# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1977346'
loop_
_audit_author_name
_audit_author_address
'Guillaume Pilet'
;UCBL
France
;
_audit_update_record             
;
2020-04-29 deposited with the CCDC.	2020-07-03 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          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   8.0075(11)
_cell_length_b                   17.5214(17)
_cell_length_c                   27.658(4)
_cell_angle_alpha                90.0
_cell_angle_beta                 94.252(11)
_cell_angle_gamma                90.0
_cell_volume                     3869.8(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 1 2/a 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z+1/2
-x+1/2,-y+1/2,-z+1/2
-x+1/2,y,-z
x+1/2,-y,z
-x+1,y+1/2,-z+1/2
x+1,-y+1/2,z+1/2

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


_cell_formula_units_Z            4

# Given Formula = C37 H31 Br2 N3 O6 
# Dc =      1.33 Fooo =   1568.00 Mu =     21.40 M =    773.48
# Found Formula = C40.67 H37.99 Br2 N3 O6.67 
# Dc =      1.43 FOOO =   1705.28 Mu =     21.47 M =    835.23

_chemical_formula_sum            'C40.67 H38 Br2 N3 O6.67'
_chemical_formula_moiety         'C40.67 H38 Br2 N3 O6.67'
_chemical_compound_source        .
_chemical_formula_weight         835.23


_cell_measurement_reflns_used    4061
_cell_measurement_theta_min      4
_cell_measurement_theta_max      29
_cell_measurement_temperature    100

_exptl_crystal_description       needle
_exptl_crystal_colour            dark
_exptl_crystal_size_min          0.033
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_max          0.692

_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1705.281
_exptl_absorpt_coefficient_mu    2.147

# Sheldrick geometric approximatio 0.73 0.93 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_T_max  0.93
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            14248
_reflns_number_total             4753
_diffrn_reflns_av_R_equivalents  0.044
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4753 
# Theoretical number of reflections is about 10980 


_diffrn_reflns_theta_min         2.803
_diffrn_reflns_theta_max         29.697
_diffrn_measured_fraction_theta_max 0.967

_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.989


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -11
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              37

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -1.03
_refine_diff_density_max         1.48


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


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_restraints     39
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3600
_oxford_refine_ls_R_factor_ref   0.0613
_refine_ls_wR_factor_ref         0.0902
_refine_ls_goodness_of_fit_ref   1.3822
_refine_ls_shift/su_max          0.0005113
_refine_ls_shift/su_mean         0.0000193


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3601
_refine_ls_R_factor_all          0.0616
_refine_ls_wR_factor_all         0.0917

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3601
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_gt          0.0917


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 15.3 11.8 12.5 4.58 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.52281(6) 0.18480(2) 0.348421(17) 0.0302 1.0000 Uani . U . . . .
C2 C 0.4966(6) 0.2855(2) 0.37331(16) 0.0245 1.0000 Uani . . . . . .
C3 C 0.5782(6) 0.3446(2) 0.35267(16) 0.0251 1.0000 Uani . . . . . .
C4 C 0.5569(6) 0.4176(2) 0.36963(15) 0.0237 1.0000 Uani . . . . . .
C5 C 0.4544(5) 0.4314(2) 0.40784(15) 0.0198 1.0000 Uani . . . . . .
C6 C 0.3769(5) 0.3690(2) 0.42848(16) 0.0227 1.0000 Uani . . . . . .
C7 C 0.3959(5) 0.2959(2) 0.41112(16) 0.0242 1.0000 Uani . . . . . .
H71 H 0.3421 0.2542 0.4242 0.0291 1.0000 Uiso R . . . . .
H61 H 0.3111 0.3779 0.4554 0.0269 1.0000 Uiso R . . . . .
C8 C 0.4288(5) 0.5088(2) 0.42455(15) 0.0205 1.0000 Uani D . . . . .
N9 N 0.3389(4) 0.52495(19) 0.46232(12) 0.0191 1.0000 Uani D . . . . .
C10 C 0.3323(5) 0.6040(2) 0.46744(14) 0.0199 1.0000 Uani D . . . . .
N11 N 0.2500 0.6404(3) 0.5000 0.0182 1.0000 Uani S T . . . .
C12 C 0.4261(5) 0.6379(2) 0.43025(14) 0.0193 1.0000 Uani . . . . . .
C13 C 0.4854(5) 0.5776(2) 0.40414(15) 0.0212 1.0000 Uani . . . . . .
H131 H 0.5504 0.5809 0.3774 0.0250 1.0000 Uiso R . . . . .
C14 C 0.4503(5) 0.7189(2) 0.41969(15) 0.0203 1.0000 Uani . . . . . .
C15 C 0.4490(5) 0.7749(2) 0.45527(15) 0.0216 1.0000 Uani . . . . . .
C16 C 0.4756(5) 0.8511(2) 0.44265(16) 0.0224 1.0000 Uani . . . . . .
O17 O 0.4747(4) 0.91088(17) 0.47413(12) 0.0270 1.0000 Uani . . . . . .
C18 C 0.4757(7) 0.8934(3) 0.52438(16) 0.0309 1.0000 Uani . . . . . .
H181 H 0.4744 0.9399 0.5423 0.0459 1.0000 Uiso R . . . . .
H182 H 0.5760 0.8649 0.5338 0.0461 1.0000 Uiso R . . . . .
H183 H 0.3775 0.8638 0.5301 0.0459 1.0000 Uiso R . . . . .
C19 C 0.5026(5) 0.8712(2) 0.39538(15) 0.0212 1.0000 Uani . . . . . .
O20 O 0.5192(4) 0.94635(17) 0.38266(12) 0.0251 1.0000 Uani . . . . . .
C21 C 0.6869(6) 0.9735(3) 0.3880(2) 0.0356 1.0000 Uani . . . . . .
H211 H 0.6916 1.0257 0.3772 0.0549 1.0000 Uiso R . . . . .
H212 H 0.7287 0.9708 0.4211 0.0550 1.0000 Uiso R . . . . .
H213 H 0.7592 0.9427 0.3687 0.0547 1.0000 Uiso R . . . . .
C22 C 0.5061(5) 0.8145(2) 0.35993(16) 0.0226 1.0000 Uani . . . . . .
C23 C 0.4804(5) 0.7386(2) 0.37207(16) 0.0236 1.0000 Uani . . . . . .
H231 H 0.4816 0.7009 0.3483 0.0279 1.0000 Uiso R . . . . .
O24 O 0.5350(5) 0.83919(19) 0.31468(12) 0.0312 1.0000 Uani . . . . . .
C25 C 0.5428(9) 0.7821(3) 0.27836(19) 0.0444 1.0000 Uani . . . . . .
H251 H 0.5681 0.8053 0.2480 0.0689 1.0000 Uiso R . . . . .
H252 H 0.6298 0.7461 0.2879 0.0688 1.0000 Uiso R . . . . .
H253 H 0.4368 0.7556 0.2734 0.0688 1.0000 Uiso R . . . . .
H151 H 0.4299 0.7616 0.4881 0.0259 1.0000 Uiso R . . . . .
H91 H 0.297(11) 0.4921(12) 0.481(2) 0.021(2) 0.5000 Uiso D . . . . .
H41 H 0.6114 0.4585 0.3558 0.0271 1.0000 Uiso R . . . . .
H31 H 0.6493 0.3347 0.3278 0.0281 1.0000 Uiso R . . . . .
O1 O 0.0175(14) 0.5047(6) 0.2416(4) 0.0472 0.3333 Uani D U . . . .
C1 C -0.1056(13) 0.3969(7) 0.2744(5) 0.0307 0.3333 Uani D U . . . .
C9 C -0.1690(14) 0.5176(6) 0.2508(5) 0.0302 0.3333 Uani D U . . . .
C11 C 0.0588(14) 0.4292(6) 0.2692(5) 0.0311 0.3333 Uani D U . . . .
C17 C -0.2351(16) 0.4406(5) 0.2474(5) 0.0311 0.3333 Uani D U . . . .
H111 H 0.1092 0.4401 0.3006 0.0368 0.3100 Uiso R . . . . .
H112 H 0.1304 0.3962 0.2528 0.0368 0.3100 Uiso R . . . . .
H11 H -0.1296 0.3938 0.3075 0.0362 0.3150 Uiso R . . . . .
H12 H -0.1050 0.3470 0.2609 0.0362 0.3150 Uiso R . . . . .
H171 H -0.3371 0.4369 0.2627 0.0363 0.3150 Uiso R . . . . .
H172 H -0.2527 0.4247 0.2146 0.0363 0.3150 Uiso R . . . . .
H92 H -0.1794 0.5385 0.2823 0.0356 0.3067 Uiso R . . . . .
H93 H -0.2225 0.5514 0.2273 0.0356 0.3067 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.264(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
Br1 . C2 . 1.911(4) yes
C2 . C3 . 1.371(7) yes
C2 . C7 . 1.379(7) yes
C3 . C4 . 1.377(6) yes
C3 . H31 . 0.941 no
C4 . C5 . 1.407(6) yes
C4 . H41 . 0.936 no
C5 . C6 . 1.399(6) yes
C5 . C8 . 1.451(5) yes
C6 . C7 . 1.381(6) yes
C6 . H61 . 0.956 no
C7 . H71 . 0.935 no
C8 . N9 . 1.342(6) yes
C8 . C13 . 1.421(6) yes
N9 . C10 . 1.393(5) yes
N9 . H91 . 0.86(2) no
C10 . N11 . 1.320(5) yes
C10 . C12 . 1.446(6) yes
C12 . C13 . 1.384(6) yes
C12 . C14 . 1.465(6) yes
C13 . H131 . 0.937 no
C14 . C15 . 1.390(6) yes
C14 . C23 . 1.400(6) yes
C15 . C16 . 1.401(6) yes
C15 . H151 . 0.961 no
C16 . O17 . 1.363(5) yes
C16 . C19 . 1.386(6) yes
O17 . C18 . 1.423(6) yes
C18 . H181 . 0.954 no
C18 . H182 . 0.965 no
C18 . H183 . 0.964 no
C19 . O20 . 1.372(5) yes
C19 . C22 . 1.398(6) yes
O20 . C21 . 1.421(6) yes
C21 . H211 . 0.963 no
C21 . H212 . 0.954 no
C21 . H213 . 0.978 no
C22 . C23 . 1.390(6) yes
C22 . O24 . 1.360(5) yes
C23 . H231 . 0.933 no
O24 . C25 . 1.423(7) yes
C25 . H251 . 0.968 no
C25 . H252 . 0.962 no
C25 . H253 . 0.968 no
O1 . C9 . 1.5500(13) yes
O1 . C11 . 1.5500(11) yes
C1 . C11 . 1.4500(13) yes
C1 . C17 . 1.4500(11) yes
C1 . H11 . 0.951 no
C1 . H12 . 0.951 no
C9 . C17 . 1.4501(11) yes
C9 . H92 . 0.954 no
C9 . H93 . 0.956 no
C11 . H111 . 0.949 no
C11 . H112 . 0.954 no
C17 . H171 . 0.949 no
C17 . H172 . 0.949 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C2 . C3 . 118.6(3) yes
Br1 . C2 . C7 . 118.8(3) yes
C3 . C2 . C7 . 122.6(4) yes
C2 . C3 . C4 . 119.0(4) yes
C2 . C3 . H31 . 119.9 no
C4 . C3 . H31 . 121.1 no
C3 . C4 . C5 . 120.6(4) yes
C3 . C4 . H41 . 120.0 no
C5 . C4 . H41 . 119.3 no
C4 . C5 . C6 . 118.2(4) yes
C4 . C5 . C8 . 120.3(4) yes
C6 . C5 . C8 . 121.5(4) yes
C5 . C6 . C7 . 121.3(4) yes
C5 . C6 . H61 . 118.5 no
C7 . C6 . H61 . 120.2 no
C6 . C7 . C2 . 118.2(4) yes
C6 . C7 . H71 . 121.7 no
C2 . C7 . H71 . 120.1 no
C5 . C8 . N9 . 122.8(4) yes
C5 . C8 . C13 . 127.6(4) yes
N9 . C8 . C13 . 109.6(4) yes
C8 . N9 . C10 . 108.4(3) yes
C8 . N9 . H91 . 125.8(14) no
C10 . N9 . H91 . 125.7(14) no
N9 . C10 . N11 . 125.1(4) yes
N9 . C10 . C12 . 108.1(3) yes
N11 . C10 . C12 . 126.7(4) yes
C10 . N11 . C10 5_556 122.1(5) yes
C10 . C12 . C13 . 105.9(4) yes
C10 . C12 . C14 . 128.6(4) yes
C13 . C12 . C14 . 125.4(4) yes
C8 . C13 . C12 . 108.0(4) yes
C8 . C13 . H131 . 125.3 no
C12 . C13 . H131 . 126.7 no
C12 . C14 . C15 . 122.3(4) yes
C12 . C14 . C23 . 117.5(4) yes
C15 . C14 . C23 . 120.2(4) yes
C14 . C15 . C16 . 119.1(4) yes
C14 . C15 . H151 . 120.6 no
C16 . C15 . H151 . 120.3 no
C15 . C16 . O17 . 124.4(4) yes
C15 . C16 . C19 . 121.0(4) yes
O17 . C16 . C19 . 114.6(4) yes
C16 . O17 . C18 . 117.3(3) yes
O17 . C18 . H181 . 108.9 no
O17 . C18 . H182 . 108.7 no
H181 . C18 . H182 . 110.0 no
O17 . C18 . H183 . 109.2 no
H181 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 110.5 no
C16 . C19 . O20 . 120.7(4) yes
C16 . C19 . C22 . 119.6(4) yes
O20 . C19 . C22 . 119.7(4) yes
C19 . O20 . C21 . 113.8(3) yes
O20 . C21 . H211 . 110.1 no
O20 . C21 . H212 . 110.2 no
H211 . C21 . H212 . 109.0 no
O20 . C21 . H213 . 110.6 no
H211 . C21 . H213 . 108.4 no
H212 . C21 . H213 . 108.5 no
C19 . C22 . C23 . 120.0(4) yes
C19 . C22 . O24 . 115.6(4) yes
C23 . C22 . O24 . 124.4(4) yes
C14 . C23 . C22 . 120.1(4) yes
C14 . C23 . H231 . 120.0 no
C22 . C23 . H231 . 119.8 no
C22 . O24 . C25 . 116.4(4) yes
O24 . C25 . H251 . 109.8 no
O24 . C25 . H252 . 109.7 no
H251 . C25 . H252 . 108.6 no
O24 . C25 . H253 . 110.7 no
H251 . C25 . H253 . 108.5 no
H252 . C25 . H253 . 109.6 no
C9 . O1 . C11 . 102.5(9) yes
C11 . C1 . C17 . 111.3(10) yes
C11 . C1 . H11 . 111.4 no
C17 . C1 . H11 . 109.7 no
C11 . C1 . H12 . 106.9 no
C17 . C1 . H12 . 108.0 no
H11 . C1 . H12 . 109.3 no
O1 . C9 . C17 . 101.8(10) yes
O1 . C9 . H92 . 110.9 no
C17 . C9 . H92 . 111.1 no
O1 . C9 . H93 . 111.6 no
C17 . C9 . H93 . 112.8 no
H92 . C9 . H93 . 108.6 no
O1 . C11 . C1 . 102.6(9) yes
O1 . C11 . H111 . 110.0 no
C1 . C11 . H111 . 108.4 no
O1 . C11 . H112 . 113.3 no
C1 . C11 . H112 . 113.1 no
H111 . C11 . H112 . 109.2 no
C9 . C17 . C1 . 102.4(10) yes
C9 . C17 . H171 . 110.9 no
C1 . C17 . H171 . 109.9 no
C9 . C17 . H172 . 111.3 no
C1 . C17 . H172 . 112.7 no
H171 . C17 . H172 . 109.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N9 . H91 . N9 5_556 121.7(18) 0.860 2.053 2.610(8) yes
C1 . H12 . C25 6_465 139 0.95 2.58 3.352(8) yes



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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1977349'
loop_
_audit_author_name
_audit_author_address
'Guillaume Pilet'
;UCBL
France
;
_audit_update_record             
;
2020-04-29 deposited with the CCDC.	2020-07-03 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          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   9.4848(13)
_cell_length_b                   11.0750(13)
_cell_length_c                   22.1993(16)
_cell_angle_alpha                77.140(8)
_cell_angle_beta                 79.573(9)
_cell_angle_gamma                73.999(11)
_cell_volume                     2167.5(4)

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

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


_cell_formula_units_Z            2

# Given Formula = C50 H57 Br2 N3 O2 
# Dc =      1.37 Fooo =    928.00 Mu =     19.13 M =    891.83
# Found Formula = C50 H57 Br2 N3 O2 
# Dc =      1.37 FOOO =    928.00 Mu =     19.13 M =    891.83

_chemical_formula_sum            'C50 H57 Br2 N3 O2'
_chemical_formula_moiety         'C50 H57 Br2 N3 O2'
_chemical_compound_source        ?
_chemical_formula_weight         891.83


_cell_measurement_reflns_used    6302
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29
_cell_measurement_temperature    100

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_min          0.107
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_max          0.530

_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    1.913

# Sheldrick geometric approximatio 0.77 0.81 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.81
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            21957
_reflns_number_total             10280
_diffrn_reflns_av_R_equivalents  0.050
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 10280 
# Theoretical number of reflections is about 24459 


_diffrn_reflns_theta_min         2.805
_diffrn_reflns_theta_max         29.747
_diffrn_measured_fraction_theta_max 0.931

_diffrn_reflns_theta_full        25.285
_diffrn_measured_fraction_theta_full 0.994


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -13
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -1.27
_refine_diff_density_max         1.10


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         6970
_refine_ls_number_restraints     0
_refine_ls_number_parameters     515
_oxford_refine_ls_R_factor_ref   0.0472
_refine_ls_wR_factor_ref         0.0434
_refine_ls_goodness_of_fit_ref   1.1691
_refine_ls_shift/su_max          0.0006731
_refine_ls_shift/su_mean         0.0000244


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        10257
_refine_ls_R_factor_all          0.0773
_refine_ls_wR_factor_all         0.0630

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7987
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_gt          0.0468

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


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 4.92 -2.45 2.50 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.85737(4) 1.20078(3) 0.321014(16) 0.0239 1.0000 Uani . . . . . .
C2 C 0.8588(3) 1.0460(3) 0.37783(15) 0.0198 1.0000 Uani . . . . . .
C3 C 0.9681(3) 0.9986(3) 0.41642(14) 0.0191 1.0000 Uani . . . . . .
C4 C 0.9669(3) 0.8865(3) 0.45919(14) 0.0183 1.0000 Uani . . . . . .
C5 C 0.8587(3) 0.8207(3) 0.46261(14) 0.0166 1.0000 Uani . . . . . .
C6 C 0.7520(3) 0.8694(3) 0.42222(14) 0.0189 1.0000 Uani . . . . . .
C7 C 0.7498(4) 0.9824(3) 0.38016(15) 0.0219 1.0000 Uani . . . . . .
C8 C 0.8626(3) 0.7007(3) 0.50636(14) 0.0163 1.0000 Uani . . . . . .
N9 N 0.8003(3) 0.6144(2) 0.49662(12) 0.0172 1.0000 Uani . . . . . .
C10 C 0.8230(3) 0.5134(3) 0.54686(14) 0.0169 1.0000 Uani . . . . . .
N11 N 0.7775(3) 0.4079(2) 0.55476(12) 0.0173 1.0000 Uani . . . . . .
C12 C 0.7081(3) 0.3874(3) 0.51183(15) 0.0188 1.0000 Uani . . . . . .
N13 N 0.6839(3) 0.4664(2) 0.45528(12) 0.0180 1.0000 Uani . . . . . .
C14 C 0.6154(3) 0.4156(3) 0.42295(15) 0.0184 1.0000 Uani . . . . . .
C15 C 0.5745(3) 0.4825(3) 0.36164(14) 0.0187 1.0000 Uani . . . . . .
C16 C 0.6415(3) 0.5789(3) 0.32736(15) 0.0199 1.0000 Uani . . . . . .
C17 C 0.5943(4) 0.6499(3) 0.27157(15) 0.0213 1.0000 Uani . . . . . .
C18 C 0.4792(4) 0.6245(3) 0.25010(14) 0.0212 1.0000 Uani . . . . . .
Br19 Br 0.40413(4) 0.72708(4) 0.176790(16) 0.0276 1.0000 Uani . . . . . .
C20 C 0.4149(4) 0.5271(3) 0.28206(15) 0.0218 1.0000 Uani . . . . . .
C21 C 0.4632(3) 0.4557(3) 0.33716(14) 0.0196 1.0000 Uani . . . . . .
C22 C 0.5929(3) 0.2991(3) 0.45933(15) 0.0191 1.0000 Uani . . . . . .
C23 C 0.6499(3) 0.2791(3) 0.51533(14) 0.0183 1.0000 Uani . . . . . .
C24 C 0.6528(3) 0.1699(3) 0.56683(15) 0.0188 1.0000 Uani . . . . . .
C25 C 0.6564(4) 0.1789(3) 0.62802(15) 0.0212 1.0000 Uani . . . . . .
C26 C 0.6566(4) 0.0752(3) 0.67716(15) 0.0215 1.0000 Uani . . . . . .
C27 C 0.6533(4) -0.0414(3) 0.66508(15) 0.0200 1.0000 Uani . . . . . .
O28 O 0.6524(3) -0.1500(2) 0.70951(10) 0.0235 1.0000 Uani . . . . . .
C29 C 0.6357(4) -0.1416(3) 0.77446(15) 0.0247 1.0000 Uani . . . . . .
C30 C 0.7813(4) -0.1446(4) 0.79489(17) 0.0287 1.0000 Uani . . . . . .
C31 C 0.7603(4) -0.1042(4) 0.85810(17) 0.0320 1.0000 Uani . . . . . .
C32 C 0.9028(5) -0.1293(4) 0.88594(19) 0.0417 1.0000 Uani . . . . . .
C33 C 1.0119(5) -0.0596(4) 0.8474(2) 0.0448 1.0000 Uani . . . . . .
C34 C 0.5760(4) -0.2558(3) 0.81041(16) 0.0266 1.0000 Uani . . . . . .
C35 C 0.4271(4) -0.2598(3) 0.79647(16) 0.0260 1.0000 Uani . . . . . .
C36 C 0.3694(4) -0.3664(4) 0.84165(17) 0.0304 1.0000 Uani . . . . . .
C37 C 0.2354(4) -0.3930(4) 0.82326(18) 0.0343 1.0000 Uani . . . . . .
C38 C 0.6511(3) -0.0528(3) 0.60420(15) 0.0192 1.0000 Uani . . . . . .
C39 C 0.6492(3) 0.0510(3) 0.55594(15) 0.0182 1.0000 Uani . . . . . .
C40 C 0.9020(3) 0.5430(3) 0.59020(14) 0.0172 1.0000 Uani . . . . . .
C41 C 0.9264(3) 0.6600(3) 0.56370(14) 0.0184 1.0000 Uani . . . . . .
C42 C 0.9384(3) 0.4666(3) 0.65083(15) 0.0193 1.0000 Uani . . . . . .
C43 C 0.9597(4) 0.3337(3) 0.66442(15) 0.0211 1.0000 Uani . . . . . .
C44 C 0.9900(4) 0.2649(3) 0.72271(15) 0.0215 1.0000 Uani . . . . . .
C45 C 0.9971(3) 0.3270(3) 0.76977(14) 0.0204 1.0000 Uani . . . . . .
O46 O 1.0260(3) 0.2488(2) 0.82556(10) 0.0238 1.0000 Uani . . . . . .
C47 C 1.0223(4) 0.3037(3) 0.87912(14) 0.0216 1.0000 Uani . . . . . .
C48 C 0.8654(4) 0.3627(3) 0.90443(15) 0.0230 1.0000 Uani . . . . . .
C49 C 0.8524(4) 0.4582(3) 0.94588(17) 0.0276 1.0000 Uani . . . . . .
C50 C 0.6948(4) 0.5092(3) 0.97428(16) 0.0278 1.0000 Uani . . . . . .
C51 C 0.6795(5) 0.6104(4) 1.01247(19) 0.0367 1.0000 Uani . . . . . .
C52 C 1.1031(4) 0.1957(3) 0.92530(15) 0.0225 1.0000 Uani . . . . . .
C53 C 1.2647(4) 0.1442(4) 0.90159(17) 0.0304 1.0000 Uani . . . . . .
C54 C 1.3532(4) 0.0472(4) 0.95020(18) 0.0317 1.0000 Uani . . . . . .
C55 C 1.3094(5) -0.0781(4) 0.9698(2) 0.0467 1.0000 Uani . . . . . .
C56 C 0.9769(3) 0.4587(3) 0.75723(15) 0.0211 1.0000 Uani . . . . . .
C57 C 0.9481(3) 0.5262(3) 0.69827(15) 0.0200 1.0000 Uani . . . . . .
H31 H 1.0419 1.0430 0.4133 0.0242 1.0000 Uiso R . . . . .
H41 H 1.0423 0.8545 0.4859 0.0231 1.0000 Uiso R . . . . .
H61 H 0.6790 0.8240 0.4237 0.0242 1.0000 Uiso R . . . . .
H71 H 0.6741 1.0170 0.3534 0.0284 1.0000 Uiso R . . . . .
H161 H 0.7202 0.5959 0.3425 0.0251 1.0000 Uiso R . . . . .
H171 H 0.6408 0.7145 0.2482 0.0258 1.0000 Uiso R . . . . .
H201 H 0.3366 0.5108 0.2665 0.0271 1.0000 Uiso R . . . . .
H211 H 0.4202 0.3877 0.3587 0.0237 1.0000 Uiso R . . . . .
H221 H 0.5475 0.2433 0.4472 0.0242 1.0000 Uiso R . . . . .
H251 H 0.6580 0.2590 0.6365 0.0259 1.0000 Uiso R . . . . .
H261 H 0.6585 0.0840 0.7186 0.0270 1.0000 Uiso R . . . . .
H291 H 0.5619 -0.0603 0.7815 0.0298 1.0000 Uiso R . . . . .
H301 H 0.8448 -0.2327 0.7971 0.0350 1.0000 Uiso R . . . . .
H302 H 0.8294 -0.0872 0.7633 0.0349 1.0000 Uiso R . . . . .
H311 H 0.6936 -0.1511 0.8876 0.0392 1.0000 Uiso R . . . . .
H312 H 0.7105 -0.0119 0.8533 0.0395 1.0000 Uiso R . . . . .
H321 H 0.8787 -0.1025 0.9276 0.0509 1.0000 Uiso R . . . . .
H322 H 0.9513 -0.2243 0.8924 0.0514 1.0000 Uiso R . . . . .
H332 H 1.0994 -0.0774 0.8694 0.0679 1.0000 Uiso R . . . . .
H331 H 0.9632 0.0324 0.8415 0.0683 1.0000 Uiso R . . . . .
H333 H 1.0426 -0.0859 0.8068 0.0679 1.0000 Uiso R . . . . .
H341 H 0.5679 -0.2556 0.8550 0.0327 1.0000 Uiso R . . . . .
H342 H 0.6490 -0.3344 0.8015 0.0333 1.0000 Uiso R . . . . .
H351 H 0.3550 -0.1770 0.8003 0.0330 1.0000 Uiso R . . . . .
H352 H 0.4378 -0.2726 0.7532 0.0326 1.0000 Uiso R . . . . .
H362 H 0.3438 -0.3441 0.8834 0.0381 1.0000 Uiso R . . . . .
H361 H 0.4504 -0.4448 0.8436 0.0377 1.0000 Uiso R . . . . .
H371 H 0.2031 -0.4596 0.8541 0.0530 1.0000 Uiso R . . . . .
H372 H 0.1552 -0.3149 0.8201 0.0529 1.0000 Uiso R . . . . .
H373 H 0.2627 -0.4202 0.7825 0.0528 1.0000 Uiso R . . . . .
H381 H 0.6511 -0.1331 0.5959 0.0241 1.0000 Uiso R . . . . .
H391 H 0.6468 0.0421 0.5143 0.0233 1.0000 Uiso R . . . . .
H411 H 0.9757 0.7062 0.5799 0.0222 1.0000 Uiso R . . . . .
H431 H 0.9537 0.2907 0.6327 0.0265 1.0000 Uiso R . . . . .
H441 H 1.0062 0.1734 0.7309 0.0275 1.0000 Uiso R . . . . .
H471 H 1.0780 0.3710 0.8663 0.0257 1.0000 Uiso R . . . . .
H482 H 0.8197 0.2945 0.9285 0.0280 1.0000 Uiso R . . . . .
H481 H 0.8107 0.4056 0.8689 0.0284 1.0000 Uiso R . . . . .
H491 H 0.9126 0.4165 0.9804 0.0331 1.0000 Uiso R . . . . .
H492 H 0.8919 0.5301 0.9210 0.0335 1.0000 Uiso R . . . . .
H501 H 0.6579 0.4372 1.0010 0.0340 1.0000 Uiso R . . . . .
H502 H 0.6343 0.5476 0.9398 0.0340 1.0000 Uiso R . . . . .
H511 H 0.5779 0.6379 1.0306 0.0569 1.0000 Uiso R . . . . .
H513 H 0.7425 0.5771 1.0458 0.0568 1.0000 Uiso R . . . . .
H512 H 0.7100 0.6841 0.9859 0.0568 1.0000 Uiso R . . . . .
H521 H 1.0963 0.2276 0.9637 0.0270 1.0000 Uiso R . . . . .
H522 H 1.0519 0.1269 0.9346 0.0272 1.0000 Uiso R . . . . .
H531 H 1.3126 0.2164 0.8867 0.0370 1.0000 Uiso R . . . . .
H532 H 1.2691 0.1042 0.8654 0.0370 1.0000 Uiso R . . . . .
H541 H 1.3376 0.0851 0.9882 0.0400 1.0000 Uiso R . . . . .
H542 H 1.4594 0.0302 0.9340 0.0399 1.0000 Uiso R . . . . .
H551 H 1.3704 -0.1365 1.0004 0.0711 1.0000 Uiso R . . . . .
H552 H 1.2069 -0.0643 0.9876 0.0709 1.0000 Uiso R . . . . .
H553 H 1.3237 -0.1185 0.9332 0.0710 1.0000 Uiso R . . . . .
H561 H 0.9813 0.5020 0.7887 0.0262 1.0000 Uiso R . . . . .
H571 H 0.9324 0.6160 0.6901 0.0240 1.0000 Uiso R . . . . .
H10 H 0.7103 0.5438 0.4445 0.0500 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       38(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          1.835(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C2 . 1.887(3) yes
C2 . C3 . 1.380(4) yes
C2 . C7 . 1.391(4) yes
C3 . C4 . 1.386(4) yes
C3 . H31 . 0.945 no
C4 . C5 . 1.396(4) yes
C4 . H41 . 0.954 no
C5 . C6 . 1.389(4) yes
C5 . C8 . 1.457(4) yes
C6 . C7 . 1.382(4) yes
C6 . H61 . 0.953 no
C7 . H71 . 0.957 no
C8 . N9 . 1.326(4) yes
C8 . C41 . 1.436(4) yes
N9 . C10 . 1.393(4) yes
C10 . N11 . 1.319(4) yes
C10 . C40 . 1.460(4) yes
N11 . C12 . 1.342(4) yes
C12 . N13 . 1.378(4) yes
C12 . C23 . 1.435(4) yes
N13 . C14 . 1.343(4) yes
N13 . H10 . 0.927 no
C14 . C15 . 1.461(4) yes
C14 . C22 . 1.409(4) yes
C15 . C16 . 1.400(4) yes
C15 . C21 . 1.397(4) yes
C16 . C17 . 1.388(4) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.384(4) yes
C17 . H171 . 0.950 no
C18 . Br19 . 1.897(3) yes
C18 . C20 . 1.379(5) yes
C20 . C21 . 1.380(5) yes
C20 . H201 . 0.948 no
C21 . H211 . 0.949 no
C22 . C23 . 1.394(4) yes
C22 . H221 . 0.950 no
C23 . C24 . 1.466(4) yes
C24 . C25 . 1.391(4) yes
C24 . C39 . 1.400(4) yes
C25 . C26 . 1.397(5) yes
C25 . H251 . 0.952 no
C26 . C27 . 1.386(4) yes
C26 . H261 . 0.951 no
C27 . O28 . 1.376(4) yes
C27 . C38 . 1.389(4) yes
O28 . C29 . 1.443(4) yes
C29 . C30 . 1.519(5) yes
C29 . C34 . 1.530(4) yes
C29 . H291 . 1.001 no
C30 . C31 . 1.529(5) yes
C30 . H301 . 0.991 no
C30 . H302 . 0.975 no
C31 . C32 . 1.518(6) yes
C31 . H311 . 0.990 no
C31 . H312 . 0.992 no
C32 . C33 . 1.491(6) yes
C32 . H321 . 1.002 no
C32 . H322 . 1.015 no
C33 . H332 . 0.989 no
C33 . H331 . 0.986 no
C33 . H333 . 0.978 no
C34 . C35 . 1.513(5) yes
C34 . H341 . 0.979 no
C34 . H342 . 0.985 no
C35 . C36 . 1.526(5) yes
C35 . H351 . 0.992 no
C35 . H352 . 0.986 no
C36 . C37 . 1.523(5) yes
C36 . H362 . 0.982 no
C36 . H361 . 0.987 no
C37 . H371 . 0.965 no
C37 . H372 . 0.980 no
C37 . H373 . 0.986 no
C38 . C39 . 1.385(4) yes
C38 . H381 . 0.948 no
C39 . H391 . 0.955 no
C40 . C41 . 1.363(4) yes
C40 . C42 . 1.465(4) yes
C41 . H411 . 0.940 no
C42 . C43 . 1.399(5) yes
C42 . C57 . 1.390(4) yes
C43 . C44 . 1.383(5) yes
C43 . H431 . 0.952 no
C44 . C45 . 1.392(5) yes
C44 . H441 . 0.962 no
C45 . O46 . 1.369(4) yes
C45 . C56 . 1.388(5) yes
O46 . C47 . 1.442(4) yes
C47 . C48 . 1.511(5) yes
C47 . C52 . 1.517(4) yes
C47 . H471 . 0.992 no
C48 . C49 . 1.516(5) yes
C48 . H482 . 0.981 no
C48 . H481 . 0.981 no
C49 . C50 . 1.517(5) yes
C49 . H491 . 0.991 no
C49 . H492 . 0.987 no
C50 . C51 . 1.512(5) yes
C50 . H501 . 0.989 no
C50 . H502 . 0.988 no
C51 . H511 . 0.968 no
C51 . H513 . 0.978 no
C51 . H512 . 0.975 no
C52 . C53 . 1.521(5) yes
C52 . H521 . 0.978 no
C52 . H522 . 0.977 no
C53 . C54 . 1.528(5) yes
C53 . H531 . 0.992 no
C53 . H532 . 0.990 no
C54 . C55 . 1.507(5) yes
C54 . H541 . 0.994 no
C54 . H542 . 0.987 no
C55 . H551 . 0.978 no
C55 . H552 . 0.965 no
C55 . H553 . 0.983 no
C56 . C57 . 1.389(4) yes
C56 . H561 . 0.943 no
C57 . H571 . 0.944 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C2 . C3 . 119.1(2) yes
Br1 . C2 . C7 . 119.5(2) yes
C3 . C2 . C7 . 121.4(3) yes
C2 . C3 . C4 . 119.0(3) yes
C2 . C3 . H31 . 119.6 no
C4 . C3 . H31 . 121.4 no
C3 . C4 . C5 . 120.8(3) yes
C3 . C4 . H41 . 118.7 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C6 . 118.8(3) yes
C4 . C5 . C8 . 119.9(3) yes
C6 . C5 . C8 . 121.3(3) yes
C5 . C6 . C7 . 121.2(3) yes
C5 . C6 . H61 . 119.3 no
C7 . C6 . H61 . 119.5 no
C2 . C7 . C6 . 118.7(3) yes
C2 . C7 . H71 . 120.4 no
C6 . C7 . H71 . 120.8 no
C5 . C8 . N9 . 121.1(3) yes
C5 . C8 . C41 . 127.5(3) yes
N9 . C8 . C41 . 111.5(3) yes
C8 . N9 . C10 . 106.2(2) yes
N9 . C10 . N11 . 125.2(3) yes
N9 . C10 . C40 . 109.7(3) yes
N11 . C10 . C40 . 125.1(3) yes
C10 . N11 . C12 . 121.1(3) yes
N11 . C12 . N13 . 125.4(3) yes
N11 . C12 . C23 . 126.7(3) yes
N13 . C12 . C23 . 107.8(3) yes
C12 . N13 . C14 . 110.0(3) yes
C12 . N13 . H10 . 121.4 no
C14 . N13 . H10 . 128.6 no
N13 . C14 . C15 . 120.7(3) yes
N13 . C14 . C22 . 108.1(3) yes
C15 . C14 . C22 . 131.3(3) yes
C14 . C15 . C16 . 120.7(3) yes
C14 . C15 . C21 . 120.7(3) yes
C16 . C15 . C21 . 118.5(3) yes
C15 . C16 . C17 . 120.8(3) yes
C15 . C16 . H161 . 119.6 no
C17 . C16 . H161 . 119.6 no
C16 . C17 . C18 . 119.1(3) yes
C16 . C17 . H171 . 120.6 no
C18 . C17 . H171 . 120.4 no
C17 . C18 . Br19 . 119.9(2) yes
C17 . C18 . C20 . 121.1(3) yes
Br19 . C18 . C20 . 119.0(2) yes
C18 . C20 . C21 . 119.7(3) yes
C18 . C20 . H201 . 119.8 no
C21 . C20 . H201 . 120.4 no
C15 . C21 . C20 . 120.7(3) yes
C15 . C21 . H211 . 119.6 no
C20 . C21 . H211 . 119.7 no
C14 . C22 . C23 . 108.7(3) yes
C14 . C22 . H221 . 125.4 no
C23 . C22 . H221 . 125.9 no
C12 . C23 . C22 . 105.4(3) yes
C12 . C23 . C24 . 126.8(3) yes
C22 . C23 . C24 . 127.7(3) yes
C23 . C24 . C25 . 122.5(3) yes
C23 . C24 . C39 . 120.4(3) yes
C25 . C24 . C39 . 117.1(3) yes
C24 . C25 . C26 . 122.4(3) yes
C24 . C25 . H251 . 118.5 no
C26 . C25 . H251 . 119.1 no
C25 . C26 . C27 . 119.3(3) yes
C25 . C26 . H261 . 120.7 no
C27 . C26 . H261 . 119.9 no
C26 . C27 . O28 . 124.7(3) yes
C26 . C27 . C38 . 119.2(3) yes
O28 . C27 . C38 . 116.1(3) yes
C27 . O28 . C29 . 119.2(2) yes
O28 . C29 . C30 . 111.8(3) yes
O28 . C29 . C34 . 105.9(3) yes
C30 . C29 . C34 . 111.1(3) yes
O28 . C29 . H291 . 108.9 no
C30 . C29 . H291 . 109.5 no
C34 . C29 . H291 . 109.7 no
C29 . C30 . C31 . 112.4(3) yes
C29 . C30 . H301 . 108.3 no
C31 . C30 . H301 . 109.6 no
C29 . C30 . H302 . 108.1 no
C31 . C30 . H302 . 109.6 no
H301 . C30 . H302 . 108.8 no
C30 . C31 . C32 . 114.2(3) yes
C30 . C31 . H311 . 108.6 no
C32 . C31 . H311 . 108.4 no
C30 . C31 . H312 . 108.5 no
C32 . C31 . H312 . 109.5 no
H311 . C31 . H312 . 107.5 no
C31 . C32 . C33 . 114.2(4) yes
C31 . C32 . H321 . 108.9 no
C33 . C32 . H321 . 107.6 no
C31 . C32 . H322 . 109.2 no
C33 . C32 . H322 . 108.5 no
H321 . C32 . H322 . 108.2 no
C32 . C33 . H332 . 109.6 no
C32 . C33 . H331 . 107.5 no
H332 . C33 . H331 . 110.0 no
C32 . C33 . H333 . 110.6 no
H332 . C33 . H333 . 109.6 no
H331 . C33 . H333 . 109.5 no
C29 . C34 . C35 . 116.0(3) yes
C29 . C34 . H341 . 108.1 no
C35 . C34 . H341 . 107.9 no
C29 . C34 . H342 . 108.0 no
C35 . C34 . H342 . 108.6 no
H341 . C34 . H342 . 107.9 no
C34 . C35 . C36 . 110.9(3) yes
C34 . C35 . H351 . 109.6 no
C36 . C35 . H351 . 108.9 no
C34 . C35 . H352 . 108.5 no
C36 . C35 . H352 . 110.6 no
H351 . C35 . H352 . 108.3 no
C35 . C36 . C37 . 113.9(3) yes
C35 . C36 . H362 . 109.0 no
C37 . C36 . H362 . 109.0 no
C35 . C36 . H361 . 107.8 no
C37 . C36 . H361 . 108.9 no
H362 . C36 . H361 . 108.0 no
C36 . C37 . H371 . 109.8 no
C36 . C37 . H372 . 109.4 no
H371 . C37 . H372 . 109.7 no
C36 . C37 . H373 . 109.1 no
H371 . C37 . H373 . 109.6 no
H372 . C37 . H373 . 109.3 no
C27 . C38 . C39 . 121.0(3) yes
C27 . C38 . H381 . 119.1 no
C39 . C38 . H381 . 120.0 no
C24 . C39 . C38 . 121.0(3) yes
C24 . C39 . H391 . 118.9 no
C38 . C39 . H391 . 120.1 no
C10 . C40 . C41 . 105.1(3) yes
C10 . C40 . C42 . 127.2(3) yes
C41 . C40 . C42 . 127.7(3) yes
C8 . C41 . C40 . 107.5(3) yes
C8 . C41 . H411 . 126.0 no
C40 . C41 . H411 . 126.5 no
C40 . C42 . C43 . 122.6(3) yes
C40 . C42 . C57 . 120.0(3) yes
C43 . C42 . C57 . 117.3(3) yes
C42 . C43 . C44 . 121.1(3) yes
C42 . C43 . H431 . 118.9 no
C44 . C43 . H431 . 120.0 no
C43 . C44 . C45 . 120.6(3) yes
C43 . C44 . H441 . 119.9 no
C45 . C44 . H441 . 119.6 no
C44 . C45 . O46 . 115.1(3) yes
C44 . C45 . C56 . 119.3(3) yes
O46 . C45 . C56 . 125.6(3) yes
C45 . O46 . C47 . 119.8(2) yes
O46 . C47 . C48 . 111.2(3) yes
O46 . C47 . C52 . 105.5(3) yes
C48 . C47 . C52 . 113.6(3) yes
O46 . C47 . H471 . 108.4 no
C48 . C47 . H471 . 109.0 no
C52 . C47 . H471 . 109.1 no
C47 . C48 . C49 . 114.3(3) yes
C47 . C48 . H482 . 108.8 no
C49 . C48 . H482 . 108.3 no
C47 . C48 . H481 . 107.9 no
C49 . C48 . H481 . 109.0 no
H482 . C48 . H481 . 108.4 no
C48 . C49 . C50 . 113.3(3) yes
C48 . C49 . H491 . 109.1 no
C50 . C49 . H491 . 107.9 no
C48 . C49 . H492 . 108.6 no
C50 . C49 . H492 . 109.2 no
H491 . C49 . H492 . 108.6 no
C49 . C50 . C51 . 113.6(3) yes
C49 . C50 . H501 . 108.8 no
C51 . C50 . H501 . 109.1 no
C49 . C50 . H502 . 107.7 no
C51 . C50 . H502 . 108.0 no
H501 . C50 . H502 . 109.6 no
C50 . C51 . H511 . 110.5 no
C50 . C51 . H513 . 110.3 no
H511 . C51 . H513 . 109.2 no
C50 . C51 . H512 . 109.6 no
H511 . C51 . H512 . 108.7 no
H513 . C51 . H512 . 108.5 no
C47 . C52 . C53 . 113.3(3) yes
C47 . C52 . H521 . 107.9 no
C53 . C52 . H521 . 109.4 no
C47 . C52 . H522 . 108.1 no
C53 . C52 . H522 . 109.5 no
H521 . C52 . H522 . 108.5 no
C52 . C53 . C54 . 114.2(3) yes
C52 . C53 . H531 . 109.1 no
C54 . C53 . H531 . 108.3 no
C52 . C53 . H532 . 108.3 no
C54 . C53 . H532 . 109.3 no
H531 . C53 . H532 . 107.4 no
C53 . C54 . C55 . 114.6(3) yes
C53 . C54 . H541 . 108.2 no
C55 . C54 . H541 . 107.2 no
C53 . C54 . H542 . 109.4 no
C55 . C54 . H542 . 108.8 no
H541 . C54 . H542 . 108.5 no
C54 . C55 . H551 . 110.9 no
C54 . C55 . H552 . 110.3 no
H551 . C55 . H552 . 109.0 no
C54 . C55 . H553 . 109.3 no
H551 . C55 . H553 . 108.2 no
H552 . C55 . H553 . 109.1 no
C45 . C56 . C57 . 119.4(3) yes
C45 . C56 . H561 . 120.3 no
C57 . C56 . H561 . 120.3 no
C42 . C57 . C56 . 122.3(3) yes
C42 . C57 . H571 . 118.5 no
C56 . C57 . H571 . 119.2 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
C33 . H331 . O46 . 140.00 0.986 2.561 3.378(5) yes
N13 . H10 . N9 . 126.00 0.927 1.952 2.605(5) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/09/18 at 11:12:58
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE N   (  13,X'S) H   (  10,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,X'S) H   ( 333,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) H   ( 373,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 482,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 492,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) H   ( 502,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 513,X'S) H   ( 512,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) H   ( 553,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/09/18 at 11:12:58
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
