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(12) 
CONT N ( 1) TO H(11) 
REST 0.031, 0.002 = H(12,U[ISO]) 
REST 0.031, 0.002 = H(11,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 1) TO H(12) 
CONT C(3) TO N ( 1) TO H(11) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 2) TO H(22) 
CONT N ( 2) TO H(21) 
REST 0.037, 0.002 = H(22,U[ISO]) 
REST 0.037, 0.002 = H(21,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 2) TO H(22) 
CONT C(3) TO N ( 2) TO H(21) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_1Br
_database_code_depnum_ccdc_archive 'CCDC 1531016'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
#==============================================================================
# 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 -0.003 -0.001 0.003 685 172 ' '
_platon_squeeze_details          
;
;

_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          
;A region of diffuse electron density is present, which appears to result
from disordered ethanol/water solvent molecules. It was not possible to 
refine this sensibly, and so PLATON-SQUEEZE was used to include this
electron density in the refinement.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. N-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement., SQUEEZE
;

_cell_length_a                   13.3818(3)
_cell_length_b                   7.12090(10)
_cell_length_c                   21.9744(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.8782(19)
_cell_angle_gamma                90
_cell_volume                     2082.94(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 2/n '
_symmetry_space_group_name_Hall  '-P 2yac'

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 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'
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'
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            2

_chemical_formula_sum            'C29 H32 Br4 N8'
_chemical_formula_moiety         'C29 H32 N8, 4(Br)'
_chemical_compound_source        synthesized
_chemical_formula_weight         812.24

_cell_measurement_reflns_used    10501
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      73.4
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.31

_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    4.917

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            23995
_reflns_number_total             4221
_diffrn_reflns_av_R_equivalents  0.040

_diffrn_reflns_theta_min         3.707
_diffrn_reflns_theta_max         74.315
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        72.829
_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_oxford_diffrn_Wilson_B_factor   2.87
_oxford_diffrn_Wilson_scale      0.11

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.57
_refine_diff_density_max         1.43

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     16
_refine_ls_number_parameters     213
_oxford_refine_ls_R_factor_ref   0.0417
_refine_ls_wR_factor_ref         0.1014
_refine_ls_goodness_of_fit_ref   0.9495
_refine_ls_shift/su_max          0.0009567
_refine_ls_shift/su_mean         0.0000443

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4221
_refine_ls_R_factor_all          0.0417
_refine_ls_wR_factor_all         0.1014

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3849
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_gt          0.0974

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.196E+04 0.329E+04 0.203E+04 852. 196. 
;

# 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
N1 N 0.91667(18) -0.5699(4) 0.54902(11) 0.0347 1.0000 Uani D . . . . .
N2 N 0.74831(19) -0.5844(4) 0.52064(11) 0.0389 1.0000 Uani D . . . . .
C3 C 0.8250(2) -0.5149(4) 0.55503(12) 0.0272 1.0000 Uani D . . . . .
C4 C 0.80706(18) -0.3759(4) 0.60317(10) 0.0226 1.0000 Uani . . . . . .
C5 C 0.87765(18) -0.2408(4) 0.62198(11) 0.0243 1.0000 Uani . . . . . .
C6 C 0.86103(18) -0.1142(3) 0.66828(10) 0.0219 1.0000 Uani . . . . . .
C7 C 0.77240(17) -0.1203(3) 0.69667(10) 0.0193 1.0000 Uani . . . . . .
C8 C 0.70167(17) -0.2578(3) 0.67764(10) 0.0214 1.0000 Uani . . . . . .
C9 C 0.71760(18) -0.3832(3) 0.63120(10) 0.0224 1.0000 Uani . . . . . .
C10 C 0.7500 0.0109(4) 0.7500 0.0184 1.0000 Uani S T . . . .
N11 N 0.40745(19) 0.6070(4) 0.62999(10) 0.0353 1.0000 Uani D . . . . .
N12 N 0.37701(19) 0.6198(4) 0.73009(10) 0.0344 1.0000 Uani D . . . . .
C13 C 0.42553(19) 0.5482(4) 0.68662(11) 0.0271 1.0000 Uani D . . . . .
C14 C 0.50405(17) 0.4046(4) 0.70231(10) 0.0224 1.0000 Uani . . . . . .
C15 C 0.52685(18) 0.2707(4) 0.65971(10) 0.0253 1.0000 Uani . . . . . .
C16 C 0.60428(18) 0.1406(4) 0.67426(10) 0.0239 1.0000 Uani . . . . . .
C17 C 0.66031(16) 0.1432(3) 0.73141(10) 0.0187 1.0000 Uani . . . . . .
C18 C 0.63656(17) 0.2794(3) 0.77320(10) 0.0223 1.0000 Uani . . . . . .
C19 C 0.55987(18) 0.4072(4) 0.75981(11) 0.0231 1.0000 Uani . . . . . .
Br1 Br 0.5000 0.5000 0.5000 0.0358 1.0000 Uani S . . . . .
Br2 Br 0.86304(2) -0.52965(5) 0.375527(13) 0.0361 1.0000 Uani . . . . . .
Br3 Br 1.0000 0.0000 0.5000 0.1014 1.0000 Uani S . . . . .
H51 H 0.9380 -0.2354 0.6045 0.0301 1.0000 Uiso R . . . . .
H61 H 0.9122 -0.0286 0.6802 0.0278 1.0000 Uiso R . . . . .
H81 H 0.6404 -0.2672 0.6952 0.0259 1.0000 Uiso R . . . . .
H91 H 0.6679 -0.4748 0.6186 0.0272 1.0000 Uiso R . . . . .
H151 H 0.4912 0.2658 0.6203 0.0311 1.0000 Uiso R . . . . .
H161 H 0.6212 0.0515 0.6447 0.0275 1.0000 Uiso R . . . . .
H181 H 0.6720 0.2845 0.8126 0.0268 1.0000 Uiso R . . . . .
H191 H 0.5431 0.4989 0.7888 0.0276 1.0000 Uiso R . . . . .
H12 H 0.9655(16) -0.541(5) 0.5752(12) 0.0412 1.0000 Uiso D . . . . .
H112 H 0.443(2) 0.568(5) 0.6026(10) 0.0411 1.0000 Uiso D . . . . .
H122 H 0.381(2) 0.571(4) 0.7656(9) 0.0411 1.0000 Uiso D . . . . .
H111 H 0.358(2) 0.682(4) 0.6195(11) 0.0416 1.0000 Uiso D . . . . .
H22 H 0.7581(18) -0.666(4) 0.4930(13) 0.0464 1.0000 Uiso D . . . . .
H23 H 0.9285(17) -0.655(4) 0.5217(13) 0.0415 1.0000 Uiso D . . . . .
H21 H 0.6907(15) -0.533(4) 0.5211(15) 0.0457 1.0000 Uiso D . . . . .
H121 H 0.332(2) 0.707(4) 0.7235(11) 0.0419 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.15(3)

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
N1 . C3 . 1.307(4) yes
N1 . H12 . 0.850(18) no
N1 . H23 . 0.880(18) no
N2 . C3 . 1.308(4) yes
N2 . H22 . 0.860(18) no
N2 . H21 . 0.853(18) no
C3 . C4 . 1.487(3) yes
C4 . C5 . 1.382(4) yes
C4 . C9 . 1.402(3) yes
C5 . C6 . 1.394(3) yes
C5 . H51 . 0.930 no
C6 . C7 . 1.396(3) yes
C6 . H61 . 0.934 no
C7 . C8 . 1.396(3) yes
C7 . C10 . 1.552(3) yes
C8 . C9 . 1.389(3) yes
C8 . H81 . 0.945 no
C9 . H91 . 0.952 no
C10 . C17 4_656 1.547(3) yes
C10 . C17 . 1.547(3) yes
N11 . C13 . 1.312(3) yes
N11 . H112 . 0.848(18) no
N11 . H111 . 0.860(18) no
N12 . C13 . 1.312(3) yes
N12 . H122 . 0.851(18) no
N12 . H121 . 0.863(18) no
C13 . C14 . 1.481(3) yes
C14 . C15 . 1.392(3) yes
C14 . C19 . 1.401(3) yes
C15 . C16 . 1.402(3) yes
C15 . H151 . 0.945 no
C16 . C17 . 1.395(3) yes
C16 . H161 . 0.952 no
C17 . C18 . 1.395(3) yes
C18 . C19 . 1.381(3) yes
C18 . H181 . 0.944 no
C19 . H191 . 0.955 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
C3 . N1 . H12 . 121.6(16) no
C3 . N1 . H23 . 120.8(15) no
H12 . N1 . H23 . 117(2) no
C3 . N2 . H22 . 119.7(16) no
C3 . N2 . H21 . 119.3(16) no
H22 . N2 . H21 . 120(2) no
N2 . C3 . N1 . 121.2(3) yes
N2 . C3 . C4 . 119.2(2) yes
N1 . C3 . C4 . 119.6(2) yes
C3 . C4 . C5 . 121.4(2) yes
C3 . C4 . C9 . 119.7(2) yes
C5 . C4 . C9 . 118.9(2) yes
C4 . C5 . C6 . 120.9(2) yes
C4 . C5 . H51 . 120.0 no
C6 . C5 . H51 . 119.1 no
C5 . C6 . C7 . 120.8(2) yes
C5 . C6 . H61 . 117.3 no
C7 . C6 . H61 . 121.8 no
C6 . C7 . C8 . 118.0(2) yes
C6 . C7 . C10 . 123.87(19) yes
C8 . C7 . C10 . 118.11(18) yes
C7 . C8 . C9 . 121.4(2) yes
C7 . C8 . H81 . 121.2 no
C9 . C8 . H81 . 117.4 no
C4 . C9 . C8 . 120.1(2) yes
C4 . C9 . H91 . 120.0 no
C8 . C9 . H91 . 120.0 no
C17 4_656 C10 . C7 . 111.17(11) yes
C17 4_656 C10 . C7 4_656 111.82(11) yes
C7 . C10 . C7 4_656 106.0(2) yes
C17 4_656 C10 . C17 . 105.0(2) yes
C7 . C10 . C17 . 111.82(11) yes
C7 4_656 C10 . C17 . 111.17(11) yes
C13 . N11 . H112 . 120.6(16) no
C13 . N11 . H111 . 121.0(15) no
H112 . N11 . H111 . 118(2) no
C13 . N12 . H122 . 121.6(16) no
C13 . N12 . H121 . 122.8(15) no
H122 . N12 . H121 . 115(2) no
N12 . C13 . N11 . 120.7(2) yes
N12 . C13 . C14 . 119.4(2) yes
N11 . C13 . C14 . 119.9(2) yes
C13 . C14 . C15 . 121.0(2) yes
C13 . C14 . C19 . 120.1(2) yes
C15 . C14 . C19 . 118.8(2) yes
C14 . C15 . C16 . 120.5(2) yes
C14 . C15 . H151 . 121.0 no
C16 . C15 . H151 . 118.5 no
C15 . C16 . C17 . 120.9(2) yes
C15 . C16 . H161 . 120.4 no
C17 . C16 . H161 . 118.7 no
C10 . C17 . C16 . 124.10(19) yes
C10 . C17 . C18 . 118.20(19) yes
C16 . C17 . C18 . 117.6(2) yes
C17 . C18 . C19 . 122.2(2) yes
C17 . C18 . H181 . 120.2 no
C19 . C18 . H181 . 117.6 no
C14 . C19 . C18 . 120.0(2) yes
C14 . C19 . H191 . 118.0 no
C18 . C19 . H191 . 122.0 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
C16 . H161 . C8 . 120.65(7) 0.952 2.525 3.120(3) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 23/10/16 at 20:14:50
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL BR   (    3 ) 
CONT H    (   12 ,X'S)  UNTIL H    (  121 ) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,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   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
END        
;

_iucr_refine_instructions_details_restraints 
;                                                                     
#
# Punched on 23/10/16 at 20:14:50
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(12) 
CONT N ( 1) TO H(23) 
REST 0.042, 0.002 = H(12,U[ISO]) 
REST 0.042, 0.002 = H(23,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 1) TO H(12) 
CONT C(3) TO N ( 1) TO H(23) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 2) TO H(22) 
CONT N ( 2) TO H(21) 
REST 0.047, 0.002 = H(22,U[ISO]) 
REST 0.047, 0.002 = H(21,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 2) TO H(22) 
CONT C(3) TO N ( 2) TO H(21) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 11) TO H(112) 
CONT N ( 11) TO H(111) 
REST 0.042, 0.002 = H(112,U[ISO]) 
REST 0.042, 0.002 = H(111,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(13) TO N ( 11) TO H(112) 
CONT C(13) TO N ( 11) TO H(111) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 12) TO H(122) 
CONT N ( 12) TO H(121) 
REST 0.041, 0.002 = H(122,U[ISO]) 
REST 0.041, 0.002 = H(121,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(13) TO N ( 12) TO H(122) 
CONT C(13) TO N ( 12) TO H(121) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_1Cl
_database_code_depnum_ccdc_archive 'CCDC 1531015'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
#==============================================================================
# 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 0.250 0.250 0.029 51 12 ' '
2 0.250 0.250 0.529 51 12 ' '
3 0.250 0.250 0.769 24 8 ' '
4 0.249 0.250 0.269 24 8 ' '
5 0.250 0.750 0.182 7 1 ' '
6 0.250 0.750 0.318 7 1 ' '
7 0.250 0.750 0.682 7 1 ' '
8 0.250 0.750 0.818 7 1 ' '
9 0.750 0.750 0.971 51 12 ' '
10 0.750 0.750 0.471 51 12 ' '
11 0.750 0.750 0.231 24 8 ' '
12 0.750 0.750 0.731 24 8 ' '
13 0.750 0.250 0.182 7 1 ' '
14 0.750 0.250 0.318 7 1 ' '
15 0.750 0.250 0.682 7 1 ' '
16 0.750 0.250 0.818 7 1 ' '
_platon_squeeze_details          
;
;

_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          
;A small amount of diffuse density remains, which could not be sensibly
modeled, and so PLATON-SQUEEZE was used to include this in the model.
Even with this, there is significant electron density located close to
each of the chloride anions (1.1 - 1.3 A away). This may be due to positional 
disorder, with a second position being present for each of the chloride anions.
Unfortunately, it was not possible to model this successfully. 

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. N-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement., SQUEEZE
;

_cell_length_a                   11.7352(2)
_cell_length_b                   11.7352(2)
_cell_length_c                   25.3812(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3495.39(18)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 4/n c c '
_symmetry_space_group_name_Hall  '-P 4a 2ac'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-y,-x,-z+1/2
y,x,z+1/2
x+1/2,-y,-z+1/2
-x+1/2,y,z+1/2
y+1/2,x+1/2,-z+1/2
-y+1/2,-x+1/2,z+1/2
y+1/2,-x,-z
-y+1/2,x,z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
-y,x+1/2,-z
y,-x+1/2,z
-x+1/2,-y+1/2,z
x+1/2,y+1/2,-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 0.0181 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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 '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

_chemical_formula_sum            'C29 H32 Cl4 N8'
_chemical_formula_moiety         'C29 H32 N8, 4(Cl)'
_chemical_compound_source        synthesized
_chemical_formula_weight         634.44

_cell_measurement_reflns_used    4671
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      73.40
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_max          0.19

_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1320
_exptl_absorpt_coefficient_mu    3.315

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            16382
_reflns_number_total             1781
_diffrn_reflns_av_R_equivalents  0.038

_diffrn_reflns_theta_min         3.483
_diffrn_reflns_theta_max         73.761
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        73.761
_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              0
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   2.83
_oxford_diffrn_Wilson_scale      0.33

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.67
_refine_diff_density_max         2.48

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1517
_refine_ls_number_restraints     8
_refine_ls_number_parameters     111
_oxford_refine_ls_R_factor_ref   0.1458
_refine_ls_wR_factor_ref         0.2419
_refine_ls_goodness_of_fit_ref   1.0381
_refine_ls_shift/su_max          0.0012904
_refine_ls_shift/su_mean         0.0001516

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1517
_refine_ls_R_factor_all          0.1458
_refine_ls_wR_factor_all         0.2419

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1449
_refine_ls_R_factor_gt           0.1440
_refine_ls_wR_factor_gt          0.2413

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.313E+04 0.471E+04 0.235E+04 601. 
;

# 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
N1 N 0.3634(7) 0.4863(6) 0.3480(3) 0.0539 1.0000 Uani D . . . . .
N2 N 0.5141(6) 0.5967(6) 0.3287(3) 0.0481 1.0000 Uani D . . . . .
C3 C 0.4688(7) 0.5158(6) 0.3554(2) 0.0323 1.0000 Uani D . . . . .
C4 C 0.5383(6) 0.4544(6) 0.3948(2) 0.0262 1.0000 Uani . . . . . .
C5 C 0.4904(6) 0.4048(6) 0.4401(3) 0.0327 1.0000 Uani . . . . . .
C6 C 0.5574(6) 0.3392(6) 0.4738(3) 0.0300 1.0000 Uani . . . . . .
C7 C 0.6721(5) 0.3233(5) 0.4641(2) 0.0191 1.0000 Uani . . . . . .
C8 C 0.7198(6) 0.3739(6) 0.4196(3) 0.0331 1.0000 Uani . . . . . .
C9 C 0.6527(6) 0.4363(6) 0.3853(3) 0.0359 1.0000 Uani . . . . . .
C10 C 0.7500 0.2500 0.5000 0.0249 1.0000 Uani S T . . . .
Cl2 Cl 0.7500 0.7500 0.35608(18) 0.0546 1.0000 Uani S T . . . .
Cl1 Cl 0.2500 0.2500 0.3938(2) 0.0553 1.0000 Uani S T . . . .
Cl3 Cl 0.5404(3) 0.2934(3) 0.25414(13) 0.0436 0.5000 Uani . . . . . .
H51 H 0.4138 0.4170 0.4478 0.0383 1.0000 Uiso R . . . . .
H61 H 0.5224 0.3030 0.5020 0.0371 1.0000 Uiso R . . . . .
H81 H 0.7977 0.3634 0.4130 0.0348 1.0000 Uiso R . . . . .
H91 H 0.6850 0.4668 0.3549 0.0411 1.0000 Uiso R . . . . .
H11 H 0.345(3) 0.416(2) 0.351(4) 0.0592 1.0000 Uiso D . . . . .
H12 H 0.321(3) 0.524(5) 0.326(3) 0.0589 1.0000 Uiso D . . . . .
H21 H 0.582(3) 0.619(6) 0.336(3) 0.0552 1.0000 Uiso D . . . . .
H22 H 0.471(2) 0.639(5) 0.310(3) 0.0551 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.17(19)

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
N1 . C3 . 1.298(11) yes
N1 . H11 . 0.86(2) no
N1 . H12 . 0.86(2) no
N2 . C3 . 1.281(10) yes
N2 . H21 . 0.86(2) no
N2 . H22 . 0.854(19) no
C3 . C4 . 1.478(8) yes
C4 . C5 . 1.407(9) yes
C4 . C9 . 1.380(10) yes
C5 . C6 . 1.393(10) yes
C5 . H51 . 0.931 no
C6 . C7 . 1.381(9) yes
C6 . H61 . 0.928 no
C7 . C8 . 1.395(10) yes
C7 . C10 . 1.551(6) yes
C8 . C9 . 1.382(10) yes
C8 . H81 . 0.937 no
C9 . H91 . 0.932 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
C3 . N1 . H11 . 119.1(19) no
C3 . N1 . H12 . 120.6(19) no
H11 . N1 . H12 . 113(5) no
C3 . N2 . H21 . 120.2(19) no
C3 . N2 . H22 . 118.7(19) no
H21 . N2 . H22 . 119(4) no
N1 . C3 . N2 . 121.1(6) yes
N1 . C3 . C4 . 119.5(7) yes
N2 . C3 . C4 . 119.4(7) yes
C3 . C4 . C5 . 122.3(6) yes
C3 . C4 . C9 . 119.6(6) yes
C5 . C4 . C9 . 117.9(6) yes
C4 . C5 . C6 . 120.3(6) yes
C4 . C5 . H51 . 119.5 no
C6 . C5 . H51 . 120.1 no
C5 . C6 . C7 . 121.0(6) yes
C5 . C6 . H61 . 118.5 no
C7 . C6 . H61 . 120.4 no
C6 . C7 . C8 . 118.6(6) yes
C6 . C7 . C10 . 123.0(5) yes
C8 . C7 . C10 . 118.4(5) yes
C7 . C8 . C9 . 120.5(7) yes
C7 . C8 . H81 . 118.7 no
C9 . C8 . H81 . 120.9 no
C8 . C9 . C4 . 121.7(7) yes
C8 . C9 . H91 . 119.5 no
C4 . C9 . H91 . 118.7 no
C7 13_646 C10 . C7 . 110.2(2) yes
C7 13_646 C10 . C7 9_566 108.1(4) yes
C7 . C10 . C7 9_566 110.2(2) yes
C7 13_646 C10 . C7 15_655 110.2(2) yes
C7 . C10 . C7 15_655 108.1(4) yes
C7 9_566 C10 . C7 15_655 110.2(2) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H61 . C8 13_646 124.8(2) 0.928 2.530 3.153(9) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 31/05/16 at 16:20:37
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL CL   (    3 ) 
CONT H    (   11 ,X'S)  UNTIL H    (   22 ) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
END 
;

_iucr_refine_instructions_details_restraints 
;                                                                            
#
# Punched on 31/05/16 at 16:20:37
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(11) 
CONT N ( 1) TO H(12) 
REST 0.059, 0.002 = H(11,U[ISO]) 
REST 0.059, 0.002 = H(12,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 1) TO H(11) 
CONT C(3) TO N ( 1) TO H(12) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 2) TO H(21) 
CONT N ( 2) TO H(22) 
REST 0.055, 0.002 = H(21,U[ISO]) 
REST 0.055, 0.002 = H(22,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 2) TO H(21) 
CONT C(3) TO N ( 2) TO H(22) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 0 6 x .
3 3 4 x .
1 1 8 x .
0 0 8 x .
2 2 0 x .
0 0 10 x .
2 2 2 x .
0 3 12 x .
1 2 8 x .
1 2 5 x .
