# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_5n
_database_code_depnum_ccdc_archive 'CCDC 1825056'
_audit_update_record             
;
2018-02-21 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2017-09-20
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 031eaa17
_chemical_name_systematic        .
_chemical_melting_point          381-383

_refine_special_details          
;
The difference map indicated the presence of diffuse electron density which
was attributed to disordered chloroform. Modelling this led to a stable
refinement. SQUEEZE could also be used to leave a void from which the
chloroform electron density was removed - this also lead to a stable
refinement in which R(%)=3.84. The data below is for the model which includes
the disordered chloroform. This was preferred over the SQUEEZED model because,
despite a higher R(%), it better represented the actual crystal structure. 
;

_cell_length_a                   25.6568(11)
_cell_length_b                   9.9841(3)
_cell_length_c                   9.9880(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.639(4)
_cell_angle_gamma                90
_cell_volume                     2546.15(17)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 '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'


_cell_formula_units_Z            8

# Given Formula = C8 H12 Cl0.38 I1 N1 O1 
# Dc =      1.45 Fooo =   1075.00 Mu =    201.86 M =    278.39
# Found Formula = C8.50 H12.50 Cl1.50 I1 N1 O1 
# Dc =      1.69 FOOO =   1256.00 Mu =    224.05 M =    324.78

_chemical_formula_sum            'C8.50 H12.50 Cl1.50 I1 N1 O1'
_chemical_formula_moiety         'C8 H12 I1 N1 O1, 0.5(C1 H1 Cl3)'
_chemical_compound_source        synthetic
_chemical_formula_weight         324.78


_cell_measurement_reflns_used    5804
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_max          0.43

_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1255.995
_exptl_absorpt_coefficient_mu    22.405

# Sheldrick geometric approximatio 0.26 0.26 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.26
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       '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)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            12571
_reflns_number_total             2661
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0520
# Number of reflections with Friedels Law is 2661 
# Theoretical number of reflections is about 5330 


_diffrn_reflns_theta_min         3.462
_diffrn_reflns_theta_max         76.202
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        76.202
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -31
_reflns_limit_h_max              32
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   3.17
_oxford_diffrn_Wilson_scale      0.22

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

_refine_diff_density_min         -1.44
_refine_diff_density_max         1.34


# 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         2659
_refine_ls_number_restraints     347
_refine_ls_number_parameters     173
_oxford_refine_ls_R_factor_ref   0.0428
_refine_ls_wR_factor_ref         0.1106
_refine_ls_goodness_of_fit_ref   0.9969
_refine_ls_shift/su_max          0.0006403
_refine_ls_shift/su_mean         0.0000258


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2659
_refine_ls_R_factor_all          0.0428
_refine_ls_wR_factor_all         0.1106

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2410
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_gt          0.1071

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² +10.97P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
I1 I 0.304566(11) 1.01563(3) 0.57563(3) 0.0432 1.0000 Uani . . . . . .
C2 C 0.32725(14) 0.8220(4) 0.6494(4) 0.0289 1.0000 Uani . . . . . .
C3 C 0.37458(14) 0.7889(4) 0.7511(4) 0.0324 1.0000 Uani . . . . . .
C4 C 0.34627(13) 0.6540(3) 0.7121(3) 0.0234 1.0000 Uani . . . . . .
C5 C 0.34215(15) 0.7023(4) 0.5635(4) 0.0310 1.0000 Uani . . . . . .
C6 C 0.29354(14) 0.7269(4) 0.7261(4) 0.0303 1.0000 Uani . . . . . .
C7 C 0.36130(13) 0.5161(3) 0.7671(3) 0.0229 1.0000 Uani . . . . . .
C8 C 0.41905(13) 0.4951(3) 0.7557(3) 0.0230 1.0000 Uani . . . . . .
O9 O 0.43626(10) 0.4728(3) 0.6465(3) 0.0333 1.0000 Uani . . . . . .
N10 N 0.45048(13) 0.5052(4) 0.8696(3) 0.0368 1.0000 Uani . . . . . .
C11 C 0.32867(14) 0.4062(4) 0.6927(4) 0.0322 1.0000 Uani . . . . . .
C31 C 0.5029(4) 0.1943(10) 0.6457(12) 0.0797 0.131(3) Uani D . P 1 -2 .
Cl32 Cl 0.4457(5) 0.1262(19) 0.7018(15) 0.0817 0.131(3) Uani D . P 1 -2 .
Cl33 Cl 0.5014(4) 0.1902(12) 0.4698(12) 0.0820 0.131(3) Uani D . P 1 -2 .
Cl34 Cl 0.5597(5) 0.118(2) 0.7242(16) 0.0763 0.131(3) Uani D . P 1 -2 .
C21 C 0.5064(3) 0.1743(7) 0.7652(8) 0.1040 0.369(3) Uani D . P 1 -1 .
Cl22 Cl 0.5581(4) 0.1217(10) 0.6734(10) 0.1282 0.369(3) Uani D . P 1 -1 .
Cl23 Cl 0.5196(5) 0.1412(14) 0.9378(8) 0.2111 0.369(3) Uani D . P 1 -1 .
Cl24 Cl 0.4460(3) 0.1071(13) 0.6996(13) 0.1714 0.369(3) Uani D . P 1 -1 .
H31 H 0.3741 0.8214 0.8420 0.0390 1.0000 Uiso R . . . . .
H32 H 0.4094 0.8014 0.7221 0.0388 1.0000 Uiso R . . . . .
H51 H 0.3746 0.7092 0.5202 0.0373 1.0000 Uiso R . . . . .
H52 H 0.3150 0.6643 0.5015 0.0370 1.0000 Uiso R . . . . .
H61 H 0.2858 0.7545 0.8154 0.0360 1.0000 Uiso R . . . . .
H62 H 0.2622 0.6907 0.6768 0.0363 1.0000 Uiso R . . . . .
H71 H 0.3554 0.5148 0.8632 0.0269 1.0000 Uiso R . . . . .
H101 H 0.4839 0.5004 0.8680 0.0441 1.0000 Uiso R . . . . .
H102 H 0.4376 0.5170 0.9450 0.0436 1.0000 Uiso R . . . . .
H111 H 0.3384 0.3203 0.7315 0.0480 1.0000 Uiso R . . . . .
H112 H 0.3350 0.4057 0.5988 0.0477 1.0000 Uiso R . . . . .
H113 H 0.2920 0.4211 0.6998 0.0479 1.0000 Uiso R . . . . .
H311 H 0.5029 0.2887 0.6759 0.0960 0.131(3) Uiso R . P 1 -2 .
H211 H 0.5041 0.2726 0.7559 0.1159 0.369(3) Uiso R . P 1 -1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.12(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
I1 . C2 . 2.129(4) yes
C2 . C3 . 1.541(5) yes
C2 . C5 . 1.541(5) yes
C2 . C6 . 1.539(5) yes
C3 . C4 . 1.562(5) yes
C3 . H31 . 0.966 no
C3 . H32 . 0.973 no
C4 . C5 . 1.555(5) yes
C4 . C6 . 1.555(5) yes
C4 . C7 . 1.517(5) yes
C5 . H51 . 0.977 no
C5 . H52 . 0.963 no
C6 . H61 . 0.972 no
C6 . H62 . 0.970 no
C7 . C8 . 1.512(5) yes
C7 . C11 . 1.528(5) yes
C7 . H71 . 0.987 no
C8 . O9 . 1.236(4) yes
C8 . N10 . 1.332(5) yes
N10 . H101 . 0.862 no
N10 . H102 . 0.860 no
C11 . H111 . 0.964 no
C11 . H112 . 0.967 no
C11 . H113 . 0.961 no
C31 . Cl32 . 1.759(5) yes
C31 . Cl33 . 1.754(5) yes
C31 . Cl34 . 1.757(5) yes
C31 . H311 . 0.990 no
C21 . Cl22 . 1.764(5) yes
C21 . Cl23 . 1.755(5) yes
C21 . Cl24 . 1.756(5) yes
C21 . H211 . 0.987 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
I1 . C2 . C3 . 126.4(3) yes
I1 . C2 . C5 . 125.9(2) yes
C3 . C2 . C5 . 88.7(3) yes
I1 . C2 . C6 . 125.8(2) yes
C3 . C2 . C6 . 89.1(3) yes
C5 . C2 . C6 . 88.9(3) yes
C2 . C3 . C4 . 72.8(2) yes
C2 . C3 . H31 . 117.8 no
C4 . C3 . H31 . 118.4 no
C2 . C3 . H32 . 117.6 no
C4 . C3 . H32 . 117.1 no
H31 . C3 . H32 . 109.4 no
C3 . C4 . C5 . 87.5(3) yes
C3 . C4 . C6 . 87.8(3) yes
C5 . C4 . C6 . 87.8(3) yes
C3 . C4 . C7 . 126.7(3) yes
C5 . C4 . C7 . 128.2(3) yes
C6 . C4 . C7 . 125.8(3) yes
C2 . C5 . C4 . 72.9(2) yes
C2 . C5 . H51 . 117.4 no
C4 . C5 . H51 . 117.6 no
C2 . C5 . H52 . 117.4 no
C4 . C5 . H52 . 118.0 no
H51 . C5 . H52 . 109.7 no
C2 . C6 . C4 . 73.0(2) yes
C2 . C6 . H61 . 117.2 no
C4 . C6 . H61 . 118.2 no
C2 . C6 . H62 . 117.1 no
C4 . C6 . H62 . 117.7 no
H61 . C6 . H62 . 109.8 no
C4 . C7 . C8 . 108.3(3) yes
C4 . C7 . C11 . 111.6(3) yes
C8 . C7 . C11 . 111.0(3) yes
C4 . C7 . H71 . 107.8 no
C8 . C7 . H71 . 108.5 no
C11 . C7 . H71 . 109.5 no
C7 . C8 . O9 . 121.9(3) yes
C7 . C8 . N10 . 116.2(3) yes
O9 . C8 . N10 . 121.9(3) yes
C8 . N10 . H101 . 120.0 no
C8 . N10 . H102 . 120.4 no
H101 . N10 . H102 . 119.5 no
C7 . C11 . H111 . 109.6 no
C7 . C11 . H112 . 109.8 no
H111 . C11 . H112 . 108.9 no
C7 . C11 . H113 . 110.3 no
H111 . C11 . H113 . 108.9 no
H112 . C11 . H113 . 109.3 no
Cl32 . C31 . Cl33 . 111.88(5) yes
Cl32 . C31 . Cl34 . 111.89(5) yes
Cl33 . C31 . Cl34 . 111.88(5) yes
Cl32 . C31 . H311 . 104.1 no
Cl33 . C31 . H311 . 109.1 no
Cl34 . C31 . H311 . 107.5 no
Cl22 . C21 . Cl23 . 111.88(5) yes
Cl22 . C21 . Cl24 . 111.89(5) yes
Cl23 . C21 . Cl24 . 111.87(5) yes
Cl22 . C21 . H211 . 106.8 no
Cl23 . C21 . H211 . 106.5 no
Cl24 . C21 . H211 . 107.6 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
N10 . H101 . O9 6_656 175 0.86 2.09 2.944(7) yes
N10 . H102 . O9 5_565 158 0.86 2.02 2.834(7) yes
C31 . H311 . O9 . 133 0.99 2.51 3.265(7) yes
C31 . H311 . N10 6_656 138 0.99 2.53 3.335(7) 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
-2 0 2 x .
-4 0 2 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_6b
_database_code_depnum_ccdc_archive 'CCDC 1825059'
_audit_update_record             
;
2018-02-21 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2017-10-30
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 070eaa17
_chemical_name_systematic        .
_chemical_melting_point          352-353

_refine_special_details          
;
The nitro group and the bicyclo[1.1.1]pentane bridgehead carbon atoms show
rotational disorder which was modelled. In order to maintain sensible
geometric and displacement parameters, same distance, thermal similarity
and vibrational restraints were necessary.
;

_cell_length_a                   7.0213(3)
_cell_length_b                   11.7894(5)
_cell_length_c                   12.2156(5)
_cell_angle_alpha                72.797(4)
_cell_angle_beta                 86.293(4)
_cell_angle_gamma                89.879(3)
_cell_volume                     963.76(7)

_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'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C8 H11 Br1 N1 O2 
# Dc =      1.61 Fooo =    468.00 Mu =     55.23 M =    233.08
# Found Formula = C8 H12 Br1 N1 O2 
# Dc =      1.61 FOOO =    472.00 Mu =     55.23 M =    234.09

_chemical_formula_sum            'C8 H12 Br1 N1 O2'
_chemical_formula_moiety         'C8 H12 Br1 N1 O2'
_chemical_compound_source        synthetic
_chemical_formula_weight         234.09


_cell_measurement_reflns_used    7769
_cell_measurement_theta_min      6
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.27

_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    5.523

# Sheldrick geometric approximatio 0.64 0.72 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.72
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       '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)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            16923
_reflns_number_total             3999
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0605
# Number of reflections with Friedels Law is 3999 
# Theoretical number of reflections is about 8100 


_diffrn_reflns_theta_min         3.797
_diffrn_reflns_theta_max         76.491
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        74.196
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              -13
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   3.29
_oxford_diffrn_Wilson_scale      0.03

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

_refine_diff_density_min         -0.68
_refine_diff_density_max         0.52


# 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         3998
_refine_ls_number_restraints     948
_refine_ls_number_parameters     311
_oxford_refine_ls_R_factor_ref   0.0378
_refine_ls_wR_factor_ref         0.0875
_refine_ls_goodness_of_fit_ref   1.0080
_refine_ls_shift/su_max          0.0010829
_refine_ls_shift/su_mean         0.0000531


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3998
_refine_ls_R_factor_all          0.0378
_refine_ls_wR_factor_all         0.0875

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3545
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_gt          0.0824

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.45P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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 0.49363(4) 0.64360(2) 0.57588(2) 0.0426 1.0000 Uani D . . . . .
C2 C 0.27607(16) 0.55431(9) 0.66507(9) 0.0331 1.0000 Uani D . . . . .
C3 C 0.2410(8) 0.5212(8) 0.79649(16) 0.0358 0.63(3) Uani D . P 3 1 .
C4 C 0.0706(2) 0.47012(14) 0.74911(13) 0.0293 1.0000 Uani D . . . . .
C5 C 0.0664(3) 0.5908(5) 0.6525(6) 0.0341 0.63(3) Uani D . P 3 1 .
C6 C 0.2184(8) 0.4270(3) 0.6700(7) 0.0357 0.63(3) Uani D . P 3 1 .
C7 C -0.1077(3) 0.40473(18) 0.81501(17) 0.0304 1.0000 Uani D . . . . .
N8 N -0.0321(3) 0.30219(13) 0.91144(13) 0.0383 1.0000 Uani D . . . . .
O9 O 0.043(2) 0.2201(8) 0.8852(3) 0.0538 0.49(3) Uani D . P 1 1 .
O10 O -0.050(2) 0.3088(8) 1.0091(4) 0.0574 0.49(3) Uani D . P 1 1 .
C11 C -0.2203(4) 0.3505(2) 0.7398(2) 0.0401 1.0000 Uani . . . . . .
C12 C -0.2273(4) 0.4839(2) 0.8683(2) 0.0386 1.0000 Uani . . . . . .
C103 C 0.2099(13) 0.5506(11) 0.7887(5) 0.0323 0.37(3) Uani D . P 3 2 .
C105 C 0.0678(4) 0.5696(9) 0.6323(6) 0.0322 0.37(3) Uani D . P 3 2 .
C106 C 0.2481(10) 0.4187(2) 0.6981(11) 0.0342 0.37(3) Uani D . P 3 2 .
O109 O -0.023(3) 0.2053(5) 0.8970(7) 0.0665 0.51(3) Uani D . P 1 2 .
O110 O 0.021(3) 0.3247(4) 0.9958(8) 0.0567 0.51(3) Uani D . P 1 2 .
Br201 Br 0.11029(4) 1.13200(3) 0.57872(2) 0.0472 1.0000 Uani D . . . . .
C202 C 0.30467(17) 1.04404(10) 0.67272(9) 0.0359 1.0000 Uani D . . . . .
C203 C 0.3035(8) 1.0130(9) 0.80430(17) 0.0375 0.53(2) Uani D . P 4 1 .
C204 C 0.4882(2) 0.96119(15) 0.76123(13) 0.0302 1.0000 Uani D . . . . .
C205 C 0.5165(4) 1.0807(5) 0.6636(6) 0.0358 0.53(2) Uani D . P 4 1 .
C206 C 0.3639(11) 0.9163(4) 0.6807(7) 0.0363 0.53(2) Uani D . P 4 1 .
C207 C 0.6498(3) 0.89691(18) 0.82944(16) 0.0305 1.0000 Uani D . . . . .
N208 N 0.5522(3) 0.79537(14) 0.92639(13) 0.0386 1.0000 Uani D . . . . .
O209 O 0.482(2) 0.7127(8) 0.9007(3) 0.0545 0.49(3) Uani D . P 2 1 .
O210 O 0.546(2) 0.8036(8) 1.0233(4) 0.0561 0.49(3) Uani D . P 2 1 .
C211 C 0.7815(4) 0.8409(2) 0.7570(2) 0.0402 1.0000 Uani . . . . . .
C212 C 0.7559(4) 0.9773(2) 0.8816(2) 0.0391 1.0000 Uani . . . . . .
C303 C 0.3372(11) 1.0435(9) 0.7962(4) 0.0354 0.47(2) Uani D . P 4 2 .
C305 C 0.5213(3) 1.0583(8) 0.6432(5) 0.0374 0.47(2) Uani D . P 4 2 .
C306 C 0.3256(11) 0.90830(17) 0.7091(9) 0.0364 0.47(2) Uani D . P 4 2 .
O309 O 0.547(2) 0.6980(5) 0.9131(7) 0.0719 0.51(3) Uani D . P 2 2 .
O310 O 0.479(2) 0.8191(4) 1.0101(8) 0.0576 0.51(3) Uani D . P 2 2 .
H31 H 0.2143 0.5855 0.8301 0.0430 0.63(3) Uiso R . P 3 1 .
H32 H 0.3244 0.4643 0.8421 0.0429 0.63(3) Uiso R . P 3 1 .
H51 H 0.0304 0.6609 0.6737 0.0408 0.63(3) Uiso R . P 3 1 .
H52 H 0.0143 0.5935 0.5796 0.0411 0.63(3) Uiso R . P 3 1 .
H61 H 0.3027 0.3634 0.7070 0.0427 0.63(3) Uiso R . P 3 1 .
H62 H 0.1758 0.4153 0.6003 0.0430 0.63(3) Uiso R . P 3 1 .
H111 H -0.3302 0.3045 0.7832 0.0595 1.0000 Uiso R . . . . .
H112 H -0.2665 0.4123 0.6763 0.0592 1.0000 Uiso R . . . . .
H113 H -0.1385 0.2997 0.7084 0.0596 1.0000 Uiso R . . . . .
H121 H -0.3297 0.4378 0.9176 0.0575 1.0000 Uiso R . . . . .
H122 H -0.1502 0.5181 0.9123 0.0577 1.0000 Uiso R . . . . .
H123 H -0.2808 0.5447 0.8081 0.0573 1.0000 Uiso R . . . . .
H1031 H 0.1610 0.6228 0.8015 0.0387 0.37(3) Uiso R . P 3 2 .
H1032 H 0.2899 0.5111 0.8499 0.0391 0.37(3) Uiso R . P 3 2 .
H1051 H 0.0079 0.6450 0.6313 0.0389 0.37(3) Uiso R . P 3 2 .
H1052 H 0.0359 0.5470 0.5653 0.0389 0.37(3) Uiso R . P 3 2 .
H1061 H 0.3325 0.3710 0.7509 0.0410 0.37(3) Uiso R . P 3 2 .
H1062 H 0.2296 0.3838 0.6369 0.0412 0.37(3) Uiso R . P 3 2 .
H2031 H 0.3195 1.0768 0.8384 0.0449 0.53(2) Uiso R . P 4 1 .
H2032 H 0.2090 0.9563 0.8499 0.0447 0.53(2) Uiso R . P 4 1 .
H2051 H 0.5432 1.1522 0.6835 0.0427 0.53(2) Uiso R . P 4 1 .
H2052 H 0.5943 1.0797 0.5949 0.0433 0.53(2) Uiso R . P 4 1 .
H2061 H 0.2696 0.8547 0.7169 0.0431 0.53(2) Uiso R . P 4 1 .
H2062 H 0.4277 0.9028 0.6135 0.0426 0.53(2) Uiso R . P 4 1 .
H2111 H 0.8741 0.7924 0.8025 0.0600 1.0000 Uiso R . . . . .
H2112 H 0.8454 0.9022 0.6953 0.0597 1.0000 Uiso R . . . . .
H2113 H 0.7083 0.7923 0.7241 0.0603 1.0000 Uiso R . . . . .
H2121 H 0.8493 0.9331 0.9316 0.0590 1.0000 Uiso R . . . . .
H2122 H 0.6690 1.0122 0.9266 0.0586 1.0000 Uiso R . . . . .
H2123 H 0.8207 1.0401 0.8200 0.0588 1.0000 Uiso R . . . . .
H3031 H 0.3835 1.1158 0.8067 0.0430 0.47(2) Uiso R . P 4 2 .
H3032 H 0.2418 1.0047 0.8569 0.0430 0.47(2) Uiso R . P 4 2 .
H3051 H 0.5812 1.1333 0.6413 0.0449 0.47(2) Uiso R . P 4 2 .
H3052 H 0.5732 1.0324 0.5791 0.0447 0.47(2) Uiso R . P 4 2 .
H3061 H 0.2260 0.8610 0.7609 0.0439 0.47(2) Uiso R . P 4 2 .
H3062 H 0.3631 0.8732 0.6486 0.0440 0.47(2) Uiso R . P 4 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.71(9)
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 . 1.9344(12) yes
C2 . C3 . 1.5391(16) yes
C2 . C5 . 1.5369(16) yes
C2 . C6 . 1.5384(16) yes
C2 . C103 . 1.5388(16) yes
C2 . C105 . 1.5374(16) yes
C2 . C106 . 1.5384(16) yes
C3 . C4 . 1.5579(15) yes
C3 . H31 . 0.976 no
C3 . H32 . 0.961 no
C4 . C5 . 1.5581(15) yes
C4 . C6 . 1.5581(15) yes
C4 . C7 . 1.522(2) yes
C4 . C7 . 1.522(2) yes
C4 . C103 . 1.5584(15) yes
C4 . C105 . 1.5575(15) yes
C4 . C106 . 1.5581(15) yes
C5 . H51 . 0.966 no
C5 . H52 . 0.976 no
C6 . H61 . 0.974 no
C6 . H62 . 0.968 no
C7 . N8 . 1.538(2) yes
C7 . C11 . 1.523(3) yes
C7 . C12 . 1.512(3) yes
N8 . O9 . 1.217(5) yes
N8 . O10 . 1.216(5) yes
N8 . O109 . 1.207(5) yes
N8 . O110 . 1.219(5) yes
C11 . H111 . 0.974 no
C11 . H112 . 0.968 no
C11 . H113 . 0.970 no
C12 . H121 . 0.963 no
C12 . H122 . 0.955 no
C12 . H123 . 0.958 no
C103 . H1031 . 0.968 no
C103 . H1032 . 0.969 no
C105 . H1051 . 0.980 no
C105 . H1052 . 0.971 no
C106 . H1061 . 0.958 no
C106 . H1062 . 0.970 no
Br201 . C202 . 1.9362(14) yes
C202 . C203 . 1.5389(16) yes
C202 . C205 . 1.5378(16) yes
C202 . C206 . 1.5384(16) yes
C202 . C303 . 1.5386(16) yes
C202 . C305 . 1.5382(16) yes
C202 . C306 . 1.5384(16) yes
C203 . C204 . 1.5588(15) yes
C203 . H2031 . 0.970 no
C203 . H2032 . 0.965 no
C204 . C205 . 1.5573(15) yes
C204 . C206 . 1.5585(15) yes
C204 . C207 . 1.517(3) yes
C204 . C207 . 1.517(3) yes
C204 . C303 . 1.5586(15) yes
C204 . C305 . 1.5573(15) yes
C204 . C306 . 1.5585(15) yes
C205 . H2051 . 0.966 no
C205 . H2052 . 0.973 no
C206 . H2061 . 0.968 no
C206 . H2062 . 0.964 no
C207 . N208 . 1.538(2) yes
C207 . C211 . 1.520(3) yes
C207 . C212 . 1.510(3) yes
N208 . O209 . 1.221(5) yes
N208 . O210 . 1.213(5) yes
N208 . O309 . 1.207(5) yes
N208 . O310 . 1.220(5) yes
C211 . H2111 . 0.957 no
C211 . H2112 . 0.962 no
C211 . H2113 . 0.958 no
C212 . H2121 . 0.968 no
C212 . H2122 . 0.966 no
C212 . H2123 . 0.974 no
C303 . H3031 . 0.959 no
C303 . H3032 . 0.972 no
C305 . H3051 . 0.974 no
C305 . H3052 . 0.971 no
C306 . H3061 . 0.968 no
C306 . H3062 . 0.971 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 . 125.69(4) yes
Br1 . C2 . C5 . 125.55(4) yes
C3 . C2 . C5 . 89.50(5) yes
Br1 . C2 . C6 . 125.62(4) yes
C3 . C2 . C6 . 89.47(5) yes
C5 . C2 . C6 . 89.51(5) yes
Br1 . C2 . C103 . 125.66(4) yes
Br1 . C2 . C105 . 125.57(4) yes
C103 . C2 . C105 . 89.48(5) yes
Br1 . C2 . C106 . 125.65(4) yes
C103 . C2 . C106 . 89.48(5) yes
C105 . C2 . C106 . 89.50(5) yes
C2 . C3 . C4 . 72.23(5) yes
C2 . C3 . H31 . 117.6 no
C4 . C3 . H31 . 117.4 no
C2 . C3 . H32 . 117.5 no
C4 . C3 . H32 . 116.6 no
H31 . C3 . H32 . 111.0 no
C3 . C4 . C5 . 88.05(5) yes
C3 . C4 . C6 . 88.07(5) yes
C5 . C4 . C6 . 88.03(5) yes
C3 . C4 . C7 . 128.39(13) yes
C5 . C4 . C7 . 123.60(13) yes
C6 . C4 . C7 . 127.81(13) yes
C7 . C4 . C103 . 127.51(13) yes
C7 . C4 . C105 . 123.62(13) yes
C103 . C4 . C105 . 88.05(5) yes
C7 . C4 . C106 . 128.66(13) yes
C103 . C4 . C106 . 88.06(5) yes
C105 . C4 . C106 . 88.06(5) yes
C2 . C5 . C4 . 72.28(5) yes
C2 . C5 . H51 . 116.3 no
C4 . C5 . H51 . 118.4 no
C2 . C5 . H52 . 116.2 no
C4 . C5 . H52 . 119.5 no
H51 . C5 . H52 . 109.8 no
C2 . C6 . C4 . 72.25(5) yes
C2 . C6 . H61 . 117.3 no
C4 . C6 . H61 . 117.3 no
C2 . C6 . H62 . 117.0 no
C4 . C6 . H62 . 118.2 no
H61 . C6 . H62 . 110.4 no
C4 . C7 . N8 . 104.73(16) yes
C4 . C7 . C11 . 111.16(17) yes
N8 . C7 . C11 . 107.72(16) yes
C4 . C7 . C12 . 111.21(17) yes
N8 . C7 . C12 . 108.90(15) yes
C11 . C7 . C12 . 112.7(2) yes
C7 . N8 . O9 . 117.96(5) yes
C7 . N8 . O10 . 118.02(5) yes
O9 . N8 . O10 . 124.02(5) yes
C7 . N8 . O109 . 117.98(5) yes
C7 . N8 . O110 . 117.96(5) yes
O109 . N8 . O110 . 123.99(5) yes
C7 . C11 . H111 . 111.3 no
C7 . C11 . H112 . 110.3 no
H111 . C11 . H112 . 108.0 no
C7 . C11 . H113 . 109.8 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 108.0 no
C7 . C12 . H121 . 109.5 no
C7 . C12 . H122 . 109.9 no
H121 . C12 . H122 . 109.3 no
C7 . C12 . H123 . 108.6 no
H121 . C12 . H123 . 108.8 no
H122 . C12 . H123 . 110.6 no
C2 . C103 . C4 . 72.23(5) yes
C2 . C103 . H1031 . 117.9 no
C4 . C103 . H1031 . 118.2 no
C2 . C103 . H1032 . 118.2 no
C4 . C103 . H1032 . 116.6 no
H1031 . C103 . H1032 . 109.7 no
C2 . C105 . C4 . 72.29(5) yes
C2 . C105 . H1051 . 116.9 no
C4 . C105 . H1051 . 118.4 no
C2 . C105 . H1052 . 117.0 no
C4 . C105 . H1052 . 118.0 no
H1051 . C105 . H1052 . 110.0 no
C2 . C106 . C4 . 72.25(5) yes
C2 . C106 . H1061 . 117.3 no
C4 . C106 . H1061 . 117.6 no
C2 . C106 . H1062 . 117.6 no
C4 . C106 . H1062 . 117.9 no
H1061 . C106 . H1062 . 109.9 no
Br201 . C202 . C203 . 125.66(4) yes
Br201 . C202 . C205 . 125.60(4) yes
C203 . C202 . C205 . 89.48(5) yes
Br201 . C202 . C206 . 125.62(4) yes
C203 . C202 . C206 . 89.49(5) yes
C205 . C202 . C206 . 89.48(5) yes
Br201 . C202 . C303 . 125.65(4) yes
Br201 . C202 . C305 . 125.60(4) yes
C303 . C202 . C305 . 89.47(5) yes
Br201 . C202 . C306 . 125.64(4) yes
C303 . C202 . C306 . 89.50(5) yes
C305 . C202 . C306 . 89.48(5) yes
C202 . C203 . C204 . 72.23(5) yes
C202 . C203 . H2031 . 118.7 no
C204 . C203 . H2031 . 117.2 no
C202 . C203 . H2032 . 118.0 no
C204 . C203 . H2032 . 116.6 no
H2031 . C203 . H2032 . 109.9 no
C203 . C204 . C205 . 88.06(5) yes
C203 . C204 . C206 . 88.05(5) yes
C205 . C204 . C206 . 88.05(5) yes
C203 . C204 . C207 . 129.09(13) yes
C205 . C204 . C207 . 123.24(13) yes
C206 . C204 . C207 . 127.44(13) yes
C207 . C204 . C303 . 128.13(13) yes
C207 . C204 . C305 . 123.11(13) yes
C303 . C204 . C305 . 88.06(5) yes
C207 . C204 . C306 . 128.52(13) yes
C303 . C204 . C306 . 88.05(5) yes
C305 . C204 . C306 . 88.06(5) yes
C202 . C205 . C204 . 72.30(5) yes
C202 . C205 . H2051 . 115.7 no
C204 . C205 . H2051 . 118.9 no
C202 . C205 . H2052 . 118.3 no
C204 . C205 . H2052 . 117.3 no
H2051 . C205 . H2052 . 110.1 no
C202 . C206 . C204 . 72.25(5) yes
C202 . C206 . H2061 . 116.0 no
C204 . C206 . H2061 . 117.2 no
C202 . C206 . H2062 . 117.5 no
C204 . C206 . H2062 . 117.5 no
H2061 . C206 . H2062 . 111.4 no
C204 . C207 . N208 . 105.00(16) yes
C204 . C207 . C211 . 111.10(17) yes
N208 . C207 . C211 . 107.43(16) yes
C204 . C207 . C212 . 111.40(17) yes
N208 . C207 . C212 . 109.06(15) yes
C211 . C207 . C212 . 112.5(2) yes
C207 . N208 . O209 . 117.95(5) yes
C207 . N208 . O210 . 118.01(5) yes
O209 . N208 . O210 . 124.01(5) yes
C207 . N208 . O309 . 117.98(5) yes
C207 . N208 . O310 . 117.97(5) yes
O309 . N208 . O310 . 123.99(5) yes
C207 . C211 . H2111 . 111.0 no
C207 . C211 . H2112 . 109.7 no
H2111 . C211 . H2112 . 109.7 no
C207 . C211 . H2113 . 109.7 no
H2111 . C211 . H2113 . 108.5 no
H2112 . C211 . H2113 . 108.2 no
C207 . C212 . H2121 . 110.5 no
C207 . C212 . H2122 . 110.8 no
H2121 . C212 . H2122 . 108.0 no
C207 . C212 . H2123 . 108.8 no
H2121 . C212 . H2123 . 109.2 no
H2122 . C212 . H2123 . 109.4 no
C202 . C303 . C204 . 72.24(5) yes
C202 . C303 . H3031 . 117.2 no
C204 . C303 . H3031 . 117.1 no
C202 . C303 . H3032 . 118.3 no
C204 . C303 . H3032 . 116.2 no
H3031 . C303 . H3032 . 111.0 no
C202 . C305 . C204 . 72.29(5) yes
C202 . C305 . H3051 . 117.5 no
C204 . C305 . H3051 . 118.4 no
C202 . C305 . H3052 . 117.6 no
C204 . C305 . H3052 . 116.9 no
H3051 . C305 . H3052 . 109.9 no
C202 . C306 . C204 . 72.25(5) yes
C202 . C306 . H3061 . 117.5 no
C204 . C306 . H3061 . 118.4 no
C202 . C306 . H3062 . 116.5 no
C204 . C306 . H3062 . 117.0 no
H3061 . C306 . H3062 . 110.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 . H121 . O209 2_567 156 0.96 2.57 3.469(6) yes
C211 . H2111 . O110 2_667 149 0.96 2.59 3.448(6) yes
C212 . H2121 . O9 2_667 154 0.97 2.58 3.479(6) yes
C212 . H2122 . O310 2_677 155 0.97 2.54 3.436(6) 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 2 2 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_13
_database_code_depnum_ccdc_archive 'CCDC 1825060'
_audit_update_record             
;
2018-02-21 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
#============================================================================== 
_audit_creation_date             2017-10-30
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 072eaa17
_chemical_name_systematic        .
_chemical_melting_point          357-358

_refine_special_details          
;
The bicyclo[1.1.1]pentane bridgehead carbon atoms show rotational 
disorder which was modelled. In order to maintain sensible geometric
and displacement parameters, same distance, thermal similarity and
vibrational restraints were necessary.
;

_cell_length_a                   14.7270(3)
_cell_length_b                   5.77560(10)
_cell_length_c                   21.9219(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.4149(18)
_cell_angle_gamma                90
_cell_volume                     1862.96(7)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C21 H29 N2 O1 
# Dc =      1.16 Fooo =    708.00 Mu =      5.49 M =    325.47
# Found Formula = C21 H30 N2 O1 
# Dc =      1.16 FOOO =    712.00 Mu =      5.49 M =    326.48

_chemical_formula_sum            'C21 H30 N2 O1'
_chemical_formula_moiety         'C21 H30 N2 O1'
_chemical_compound_source        synthetic
_chemical_formula_weight         326.48


_cell_measurement_reflns_used    8824
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.19
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.549

# Sheldrick geometric approximatio 0.89 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       '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)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            19286
_reflns_number_total             3885
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0314
# Number of reflections with Friedels Law is 3885 
# Theoretical number of reflections is about 7811 


_diffrn_reflns_theta_min         3.547
_diffrn_reflns_theta_max         76.317
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.791
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -18
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_oxford_diffrn_Wilson_B_factor   2.36
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.22
_refine_diff_density_max         0.22


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     462
_refine_ls_number_parameters     263
_oxford_refine_ls_R_factor_ref   0.0408
_refine_ls_wR_factor_ref         0.0984
_refine_ls_goodness_of_fit_ref   0.9976
_refine_ls_shift/su_max          0.0006095
_refine_ls_shift/su_mean         0.0000857


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3885
_refine_ls_R_factor_all          0.0408
_refine_ls_wR_factor_all         0.0984

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3559
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_gt          0.0948

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.65P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.56785(17) 0.1205(6) 0.36385(14) 0.0456 0.520(12) Uani D . P 1 1 .
C2 C 0.6241(4) 0.3447(8) 0.36822(12) 0.0412 0.520(12) Uani D . P 1 1 .
C3 C 0.61710(9) 0.2590(3) 0.43491(11) 0.0263 0.520(12) Uani D . P 1 1 .
C4 C 0.51525(16) 0.2091(11) 0.41831(16) 0.0467 0.520(12) Uani D . P 1 1 .
C5 C 0.6369(4) 0.0135(6) 0.4104(2) 0.0438 0.520(12) Uani D . P 1 1 .
C6 C 0.65653(6) 0.36988(18) 0.49160(4) 0.0309 1.0000 Uani D . . . . .
C7 C 0.75727(7) 0.42196(18) 0.48519(4) 0.0250 1.0000 Uani D . . . . .
N8 N 0.80019(6) 0.53737(14) 0.53885(4) 0.0216 1.0000 Uani . . . . . .
C9 C 0.77730(7) 0.78510(18) 0.53831(4) 0.0232 1.0000 Uani . . . . . .
C10 C 0.82010(6) 0.90982(18) 0.59371(4) 0.0227 1.0000 Uani . . . . . .
C11 C 0.92298(6) 0.87988(17) 0.59599(4) 0.0198 1.0000 Uani . . . . . .
C12 C 0.94662(7) 0.62355(17) 0.59261(4) 0.0227 1.0000 Uani . . . . . .
C13 C 0.89929(7) 0.51485(17) 0.53661(5) 0.0232 1.0000 Uani . . . . . .
N14 N 0.96732(5) 0.99254(15) 0.65018(4) 0.0214 1.0000 Uani . . . . . .
C15 C 1.05309(7) 1.07883(19) 0.64557(5) 0.0264 1.0000 Uani . . . . . .
O16 O 1.09232(5) 1.07314(17) 0.59749(4) 0.0373 1.0000 Uani . . . . . .
C17 C 1.09723(8) 1.1821(3) 0.70322(5) 0.0379 1.0000 Uani . . . . . .
C18 C 1.17417(9) 1.3448(3) 0.69118(6) 0.0472 1.0000 Uani . . . . . .
C19 C 0.92330(6) 0.98598(17) 0.70762(4) 0.0209 1.0000 Uani . . . . . .
C20 C 0.93728(7) 0.80240(19) 0.74774(5) 0.0258 1.0000 Uani . . . . . .
C21 C 0.89411(7) 0.7994(2) 0.80312(5) 0.0287 1.0000 Uani . . . . . .
C22 C 0.83733(7) 0.9799(2) 0.81850(5) 0.0269 1.0000 Uani . . . . . .
C23 C 0.82303(7) 1.1620(2) 0.77810(5) 0.0281 1.0000 Uani . . . . . .
C24 C 0.86543(7) 1.16495(18) 0.72271(5) 0.0254 1.0000 Uani . . . . . .
C101 C 0.56761(18) 0.1272(7) 0.36175(14) 0.0439 0.480(12) Uani D . P 1 2 .
C102 C 0.5953(5) 0.3820(7) 0.37148(17) 0.0475 0.480(12) Uani D . P 1 2 .
C103 C 0.61661(10) 0.2612(4) 0.43359(12) 0.0316 0.480(12) Uani D . P 1 2 .
C104 C 0.5232(3) 0.1379(11) 0.42406(16) 0.0447 0.480(12) Uani D . P 1 2 .
C105 C 0.6568(3) 0.0599(10) 0.3963(2) 0.0440 0.480(12) Uani D . P 1 2 .
H11 H 0.5421 0.0463 0.3265 0.0553 0.520(12) Uiso R . P 1 1 .
H21 H 0.6857 0.3328 0.3520 0.0475 0.520(12) Uiso R . P 1 1 .
H22 H 0.5929 0.4951 0.3572 0.0496 0.520(12) Uiso R . P 1 1 .
H41 H 0.4830 0.0891 0.4425 0.0553 0.520(12) Uiso R . P 1 1 .
H42 H 0.4766 0.3437 0.4103 0.0559 0.520(12) Uiso R . P 1 1 .
H51 H 0.7005 -0.0127 0.3972 0.0537 0.520(12) Uiso R . P 1 1 .
H52 H 0.6148 -0.1123 0.4352 0.0525 0.520(12) Uiso R . P 1 1 .
H61 H 0.6478 0.2725 0.5282 0.0375 0.520(12) Uiso R . P 1 1 .
H62 H 0.6250 0.5168 0.4962 0.0381 0.520(12) Uiso R . P 1 1 .
H63 H 0.6522 0.2563 0.5257 0.0375 0.480(12) Uiso R . P 1 2 .
H64 H 0.6232 0.5092 0.5021 0.0379 0.480(12) Uiso R . P 1 2 .
H71 H 0.7897 0.2750 0.4795 0.0298 1.0000 Uiso R . . . . .
H72 H 0.7654 0.5163 0.4486 0.0297 1.0000 Uiso R . . . . .
H91 H 0.7989 0.8567 0.5005 0.0271 1.0000 Uiso R . . . . .
H92 H 0.7103 0.8016 0.5391 0.0287 1.0000 Uiso R . . . . .
H101 H 0.7966 0.8445 0.6308 0.0263 1.0000 Uiso R . . . . .
H102 H 0.8041 1.0760 0.5921 0.0275 1.0000 Uiso R . . . . .
H111 H 0.9469 0.9564 0.5606 0.0228 1.0000 Uiso R . . . . .
H121 H 1.0129 0.6046 0.5907 0.0276 1.0000 Uiso R . . . . .
H122 H 0.9264 0.5445 0.6294 0.0265 1.0000 Uiso R . . . . .
H131 H 0.9146 0.3506 0.5351 0.0284 1.0000 Uiso R . . . . .
H132 H 0.9208 0.5917 0.4992 0.0270 1.0000 Uiso R . . . . .
H171 H 1.1179 1.0542 0.7277 0.0483 1.0000 Uiso R . . . . .
H172 H 1.0520 1.2591 0.7275 0.0474 1.0000 Uiso R . . . . .
H181 H 1.2013 1.4053 0.7291 0.0689 1.0000 Uiso R . . . . .
H182 H 1.2210 1.2638 0.6698 0.0717 1.0000 Uiso R . . . . .
H183 H 1.1531 1.4770 0.6656 0.0725 1.0000 Uiso R . . . . .
H201 H 0.9762 0.6800 0.7366 0.0319 1.0000 Uiso R . . . . .
H211 H 0.9044 0.6733 0.8306 0.0334 1.0000 Uiso R . . . . .
H221 H 0.8081 0.9741 0.8561 0.0323 1.0000 Uiso R . . . . .
H231 H 0.7832 1.2878 0.7875 0.0341 1.0000 Uiso R . . . . .
H241 H 0.8554 1.2903 0.6950 0.0314 1.0000 Uiso R . . . . .
H1011 H 0.5412 0.0570 0.3241 0.0533 0.480(12) Uiso R . P 1 2 .
H1021 H 0.6488 0.4397 0.3490 0.0570 0.480(12) Uiso R . P 1 2 .
H1022 H 0.5474 0.4976 0.3734 0.0565 0.480(12) Uiso R . P 1 2 .
H1041 H 0.5159 -0.0110 0.4441 0.0533 0.480(12) Uiso R . P 1 2 .
H1042 H 0.4672 0.2316 0.4270 0.0546 0.480(12) Uiso R . P 1 2 .
H1051 H 0.7131 0.0940 0.3758 0.0531 0.480(12) Uiso R . P 1 2 .
H1052 H 0.6592 -0.0979 0.4161 0.0534 0.480(12) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.78(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.538(2) yes
C1 . C4 . 1.538(2) yes
C1 . C5 . 1.540(2) yes
C1 . H11 . 0.985 no
C2 . C3 . 1.551(2) yes
C2 . H21 . 0.990 no
C2 . H22 . 1.007 no
C3 . C4 . 1.555(2) yes
C3 . C5 . 1.548(2) yes
C3 . C6 . 1.494(3) yes
C4 . H41 . 1.005 no
C4 . H42 . 0.975 no
C5 . H51 . 1.003 no
C5 . H52 . 0.971 no
C6 . C7 . 1.5261(13) yes
C6 . H61 . 0.992 no
C6 . H62 . 0.975 no
C6 . C7 . 1.5261(13) yes
C6 . C103 . 1.515(3) yes
C6 . H63 . 0.998 no
C6 . H64 . 0.975 no
C7 . N8 . 1.4713(11) yes
C7 . H71 . 0.985 no
C7 . H72 . 0.981 no
N8 . C9 . 1.4699(13) yes
N8 . C13 . 1.4681(12) yes
C9 . C10 . 1.5254(13) yes
C9 . H91 . 0.991 no
C9 . H92 . 0.992 no
C10 . C11 . 1.5237(13) yes
C10 . H101 . 0.974 no
C10 . H102 . 0.989 no
C11 . C12 . 1.5233(13) yes
C11 . N14 . 1.4819(12) yes
C11 . H111 . 0.972 no
C12 . C13 . 1.5215(13) yes
C12 . H121 . 0.984 no
C12 . H122 . 0.983 no
C13 . H131 . 0.976 no
C13 . H132 . 0.996 no
N14 . C15 . 1.3655(13) yes
N14 . C19 . 1.4409(12) yes
C15 . O16 . 1.2237(13) yes
C15 . C17 . 1.5185(15) yes
C17 . C18 . 1.5040(17) yes
C17 . H171 . 0.956 no
C17 . H172 . 0.978 no
C18 . H181 . 0.972 no
C18 . H182 . 0.971 no
C18 . H183 . 0.990 no
C19 . C20 . 1.3874(14) yes
C19 . C24 . 1.3884(14) yes
C20 . C21 . 1.3940(14) yes
C20 . H201 . 0.949 no
C21 . C22 . 1.3870(16) yes
C21 . H211 . 0.953 no
C22 . C23 . 1.3852(16) yes
C22 . H221 . 0.947 no
C23 . C24 . 1.3888(14) yes
C23 . H231 . 0.962 no
C24 . H241 . 0.953 no
C101 . C102 . 1.540(2) yes
C101 . C104 . 1.540(2) yes
C101 . C105 . 1.539(2) yes
C101 . H1011 . 0.986 no
C102 . C103 . 1.550(2) yes
C102 . H1021 . 1.004 no
C102 . H1022 . 0.973 no
C103 . C104 . 1.555(2) yes
C103 . C105 . 1.553(2) yes
C104 . H1041 . 0.974 no
C104 . H1042 . 0.990 no
C105 . H1051 . 0.980 no
C105 . H1052 . 1.009 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C4 . 87.67(5) yes
C2 . C1 . C5 . 87.57(5) yes
C4 . C1 . C5 . 87.63(5) yes
C2 . C1 . H11 . 127.3 no
C4 . C1 . H11 . 126.9 no
C5 . C1 . H11 . 126.6 no
C1 . C2 . C3 . 74.53(5) yes
C1 . C2 . H21 . 114.8 no
C3 . C2 . H21 . 114.5 no
C1 . C2 . H22 . 118.2 no
C3 . C2 . H22 . 116.9 no
H21 . C2 . H22 . 112.9 no
C2 . C3 . C4 . 86.58(5) yes
C2 . C3 . C5 . 86.80(5) yes
C4 . C3 . C5 . 86.71(5) yes
C2 . C3 . C6 . 127.49(5) yes
C4 . C3 . C6 . 127.70(5) yes
C5 . C3 . C6 . 127.52(5) yes
C1 . C4 . C3 . 74.40(5) yes
C1 . C4 . H41 . 116.5 no
C3 . C4 . H41 . 118.5 no
C1 . C4 . H42 . 115.8 no
C3 . C4 . H42 . 116.4 no
H41 . C4 . H42 . 111.1 no
C1 . C5 . C3 . 74.56(5) yes
C1 . C5 . H51 . 117.9 no
C3 . C5 . H51 . 115.4 no
C1 . C5 . H52 . 116.4 no
C3 . C5 . H52 . 114.8 no
H51 . C5 . H52 . 112.7 no
C3 . C6 . C7 . 110.69(5) yes
C3 . C6 . H61 . 111.7 no
C7 . C6 . H61 . 110.2 no
C3 . C6 . H62 . 106.8 no
C7 . C6 . H62 . 107.9 no
H61 . C6 . H62 . 109.4 no
C7 . C6 . C103 . 110.41(5) yes
C7 . C6 . H63 . 106.9 no
C103 . C6 . H63 . 108.8 no
C7 . C6 . H64 . 111.1 no
C103 . C6 . H64 . 111.0 no
H63 . C6 . H64 . 108.5 no
C6 . C7 . N8 . 113.72(7) yes
C6 . C7 . H71 . 108.7 no
N8 . C7 . H71 . 107.3 no
C6 . C7 . H72 . 109.7 no
N8 . C7 . H72 . 109.8 no
H71 . C7 . H72 . 107.4 no
C7 . N8 . C9 . 110.12(8) yes
C7 . N8 . C13 . 109.11(7) yes
C9 . N8 . C13 . 108.30(8) yes
N8 . C9 . C10 . 111.49(8) yes
N8 . C9 . H91 . 109.3 no
C10 . C9 . H91 . 109.4 no
N8 . C9 . H92 . 108.7 no
C10 . C9 . H92 . 108.6 no
H91 . C9 . H92 . 109.2 no
C9 . C10 . C11 . 110.45(8) yes
C9 . C10 . H101 . 109.4 no
C11 . C10 . H101 . 108.5 no
C9 . C10 . H102 . 109.9 no
C11 . C10 . H102 . 110.3 no
H101 . C10 . H102 . 108.3 no
C10 . C11 . C12 . 109.74(8) yes
C10 . C11 . N14 . 112.35(7) yes
C12 . C11 . N14 . 111.82(8) yes
C10 . C11 . H111 . 108.4 no
C12 . C11 . H111 . 108.2 no
N14 . C11 . H111 . 106.1 no
C11 . C12 . C13 . 110.02(8) yes
C11 . C12 . H121 . 109.8 no
C13 . C12 . H121 . 109.9 no
C11 . C12 . H122 . 109.5 no
C13 . C12 . H122 . 109.0 no
H121 . C12 . H122 . 108.6 no
C12 . C13 . N8 . 111.03(8) yes
C12 . C13 . H131 . 109.3 no
N8 . C13 . H131 . 108.6 no
C12 . C13 . H132 . 109.3 no
N8 . C13 . H132 . 109.8 no
H131 . C13 . H132 . 108.8 no
C11 . N14 . C15 . 118.60(8) yes
C11 . N14 . C19 . 119.32(7) yes
C15 . N14 . C19 . 121.73(8) yes
N14 . C15 . O16 . 121.71(10) yes
N14 . C15 . C17 . 116.53(9) yes
O16 . C15 . C17 . 121.75(9) yes
C15 . C17 . C18 . 113.51(10) yes
C15 . C17 . H171 . 106.2 no
C18 . C17 . H171 . 110.9 no
C15 . C17 . H172 . 110.7 no
C18 . C17 . H172 . 110.3 no
H171 . C17 . H172 . 104.7 no
C17 . C18 . H181 . 111.1 no
C17 . C18 . H182 . 109.8 no
H181 . C18 . H182 . 108.2 no
C17 . C18 . H183 . 111.2 no
H181 . C18 . H183 . 108.4 no
H182 . C18 . H183 . 108.0 no
N14 . C19 . C20 . 120.92(9) yes
N14 . C19 . C24 . 119.46(9) yes
C20 . C19 . C24 . 119.61(9) yes
C19 . C20 . C21 . 120.05(9) yes
C19 . C20 . H201 . 118.8 no
C21 . C20 . H201 . 121.2 no
C20 . C21 . C22 . 120.26(10) yes
C20 . C21 . H211 . 119.6 no
C22 . C21 . H211 . 120.2 no
C21 . C22 . C23 . 119.49(9) yes
C21 . C22 . H221 . 119.1 no
C23 . C22 . H221 . 121.4 no
C22 . C23 . C24 . 120.44(10) yes
C22 . C23 . H231 . 121.0 no
C24 . C23 . H231 . 118.6 no
C23 . C24 . C19 . 120.14(10) yes
C23 . C24 . H241 . 120.3 no
C19 . C24 . H241 . 119.6 no
C102 . C101 . C104 . 87.64(5) yes
C102 . C101 . C105 . 87.57(5) yes
C104 . C101 . C105 . 87.67(5) yes
C102 . C101 . H1011 . 127.0 no
C104 . C101 . H1011 . 126.3 no
C105 . C101 . H1011 . 127.4 no
C101 . C102 . C103 . 74.57(5) yes
C101 . C102 . H1021 . 117.3 no
C103 . C102 . H1021 . 116.5 no
C101 . C102 . H1022 . 118.3 no
C103 . C102 . H1022 . 113.1 no
H1021 . C102 . H1022 . 112.3 no
C102 . C103 . C6 . 127.44(5) yes
C102 . C103 . C104 . 86.73(5) yes
C6 . C103 . C104 . 127.76(5) yes
C102 . C103 . C105 . 86.70(5) yes
C6 . C103 . C105 . 127.51(5) yes
C104 . C103 . C105 . 86.64(5) yes
C101 . C104 . C103 . 74.40(5) yes
C101 . C104 . H1041 . 115.1 no
C103 . C104 . H1041 . 117.2 no
C101 . C104 . H1042 . 117.7 no
C103 . C104 . H1042 . 118.3 no
H1041 . C104 . H1042 . 110.2 no
C101 . C105 . C103 . 74.52(5) yes
C101 . C105 . H1051 . 116.4 no
C103 . C105 . H1051 . 116.1 no
C101 . C105 . H1052 . 116.9 no
C103 . C105 . H1052 . 117.2 no
H1051 . C105 . H1052 . 111.3 no


####################################################################### 
# 
# 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_5r
_database_code_depnum_ccdc_archive 'CCDC 1825057'
_audit_update_record             
;
2018-02-21 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2017-09-18
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 052eaa17-c
_chemical_name_systematic        .
_chemical_melting_point          '349 (decomposition)'

_refine_special_details          
;
Crystallisation from dichloromethane/hexane (roughly 1:4) affords 2 
polymorphs. The initially formed polymorph (the kinetic structure)
is needle-like with the following cell parameters: P21/n, a = 10.0114, 
b = 6.9132, c = 18.1356, beta = 92.252. At temperatures below 240K, the 
diffraction pattern exhibited streaking (in some cases this could be resolved 
as very weak satellites) between the reflections for all crystals screened 
(roughly 15 in total). We attribute this to a phase change, possibly to a
modulated structure which could not be resolved at 100K. Integration of the data
and model refinement did not give a satisfactory solution and the structure 
exhibited significant translational disorder along the b-axis. Attempted 
modelling of this with a split-site model did not lead to a stable refinement.

After leaving these crystals in the aforementioned solution for approximately
1 week, these needles gradually formed large blocks (possibly a more 
thermodynamically favoured structure) which did not exhibit a phase transition
or any artifacts in the diffraction pattern - the data below is for this
polymorph.
;

_cell_length_a                   12.8692(2)
_cell_length_b                   8.45340(10)
_cell_length_c                   11.4743(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.0055(15)
_cell_angle_gamma                90
_cell_volume                     1232.88(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C12 H12 I1 N1 O2 
# Dc =      1.77 Fooo =    640.00 Mu =    203.00 M =    329.14
# Found Formula = C12 H12 I1 N1 O2 
# Dc =      1.77 FOOO =    640.00 Mu =    203.00 M =    329.14

_chemical_formula_sum            'C12 H12 I1 N1 O2'
_chemical_formula_moiety         'C12 H12 I1 N1 O2'
_chemical_compound_source        synthetic
_chemical_formula_weight         329.14


_cell_measurement_reflns_used    15554
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.13
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_max          0.38

_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    20.300

# Sheldrick geometric approximatio 0.01 0.07 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.00
_exptl_absorpt_correction_T_max  0.07
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       '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)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            26750
_reflns_number_total             2580
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0358
# Number of reflections with Friedels Law is 2580 
# Theoretical number of reflections is about 5157 


_diffrn_reflns_theta_min         6.288
_diffrn_reflns_theta_max         76.128
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        76.128
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.12
_oxford_diffrn_Wilson_scale      0.06

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

_refine_diff_density_min         -0.99
_refine_diff_density_max         0.86


# 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         2575
_refine_ls_number_restraints     0
_refine_ls_number_parameters     145
_oxford_refine_ls_R_factor_ref   0.0278
_refine_ls_wR_factor_ref         0.0760
_refine_ls_goodness_of_fit_ref   1.0008
_refine_ls_shift/su_max          0.0012215
_refine_ls_shift/su_mean         0.0000258


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2575
_refine_ls_R_factor_all          0.0278
_refine_ls_wR_factor_all         0.0760

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2525
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_gt          0.0756

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.54P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
I1 I 0.600534(13) 0.29189(2) 0.563690(16) 0.0300 1.0000 Uani . . . . . .
C2 C 0.4461(2) 0.2402(3) 0.6002(2) 0.0219 1.0000 Uani . . . . . .
C3 C 0.3767(2) 0.3435(4) 0.6681(3) 0.0285 1.0000 Uani . . . . . .
C4 C 0.3134(2) 0.1900(3) 0.6278(2) 0.0224 1.0000 Uani . . . . . .
C5 C 0.4163(2) 0.0952(3) 0.6683(3) 0.0269 1.0000 Uani . . . . . .
C6 C 0.3499(2) 0.2096(3) 0.5054(3) 0.0254 1.0000 Uani . . . . . .
C7 C 0.2032(2) 0.1468(3) 0.6473(3) 0.0281 1.0000 Uani . . . . . .
C8 C 0.1684(2) -0.0050(3) 0.5836(2) 0.0234 1.0000 Uani . . . . . .
C9 C 0.1212(2) -0.0014(3) 0.4652(2) 0.0251 1.0000 Uani . . . . . .
C10 C 0.0896(2) -0.1397(3) 0.4051(2) 0.0249 1.0000 Uani . . . . . .
C11 C 0.1073(2) -0.2815(3) 0.4654(3) 0.0230 1.0000 Uani . . . . . .
N12 N 0.07273(19) -0.4281(3) 0.4030(2) 0.0296 1.0000 Uani . . . . . .
O13 O 0.0095(2) -0.4188(3) 0.3117(2) 0.0423 1.0000 Uani . . . . . .
O14 O 0.1085(2) -0.5543(3) 0.4453(2) 0.0450 1.0000 Uani . . . . . .
C15 C 0.1553(2) -0.2900(3) 0.5822(3) 0.0263 1.0000 Uani . . . . . .
C16 C 0.1851(2) -0.1495(4) 0.6401(2) 0.0262 1.0000 Uani . . . . . .
H32 H 0.3991 0.3575 0.7540 0.0342 1.0000 Uiso R . . . . .
H31 H 0.3509 0.4423 0.6305 0.0342 1.0000 Uiso R . . . . .
H51 H 0.4422 0.0907 0.7531 0.0325 1.0000 Uiso R . . . . .
H52 H 0.4214 -0.0089 0.6333 0.0321 1.0000 Uiso R . . . . .
H62 H 0.3231 0.2987 0.4571 0.0305 1.0000 Uiso R . . . . .
H61 H 0.3511 0.1174 0.4576 0.0295 1.0000 Uiso R . . . . .
H72 H 0.2026 0.1301 0.7293 0.0346 1.0000 Uiso R . . . . .
H71 H 0.1541 0.2294 0.6183 0.0343 1.0000 Uiso R . . . . .
H91 H 0.1100 0.0964 0.4269 0.0302 1.0000 Uiso R . . . . .
H101 H 0.0578 -0.1375 0.3269 0.0306 1.0000 Uiso R . . . . .
H151 H 0.1667 -0.3876 0.6202 0.0322 1.0000 Uiso R . . . . .
H161 H 0.2170 -0.1529 0.7197 0.0314 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.29(6)
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
I1 . C2 . 2.139(3) yes
C2 . C3 . 1.545(4) yes
C2 . C5 . 1.535(4) yes
C2 . C6 . 1.537(4) yes
C3 . C4 . 1.563(4) yes
C3 . H32 . 0.990 no
C3 . H31 . 0.974 no
C4 . C5 . 1.555(4) yes
C4 . C6 . 1.558(4) yes
C4 . C7 . 1.514(4) yes
C5 . H51 . 0.979 no
C5 . H52 . 0.974 no
C6 . H62 . 0.966 no
C6 . H61 . 0.955 no
C7 . C8 . 1.510(4) yes
C7 . H72 . 0.953 no
C7 . H71 . 0.965 no
C8 . C9 . 1.400(4) yes
C8 . C16 . 1.384(4) yes
C9 . C10 . 1.385(4) yes
C9 . H91 . 0.936 no
C10 . C11 . 1.385(4) yes
C10 . H101 . 0.926 no
C11 . N12 . 1.465(3) yes
C11 . C15 . 1.387(4) yes
N12 . O13 . 1.224(4) yes
N12 . O14 . 1.231(4) yes
C15 . C16 . 1.385(4) yes
C15 . H151 . 0.934 no
C16 . H161 . 0.942 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
I1 . C2 . C3 . 127.72(19) yes
I1 . C2 . C5 . 125.23(19) yes
C3 . C2 . C5 . 89.1(2) yes
I1 . C2 . C6 . 124.48(19) yes
C3 . C2 . C6 . 89.2(2) yes
C5 . C2 . C6 . 89.3(2) yes
C2 . C3 . C4 . 72.36(19) yes
C2 . C3 . H32 . 117.9 no
C4 . C3 . H32 . 116.8 no
C2 . C3 . H31 . 116.5 no
C4 . C3 . H31 . 117.1 no
H32 . C3 . H31 . 111.3 no
C3 . C4 . C5 . 87.7(2) yes
C3 . C4 . C6 . 87.8(2) yes
C5 . C4 . C6 . 87.8(2) yes
C3 . C4 . C7 . 127.8(2) yes
C5 . C4 . C7 . 127.2(2) yes
C6 . C4 . C7 . 125.5(2) yes
C2 . C5 . C4 . 72.85(19) yes
C2 . C5 . H51 . 117.6 no
C4 . C5 . H51 . 117.3 no
C2 . C5 . H52 . 118.3 no
C4 . C5 . H52 . 116.8 no
H51 . C5 . H52 . 109.9 no
C2 . C6 . C4 . 72.72(19) yes
C2 . C6 . H62 . 116.8 no
C4 . C6 . H62 . 118.0 no
C2 . C6 . H61 . 117.4 no
C4 . C6 . H61 . 117.7 no
H62 . C6 . H61 . 110.1 no
C4 . C7 . C8 . 110.3(2) yes
C4 . C7 . H72 . 109.6 no
C8 . C7 . H72 . 107.7 no
C4 . C7 . H71 . 110.6 no
C8 . C7 . H71 . 108.6 no
H72 . C7 . H71 . 110.0 no
C7 . C8 . C9 . 120.1(3) yes
C7 . C8 . C16 . 120.8(2) yes
C9 . C8 . C16 . 119.1(2) yes
C8 . C9 . C10 . 120.9(3) yes
C8 . C9 . H91 . 119.1 no
C10 . C9 . H91 . 120.0 no
C9 . C10 . C11 . 118.0(2) yes
C9 . C10 . H101 . 121.0 no
C11 . C10 . H101 . 120.9 no
C10 . C11 . N12 . 118.3(3) yes
C10 . C11 . C15 . 122.7(2) yes
N12 . C11 . C15 . 118.9(2) yes
C11 . N12 . O13 . 118.3(3) yes
C11 . N12 . O14 . 118.3(2) yes
O13 . N12 . O14 . 123.4(3) yes
C11 . C15 . C16 . 117.9(2) yes
C11 . C15 . H151 . 120.7 no
C16 . C15 . H151 . 121.5 no
C15 . C16 . C8 . 121.4(2) yes
C15 . C16 . H161 . 119.0 no
C8 . C16 . H161 . 119.5 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
C10 . H101 . O13 4_555 133 0.93 2.50 3.211(4) 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 2 x .
1 1 2 x .
-3 1 2 x .
0 1 2 x .
0 10 0 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_5s
_database_code_depnum_ccdc_archive 'CCDC 1825058'
_audit_update_record             
;
2018-02-21 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2017-07-16
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 041eaa17
_chemical_name_systematic        .
_chemical_melting_point          357-359

_refine_special_details          
;
Crystals of this compound (crystallised from hexane) shattered 
upon cooling to 150K, possibly due to a phase transition. Slow
cooling from room temperature to 150K also resulted in shattering.
The crystals were stable at 200K and data was collected at this
temperature.

The CF3 group clearly occupies 3 distinct positions as seen in 
the Fourier difference map. In order to maintain sensible geometric
and displacement parameters, same distance, thermal similarity and
vibrational restraints were necessary for a stable refinement.
;

_cell_length_a                   5.6020(3)
_cell_length_b                   8.9978(5)
_cell_length_c                   13.3874(9)
_cell_angle_alpha                95.953(5)
_cell_angle_beta                 98.695(5)
_cell_angle_gamma                98.785(5)
_cell_volume                     653.64(7)

_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'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C13 H12 F3 I1 
# Dc =      1.79 Fooo =    340.00 Mu =    193.90 M =    352.14
# Found Formula = C13 H12 F3 I1 
# Dc =      1.79 FOOO =    340.00 Mu =    193.90 M =    352.14

_chemical_formula_sum            'C13 H12 F3 I1'
_chemical_formula_moiety         'C13 H12 F3 I1'
_chemical_compound_source        synthetic
_chemical_formula_weight         352.14


_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    200

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_max          0.49

_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    19.390

# Sheldrick geometric approximatio 0.26 0.31 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.16
_exptl_absorpt_correction_T_max  0.31
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       '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)'
_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      200
_diffrn_reflns_number            5134
_reflns_number_total             2669
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0426
# Number of reflections with Friedels Law is 2669 
# Theoretical number of reflections is about 5470 


_diffrn_reflns_theta_min         5.016
_diffrn_reflns_theta_max         76.150
_diffrn_measured_fraction_theta_max 0.977

_diffrn_reflns_theta_full        66.251
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   3.72
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.94
_refine_diff_density_max         0.75


# 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         2661
_refine_ls_number_restraints     280
_refine_ls_number_parameters     211
_oxford_refine_ls_R_factor_ref   0.0388
_refine_ls_wR_factor_ref         0.0990
_refine_ls_goodness_of_fit_ref   0.9928
_refine_ls_shift/su_max          0.0003355
_refine_ls_shift/su_mean         0.0000268


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2662
_refine_ls_R_factor_all          0.0388
_refine_ls_wR_factor_all         0.0992

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2443
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_gt          0.0947

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.69P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
I1 I 0.03796(5) 0.26735(3) 0.40078(2) 0.0522 1.0000 Uani . . . . . .
C2 C 0.2373(7) 0.2627(4) 0.5493(3) 0.0386 1.0000 Uani . . . . . .
C3 C 0.4318(9) 0.3898(5) 0.6131(4) 0.0503 1.0000 Uani . . . . . .
C4 C 0.4040(7) 0.2551(4) 0.6773(3) 0.0382 1.0000 Uani . . . . . .
C5 C 0.1215(8) 0.2387(5) 0.6449(3) 0.0438 1.0000 Uani . . . . . .
C6 C 0.4051(8) 0.1483(5) 0.5779(3) 0.0425 1.0000 Uani . . . . . .
C7 C 0.5394(8) 0.2471(5) 0.7832(3) 0.0475 1.0000 Uani . . . . . .
C8 C 0.4594(7) 0.0960(5) 0.8176(3) 0.0405 1.0000 Uani . . . . . .
C9 C 0.5664(8) -0.0292(6) 0.7916(4) 0.0498 1.0000 Uani . . . . . .
C10 C 0.4894(9) -0.1691(6) 0.8190(4) 0.0525 1.0000 Uani . . . . . .
C11 C 0.2962(7) -0.1884(4) 0.8746(3) 0.0442 1.0000 Uani D . . . . .
C12 C 0.1873(9) -0.0662(6) 0.8998(3) 0.0512 1.0000 Uani . . . . . .
C13 C 0.2676(9) 0.0741(5) 0.8729(3) 0.0483 1.0000 Uani . . . . . .
C14 C 0.2094(6) -0.3398(3) 0.9039(2) 0.0685 1.0000 Uani D . . . . .
F15 F 0.0259(18) -0.4210(7) 0.8350(5) 0.0852 0.469(13) Uani D . P 1 1 .
F16 F 0.3864(12) -0.4242(7) 0.9144(9) 0.0847 0.469(13) Uani D . P 1 1 .
F17 F 0.126(2) -0.3299(5) 0.9929(5) 0.0664 0.469(13) Uani D . P 1 1 .
F115 F 0.120(2) -0.4441(6) 0.8230(4) 0.0785 0.386(12) Uani D . P 1 2 .
F116 F 0.3893(11) -0.3943(8) 0.9594(8) 0.0709 0.386(12) Uani D . P 1 2 .
F117 F 0.0309(18) -0.3371(6) 0.9600(8) 0.0746 0.386(12) Uani D . P 1 2 .
F215 F 0.291(4) -0.4518(6) 0.8520(13) 0.0708 0.145(6) Uani D . P 1 3 .
F216 F 0.283(4) -0.3477(9) 1.0027(6) 0.0731 0.145(6) Uani D . P 1 3 .
F217 F -0.0365(12) -0.3763(12) 0.8869(16) 0.0738 0.145(6) Uani D . P 1 3 .
H31 H 0.5872 0.4133 0.5890 0.0598 1.0000 Uiso R . . . . .
H32 H 0.3775 0.4828 0.6365 0.0602 1.0000 Uiso R . . . . .
H51 H 0.0246 0.1405 0.6475 0.0531 1.0000 Uiso R . . . . .
H52 H 0.0424 0.3186 0.6722 0.0531 1.0000 Uiso R . . . . .
H61 H 0.3269 0.0423 0.5731 0.0512 1.0000 Uiso R . . . . .
H62 H 0.5591 0.1544 0.5517 0.0512 1.0000 Uiso R . . . . .
H71 H 0.7154 0.2636 0.7825 0.0572 1.0000 Uiso R . . . . .
H72 H 0.5002 0.3269 0.8299 0.0572 1.0000 Uiso R . . . . .
H91 H 0.6928 -0.0185 0.7544 0.0601 1.0000 Uiso R . . . . .
H101 H 0.5650 -0.2507 0.8012 0.0631 1.0000 Uiso R . . . . .
H121 H 0.0549 -0.0792 0.9345 0.0608 1.0000 Uiso R . . . . .
H131 H 0.1912 0.1558 0.8920 0.0580 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.9(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
I1 . C2 . 2.136(4) yes
C2 . C3 . 1.536(5) yes
C2 . C5 . 1.540(6) yes
C2 . C6 . 1.536(6) yes
C3 . C4 . 1.559(6) yes
C3 . H31 . 0.975 no
C3 . H32 . 0.971 no
C4 . C5 . 1.556(6) yes
C4 . C6 . 1.560(5) yes
C4 . C7 . 1.518(6) yes
C5 . H51 . 0.970 no
C5 . H52 . 0.969 no
C6 . H61 . 0.979 no
C6 . H62 . 0.975 no
C7 . C8 . 1.506(6) yes
C7 . H71 . 0.976 no
C7 . H72 . 0.975 no
C8 . C9 . 1.392(6) yes
C8 . C13 . 1.395(6) yes
C9 . C10 . 1.372(7) yes
C9 . H91 . 0.924 no
C10 . C11 . 1.403(6) yes
C10 . H101 . 0.930 no
C11 . C12 . 1.373(6) yes
C11 . C14 . 1.488(3) yes
C12 . C13 . 1.376(7) yes
C12 . H121 . 0.932 no
C13 . H131 . 0.938 no
C14 . F15 . 1.336(5) yes
C14 . F16 . 1.338(5) yes
C14 . F17 . 1.343(5) yes
C14 . F115 . 1.336(5) yes
C14 . F116 . 1.344(5) yes
C14 . F117 . 1.340(5) yes
C14 . F215 . 1.342(6) yes
C14 . F216 . 1.336(6) yes
C14 . F217 . 1.345(6) 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
I1 . C2 . C3 . 127.0(3) yes
I1 . C2 . C5 . 125.1(3) yes
C3 . C2 . C5 . 89.3(3) yes
I1 . C2 . C6 . 125.4(3) yes
C3 . C2 . C6 . 89.0(3) yes
C5 . C2 . C6 . 89.2(3) yes
C2 . C3 . C4 . 72.8(3) yes
C2 . C3 . H31 . 117.3 no
C4 . C3 . H31 . 116.7 no
C2 . C3 . H32 . 117.3 no
C4 . C3 . H32 . 118.5 no
H31 . C3 . H32 . 110.1 no
C3 . C4 . C5 . 87.9(3) yes
C3 . C4 . C6 . 87.3(3) yes
C5 . C4 . C6 . 87.8(3) yes
C3 . C4 . C7 . 127.6(3) yes
C5 . C4 . C7 . 126.3(4) yes
C6 . C4 . C7 . 126.8(4) yes
C2 . C5 . C4 . 72.8(3) yes
C2 . C5 . H51 . 118.3 no
C4 . C5 . H51 . 116.9 no
C2 . C5 . H52 . 117.6 no
C4 . C5 . H52 . 117.6 no
H51 . C5 . H52 . 109.8 no
C2 . C6 . C4 . 72.8(3) yes
C2 . C6 . H61 . 116.9 no
C4 . C6 . H61 . 117.7 no
C2 . C6 . H62 . 118.3 no
C4 . C6 . H62 . 117.0 no
H61 . C6 . H62 . 110.1 no
C4 . C7 . C8 . 110.7(3) yes
C4 . C7 . H71 . 109.1 no
C8 . C7 . H71 . 110.3 no
C4 . C7 . H72 . 108.0 no
C8 . C7 . H72 . 108.8 no
H71 . C7 . H72 . 109.7 no
C7 . C8 . C9 . 121.3(4) yes
C7 . C8 . C13 . 121.3(4) yes
C9 . C8 . C13 . 117.3(4) yes
C8 . C9 . C10 . 122.1(4) yes
C8 . C9 . H91 . 119.3 no
C10 . C9 . H91 . 118.6 no
C9 . C10 . C11 . 119.6(4) yes
C9 . C10 . H101 . 120.3 no
C11 . C10 . H101 . 120.0 no
C10 . C11 . C12 . 118.9(4) yes
C10 . C11 . C14 . 120.1(3) yes
C12 . C11 . C14 . 121.0(3) yes
C11 . C12 . C13 . 121.1(4) yes
C11 . C12 . H121 . 119.3 no
C13 . C12 . H121 . 119.6 no
C8 . C13 . C12 . 121.1(4) yes
C8 . C13 . H131 . 119.8 no
C12 . C13 . H131 . 119.2 no
C11 . C14 . F15 . 112.40(5) yes
C11 . C14 . F16 . 112.45(5) yes
F15 . C14 . F16 . 106.40(5) yes
C11 . C14 . F17 . 112.41(5) yes
F15 . C14 . F17 . 106.34(5) yes
F16 . C14 . F17 . 106.37(5) yes
C11 . C14 . F115 . 112.42(5) yes
C11 . C14 . F116 . 112.38(5) yes
F115 . C14 . F116 . 106.35(5) yes
C11 . C14 . F117 . 112.44(5) yes
F115 . C14 . F117 . 106.41(5) yes
F116 . C14 . F117 . 106.36(5) yes
C11 . C14 . F215 . 112.42(5) yes
C11 . C14 . F216 . 112.43(5) yes
F215 . C14 . F216 . 106.37(5) yes
C11 . C14 . F217 . 112.41(5) yes
F215 . C14 . F217 . 106.36(5) yes
F216 . C14 . F217 . 106.37(5) 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
-2 -1 8 x .
-2 -2 8 x .
-2 -1 7 x .
3 -6 1 x .
3 -5 2 x .
-2 -1 6 x .
-3 -1 7 x .
