# Electronic Supplementary Material (ESI) for ChemComm.
# 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_IColl2PF6-300K
_database_code_depnum_ccdc_archive 'CCDC 1853983'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 130lcm18
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   8.0754(2)
_cell_length_b                   8.3550(3)
_cell_length_c                   15.6634(7)
_cell_angle_alpha                99.537(3)
_cell_angle_beta                 98.842(3)
_cell_angle_gamma                98.269(3)
_cell_volume                     1014.16(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
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'
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'
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'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 '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 = C16 H22 F6 I1 N2 P1 
# Dc =      1.68 Fooo =    508.00 Mu =    136.80 M =    514.23
# Found Formula = C16 H22.00 F6 I1 N2 P1 
# Dc =      1.68 FOOO =    508.00 Mu =    136.80 M =    514.23

_chemical_formula_sum            'C16 H22 F6 I N2 P'
_chemical_formula_moiety         'C16 H22 I N2, F6 P'
_chemical_compound_source        .
_chemical_formula_weight         514.23


_cell_measurement_reflns_used    5716
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    300

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_max          0.23

_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             507.998
_exptl_absorpt_coefficient_mu    13.680

# Sheldrick geometric approximatio 0.07 0.38 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.10
_exptl_absorpt_correction_T_max  0.38
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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      300
_diffrn_reflns_number            9190
_reflns_number_total             4174
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0447
# Number of reflections with Friedels Law is 4174 
# Theoretical number of reflections is about 8475 


_diffrn_reflns_theta_min         5.452
_diffrn_reflns_theta_max         76.049
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        72.500
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   3.85
_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         -0.80
_refine_diff_density_max         1.02


# 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     0
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4173
_oxford_refine_ls_R_factor_ref   0.0404
_refine_ls_wR_factor_ref         0.1042
_refine_ls_goodness_of_fit_ref   0.9047
_refine_ls_shift/su_max          0.0004285
_refine_ls_shift/su_mean         0.0000117


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4173
_refine_ls_R_factor_all          0.0404
_refine_ls_wR_factor_all         0.1042

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3899
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_gt          0.1015


_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 + 1.24P] 
 ,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 0.48038(3) 0.52009(3) 0.224666(14) 0.0496 1.0000 Uani . . . . . .
N11 N 0.3518(4) 0.5395(4) 0.0853(2) 0.0520 1.0000 Uani . . . . . .
C12 C 0.2656(6) 0.4033(5) 0.0285(3) 0.0562 1.0000 Uani . . . . . .
C13 C 0.1760(6) 0.4145(6) -0.0522(3) 0.0616 1.0000 Uani . . . . . .
C14 C 0.1728(6) 0.5644(6) -0.0770(3) 0.0591 1.0000 Uani . . . . . .
C15 C 0.2645(6) 0.7022(6) -0.0184(3) 0.0627 1.0000 Uani . . . . . .
C16 C 0.3539(6) 0.6893(5) 0.0621(3) 0.0572 1.0000 Uani . . . . . .
C17 C 0.2685(8) 0.2384(6) 0.0551(3) 0.0765 1.0000 Uani . . . . . .
C18 C 0.0745(7) 0.5753(8) -0.1653(3) 0.0773 1.0000 Uani . . . . . .
C19 C 0.4540(8) 0.8399(6) 0.1250(4) 0.0775 1.0000 Uani . . . . . .
N21 N 0.6061(4) 0.4963(4) 0.3617(2) 0.0504 1.0000 Uani . . . . . .
C22 C 0.6541(6) 0.6307(5) 0.4272(3) 0.0556 1.0000 Uani . . . . . .
C23 C 0.7378(6) 0.6171(6) 0.5083(3) 0.0627 1.0000 Uani . . . . . .
C24 C 0.7787(6) 0.4687(6) 0.5242(3) 0.0620 1.0000 Uani . . . . . .
C25 C 0.7267(6) 0.3335(6) 0.4568(3) 0.0612 1.0000 Uani . . . . . .
C26 C 0.6391(5) 0.3478(5) 0.3756(3) 0.0545 1.0000 Uani . . . . . .
C27 C 0.6141(8) 0.7927(6) 0.4096(4) 0.0742 1.0000 Uani . . . . . .
C28 C 0.8771(8) 0.4553(9) 0.6126(4) 0.0823 1.0000 Uani . . . . . .
C29 C 0.5807(7) 0.1989(6) 0.3038(4) 0.0731 1.0000 Uani . . . . . .
P1 P 0.03725(16) -0.01929(16) 0.26893(9) 0.0700 1.0000 Uani . . . . . .
F11 F -0.0458(8) 0.0879(9) 0.3347(5) 0.1735 1.0000 Uani . . . . . .
F12 F -0.1080(8) -0.0023(9) 0.1931(5) 0.1702 1.0000 Uani . . . . . .
F13 F 0.1495(7) 0.1434(7) 0.2583(4) 0.1483 1.0000 Uani . . . . . .
F14 F 0.1820(9) -0.0323(8) 0.3436(5) 0.1727 1.0000 Uani . . . . . .
F15 F -0.0799(8) -0.1818(7) 0.2757(5) 0.1582 1.0000 Uani . . . . . .
F16 F 0.1178(8) -0.1274(11) 0.2045(6) 0.2244 1.0000 Uani . . . . . .
H171 H 0.2224 0.1501 0.0067 0.1151 1.0000 Uiso R . . . . .
H173 H 0.2062 0.2288 0.1029 0.1148 1.0000 Uiso R . . . . .
H172 H 0.3849 0.2266 0.0765 0.1148 1.0000 Uiso R . . . . .
H131 H 0.1150 0.3208 -0.0904 0.0740 1.0000 Uiso R . . . . .
H151 H 0.2646 0.8070 -0.0331 0.0748 1.0000 Uiso R . . . . .
H193 H 0.5712 0.8304 0.1388 0.1161 1.0000 Uiso R . . . . .
H192 H 0.4100 0.8577 0.1787 0.1160 1.0000 Uiso R . . . . .
H191 H 0.4431 0.9352 0.0981 0.1158 1.0000 Uiso R . . . . .
H181 H 0.1232 0.5256 -0.2117 0.1160 1.0000 Uiso R . . . . .
H182 H 0.0735 0.6891 -0.1686 0.1159 1.0000 Uiso R . . . . .
H183 H -0.0407 0.5202 -0.1716 0.1160 1.0000 Uiso R . . . . .
H271 H 0.6458 0.8711 0.4639 0.1107 1.0000 Uiso R . . . . .
H273 H 0.4955 0.7832 0.3888 0.1109 1.0000 Uiso R . . . . .
H272 H 0.6770 0.8272 0.3664 0.1111 1.0000 Uiso R . . . . .
H231 H 0.7652 0.7101 0.5525 0.0747 1.0000 Uiso R . . . . .
H281 H 0.8904 0.3412 0.6136 0.1233 1.0000 Uiso R . . . . .
H282 H 0.9898 0.5211 0.6243 0.1233 1.0000 Uiso R . . . . .
H283 H 0.8201 0.4901 0.6598 0.1233 1.0000 Uiso R . . . . .
H251 H 0.7512 0.2301 0.4652 0.0733 1.0000 Uiso R . . . . .
H291 H 0.6395 0.2086 0.2555 0.1102 1.0000 Uiso R . . . . .
H292 H 0.4587 0.1808 0.2815 0.1100 1.0000 Uiso R . . . . .
H293 H 0.6083 0.1027 0.3254 0.1101 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.40(7)
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 . N11 . 2.310(3) yes
I1 . N21 . 2.282(3) yes
N11 . C12 . 1.348(5) yes
N11 . C16 . 1.359(6) yes
C12 . C13 . 1.381(6) yes
C12 . C17 . 1.506(6) yes
C13 . C14 . 1.375(7) yes
C13 . H131 . 0.925 no
C14 . C15 . 1.383(7) yes
C14 . C18 . 1.508(6) yes
C15 . C16 . 1.382(6) yes
C15 . H151 . 0.941 no
C16 . C19 . 1.502(6) yes
C17 . H171 . 0.952 no
C17 . H173 . 0.972 no
C17 . H172 . 0.972 no
C18 . H181 . 0.943 no
C18 . H182 . 0.962 no
C18 . H183 . 0.960 no
C19 . H193 . 0.955 no
C19 . H192 . 0.960 no
C19 . H191 . 0.969 no
N21 . C22 . 1.354(5) yes
N21 . C26 . 1.350(6) yes
C22 . C23 . 1.375(6) yes
C23 . C24 . 1.379(7) yes
C23 . H231 . 0.926 no
C24 . C25 . 1.378(7) yes
C25 . C26 . 1.389(6) yes
C25 . H251 . 0.939 no
C27 . C22 . 1.495(6) yes
C27 . H271 . 0.959 no
C27 . H273 . 0.951 no
C27 . H272 . 0.963 no
C28 . C24 . 1.517(6) yes
C28 . H281 . 0.976 no
C28 . H282 . 0.967 no
C28 . H283 . 0.957 no
C29 . C26 . 1.496(6) yes
C29 . H291 . 0.962 no
C29 . H292 . 0.974 no
C29 . H293 . 0.963 no
P1 . F11 . 1.547(5) yes
P1 . F12 . 1.576(6) yes
P1 . F13 . 1.570(5) yes
P1 . F14 . 1.550(5) yes
P1 . F15 . 1.568(5) yes
P1 . F16 . 1.526(5) 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
N11 . I1 . N21 . 179.06(11) yes
I1 . N11 . C12 . 120.1(3) yes
I1 . N11 . C16 . 120.1(3) yes
C12 . N11 . C16 . 119.6(3) yes
N11 . C12 . C13 . 120.8(4) yes
N11 . C12 . C17 . 118.5(4) yes
C13 . C12 . C17 . 120.7(4) yes
C12 . C13 . C14 . 121.0(4) yes
C12 . C13 . H131 . 120.5 no
C14 . C13 . H131 . 118.5 no
C13 . C14 . C15 . 117.1(4) yes
C13 . C14 . C18 . 120.6(5) yes
C15 . C14 . C18 . 122.2(5) yes
C14 . C15 . C16 . 121.3(4) yes
C14 . C15 . H151 . 119.4 no
C16 . C15 . H151 . 119.3 no
C15 . C16 . N11 . 120.1(4) yes
C15 . C16 . C19 . 120.7(4) yes
N11 . C16 . C19 . 119.2(4) yes
C12 . C17 . H171 . 111.5 no
C12 . C17 . H173 . 110.7 no
H171 . C17 . H173 . 109.8 no
C12 . C17 . H172 . 110.2 no
H171 . C17 . H172 . 107.6 no
H173 . C17 . H172 . 107.0 no
C14 . C18 . H181 . 111.2 no
C14 . C18 . H182 . 109.5 no
H181 . C18 . H182 . 109.4 no
C14 . C18 . H183 . 109.3 no
H181 . C18 . H183 . 108.9 no
H182 . C18 . H183 . 108.5 no
C16 . C19 . H193 . 111.0 no
C16 . C19 . H192 . 111.3 no
H193 . C19 . H192 . 108.8 no
C16 . C19 . H191 . 108.6 no
H193 . C19 . H191 . 110.0 no
H192 . C19 . H191 . 107.1 no
I1 . N21 . C22 . 120.4(3) yes
I1 . N21 . C26 . 119.1(3) yes
C22 . N21 . C26 . 120.4(3) yes
C27 . C22 . N21 . 118.9(4) yes
C27 . C22 . C23 . 121.0(4) yes
N21 . C22 . C23 . 120.1(4) yes
C22 . C23 . C24 . 121.2(4) yes
C22 . C23 . H231 . 118.3 no
C24 . C23 . H231 . 120.5 no
C28 . C24 . C23 . 121.1(5) yes
C28 . C24 . C25 . 121.4(5) yes
C23 . C24 . C25 . 117.5(4) yes
C24 . C25 . C26 . 120.9(4) yes
C24 . C25 . H251 . 120.0 no
C26 . C25 . H251 . 119.1 no
C29 . C26 . C25 . 120.1(4) yes
C29 . C26 . N21 . 120.1(4) yes
C25 . C26 . N21 . 119.9(4) yes
C22 . C27 . H271 . 107.9 no
C22 . C27 . H273 . 110.1 no
H271 . C27 . H273 . 109.0 no
C22 . C27 . H272 . 109.5 no
H271 . C27 . H272 . 110.5 no
H273 . C27 . H272 . 109.8 no
C24 . C28 . H281 . 110.5 no
C24 . C28 . H282 . 111.1 no
H281 . C28 . H282 . 107.6 no
C24 . C28 . H283 . 111.8 no
H281 . C28 . H283 . 107.3 no
H282 . C28 . H283 . 108.4 no
C26 . C29 . H291 . 110.4 no
C26 . C29 . H292 . 112.7 no
H291 . C29 . H292 . 108.5 no
C26 . C29 . H293 . 109.6 no
H291 . C29 . H293 . 106.7 no
H292 . C29 . H293 . 108.7 no
F11 . P1 . F12 . 88.3(4) yes
F11 . P1 . F13 . 88.0(4) yes
F12 . P1 . F13 . 91.3(3) yes
F11 . P1 . F14 . 91.4(4) yes
F12 . P1 . F14 . 178.8(3) yes
F13 . P1 . F14 . 87.6(3) yes
F11 . P1 . F15 . 92.5(4) yes
F12 . P1 . F15 . 86.3(4) yes
F13 . P1 . F15 . 177.6(3) yes
F14 . P1 . F15 . 94.8(4) yes
F11 . P1 . F16 . 179.1(5) yes
F12 . P1 . F16 . 91.8(5) yes
F13 . P1 . F16 . 92.8(4) yes
F14 . P1 . F16 . 88.5(5) yes
F15 . P1 . F16 . 86.7(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
-2 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_IColl2PF6-100K
_database_code_depnum_ccdc_archive 'CCDC 1853984'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 131lcm18
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   7.9723(2)
_cell_length_b                   8.2018(3)
_cell_length_c                   15.4695(5)
_cell_angle_alpha                99.377(3)
_cell_angle_beta                 97.639(2)
_cell_angle_gamma                100.448(2)
_cell_volume                     967.59(5)

_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
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'
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'
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'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 '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 = C16 H22 F6 I1 N2 P1 
# Dc =      1.76 Fooo =    508.00 Mu =    143.38 M =    514.23
# Found Formula = C16 H22.00 F6 I1 N2 P1 
# Dc =      1.76 FOOO =    508.00 Mu =    143.38 M =    514.23

_chemical_formula_sum            'C16 H22 F6 I N2 P'
_chemical_formula_moiety         'C16 H22 I N2, F6 P'
_chemical_compound_source        .
_chemical_formula_weight         514.23


_cell_measurement_reflns_used    5377
_cell_measurement_theta_min      6
_cell_measurement_theta_max      76
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_max          0.23

_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             507.998
_exptl_absorpt_coefficient_mu    14.338

# Sheldrick geometric approximatio 0.07 0.37 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.37
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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      100
_diffrn_reflns_number            8478
_reflns_number_total             3933
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0350
# Number of reflections with Friedels Law is 3933 
# Theoretical number of reflections is about 8059 


_diffrn_reflns_theta_min         5.589
_diffrn_reflns_theta_max         75.791
_diffrn_measured_fraction_theta_max 0.975

_diffrn_reflns_theta_full        72.500
_diffrn_measured_fraction_theta_full 0.992


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   1.15
_oxford_diffrn_Wilson_scale      0.07

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

_refine_diff_density_min         -1.18
_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_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3932
_oxford_refine_ls_R_factor_ref   0.0330
_refine_ls_wR_factor_ref         0.0840
_refine_ls_goodness_of_fit_ref   1.0534
_refine_ls_shift/su_max          0.0005777
_refine_ls_shift/su_mean         0.0000138


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3932
_refine_ls_R_factor_all          0.0330
_refine_ls_wR_factor_all         0.0840

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3850
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_gt          0.0836


_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) + ( 0.04P)² + 4.08P] 
 ,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 0.48050(3) 0.51838(3) 0.220751(13) 0.0135 1.0000 Uani . . . . . .
N11 N 0.3504(4) 0.5342(4) 0.08041(19) 0.0171 1.0000 Uani . . . . . .
C12 C 0.2540(5) 0.3919(5) 0.0255(2) 0.0184 1.0000 Uani . . . . . .
C13 C 0.1620(5) 0.4012(5) -0.0556(2) 0.0191 1.0000 Uani . . . . . .
C14 C 0.1672(5) 0.5565(5) -0.0825(2) 0.0189 1.0000 Uani . . . . . .
C15 C 0.2685(5) 0.6981(5) -0.0254(3) 0.0211 1.0000 Uani . . . . . .
C16 C 0.3600(5) 0.6863(5) 0.0554(2) 0.0187 1.0000 Uani . . . . . .
C17 C 0.2475(6) 0.2250(5) 0.0538(3) 0.0239 1.0000 Uani . . . . . .
C18 C 0.0665(5) 0.5652(5) -0.1701(2) 0.0236 1.0000 Uani . . . . . .
C19 C 0.4708(5) 0.8395(5) 0.1168(3) 0.0230 1.0000 Uani . . . . . .
N21 N 0.6050(4) 0.4935(4) 0.35775(19) 0.0169 1.0000 Uani . . . . . .
C22 C 0.6509(5) 0.6306(5) 0.4255(2) 0.0185 1.0000 Uani . . . . . .
C23 C 0.7346(5) 0.6164(5) 0.5075(2) 0.0197 1.0000 Uani . . . . . .
C24 C 0.7746(5) 0.4636(5) 0.5217(2) 0.0200 1.0000 Uani . . . . . .
C25 C 0.7238(5) 0.3262(5) 0.4515(2) 0.0188 1.0000 Uani . . . . . .
C26 C 0.6383(5) 0.3422(5) 0.3706(2) 0.0184 1.0000 Uani . . . . . .
C27 C 0.6124(5) 0.7966(5) 0.4096(3) 0.0232 1.0000 Uani . . . . . .
C28 C 0.8710(5) 0.4495(5) 0.6094(2) 0.0244 1.0000 Uani . . . . . .
C29 C 0.5831(5) 0.1923(5) 0.2951(2) 0.0217 1.0000 Uani . . . . . .
P1 P 0.04188(12) -0.01159(12) 0.27349(6) 0.0204 1.0000 Uani . . . . . .
F11 F -0.0541(4) 0.0851(4) 0.34361(19) 0.0370 1.0000 Uani . . . . . .
F12 F -0.1018(4) 0.0044(4) 0.19380(18) 0.0370 1.0000 Uani . . . . . .
F13 F 0.1551(3) 0.1660(3) 0.26563(17) 0.0318 1.0000 Uani . . . . . .
F14 F 0.1861(4) -0.0257(4) 0.35252(19) 0.0385 1.0000 Uani . . . . . .
F15 F -0.0727(4) -0.1882(3) 0.2805(2) 0.0380 1.0000 Uani . . . . . .
F16 F 0.1380(4) -0.1068(4) 0.2030(2) 0.0442 1.0000 Uani . . . . . .
H171 H 0.1828 0.1365 0.0074 0.0360 1.0000 Uiso R . . . . .
H173 H 0.1936 0.2250 0.1056 0.0363 1.0000 Uiso R . . . . .
H172 H 0.3620 0.2037 0.0678 0.0359 1.0000 Uiso R . . . . .
H131 H 0.0963 0.3039 -0.0916 0.0230 1.0000 Uiso R . . . . .
H151 H 0.2734 0.8042 -0.0413 0.0251 1.0000 Uiso R . . . . .
H193 H 0.5876 0.8253 0.1306 0.0337 1.0000 Uiso R . . . . .
H192 H 0.4241 0.8620 0.1703 0.0341 1.0000 Uiso R . . . . .
H191 H 0.4695 0.9343 0.0877 0.0337 1.0000 Uiso R . . . . .
H181 H 0.1133 0.5125 -0.2184 0.0349 1.0000 Uiso R . . . . .
H182 H 0.0675 0.6817 -0.1738 0.0350 1.0000 Uiso R . . . . .
H183 H -0.0505 0.5081 -0.1733 0.0351 1.0000 Uiso R . . . . .
H271 H 0.6393 0.8745 0.4649 0.0350 1.0000 Uiso R . . . . .
H273 H 0.4933 0.7836 0.3859 0.0353 1.0000 Uiso R . . . . .
H272 H 0.6815 0.8385 0.3682 0.0350 1.0000 Uiso R . . . . .
H231 H 0.7644 0.7087 0.5531 0.0238 1.0000 Uiso R . . . . .
H281 H 0.8943 0.3383 0.6082 0.0373 1.0000 Uiso R . . . . .
H282 H 0.9807 0.5277 0.6233 0.0378 1.0000 Uiso R . . . . .
H283 H 0.8075 0.4732 0.6566 0.0378 1.0000 Uiso R . . . . .
H251 H 0.7489 0.2218 0.4581 0.0228 1.0000 Uiso R . . . . .
H291 H 0.6428 0.2073 0.2458 0.0330 1.0000 Uiso R . . . . .
H292 H 0.4603 0.1708 0.2729 0.0333 1.0000 Uiso R . . . . .
H293 H 0.6089 0.0921 0.3148 0.0328 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.97(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
I1 . N11 . 2.313(3) yes
I1 . N21 . 2.275(3) yes
N11 . C12 . 1.361(5) yes
N11 . C16 . 1.357(5) yes
C12 . C13 . 1.388(5) yes
C12 . C17 . 1.498(5) yes
C13 . C14 . 1.398(5) yes
C13 . H131 . 0.920 no
C14 . C15 . 1.385(6) yes
C14 . C18 . 1.500(5) yes
C15 . C16 . 1.389(5) yes
C15 . H151 . 0.938 no
C16 . C19 . 1.499(5) yes
C17 . H171 . 0.951 no
C17 . H173 . 0.958 no
C17 . H172 . 0.964 no
C18 . H181 . 0.954 no
C18 . H182 . 0.965 no
C18 . H183 . 0.956 no
C19 . H193 . 0.960 no
C19 . H192 . 0.957 no
C19 . H191 . 0.961 no
N21 . C22 . 1.365(5) yes
N21 . C26 . 1.355(5) yes
C22 . C23 . 1.385(5) yes
C23 . C24 . 1.392(6) yes
C23 . H231 . 0.919 no
C24 . C25 . 1.389(5) yes
C25 . C26 . 1.381(5) yes
C25 . H251 . 0.932 no
C27 . C22 . 1.499(5) yes
C27 . H271 . 0.953 no
C27 . H273 . 0.952 no
C27 . H272 . 0.963 no
C28 . C24 . 1.501(5) yes
C28 . H281 . 0.961 no
C28 . H282 . 0.962 no
C28 . H283 . 0.956 no
C29 . C26 . 1.506(5) yes
C29 . H291 . 0.964 no
C29 . H292 . 0.968 no
C29 . H293 . 0.968 no
P1 . F11 . 1.597(3) yes
P1 . F12 . 1.607(3) yes
P1 . F13 . 1.601(3) yes
P1 . F14 . 1.597(3) yes
P1 . F15 . 1.594(3) yes
P1 . F16 . 1.597(3) 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
N11 . I1 . N21 . 178.11(11) yes
I1 . N11 . C12 . 119.6(2) yes
I1 . N11 . C16 . 120.1(2) yes
C12 . N11 . C16 . 120.2(3) yes
N11 . C12 . C13 . 120.4(3) yes
N11 . C12 . C17 . 119.3(3) yes
C13 . C12 . C17 . 120.3(3) yes
C12 . C13 . C14 . 120.7(3) yes
C12 . C13 . H131 . 119.3 no
C14 . C13 . H131 . 120.1 no
C13 . C14 . C15 . 117.2(3) yes
C13 . C14 . C18 . 120.2(3) yes
C15 . C14 . C18 . 122.5(4) yes
C14 . C15 . C16 . 121.3(4) yes
C14 . C15 . H151 . 119.2 no
C16 . C15 . H151 . 119.5 no
C15 . C16 . N11 . 120.2(3) yes
C15 . C16 . C19 . 121.2(3) yes
N11 . C16 . C19 . 118.6(3) yes
C12 . C17 . H171 . 110.0 no
C12 . C17 . H173 . 109.4 no
H171 . C17 . H173 . 109.4 no
C12 . C17 . H172 . 111.1 no
H171 . C17 . H172 . 108.4 no
H173 . C17 . H172 . 108.6 no
C14 . C18 . H181 . 111.0 no
C14 . C18 . H182 . 109.6 no
H181 . C18 . H182 . 110.0 no
C14 . C18 . H183 . 108.3 no
H181 . C18 . H183 . 109.2 no
H182 . C18 . H183 . 108.6 no
C16 . C19 . H193 . 111.1 no
C16 . C19 . H192 . 110.2 no
H193 . C19 . H192 . 110.0 no
C16 . C19 . H191 . 108.0 no
H193 . C19 . H191 . 109.4 no
H192 . C19 . H191 . 108.1 no
I1 . N21 . C22 . 120.4(2) yes
I1 . N21 . C26 . 119.3(2) yes
C22 . N21 . C26 . 120.3(3) yes
C27 . C22 . N21 . 119.3(3) yes
C27 . C22 . C23 . 120.7(3) yes
N21 . C22 . C23 . 120.0(3) yes
C22 . C23 . C24 . 120.8(3) yes
C22 . C23 . H231 . 119.8 no
C24 . C23 . H231 . 119.4 no
C28 . C24 . C23 . 120.8(3) yes
C28 . C24 . C25 . 121.6(4) yes
C23 . C24 . C25 . 117.6(3) yes
C24 . C25 . C26 . 120.9(4) yes
C24 . C25 . H251 . 120.3 no
C26 . C25 . H251 . 118.9 no
C29 . C26 . C25 . 120.4(3) yes
C29 . C26 . N21 . 119.1(3) yes
C25 . C26 . N21 . 120.4(3) yes
C22 . C27 . H271 . 108.5 no
C22 . C27 . H273 . 110.3 no
H271 . C27 . H273 . 109.3 no
C22 . C27 . H272 . 109.7 no
H271 . C27 . H272 . 109.9 no
H273 . C27 . H272 . 109.1 no
C24 . C28 . H281 . 111.3 no
C24 . C28 . H282 . 110.3 no
H281 . C28 . H282 . 107.1 no
C24 . C28 . H283 . 111.6 no
H281 . C28 . H283 . 108.2 no
H282 . C28 . H283 . 108.2 no
C26 . C29 . H291 . 112.1 no
C26 . C29 . H292 . 111.8 no
H291 . C29 . H292 . 107.5 no
C26 . C29 . H293 . 110.0 no
H291 . C29 . H293 . 107.2 no
H292 . C29 . H293 . 107.9 no
F11 . P1 . F12 . 89.95(16) yes
F11 . P1 . F13 . 89.53(15) yes
F12 . P1 . F13 . 89.70(14) yes
F11 . P1 . F14 . 90.13(17) yes
F12 . P1 . F14 . 179.37(16) yes
F13 . P1 . F14 . 89.67(15) yes
F11 . P1 . F15 . 90.40(16) yes
F12 . P1 . F15 . 89.62(16) yes
F13 . P1 . F15 . 179.32(15) yes
F14 . P1 . F15 . 91.00(16) yes
F11 . P1 . F16 . 179.48(18) yes
F12 . P1 . F16 . 89.77(17) yes
F13 . P1 . F16 . 90.03(16) yes
F14 . P1 . F16 . 90.14(17) yes
F15 . P1 . F16 . 90.03(17) 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 .
####################################################################### 
# 
# 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_IColl2ClO4-II-300K
_database_code_depnum_ccdc_archive 'CCDC 1853991'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 099lcm18
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
On initial refinement, displacement ellipsoids for the perchlorate ion 
associated were decidedly prolate.  Because of this disorder, same 
distance, vibrational and thermal similarity restraints were required 
to maintian a sensible model for the anion.
;

_cell_length_a                   29.1018(8)
_cell_length_b                   8.5668(2)
_cell_length_c                   15.9883(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.803(3)
_cell_angle_gamma                90
_cell_volume                     3915.39(19)

_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
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'
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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C16 H22 Cl1 I1 N2 O4 
# Dc =      1.59 Fooo =   1872.00 Mu =    142.93 M =    468.72
# Found Formula = C16 H22 Cl1 I1 N2 O4.00 
# Dc =      1.59 FOOO =   1872.00 Mu =    142.93 M =    468.72

_chemical_formula_sum            'C16 H22 Cl I N2 O4'
_chemical_formula_moiety         'C16 H22 I N2, Cl O4'
_chemical_compound_source        .
_chemical_formula_weight         468.72


_cell_measurement_reflns_used    4166
_cell_measurement_theta_min      5
_cell_measurement_theta_max      75
_cell_measurement_temperature    300

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.041
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_max          0.211

_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1872.000
_exptl_absorpt_coefficient_mu    14.293

# Sheldrick geometric approximatio 0.11 0.56 
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
; 
 Gaussian Integration (Busing and Levy, 1957) 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 -4 0.0600
0 1 5 0.0800
-1 1 0 0.1000
1 -1 1 0.0600
1 0 0 0.0010
-1 0 0 0.0400
0 0 -1 0.0800

_exptl_absorpt_correction_T_min  0.139
_exptl_absorpt_correction_T_max  0.737
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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      300
_diffrn_reflns_number            11165
_reflns_number_total             4035
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.0517
# Number of reflections with Friedels Law is 4035 
# Theoretical number of reflections is about 8192 


_diffrn_reflns_theta_min         5.391
_diffrn_reflns_theta_max         76.164
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        73.879
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -36
_reflns_limit_h_max              35
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.59
_refine_diff_density_max         0.43


# 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     88
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4027
_oxford_refine_ls_R_factor_ref   0.0441
_refine_ls_wR_factor_ref         0.1016
_refine_ls_goodness_of_fit_ref   1.0051
_refine_ls_shift/su_max          0.0002712
_refine_ls_shift/su_mean         0.0000244


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4028
_refine_ls_R_factor_all          0.0441
_refine_ls_wR_factor_all         0.1018

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3283
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_gt          0.0909


_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 + 2.07P] 
 ,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 0.7500 0.2500 0.5000 0.0769 1.0000 Uani S . . . . .
N11 N 0.74648(12) 0.0058(4) 0.4408(2) 0.0718 1.0000 Uani . . . . . .
C12 C 0.78544(15) -0.0812(6) 0.4458(3) 0.0746 1.0000 Uani . . . . . .
C13 C 0.78405(17) -0.2199(6) 0.4025(3) 0.0819 1.0000 Uani . . . . . .
C14 C 0.74319(19) -0.2717(6) 0.3523(3) 0.0846 1.0000 Uani . . . . . .
C15 C 0.70377(18) -0.1819(7) 0.3509(3) 0.0880 1.0000 Uani . . . . . .
C16 C 0.70528(17) -0.0449(6) 0.3950(3) 0.0831 1.0000 Uani . . . . . .
C17 C 0.83059(17) -0.0222(7) 0.4978(4) 0.0957 1.0000 Uani . . . . . .
C18 C 0.7407(3) -0.4201(8) 0.2999(4) 0.1225 1.0000 Uani . . . . . .
C19 C 0.6617(2) 0.0519(9) 0.3934(5) 0.1200 1.0000 Uani . . . . . .
I2 I 0.5000 0.5000 0.5000 0.0791 1.0000 Uani S . . . . .
N21 N 0.53480(12) 0.4698(4) 0.3838(3) 0.0773 1.0000 Uani . . . . . .
C22 C 0.54983(16) 0.5960(5) 0.3466(4) 0.0843 1.0000 Uani . . . . . .
C23 C 0.57431(17) 0.5774(6) 0.2818(4) 0.0912 1.0000 Uani . . . . . .
C24 C 0.58413(16) 0.4314(7) 0.2531(3) 0.0901 1.0000 Uani . . . . . .
C25 C 0.56681(18) 0.3061(6) 0.2915(4) 0.0902 1.0000 Uani . . . . . .
C26 C 0.54230(16) 0.3242(5) 0.3559(3) 0.0812 1.0000 Uani . . . . . .
C27 C 0.5398(3) 0.7551(6) 0.3763(5) 0.1119 1.0000 Uani . . . . . .
C28 C 0.6120(2) 0.4108(10) 0.1846(4) 0.1213 1.0000 Uani . . . . . .
C29 C 0.5230(3) 0.1871(6) 0.3955(4) 0.1145 1.0000 Uani . . . . . .
Cl1 Cl 0.61012(5) 0.06625(17) 0.62601(9) 0.0971 1.0000 Uani D U . . . .
O11 O 0.6058(6) 0.2106(8) 0.5885(7) 0.1967 0.625(9) Uani D U P 1 1 .
O12 O 0.5827(4) 0.0631(12) 0.6891(7) 0.1646 0.625(9) Uani D U P 1 1 .
O13 O 0.5931(5) -0.0449(11) 0.5647(6) 0.1770 0.625(9) Uani D U P 1 1 .
O14 O 0.6545(3) 0.031(2) 0.6621(9) 0.2547 0.625(9) Uani D U P 1 1 .
O111 O 0.5687(5) 0.141(2) 0.6057(13) 0.2254 0.375(9) Uani D U P 1 2 .
O112 O 0.6168(8) 0.001(2) 0.7051(6) 0.2373 0.375(9) Uani D U P 1 2 .
O113 O 0.6144(6) -0.0460(19) 0.5660(10) 0.1622 0.375(9) Uani D U P 1 2 .
O114 O 0.6465(5) 0.1732(19) 0.6270(12) 0.1726 0.375(9) Uani D U P 1 2 .
H131 H 0.8109 -0.2787 0.4078 0.0981 1.0000 Uiso R . . . . .
H151 H 0.6752 -0.2168 0.3196 0.1060 1.0000 Uiso R . . . . .
H171 H 0.8538 -0.1013 0.4990 0.1437 1.0000 Uiso R . . . . .
H172 H 0.8400 0.0709 0.4721 0.1437 1.0000 Uiso R . . . . .
H173 H 0.8262 -0.0002 0.5545 0.1435 1.0000 Uiso R . . . . .
H181 H 0.7166 -0.4864 0.3127 0.1840 1.0000 Uiso R . . . . .
H182 H 0.7333 -0.3935 0.2406 0.1840 1.0000 Uiso R . . . . .
H183 H 0.7701 -0.4738 0.3117 0.1840 1.0000 Uiso R . . . . .
H191 H 0.6581 0.0732 0.4500 0.1801 1.0000 Uiso R . . . . .
H192 H 0.6640 0.1493 0.3654 0.1797 1.0000 Uiso R . . . . .
H193 H 0.6348 -0.0040 0.3650 0.1798 1.0000 Uiso R . . . . .
H231 H 0.5836 0.6651 0.2562 0.1089 1.0000 Uiso R . . . . .
H251 H 0.5716 0.2053 0.2729 0.1078 1.0000 Uiso R . . . . .
H271 H 0.5531 0.8303 0.3450 0.1679 1.0000 Uiso R . . . . .
H272 H 0.5530 0.7653 0.4356 0.1677 1.0000 Uiso R . . . . .
H273 H 0.5066 0.7701 0.3675 0.1677 1.0000 Uiso R . . . . .
H281 H 0.5972 0.3340 0.1456 0.1820 1.0000 Uiso R . . . . .
H282 H 0.6428 0.3775 0.2097 0.1819 1.0000 Uiso R . . . . .
H283 H 0.6137 0.5093 0.1564 0.1821 1.0000 Uiso R . . . . .
H291 H 0.4898 0.1969 0.3906 0.1718 1.0000 Uiso R . . . . .
H292 H 0.5380 0.1798 0.4541 0.1718 1.0000 Uiso R . . . . .
H293 H 0.5295 0.0961 0.3660 0.1718 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.847(11)
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 . N11 4_656 2.291(4) yes
I1 . N11 . 2.291(4) yes
N11 . C12 . 1.347(5) yes
N11 . C16 . 1.354(6) yes
C12 . C13 . 1.372(7) yes
C12 . C17 . 1.504(7) yes
C13 . C14 . 1.378(7) yes
C13 . H131 . 0.920 no
C14 . C15 . 1.378(7) yes
C14 . C18 . 1.517(7) yes
C15 . C16 . 1.366(7) yes
C15 . H151 . 0.935 no
C16 . C19 . 1.511(7) yes
C17 . H171 . 0.955 no
C17 . H172 . 0.960 no
C17 . H173 . 0.959 no
C18 . H181 . 0.955 no
C18 . H182 . 0.959 no
C18 . H183 . 0.959 no
C19 . H191 . 0.949 no
C19 . H192 . 0.956 no
C19 . H193 . 0.956 no
I2 . N21 2_666 2.291(4) yes
I2 . N21 . 2.291(4) yes
N21 . C22 . 1.346(6) yes
N21 . C26 . 1.356(5) yes
C22 . C23 . 1.373(8) yes
C22 . C27 . 1.490(6) yes
C23 . C24 . 1.381(7) yes
C23 . H231 . 0.920 no
C24 . C25 . 1.378(8) yes
C24 . C28 . 1.489(8) yes
C25 . C26 . 1.367(8) yes
C25 . H251 . 0.933 no
C26 . C29 . 1.493(8) yes
C27 . H271 . 0.942 no
C27 . H272 . 0.958 no
C27 . H273 . 0.957 no
C28 . H281 . 0.953 no
C28 . H282 . 0.955 no
C28 . H283 . 0.962 no
C29 . H291 . 0.957 no
C29 . H292 . 0.959 no
C29 . H293 . 0.948 no
Cl1 . O11 . 1.369(6) yes
Cl1 . O12 . 1.399(6) yes
Cl1 . O13 . 1.390(6) yes
Cl1 . O14 . 1.345(6) yes
Cl1 . O111 . 1.350(7) yes
Cl1 . O112 . 1.362(7) yes
Cl1 . O113 . 1.380(7) yes
Cl1 . O114 . 1.397(7) 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
N11 4_656 I1 . N11 . 179.99 yes
I1 . N11 . C12 . 120.6(3) yes
I1 . N11 . C16 . 118.9(3) yes
C12 . N11 . C16 . 120.4(4) yes
N11 . C12 . C13 . 120.3(4) yes
N11 . C12 . C17 . 119.0(4) yes
C13 . C12 . C17 . 120.7(4) yes
C12 . C13 . C14 . 120.9(4) yes
C12 . C13 . H131 . 118.9 no
C14 . C13 . H131 . 120.2 no
C13 . C14 . C15 . 117.1(5) yes
C13 . C14 . C18 . 122.6(5) yes
C15 . C14 . C18 . 120.4(5) yes
C14 . C15 . C16 . 121.7(5) yes
C14 . C15 . H151 . 119.0 no
C16 . C15 . H151 . 119.3 no
C15 . C16 . N11 . 119.6(4) yes
C15 . C16 . C19 . 121.1(5) yes
N11 . C16 . C19 . 119.3(5) yes
C12 . C17 . H171 . 108.3 no
C12 . C17 . H172 . 109.4 no
H171 . C17 . H172 . 109.9 no
C12 . C17 . H173 . 109.3 no
H171 . C17 . H173 . 109.9 no
H172 . C17 . H173 . 109.9 no
C14 . C18 . H181 . 109.9 no
C14 . C18 . H182 . 109.1 no
H181 . C18 . H182 . 108.4 no
C14 . C18 . H183 . 110.2 no
H181 . C18 . H183 . 109.7 no
H182 . C18 . H183 . 109.5 no
C16 . C19 . H191 . 109.4 no
C16 . C19 . H192 . 110.8 no
H191 . C19 . H192 . 108.0 no
C16 . C19 . H193 . 110.0 no
H191 . C19 . H193 . 108.8 no
H192 . C19 . H193 . 109.8 no
N21 2_666 I2 . N21 . 179.99 yes
I2 . N21 . C22 . 119.8(3) yes
I2 . N21 . C26 . 119.6(3) yes
C22 . N21 . C26 . 120.5(4) yes
N21 . C22 . C23 . 119.9(4) yes
N21 . C22 . C27 . 119.7(5) yes
C23 . C22 . C27 . 120.5(5) yes
C22 . C23 . C24 . 121.7(5) yes
C22 . C23 . H231 . 118.6 no
C24 . C23 . H231 . 119.7 no
C23 . C24 . C25 . 116.2(5) yes
C23 . C24 . C28 . 121.8(6) yes
C25 . C24 . C28 . 122.0(5) yes
C24 . C25 . C26 . 122.3(5) yes
C24 . C25 . H251 . 119.4 no
C26 . C25 . H251 . 118.3 no
C25 . C26 . N21 . 119.4(5) yes
C25 . C26 . C29 . 121.4(4) yes
N21 . C26 . C29 . 119.2(5) yes
C22 . C27 . H271 . 109.4 no
C22 . C27 . H272 . 109.4 no
H271 . C27 . H272 . 109.4 no
C22 . C27 . H273 . 109.2 no
H271 . C27 . H273 . 109.5 no
H272 . C27 . H273 . 109.9 no
C24 . C28 . H281 . 108.8 no
C24 . C28 . H282 . 108.9 no
H281 . C28 . H282 . 110.0 no
C24 . C28 . H283 . 108.9 no
H281 . C28 . H283 . 110.7 no
H282 . C28 . H283 . 109.4 no
C26 . C29 . H291 . 110.5 no
C26 . C29 . H292 . 109.0 no
H291 . C29 . H292 . 110.7 no
C26 . C29 . H293 . 108.1 no
H291 . C29 . H293 . 108.9 no
H292 . C29 . H293 . 109.6 no
O11 . Cl1 . O12 . 108.4(5) yes
O11 . Cl1 . O13 . 108.6(6) yes
O12 . Cl1 . O13 . 108.6(6) yes
O11 . Cl1 . O14 . 113.0(6) yes
O12 . Cl1 . O14 . 108.6(6) yes
O13 . Cl1 . O14 . 109.6(6) yes
O111 . Cl1 . O112 . 112.7(8) yes
O111 . Cl1 . O113 . 110.9(7) yes
O112 . Cl1 . O113 . 110.1(7) yes
O111 . Cl1 . O114 . 109.2(8) yes
O112 . Cl1 . O114 . 106.3(7) yes
O113 . Cl1 . O114 . 107.4(7) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C18 . H183 . O14 4_646 164 0.96 2.21 3.144(8) yes
C23 . H231 . O12 6_564 161 0.92 2.56 3.446(8) yes
C25 . H251 . O112 6_554 153 0.93 2.56 3.422(8) yes
C27 . H273 . O111 2_666 159 0.96 2.43 3.344(8) yes
C29 . H292 . O111 . 173 0.96 2.44 3.398(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
-26 6 8 x .
8 0 2 x .
6 0 2 x .
4 0 2 x .
-4 0 2 x .
-1 1 4 x .
3 1 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_CollHBr
_database_code_depnum_ccdc_archive 'CCDC 1853997'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-15
_audit_creation_method           CRYSTALS_ver_14.61_build_6156

_oxford_structure_analysis_title 119lcm18
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
The data were originally indexed with a hexagonal cell (a = 8:623 Å, 
c = 6:898 Å, volume = 443.9 Å³), but a solution in the indicated 
space group P6₃/mmc yielded a highly disordered model.  Inspection 
of the data suggested the possibility of an alternative, lower symmetry
monoclinic spacegroup with twinning by pseudo-merohedry with the two 
components related by a rotation of 180° rotation about [1 1 0] direct 
lattice direction according to the twin law:

                      (0:5  0:5  0:0)
                      (1:5  0:5  0:0)
                      (0:0  0:0 -1:0)

This solution exhibited prolate ellipsoids and the relative size suggests 
there may still be a small degree of disorder present.  It was thought 
that the two-fold rotation axis that relates the two halves of the 
collidinium cation could be responsible for these and the true symmetry 
could be actually be even lower, Cc or even P1, but the quality of the 
data due to the twinning meant it was not possible to confirm this and even 
in C2/c the refinement was unstable and required shift limiting restraints
for convergence, a problem that would be exacerbated in a lower symmetry
space group.  Although questions regarding the space group remain, the
structure solution is adequate for the purposes discussed.
;

_cell_length_a                   8.6217(6)
_cell_length_b                   14.9357(9)
_cell_length_c                   6.8943(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.007(5)
_cell_angle_gamma                90
_cell_volume                     887.79(10)

_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 0.0033 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'
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 = C16 H24 Br2 N2 
# Dc =      3.02 Fooo =    816.00 Mu =     91.18 M =    404.19
# Found Formula = C8 H12 Br1 N1 
# Dc =      1.51 FOOO =    408.00 Mu =     45.59 M =    202.09

_chemical_formula_sum            'C8 H12 Br N'
_chemical_formula_moiety         'C8 H12 N, Br'
_chemical_compound_source        ?
_chemical_formula_weight         202.09


_cell_measurement_reflns_used    1867
_cell_measurement_theta_min      3
_cell_measurement_theta_max      24
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.28

_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    4.559

# Sheldrick geometric approximatio 0.40 0.66 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.66
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       '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            8473
_reflns_number_total             1217
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0506
# Number of reflections without Friedels Law is 2341 
# Number of reflections with Friedels Law is 1217 
# Theoretical number of reflections is about 933 


_diffrn_reflns_theta_min         2.728
_diffrn_reflns_theta_max         29.826
_diffrn_measured_fraction_theta_max 0.957

_diffrn_reflns_theta_full        26.545
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -20
_reflns_limit_k_max              0
_reflns_limit_l_min              -9
_reflns_limit_l_max              0

_oxford_diffrn_Wilson_B_factor   5.09
_oxford_diffrn_Wilson_scale      0.17

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

_refine_diff_density_min         -0.81
_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         938
_refine_ls_number_restraints     88
_refine_ls_number_parameters     53
_oxford_refine_ls_R_factor_ref   0.0592
_refine_ls_wR_factor_ref         0.1048
_refine_ls_goodness_of_fit_ref   0.9991
_refine_ls_shift/su_max          0.0005252
_refine_ls_shift/su_mean         0.0000460


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        938
_refine_ls_R_factor_all          0.0592
_refine_ls_wR_factor_all         0.1048

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                711
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_gt          0.0884

# 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) + ( 0.03P)² + 5.63P] 
 ,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 0.0000 0.83373(10) 0.7500 0.0685 1.0000 Uani S T . . . .
N1 N 0.000000(7) 0.5924(8) 0.750000(7) 0.0764 1.0000 Uani S T . . . .
C2 C -0.1407(9) 0.5428(8) 0.7495(8) 0.0663 1.0000 Uani . . . . . .
C3 C -0.1362(9) 0.4539(6) 0.7502(8) 0.0530 1.0000 Uani . . . . . .
C4 C 0.0000 0.4083(9) 0.7500 0.0710 1.0000 Uani S T . . . .
C7 C -0.2883(13) 0.5953(11) 0.7467(12) 0.1301 1.0000 Uani . . . . . .
C8 C 0.000000(10) 0.3097(11) 0.750000(10) 0.1298 1.0000 Uani S T . . . .
H11 H 0.0000 0.6502 0.7500 0.0909 1.0000 Uiso RS . . . . .
H31 H -0.2278 0.4220 0.7476 0.0637 1.0000 Uiso R . . . . .
H71 H -0.3742 0.5560 0.7377 0.1948 1.0000 Uiso R . . . . .
H72 H -0.2994 0.6294 0.8639 0.1947 1.0000 Uiso R . . . . .
H73 H -0.2935 0.6354 0.6393 0.1948 1.0000 Uiso R . . . . .
H81 H 0.1039 0.2885 0.7499 0.1559 0.5000 Uiso R . . . . .
H82 H -0.0519 0.2885 0.8626 0.1559 0.5000 Uiso R . . . . .
H83 H -0.0520 0.2885 0.6375 0.1559 0.5000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.62(8)

loop_
_oxford_twin_element_scale_factors
0.43(3)
0.57(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 6_556 1.421(12) yes
N1 . C2 . 1.421(12) yes
N1 . H11 . 0.863 no
C2 . C3 . 1.329(12) yes
C2 . C7 . 1.496(10) yes
C3 . C4 . 1.357(11) yes
C3 . H31 . 0.922 no
C4 . C8 . 1.47(2) yes
C7 . H71 . 0.947 no
C7 . H72 . 0.959 no
C7 . H73 . 0.953 no
C8 . H83 6_556 0.950 no
C8 . H82 6_556 0.950 no
C8 . H81 6_556 0.950 no
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C8 . H83 . 0.950 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 6_556 N1 . C2 . 117.2(10) yes
C2 6_556 N1 . H11 . 121.4 no
C2 . N1 . H11 . 121.4 no
N1 . C2 . C3 . 119.8(7) yes
N1 . C2 . C7 . 116.9(11) yes
C3 . C2 . C7 . 123.3(11) yes
C2 . C3 . C4 . 121.7(7) yes
C2 . C3 . H31 . 119.5 no
C4 . C3 . H31 . 118.8 no
C3 6_556 C4 . C3 . 119.9(11) yes
C3 6_556 C4 . C8 . 120.1(6) yes
C3 . C4 . C8 . 120.1(6) yes
C2 . C7 . H71 . 109.9 no
C2 . C7 . H72 . 110.6 no
H71 . C7 . H72 . 107.8 no
C2 . C7 . H73 . 112.3 no
H71 . C7 . H73 . 107.6 no
H72 . C7 . H73 . 108.5 no
C4 . C8 . H83 6_556 109.5 no
C4 . C8 . H82 6_556 109.5 no
H83 6_556 C8 . H82 6_556 109.5 no
C4 . C8 . H81 6_556 109.5 no
H83 6_556 C8 . H81 6_556 109.5 no
H82 6_556 C8 . H81 6_556 109.5 no
C4 . C8 . H81 . 109.5 no
H83 6_556 C8 . H81 . 56.3 no
H82 6_556 C8 . H81 . 56.3 no
H81 6_556 C8 . H81 . 141.1 no
C4 . C8 . H82 . 109.5 no
H83 6_556 C8 . H82 . 56.3 no
H82 6_556 C8 . H82 . 141.1 no
H81 6_556 C8 . H82 . 56.3 no
H81 . C8 . H82 . 109.5 no
C4 . C8 . H83 . 109.5 no
H83 6_556 C8 . H83 . 141.1 no
H82 6_556 C8 . H83 . 56.3 no
H81 6_556 C8 . H83 . 56.3 no
H81 . C8 . H83 . 109.5 no
H82 . C8 . H83 . 109.5 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_BrColl2BF4-300K
_database_code_depnum_ccdc_archive 'CCDC 1853995'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 099KEC14-300K
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
On initial refinement, displacement ellipsoids for the perchlorate ion 
associated were decidedly prolate.  Because of this disorder, same 
distance, vibrational and thermal similarity restraints were required 
to maintian a sensible model for the anion.
;

_cell_length_a                   29.0149(3)
_cell_length_b                   8.50144(7)
_cell_length_c                   15.54176(17)
_cell_angle_alpha                90
_cell_angle_beta                 100.7977(10)
_cell_angle_gamma                90
_cell_volume                     3765.79(7)

_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'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 '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'
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'
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            8

# Given Formula = C16 H20 B1 Br1 F4 N2 
# Dc =      1.44 Fooo =   1648.00 Mu =     33.21 M =    407.06
# Found Formula = C16 H22 B1 Br1 F4.00 N2 
# Dc =      1.44 FOOO =   1664.00 Mu =     33.21 M =    409.07

_chemical_formula_sum            'C16 H22 B Br F4 N2'
_chemical_formula_moiety         'C16 H22 Br N2, B F4'
_chemical_compound_source        .
_chemical_formula_weight         409.07


_cell_measurement_reflns_used    22418
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.29
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_max          0.34

_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1664.000
_exptl_absorpt_coefficient_mu    3.321

# Sheldrick geometric approximatio 0.36 0.38 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.27
_exptl_absorpt_correction_T_max  0.38
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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      300
_diffrn_reflns_number            41023
_reflns_number_total             3935
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0308
# Number of reflections with Friedels Law is 3935 
# Theoretical number of reflections is about 7902 


_diffrn_reflns_theta_min         3.101
_diffrn_reflns_theta_max         76.390
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.863
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -36
_reflns_limit_h_max              35
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   5.44
_oxford_diffrn_Wilson_scale      0.19

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

_refine_diff_density_min         -0.32
_refine_diff_density_max         0.33


# 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     88
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3920
_oxford_refine_ls_R_factor_ref   0.0367
_refine_ls_wR_factor_ref         0.1023
_refine_ls_goodness_of_fit_ref   1.0071
_refine_ls_shift/su_max          0.0003091
_refine_ls_shift/su_mean         0.0000245


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3920
_refine_ls_R_factor_all          0.0367
_refine_ls_wR_factor_all         0.1023

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3575
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_gt          0.0997


_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 + 1.50P] 
 ,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 0.7500 0.2500 0.5000 0.0686 1.0000 Uani S . . . . .
N11 N 0.74710(6) 0.0212(2) 0.44437(11) 0.0670 1.0000 Uani . . . . . .
C12 C 0.78667(8) -0.0638(3) 0.44893(14) 0.0700 1.0000 Uani . . . . . .
C13 C 0.78509(9) -0.2059(3) 0.40556(17) 0.0772 1.0000 Uani . . . . . .
C14 C 0.74408(10) -0.2615(3) 0.35668(17) 0.0793 1.0000 Uani . . . . . .
C15 C 0.70434(9) -0.1723(3) 0.35489(16) 0.0818 1.0000 Uani . . . . . .
C16 C 0.70562(8) -0.0323(3) 0.39984(15) 0.0746 1.0000 Uani . . . . . .
C17 C 0.83157(9) 0.0005(3) 0.5012(2) 0.0928 1.0000 Uani . . . . . .
C18 C 0.74226(13) -0.4139(4) 0.3058(2) 0.1125 1.0000 Uani . . . . . .
C19 C 0.66233(10) 0.0654(4) 0.3987(2) 0.1055 1.0000 Uani . . . . . .
Br2 Br 0.5000 0.5000 0.5000 0.0806 1.0000 Uani S . . . . .
N21 N 0.53353(8) 0.4764(2) 0.39050(16) 0.0813 1.0000 Uani . . . . . .
C22 C 0.54780(9) 0.6064(3) 0.3519(2) 0.0869 1.0000 Uani . . . . . .
C23 C 0.57181(10) 0.5912(4) 0.2848(2) 0.0954 1.0000 Uani . . . . . .
C24 C 0.58180(10) 0.4444(4) 0.2542(2) 0.0963 1.0000 Uani . . . . . .
C25 C 0.56576(11) 0.3147(4) 0.2938(2) 0.0981 1.0000 Uani . . . . . .
C26 C 0.54159(10) 0.3316(3) 0.3613(2) 0.0891 1.0000 Uani . . . . . .
C27 C 0.53639(16) 0.7647(3) 0.3844(3) 0.1163 1.0000 Uani . . . . . .
C28 C 0.60905(14) 0.4266(6) 0.1824(3) 0.1270 1.0000 Uani . . . . . .
C29 C 0.52371(17) 0.1923(3) 0.4025(3) 0.1250 1.0000 Uani . . . . . .
B1 B 0.61102(14) 0.0502(5) 0.6339(2) 0.1025 1.0000 Uani D U . . . .
F11 F 0.6176(4) 0.1877(6) 0.6081(6) 0.2221 0.580(7) Uani D U P 1 1 .
F12 F 0.5823(2) 0.0507(7) 0.6917(4) 0.1641 0.580(7) Uani D U P 1 1 .
F13 F 0.5929(3) -0.0451(8) 0.5691(3) 0.1958 0.580(7) Uani D U P 1 1 .
F14 F 0.64851(18) -0.0262(10) 0.6756(5) 0.2056 0.580(7) Uani D U P 1 1 .
F111 F 0.5778(3) 0.1490(13) 0.5983(7) 0.2588 0.420(7) Uani D U P 1 2 .
F112 F 0.6096(6) 0.0116(14) 0.7103(4) 0.2909 0.420(7) Uani D U P 1 2 .
F113 F 0.6163(4) -0.0595(10) 0.5798(6) 0.1952 0.420(7) Uani D U P 1 2 .
F114 F 0.6506(3) 0.1435(12) 0.6403(7) 0.2075 0.420(7) Uani D U P 1 2 .
H131 H 0.8120 -0.2612 0.4075 0.0927 1.0000 Uiso R . . . . .
H151 H 0.6755 -0.2073 0.3228 0.0983 1.0000 Uiso R . . . . .
H171 H 0.8550 -0.0738 0.5031 0.1391 1.0000 Uiso R . . . . .
H172 H 0.8398 0.0942 0.4751 0.1382 1.0000 Uiso R . . . . .
H173 H 0.8270 0.0246 0.5593 0.1377 1.0000 Uiso R . . . . .
H181 H 0.7164 -0.4741 0.3147 0.1694 1.0000 Uiso R . . . . .
H182 H 0.7394 -0.3933 0.2456 0.1693 1.0000 Uiso R . . . . .
H183 H 0.7698 -0.4755 0.3249 0.1691 1.0000 Uiso R . . . . .
H191 H 0.6600 0.0873 0.4567 0.1576 1.0000 Uiso R . . . . .
H192 H 0.6644 0.1646 0.3728 0.1576 1.0000 Uiso R . . . . .
H193 H 0.6337 0.0151 0.3716 0.1570 1.0000 Uiso R . . . . .
H231 H 0.5803 0.6827 0.2584 0.1128 1.0000 Uiso R . . . . .
H251 H 0.5709 0.2148 0.2734 0.1171 1.0000 Uiso R . . . . .
H271 H 0.5474 0.8447 0.3530 0.1736 1.0000 Uiso R . . . . .
H272 H 0.5499 0.7828 0.4448 0.1731 1.0000 Uiso R . . . . .
H273 H 0.5034 0.7781 0.3779 0.1730 1.0000 Uiso R . . . . .
H281 H 0.5916 0.3667 0.1355 0.1902 1.0000 Uiso R . . . . .
H282 H 0.6375 0.3747 0.2058 0.1893 1.0000 Uiso R . . . . .
H283 H 0.6163 0.5263 0.1632 0.1898 1.0000 Uiso R . . . . .
H291 H 0.4911 0.2053 0.4023 0.1879 1.0000 Uiso R . . . . .
H292 H 0.5414 0.1824 0.4600 0.1875 1.0000 Uiso R . . . . .
H293 H 0.5282 0.1028 0.3689 0.1875 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       95(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          2.64(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
Br1 . N11 4_656 2.1239(18) yes
Br1 . N11 . 2.1239(18) yes
N11 . C12 . 1.347(3) yes
N11 . C16 . 1.350(3) yes
C12 . C13 . 1.380(3) yes
C12 . C17 . 1.503(4) yes
C13 . C14 . 1.371(4) yes
C13 . H131 . 0.908 no
C14 . C15 . 1.376(4) yes
C14 . C18 . 1.513(4) yes
C15 . C16 . 1.377(4) yes
C15 . H151 . 0.938 no
C16 . C19 . 1.503(4) yes
C17 . H171 . 0.925 no
C17 . H172 . 0.945 no
C17 . H173 . 0.959 no
C18 . H181 . 0.940 no
C18 . H182 . 0.941 no
C18 . H183 . 0.955 no
C19 . H191 . 0.935 no
C19 . H192 . 0.941 no
C19 . H193 . 0.959 no
Br2 . N21 2_666 2.122(3) yes
Br2 . N21 . 2.122(3) yes
N21 . C22 . 1.358(4) yes
N21 . C26 . 1.348(3) yes
C22 . C23 . 1.364(4) yes
C22 . C27 . 1.496(4) yes
C23 . C24 . 1.385(4) yes
C23 . H231 . 0.934 no
C24 . C25 . 1.385(5) yes
C24 . C28 . 1.491(5) yes
C25 . C26 . 1.374(5) yes
C25 . H251 . 0.929 no
C26 . C29 . 1.486(5) yes
C27 . H271 . 0.928 no
C27 . H272 . 0.960 no
C27 . H273 . 0.949 no
C28 . H281 . 0.952 no
C28 . H282 . 0.946 no
C28 . H283 . 0.935 no
C29 . H291 . 0.952 no
C29 . H292 . 0.947 no
C29 . H293 . 0.946 no
B1 . F11 . 1.262(5) yes
B1 . F12 . 1.335(5) yes
B1 . F13 . 1.323(5) yes
B1 . F14 . 1.327(5) yes
B1 . F111 . 1.319(6) yes
B1 . F112 . 1.239(6) yes
B1 . F113 . 1.284(6) yes
B1 . F114 . 1.385(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
N11 4_656 Br1 . N11 . 179.99 yes
Br1 . N11 . C12 . 120.10(16) yes
Br1 . N11 . C16 . 118.75(15) yes
C12 . N11 . C16 . 121.0(2) yes
N11 . C12 . C13 . 119.6(2) yes
N11 . C12 . C17 . 118.5(2) yes
C13 . C12 . C17 . 121.9(2) yes
C12 . C13 . C14 . 121.3(2) yes
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 119.5 no
C13 . C14 . C15 . 117.3(2) yes
C13 . C14 . C18 . 121.8(3) yes
C15 . C14 . C18 . 120.9(3) yes
C14 . C15 . C16 . 121.6(3) yes
C14 . C15 . H151 . 119.7 no
C16 . C15 . H151 . 118.7 no
C15 . C16 . N11 . 119.2(2) yes
C15 . C16 . C19 . 121.9(2) yes
N11 . C16 . C19 . 118.8(2) yes
C12 . C17 . H171 . 109.0 no
C12 . C17 . H172 . 109.7 no
H171 . C17 . H172 . 110.2 no
C12 . C17 . H173 . 109.2 no
H171 . C17 . H173 . 110.3 no
H172 . C17 . H173 . 108.4 no
C14 . C18 . H181 . 109.9 no
C14 . C18 . H182 . 110.4 no
H181 . C18 . H182 . 108.9 no
C14 . C18 . H183 . 111.2 no
H181 . C18 . H183 . 107.5 no
H182 . C18 . H183 . 108.9 no
C16 . C19 . H191 . 108.0 no
C16 . C19 . H192 . 112.3 no
H191 . C19 . H192 . 104.9 no
C16 . C19 . H193 . 114.4 no
H191 . C19 . H193 . 107.4 no
H192 . C19 . H193 . 109.3 no
N21 2_666 Br2 . N21 . 179.99 yes
Br2 . N21 . C22 . 120.06(18) yes
Br2 . N21 . C26 . 119.4(2) yes
C22 . N21 . C26 . 120.5(3) yes
N21 . C22 . C23 . 120.1(2) yes
N21 . C22 . C27 . 118.5(3) yes
C23 . C22 . C27 . 121.3(3) yes
C22 . C23 . C24 . 121.2(3) yes
C22 . C23 . H231 . 118.2 no
C24 . C23 . H231 . 120.6 no
C23 . C24 . C25 . 117.0(3) yes
C23 . C24 . C28 . 121.6(4) yes
C25 . C24 . C28 . 121.4(3) yes
C24 . C25 . C26 . 121.2(3) yes
C24 . C25 . H251 . 119.1 no
C26 . C25 . H251 . 119.6 no
C25 . C26 . N21 . 119.8(3) yes
C25 . C26 . C29 . 121.0(3) yes
N21 . C26 . C29 . 119.1(3) yes
C22 . C27 . H271 . 111.2 no
C22 . C27 . H272 . 113.5 no
H271 . C27 . H272 . 106.3 no
C22 . C27 . H273 . 110.7 no
H271 . C27 . H273 . 107.2 no
H272 . C27 . H273 . 107.7 no
C24 . C28 . H281 . 110.2 no
C24 . C28 . H282 . 107.8 no
H281 . C28 . H282 . 110.2 no
C24 . C28 . H283 . 109.1 no
H281 . C28 . H283 . 111.1 no
H282 . C28 . H283 . 108.3 no
C26 . C29 . H291 . 109.5 no
C26 . C29 . H292 . 107.8 no
H291 . C29 . H292 . 112.1 no
C26 . C29 . H293 . 107.8 no
H291 . C29 . H293 . 109.4 no
H292 . C29 . H293 . 110.1 no
F11 . B1 . F12 . 111.3(5) yes
F11 . B1 . F13 . 112.8(5) yes
F12 . B1 . F13 . 107.7(5) yes
F11 . B1 . F14 . 116.7(6) yes
F12 . B1 . F14 . 103.4(5) yes
F13 . B1 . F14 . 104.2(5) yes
F111 . B1 . F112 . 114.8(7) yes
F111 . B1 . F113 . 110.8(6) yes
F112 . B1 . F113 . 117.7(7) yes
F111 . B1 . F114 . 101.3(6) yes
F112 . B1 . F114 . 105.0(6) yes
F113 . B1 . F114 . 105.3(6) yes


####################################################################### 
# 
# 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_IColl2ClO4-I-300K
_database_code_depnum_ccdc_archive 'CCDC 1853987'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 139lcm18-300K
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
On initial refinement, displacement ellipsoids for the perchlorate ion 
associated with Cl2 were decidedly prolate.  This included the central 
chloride, so the perchlorate moved to a general position close to the 
inversion centre, with the occupancy fixed to a half.  Because of this 
disorder, same distance, vibrational and thermal similarity restraints 
were required to maintian a sensible model for the anion.
;

_cell_length_a                   27.9017(9)
_cell_length_b                   11.0678(2)
_cell_length_c                   23.4625(8)
_cell_angle_alpha                90
_cell_angle_beta                 126.566(5)
_cell_angle_gamma                90
_cell_volume                     5819.3(5)

_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
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'
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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            12

# Given Formula = C18.67 H25.67 Cl1.17 I1.17 N2.33 O4.67 
# Dc =      1.87 Fooo =   3276.00 Mu =    168.29 M =    546.84
# Found Formula = C16 H22.00 Cl1 I1 N2 O4 
# Dc =      1.60 FOOO =   2807.98 Mu =    144.25 M =    468.72

_chemical_formula_sum            'C16 H22 Cl I N2 O4'
_chemical_formula_moiety         'C16 H22 I N2, Cl O4'
_chemical_compound_source        .
_chemical_formula_weight         468.72


_cell_measurement_reflns_used    17899
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.11
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2807.984
_exptl_absorpt_coefficient_mu    14.425

# Sheldrick geometric approximatio 0.07 0.20 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.08
_exptl_absorpt_correction_T_max  0.20
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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      300
_diffrn_reflns_number            37010
_reflns_number_total             6063
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0467
# Number of reflections with Friedels Law is 6063 
# Theoretical number of reflections is about 12199 


_diffrn_reflns_theta_min         3.940
_diffrn_reflns_theta_max         76.310
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.310
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -34
_reflns_limit_h_max              28
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   4.57
_oxford_diffrn_Wilson_scale      0.81

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

_refine_diff_density_min         -0.79
_refine_diff_density_max         0.41


# 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     44
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6055
_oxford_refine_ls_R_factor_ref   0.0330
_refine_ls_wR_factor_ref         0.0805
_refine_ls_goodness_of_fit_ref   1.0316
_refine_ls_shift/su_max          0.0009910
_refine_ls_shift/su_mean         0.0000325


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6055
_refine_ls_R_factor_all          0.0330
_refine_ls_wR_factor_all         0.0805

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5397
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_gt          0.0765


_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) + ( 0.04P)² + 7.56P] 
 ,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 0.5000 0.0000 0.5000 0.0514 1.0000 Uani S . . . . .
N11 N 0.57693(10) 0.1190(2) 0.58639(11) 0.0508 1.0000 Uani . . . . . .
C12 C 0.58293(13) 0.2324(3) 0.57027(15) 0.0545 1.0000 Uani . . . . . .
C13 C 0.63357(13) 0.2991(3) 0.61873(16) 0.0595 1.0000 Uani . . . . . .
C14 C 0.67760(13) 0.2512(3) 0.68477(16) 0.0599 1.0000 Uani . . . . . .
C15 C 0.66910(13) 0.1370(3) 0.70023(15) 0.0596 1.0000 Uani . . . . . .
C16 C 0.61871(13) 0.0711(3) 0.65123(15) 0.0546 1.0000 Uani . . . . . .
C17 C 0.53369(15) 0.2862(3) 0.50020(17) 0.0714 1.0000 Uani . . . . . .
C18 C 0.73282(16) 0.3236(4) 0.7377(2) 0.0832 1.0000 Uani . . . . . .
C19 C 0.60807(18) -0.0521(3) 0.66904(19) 0.0753 1.0000 Uani . . . . . .
I2 I 0.793537(9) 0.05320(2) 0.642851(10) 0.0611 1.0000 Uani . . . . . .
N21 N 0.71995(12) 0.1769(3) 0.55766(14) 0.0626 1.0000 Uani . . . . . .
C22 C 0.66792(16) 0.1278(4) 0.5028(2) 0.0727 1.0000 Uani . . . . . .
C23 C 0.62487(17) 0.2012(4) 0.4488(2) 0.0774 1.0000 Uani . . . . . .
C24 C 0.63336(17) 0.3231(4) 0.44847(19) 0.0730 1.0000 Uani . . . . . .
C25 C 0.68668(17) 0.3698(3) 0.5049(2) 0.0708 1.0000 Uani . . . . . .
C26 C 0.72976(16) 0.2968(3) 0.55941(18) 0.0643 1.0000 Uani . . . . . .
C27 C 0.6583(2) -0.0059(4) 0.5025(3) 0.1092 1.0000 Uani . . . . . .
C28 C 0.5861(2) 0.4015(5) 0.3891(3) 0.0980 1.0000 Uani . . . . . .
C29 C 0.78716(19) 0.3510(4) 0.6210(2) 0.0863 1.0000 Uani . . . . . .
N31 N 0.87081(11) -0.0705(2) 0.72565(13) 0.0589 1.0000 Uani . . . . . .
C32 C 0.91235(15) -0.0280(3) 0.79205(17) 0.0648 1.0000 Uani . . . . . .
C33 C 0.96165(14) -0.0965(4) 0.83983(17) 0.0676 1.0000 Uani . . . . . .
C34 C 0.97034(14) -0.2082(4) 0.82231(18) 0.0674 1.0000 Uani . . . . . .
C35 C 0.92696(15) -0.2511(3) 0.75437(18) 0.0677 1.0000 Uani . . . . . .
C36 C 0.87724(15) -0.1819(3) 0.70670(17) 0.0643 1.0000 Uani . . . . . .
C37 C 0.9033(2) 0.0944(4) 0.8120(2) 0.0940 1.0000 Uani . . . . . .
C38 C 1.02474(17) -0.2830(5) 0.8741(2) 0.0898 1.0000 Uani . . . . . .
C39 C 0.83010(18) -0.2289(4) 0.6334(2) 0.0872 1.0000 Uani . . . . . .
Cl1 Cl 0.65331(4) 0.64947(7) 0.56538(4) 0.0679 1.0000 Uani . . . . . .
O11 O 0.6394(2) 0.7588(3) 0.5829(2) 0.1223 1.0000 Uani . . . . . .
O12 O 0.60144(14) 0.5753(3) 0.52621(18) 0.1012 1.0000 Uani . . . . . .
O13 O 0.67269(17) 0.6739(3) 0.5223(2) 0.1071 1.0000 Uani . . . . . .
O14 O 0.69859(16) 0.5853(3) 0.62714(17) 0.1111 1.0000 Uani . . . . . .
Cl2 Cl 0.5117(2) 0.0981(2) 0.2560(5) 0.1104 0.5000 Uani D U . 1 -1 .
O21 O 0.4892(5) 0.1293(12) 0.2923(8) 0.1861 0.5000 Uani D U . 1 -1 .
O22 O 0.4723(5) 0.0254(11) 0.1995(6) 0.2316 0.5000 Uani D U . 1 -1 .
O23 O 0.5253(7) 0.1979(8) 0.2356(8) 0.1990 0.5000 Uani D U . 1 -1 .
O24 O 0.5635(4) 0.0315(10) 0.3012(6) 0.1405 0.5000 Uani D U . 1 -1 .
H231 H 0.5896 0.1663 0.4113 0.0929 1.0000 Uiso R . . . . .
H251 H 0.6940 0.4515 0.5070 0.0845 1.0000 Uiso R . . . . .
H271 H 0.6598 -0.0294 0.5424 0.1638 1.0000 Uiso R . . . . .
H272 H 0.6886 -0.0491 0.5047 0.1636 1.0000 Uiso R . . . . .
H273 H 0.6204 -0.0269 0.4594 0.1637 1.0000 Uiso R . . . . .
H281 H 0.5928 0.4827 0.4043 0.1469 1.0000 Uiso R . . . . .
H282 H 0.5874 0.3947 0.3494 0.1471 1.0000 Uiso R . . . . .
H283 H 0.5476 0.3774 0.3747 0.1470 1.0000 Uiso R . . . . .
H291 H 0.7928 0.3289 0.6647 0.1292 1.0000 Uiso R . . . . .
H292 H 0.8205 0.3230 0.6221 0.1291 1.0000 Uiso R . . . . .
H293 H 0.7855 0.4365 0.6178 0.1288 1.0000 Uiso R . . . . .
H331 H 0.9903 -0.0664 0.8847 0.0814 1.0000 Uiso R . . . . .
H351 H 0.9315 -0.3275 0.7399 0.0804 1.0000 Uiso R . . . . .
H371 H 0.8645 0.0970 0.8014 0.1407 1.0000 Uiso R . . . . .
H372 H 0.9053 0.1563 0.7848 0.1407 1.0000 Uiso R . . . . .
H373 H 0.9326 0.1091 0.8613 0.1408 1.0000 Uiso R . . . . .
H381 H 1.0359 -0.2711 0.9209 0.1350 1.0000 Uiso R . . . . .
H382 H 1.0566 -0.2595 0.8722 0.1354 1.0000 Uiso R . . . . .
H383 H 1.0169 -0.3673 0.8624 0.1352 1.0000 Uiso R . . . . .
H391 H 0.7924 -0.2234 0.6251 0.1305 1.0000 Uiso R . . . . .
H392 H 0.8278 -0.1832 0.5972 0.1306 1.0000 Uiso R . . . . .
H393 H 0.8379 -0.3105 0.6293 0.1304 1.0000 Uiso R . . . . .
H131 H 0.6368 0.3770 0.6071 0.0700 1.0000 Uiso R . . . . .
H151 H 0.6976 0.1028 0.7444 0.0712 1.0000 Uiso R . . . . .
H171 H 0.5426 0.3701 0.5000 0.1067 1.0000 Uiso R . . . . .
H172 H 0.5309 0.2432 0.4623 0.1070 1.0000 Uiso R . . . . .
H173 H 0.4964 0.2795 0.4946 0.1069 1.0000 Uiso R . . . . .
H181 H 0.7420 0.3211 0.7838 0.1254 1.0000 Uiso R . . . . .
H182 H 0.7272 0.4052 0.7231 0.1247 1.0000 Uiso R . . . . .
H183 H 0.7660 0.2940 0.7392 0.1253 1.0000 Uiso R . . . . .
H191 H 0.5708 -0.0570 0.6640 0.1127 1.0000 Uiso R . . . . .
H192 H 0.6068 -0.1121 0.6390 0.1133 1.0000 Uiso R . . . . .
H193 H 0.6393 -0.0725 0.7173 0.1126 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.228(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 . N11 2_656 2.295(2) yes
I1 . N11 . 2.295(2) yes
N11 . C12 . 1.350(4) yes
N11 . C16 . 1.357(3) yes
C12 . C13 . 1.385(4) yes
C12 . C17 . 1.501(4) yes
C13 . C14 . 1.387(4) yes
C13 . H131 . 0.926 no
C14 . C15 . 1.374(5) yes
C14 . C18 . 1.509(4) yes
C15 . C16 . 1.381(4) yes
C15 . H151 . 0.932 no
C16 . C19 . 1.506(5) yes
C17 . H171 . 0.962 no
C17 . H172 . 0.969 no
C17 . H173 . 0.971 no
C18 . H181 . 0.954 no
C18 . H182 . 0.946 no
C18 . H183 . 0.961 no
C19 . H191 . 0.976 no
C19 . H192 . 0.954 no
C19 . H193 . 0.958 no
I2 . N21 . 2.280(3) yes
I2 . N31 . 2.303(3) yes
N21 . C22 . 1.354(5) yes
N21 . C26 . 1.350(5) yes
C22 . C23 . 1.376(5) yes
C22 . C27 . 1.504(6) yes
C23 . C24 . 1.370(6) yes
C23 . H231 . 0.927 no
C24 . C25 . 1.374(6) yes
C24 . C28 . 1.497(5) yes
C25 . C26 . 1.379(5) yes
C25 . H251 . 0.922 no
C26 . C29 . 1.502(5) yes
C27 . H271 . 0.946 no
C27 . H272 . 0.946 no
C27 . H273 . 0.959 no
C28 . H281 . 0.943 no
C28 . H282 . 0.955 no
C28 . H283 . 0.952 no
C29 . H291 . 0.973 no
C29 . H292 . 0.966 no
C29 . H293 . 0.948 no
N31 . C32 . 1.357(4) yes
N31 . C36 . 1.359(5) yes
C32 . C33 . 1.374(5) yes
C32 . C37 . 1.502(6) yes
C33 . C34 . 1.369(6) yes
C33 . H331 . 0.925 no
C34 . C35 . 1.390(5) yes
C34 . C38 . 1.506(5) yes
C35 . C36 . 1.383(5) yes
C35 . H351 . 0.948 no
C36 . C39 . 1.505(5) yes
C37 . H371 . 0.957 no
C37 . H372 . 0.959 no
C37 . H373 . 0.952 no
C38 . H381 . 0.956 no
C38 . H382 . 0.952 no
C38 . H383 . 0.960 no
C39 . H391 . 0.951 no
C39 . H392 . 0.956 no
C39 . H393 . 0.947 no
Cl1 . O11 . 1.406(3) yes
Cl1 . O12 . 1.424(3) yes
Cl1 . O13 . 1.427(3) yes
Cl1 . O14 . 1.421(3) yes
Cl2 . O21 . 1.370(8) yes
Cl2 . O22 . 1.369(6) yes
Cl2 . O23 . 1.345(7) yes
Cl2 . O24 . 1.390(7) 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
N11 2_656 I1 . N11 . 179.99 yes
I1 . N11 . C12 . 119.55(18) yes
I1 . N11 . C16 . 119.5(2) yes
C12 . N11 . C16 . 120.7(2) yes
N11 . C12 . C13 . 120.1(3) yes
N11 . C12 . C17 . 119.4(3) yes
C13 . C12 . C17 . 120.5(3) yes
C12 . C13 . C14 . 120.4(3) yes
C12 . C13 . H131 . 119.0 no
C14 . C13 . H131 . 120.6 no
C13 . C14 . C15 . 118.0(3) yes
C13 . C14 . C18 . 120.5(3) yes
C15 . C14 . C18 . 121.5(3) yes
C14 . C15 . C16 . 121.1(3) yes
C14 . C15 . H151 . 120.1 no
C16 . C15 . H151 . 118.8 no
C15 . C16 . N11 . 119.7(3) yes
C15 . C16 . C19 . 121.3(3) yes
N11 . C16 . C19 . 119.0(3) yes
C12 . C17 . H171 . 108.5 no
C12 . C17 . H172 . 109.3 no
H171 . C17 . H172 . 110.5 no
C12 . C17 . H173 . 109.0 no
H171 . C17 . H173 . 109.4 no
H172 . C17 . H173 . 110.0 no
C14 . C18 . H181 . 111.8 no
C14 . C18 . H182 . 110.0 no
H181 . C18 . H182 . 108.2 no
C14 . C18 . H183 . 109.8 no
H181 . C18 . H183 . 110.2 no
H182 . C18 . H183 . 106.7 no
C16 . C19 . H191 . 112.9 no
C16 . C19 . H192 . 110.6 no
H191 . C19 . H192 . 107.7 no
C16 . C19 . H193 . 110.5 no
H191 . C19 . H193 . 106.5 no
H192 . C19 . H193 . 108.4 no
N21 . I2 . N31 . 176.46(10) yes
I2 . N21 . C22 . 119.2(2) yes
I2 . N21 . C26 . 120.2(2) yes
C22 . N21 . C26 . 120.4(3) yes
N21 . C22 . C23 . 119.5(4) yes
N21 . C22 . C27 . 119.2(3) yes
C23 . C22 . C27 . 121.4(4) yes
C22 . C23 . C24 . 121.8(4) yes
C22 . C23 . H231 . 118.6 no
C24 . C23 . H231 . 119.6 no
C23 . C24 . C25 . 117.2(3) yes
C23 . C24 . C28 . 121.1(4) yes
C25 . C24 . C28 . 121.7(4) yes
C24 . C25 . C26 . 121.2(4) yes
C24 . C25 . H251 . 119.9 no
C26 . C25 . H251 . 118.8 no
C25 . C26 . N21 . 119.9(3) yes
C25 . C26 . C29 . 119.9(3) yes
N21 . C26 . C29 . 120.2(3) yes
C22 . C27 . H271 . 111.4 no
C22 . C27 . H272 . 110.2 no
H271 . C27 . H272 . 107.1 no
C22 . C27 . H273 . 109.0 no
H271 . C27 . H273 . 110.4 no
H272 . C27 . H273 . 108.8 no
C24 . C28 . H281 . 109.6 no
C24 . C28 . H282 . 109.7 no
H281 . C28 . H282 . 109.3 no
C24 . C28 . H283 . 110.4 no
H281 . C28 . H283 . 109.2 no
H282 . C28 . H283 . 108.6 no
C26 . C29 . H291 . 108.8 no
C26 . C29 . H292 . 110.8 no
H291 . C29 . H292 . 110.1 no
C26 . C29 . H293 . 110.5 no
H291 . C29 . H293 . 107.6 no
H292 . C29 . H293 . 109.0 no
I2 . N31 . C32 . 119.5(2) yes
I2 . N31 . C36 . 120.2(2) yes
C32 . N31 . C36 . 120.1(3) yes
N31 . C32 . C33 . 120.0(3) yes
N31 . C32 . C37 . 118.9(3) yes
C33 . C32 . C37 . 121.1(3) yes
C32 . C33 . C34 . 121.6(3) yes
C32 . C33 . H331 . 119.7 no
C34 . C33 . H331 . 118.7 no
C33 . C34 . C35 . 117.6(3) yes
C33 . C34 . C38 . 121.9(3) yes
C35 . C34 . C38 . 120.5(4) yes
C34 . C35 . C36 . 120.5(4) yes
C34 . C35 . H351 . 120.3 no
C36 . C35 . H351 . 119.2 no
C35 . C36 . N31 . 120.1(3) yes
C35 . C36 . C39 . 120.4(3) yes
N31 . C36 . C39 . 119.5(3) yes
C32 . C37 . H371 . 108.7 no
C32 . C37 . H372 . 110.5 no
H371 . C37 . H372 . 108.0 no
C32 . C37 . H373 . 110.6 no
H371 . C37 . H373 . 109.1 no
H372 . C37 . H373 . 109.9 no
C34 . C38 . H381 . 109.4 no
C34 . C38 . H382 . 109.3 no
H381 . C38 . H382 . 110.1 no
C34 . C38 . H383 . 110.8 no
H381 . C38 . H383 . 109.1 no
H382 . C38 . H383 . 108.1 no
C36 . C39 . H391 . 108.6 no
C36 . C39 . H392 . 112.5 no
H391 . C39 . H392 . 107.6 no
C36 . C39 . H393 . 110.4 no
H391 . C39 . H393 . 109.4 no
H392 . C39 . H393 . 108.3 no
O11 . Cl1 . O12 . 109.5(2) yes
O11 . Cl1 . O13 . 109.4(2) yes
O12 . Cl1 . O13 . 108.7(2) yes
O11 . Cl1 . O14 . 111.4(2) yes
O12 . Cl1 . O14 . 108.3(2) yes
O13 . Cl1 . O14 . 109.6(3) yes
O21 . Cl2 . O22 . 110.4(7) yes
O23 . Cl2 . O21 . 110.2(6) yes
O23 . Cl2 . O22 . 111.9(7) yes
O24 . Cl2 . O21 . 108.2(7) yes
O24 . Cl2 . O22 . 107.3(5) yes
O23 . Cl2 . O24 . 108.8(7) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C23 . H231 . O21 . 164 0.93 2.55 3.447(6) yes
C35 . H351 . O24 4_646 176 0.95 2.49 3.437(6) yes
C38 . H383 . O22 4_646 142 0.96 2.41 3.219(6) yes
C19 . H191 . O21 2_656 151 0.98 2.56 3.443(6) yes
C19 . H192 . O11 1_545 160 0.95 2.45 3.365(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
2 0 2 x .
-6 0 6 x .
-5 1 4 x .
-2 0 4 x .
3 1 0 x .
4 0 0 x .
-3 13 2 x .
-32 0 10 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_BrColl2ClO4-I-100K
_database_code_depnum_ccdc_archive 'CCDC 1853990'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-20
_audit_creation_method           CRYSTALS_ver_14.61_build_6156

_oxford_structure_analysis_title 127lcm18
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   26.7649(4)
_cell_length_b                   10.8741(1)
_cell_length_c                   23.3335(3)
_cell_angle_alpha                90
_cell_angle_beta                 126.930(2)
_cell_angle_gamma                90
_cell_volume                     5428.59(19)

_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
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'
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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            12

# Given Formula = C16 H22 Br1 Cl1 N2 O4 
# Dc =      1.55 Fooo =   2592.00 Mu =     46.54 M =    421.72
# Found Formula = C16 H22 Br1 Cl1 N2 O4 
# Dc =      1.55 FOOO =   2592.00 Mu =     46.54 M =    421.72

_chemical_formula_sum            'C16 H22 Br1 Cl1 N2 O4'
_chemical_formula_moiety         'C16 H22 Br1 N2, Cl O4'
_chemical_compound_source        .
_chemical_formula_weight         421.72


_cell_measurement_reflns_used    21564
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_max          0.34

_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2592
_exptl_absorpt_coefficient_mu    4.654

# Sheldrick geometric approximatio 0.36 0.66 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.26
_exptl_absorpt_correction_T_max  0.66
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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            32349
_reflns_number_total             5654
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0376
# Number of reflections with Friedels Law is 5654 
# Theoretical number of reflections is about 11352 


_diffrn_reflns_theta_min         4.001
_diffrn_reflns_theta_max         76.122
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.600
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -33
_reflns_limit_h_max              26
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.72


# 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         5654
_refine_ls_number_restraints     0
_refine_ls_number_parameters     327
_oxford_refine_ls_R_factor_ref   0.0255
_refine_ls_wR_factor_ref         0.0666
_refine_ls_goodness_of_fit_ref   1.0181
_refine_ls_shift/su_max          0.0024402
_refine_ls_shift/su_mean         0.0000916


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5654
_refine_ls_R_factor_all          0.0255
_refine_ls_wR_factor_all         0.0666

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5559
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_gt          0.0662

# 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) + ( 0.04P)² + 9.20P] 
 ,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 0.5000 0.0000 0.5000 0.0160 1.0000 Uani S . . . . .
N11 N 0.57353(6) 0.11247(13) 0.58171(7) 0.0166 1.0000 Uani . . . . . .
C12 C 0.58119(7) 0.22683(16) 0.56508(9) 0.0177 1.0000 Uani . . . . . .
C13 C 0.63308(8) 0.29598(16) 0.61583(9) 0.0197 1.0000 Uani . . . . . .
C14 C 0.67701(8) 0.24971(16) 0.68464(9) 0.0196 1.0000 Uani . . . . . .
C15 C 0.66639(8) 0.13345(16) 0.70024(9) 0.0202 1.0000 Uani . . . . . .
C16 C 0.61438(8) 0.06564(16) 0.64861(9) 0.0185 1.0000 Uani . . . . . .
C17 C 0.53104(8) 0.27784(17) 0.49229(9) 0.0219 1.0000 Uani . . . . . .
C18 C 0.73326(8) 0.32351(18) 0.74083(10) 0.0253 1.0000 Uani . . . . . .
C19 C 0.60055(9) -0.05761(16) 0.66474(9) 0.0243 1.0000 Uani . . . . . .
Br2 Br 0.796749(7) 0.052032(15) 0.644885(8) 0.0178 1.0000 Uani . . . . . .
N21 N 0.72823(6) 0.17017(14) 0.56491(7) 0.0187 1.0000 Uani . . . . . .
C22 C 0.67505(8) 0.12072(17) 0.50639(9) 0.0227 1.0000 Uani . . . . . .
C23 C 0.63082(8) 0.19675(17) 0.45137(9) 0.0226 1.0000 Uani . . . . . .
C24 C 0.64015(8) 0.32306(17) 0.45405(9) 0.0209 1.0000 Uani . . . . . .
C25 C 0.69546(8) 0.36985(16) 0.51435(9) 0.0211 1.0000 Uani . . . . . .
C26 C 0.73899(8) 0.29285(16) 0.56994(9) 0.0191 1.0000 Uani . . . . . .
C27 C 0.66608(10) -0.01596(19) 0.50307(12) 0.0384 1.0000 Uani . . . . . .
C28 C 0.59169(9) 0.40451(18) 0.39377(10) 0.0260 1.0000 Uani . . . . . .
C29 C 0.79784(8) 0.34280(18) 0.63642(10) 0.0258 1.0000 Uani . . . . . .
N31 N 0.86978(6) -0.06775(13) 0.72395(7) 0.0177 1.0000 Uani . . . . . .
C32 C 0.91077(8) -0.02690(17) 0.79235(9) 0.0197 1.0000 Uani . . . . . .
C33 C 0.96140(8) -0.09877(17) 0.84237(9) 0.0211 1.0000 Uani . . . . . .
C34 C 0.97168(8) -0.21246(17) 0.82354(9) 0.0213 1.0000 Uani . . . . . .
C35 C 0.92818(8) -0.25172(16) 0.75301(9) 0.0211 1.0000 Uani . . . . . .
C36 C 0.87704(8) -0.17910(16) 0.70384(9) 0.0201 1.0000 Uani . . . . . .
C37 C 0.89925(9) 0.09574(18) 0.81181(9) 0.0266 1.0000 Uani . . . . . .
C38 C 1.02737(8) -0.28966(19) 0.87723(10) 0.0272 1.0000 Uani . . . . . .
C39 C 0.82888(8) -0.22230(18) 0.62853(9) 0.0258 1.0000 Uani . . . . . .
Cl1 Cl 0.652739(17) 0.64747(3) 0.56374(2) 0.0188 1.0000 Uani . . . . . .
O11 O 0.63771(7) 0.76102(13) 0.58189(8) 0.0316 1.0000 Uani . . . . . .
O12 O 0.59775(6) 0.57043(13) 0.52384(7) 0.0279 1.0000 Uani . . . . . .
O13 O 0.67373(6) 0.67300(12) 0.52069(7) 0.0266 1.0000 Uani . . . . . .
O14 O 0.70149(6) 0.58380(13) 0.62838(7) 0.0299 1.0000 Uani . . . . . .
Cl2 Cl 0.5000 0.10899(6) 0.2500 0.0264 1.0000 Uani S T . . . .
H231 H 0.5939 0.1626 0.4123 0.0275 1.0000 Uiso R . . . . .
H251 H 0.7032 0.4541 0.5179 0.0234 1.0000 Uiso R . . . . .
H271 H 0.6658 -0.0393 0.5430 0.0584 1.0000 Uiso R . . . . .
H272 H 0.6988 -0.0588 0.5069 0.0586 1.0000 Uiso R . . . . .
H273 H 0.6272 -0.0369 0.4602 0.0590 1.0000 Uiso R . . . . .
H281 H 0.6030 0.4893 0.4057 0.0390 1.0000 Uiso R . . . . .
H282 H 0.5892 0.3895 0.3522 0.0387 1.0000 Uiso R . . . . .
H283 H 0.5519 0.3909 0.3825 0.0399 1.0000 Uiso R . . . . .
H291 H 0.8015 0.3169 0.6772 0.0391 1.0000 Uiso R . . . . .
H292 H 0.8333 0.3163 0.6396 0.0385 1.0000 Uiso R . . . . .
H293 H 0.7973 0.4303 0.6340 0.0392 1.0000 Uiso R . . . . .
H331 H 0.9882 -0.0707 0.8894 0.0251 1.0000 Uiso R . . . . .
H351 H 0.9335 -0.3280 0.7399 0.0250 1.0000 Uiso R . . . . .
H371 H 0.8566 0.1007 0.7976 0.0389 1.0000 Uiso R . . . . .
H372 H 0.9067 0.1610 0.7894 0.0390 1.0000 Uiso R . . . . .
H373 H 0.9255 0.1058 0.8623 0.0398 1.0000 Uiso R . . . . .
H381 H 1.0284 -0.2979 0.9194 0.0413 1.0000 Uiso R . . . . .
H382 H 1.0655 -0.2520 0.8902 0.0417 1.0000 Uiso R . . . . .
H383 H 1.0237 -0.3704 0.8586 0.0417 1.0000 Uiso R . . . . .
H391 H 0.7879 -0.2230 0.6173 0.0385 1.0000 Uiso R . . . . .
H392 H 0.8283 -0.1721 0.5932 0.0388 1.0000 Uiso R . . . . .
H393 H 0.8378 -0.3047 0.6234 0.0384 1.0000 Uiso R . . . . .
H131 H 0.6381 0.3740 0.6044 0.0235 1.0000 Uiso R . . . . .
H151 H 0.6932 0.1015 0.7461 0.0243 1.0000 Uiso R . . . . .
H171 H 0.5413 0.3594 0.4884 0.0318 1.0000 Uiso R . . . . .
H172 H 0.5268 0.2277 0.4550 0.0317 1.0000 Uiso R . . . . .
H173 H 0.4920 0.2799 0.4863 0.0318 1.0000 Uiso R . . . . .
H181 H 0.7302 0.3445 0.7793 0.0384 1.0000 Uiso R . . . . .
H182 H 0.7350 0.3976 0.7210 0.0380 1.0000 Uiso R . . . . .
H183 H 0.7708 0.2778 0.7602 0.0385 1.0000 Uiso R . . . . .
H191 H 0.5593 -0.0591 0.6551 0.0359 1.0000 Uiso R . . . . .
H192 H 0.6038 -0.1202 0.6382 0.0372 1.0000 Uiso R . . . . .
H193 H 0.6292 -0.0742 0.7142 0.0376 1.0000 Uiso R . . . . .
O21 O 0.48471(8) 0.1847(2) 0.28725(10) 0.0541 1.0000 Uani . . . . . .
O22 O 0.44665(9) 0.03294(16) 0.19953(9) 0.0508 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.345(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . N11 2_656 2.1201(14) yes
Br1 . N11 . 2.1201(14) yes
N11 . C12 . 1.354(2) yes
N11 . C16 . 1.357(2) yes
C12 . C13 . 1.386(2) yes
C12 . C17 . 1.502(2) yes
C13 . C14 . 1.395(2) yes
C13 . H131 . 0.923 no
C14 . C15 . 1.391(2) yes
C14 . C18 . 1.502(2) yes
C15 . C16 . 1.385(2) yes
C15 . H151 . 0.926 no
C16 . C19 . 1.497(2) yes
C17 . H171 . 0.949 no
C17 . H172 . 0.973 no
C17 . H173 . 0.970 no
C18 . H181 . 0.975 no
C18 . H182 . 0.944 no
C18 . H183 . 0.956 no
C19 . H191 . 0.985 no
C19 . H192 . 0.959 no
C19 . H193 . 0.942 no
Br2 . N21 . 2.0937(14) yes
Br2 . N31 . 2.1418(14) yes
N21 . C22 . 1.358(2) yes
N21 . C26 . 1.355(2) yes
C22 . C23 . 1.381(3) yes
C22 . C27 . 1.500(3) yes
C23 . C24 . 1.391(3) yes
C23 . H231 . 0.929 no
C24 . C25 . 1.388(2) yes
C24 . C28 . 1.501(2) yes
C25 . C26 . 1.387(2) yes
C25 . H251 . 0.932 no
C26 . C29 . 1.499(2) yes
C27 . H271 . 0.970 no
C27 . H272 . 0.948 no
C27 . H273 . 0.941 no
C28 . H281 . 0.958 no
C28 . H282 . 0.945 no
C28 . H283 . 0.944 no
C29 . H291 . 0.940 no
C29 . H292 . 0.950 no
C29 . H293 . 0.953 no
N31 . C32 . 1.358(2) yes
N31 . C36 . 1.354(2) yes
C32 . C33 . 1.382(2) yes
C32 . C37 . 1.499(2) yes
C33 . C34 . 1.394(3) yes
C33 . H331 . 0.930 no
C34 . C35 . 1.394(2) yes
C34 . C38 . 1.501(2) yes
C35 . C36 . 1.388(2) yes
C35 . H351 . 0.925 no
C36 . C39 . 1.499(2) yes
C37 . H371 . 0.980 no
C37 . H372 . 0.971 no
C37 . H373 . 0.948 no
C38 . H381 . 0.972 no
C38 . H382 . 0.964 no
C38 . H383 . 0.958 no
C39 . H391 . 0.963 no
C39 . H392 . 0.980 no
C39 . H393 . 0.953 no
Cl1 . O11 . 1.4390(14) yes
Cl1 . O12 . 1.4451(13) yes
Cl1 . O13 . 1.4422(13) yes
Cl1 . O14 . 1.4464(13) yes
Cl2 . O22 6_655 1.4454(16) yes
Cl2 . O21 6_655 1.4244(17) yes
Cl2 . O21 . 1.4244(17) yes
Cl2 . O22 . 1.4454(16) 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
N11 2_656 Br1 . N11 . 179.995 yes
Br1 . N11 . C12 . 119.38(11) yes
Br1 . N11 . C16 . 119.28(11) yes
C12 . N11 . C16 . 121.21(14) yes
N11 . C12 . C13 . 119.99(15) yes
N11 . C12 . C17 . 118.49(15) yes
C13 . C12 . C17 . 121.46(15) yes
C12 . C13 . C14 . 120.46(16) yes
C12 . C13 . H131 . 119.8 no
C14 . C13 . H131 . 119.8 no
C13 . C14 . C15 . 117.75(16) yes
C13 . C14 . C18 . 121.44(16) yes
C15 . C14 . C18 . 120.80(16) yes
C14 . C15 . C16 . 120.85(15) yes
C14 . C15 . H151 . 120.3 no
C16 . C15 . H151 . 118.8 no
C15 . C16 . N11 . 119.67(15) yes
C15 . C16 . C19 . 121.94(15) yes
N11 . C16 . C19 . 118.37(15) yes
C12 . C17 . H171 . 109.9 no
C12 . C17 . H172 . 110.4 no
H171 . C17 . H172 . 108.8 no
C12 . C17 . H173 . 108.9 no
H171 . C17 . H173 . 108.3 no
H172 . C17 . H173 . 110.4 no
C14 . C18 . H181 . 109.5 no
C14 . C18 . H182 . 110.3 no
H181 . C18 . H182 . 107.8 no
C14 . C18 . H183 . 110.6 no
H181 . C18 . H183 . 109.3 no
H182 . C18 . H183 . 109.3 no
C16 . C19 . H191 . 111.7 no
C16 . C19 . H192 . 109.9 no
H191 . C19 . H192 . 111.5 no
C16 . C19 . H193 . 109.7 no
H191 . C19 . H193 . 104.5 no
H192 . C19 . H193 . 109.4 no
N21 . Br2 . N31 . 176.56(5) yes
Br2 . N21 . C22 . 118.74(12) yes
Br2 . N21 . C26 . 120.01(11) yes
C22 . N21 . C26 . 121.12(15) yes
N21 . C22 . C23 . 119.53(16) yes
N21 . C22 . C27 . 118.87(16) yes
C23 . C22 . C27 . 121.60(16) yes
C22 . C23 . C24 . 121.26(16) yes
C22 . C23 . H231 . 119.0 no
C24 . C23 . H231 . 119.7 no
C23 . C24 . C25 . 117.45(16) yes
C23 . C24 . C28 . 120.65(16) yes
C25 . C24 . C28 . 121.90(17) yes
C24 . C25 . C26 . 120.76(16) yes
C24 . C25 . H251 . 119.7 no
C26 . C25 . H251 . 119.6 no
C25 . C26 . N21 . 119.85(15) yes
C25 . C26 . C29 . 121.26(16) yes
N21 . C26 . C29 . 118.88(15) yes
C22 . C27 . H271 . 107.6 no
C22 . C27 . H272 . 111.9 no
H271 . C27 . H272 . 108.7 no
C22 . C27 . H273 . 109.6 no
H271 . C27 . H273 . 108.5 no
H272 . C27 . H273 . 110.5 no
C24 . C28 . H281 . 110.6 no
C24 . C28 . H282 . 110.4 no
H281 . C28 . H282 . 106.2 no
C24 . C28 . H283 . 111.4 no
H281 . C28 . H283 . 109.8 no
H282 . C28 . H283 . 108.4 no
C26 . C29 . H291 . 110.2 no
C26 . C29 . H292 . 110.5 no
H291 . C29 . H292 . 109.7 no
C26 . C29 . H293 . 109.4 no
H291 . C29 . H293 . 110.3 no
H292 . C29 . H293 . 106.7 no
Br2 . N31 . C32 . 119.21(12) yes
Br2 . N31 . C36 . 119.48(11) yes
C32 . N31 . C36 . 121.13(15) yes
N31 . C32 . C33 . 119.83(16) yes
N31 . C32 . C37 . 118.62(15) yes
C33 . C32 . C37 . 121.54(15) yes
C32 . C33 . C34 . 120.98(16) yes
C32 . C33 . H331 . 118.7 no
C34 . C33 . H331 . 120.3 no
C33 . C34 . C35 . 117.43(16) yes
C33 . C34 . C38 . 121.22(16) yes
C35 . C34 . C38 . 121.35(17) yes
C34 . C35 . C36 . 120.73(16) yes
C34 . C35 . H351 . 118.7 no
C36 . C35 . H351 . 120.6 no
C35 . C36 . N31 . 119.86(15) yes
C35 . C36 . C39 . 121.13(16) yes
N31 . C36 . C39 . 119.01(15) yes
C32 . C37 . H371 . 110.8 no
C32 . C37 . H372 . 109.9 no
H371 . C37 . H372 . 110.7 no
C32 . C37 . H373 . 110.2 no
H371 . C37 . H373 . 104.9 no
H372 . C37 . H373 . 110.3 no
C34 . C38 . H381 . 107.9 no
C34 . C38 . H382 . 110.9 no
H381 . C38 . H382 . 109.9 no
C34 . C38 . H383 . 110.8 no
H381 . C38 . H383 . 107.9 no
H382 . C38 . H383 . 109.4 no
C36 . C39 . H391 . 111.0 no
C36 . C39 . H392 . 112.2 no
H391 . C39 . H392 . 109.6 no
C36 . C39 . H393 . 109.7 no
H391 . C39 . H393 . 106.8 no
H392 . C39 . H393 . 107.3 no
O11 . Cl1 . O12 . 109.30(9) yes
O11 . Cl1 . O13 . 109.55(8) yes
O12 . Cl1 . O13 . 109.58(8) yes
O11 . Cl1 . O14 . 109.89(9) yes
O12 . Cl1 . O14 . 109.01(8) yes
O13 . Cl1 . O14 . 109.50(8) yes
O22 6_655 Cl2 . O21 6_655 108.82(11) yes
O22 6_655 Cl2 . O21 . 109.82(12) yes
O21 6_655 Cl2 . O21 . 109.36(19) yes
O22 6_655 Cl2 . O22 . 110.20(14) yes
O21 6_655 Cl2 . O22 . 109.82(12) yes
O21 . Cl2 . O22 . 108.82(11) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C23 . H231 . O22 6_655 140 0.93 2.56 3.331(3) yes
C25 . H251 . O13 . 151 0.93 2.52 3.366(3) yes
C35 . H351 . O22 7_545 178 0.93 2.52 3.449(3) yes
C15 . H151 . O14 8_646 154 0.93 2.58 3.434(3) yes
C17 . H171 . O12 . 161 0.95 2.59 3.503(3) yes
C19 . H192 . O11 1_545 163 0.96 2.38 3.306(3) yes


####################################################################### 
# 
# 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_BrColl2BF4-100K
_database_code_depnum_ccdc_archive 'CCDC 1853996'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 099KEC14-100K
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
On initial refinement, displacement ellipsoids for one half IColl2 
cation were decidedly prolate.  This included the central 
iodine, so the cation was moved to a general position close to the 
inversion centre, with the occupancy fixed to a half.  Despite this 
disorder restraints were not necessary and the structure was refined 
freely.
;

_cell_length_a                   28.9753(5)
_cell_length_b                   8.47823(11)
_cell_length_c                   15.0337(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.8782(19)
_cell_angle_gamma                90
_cell_volume                     3600.28(11)

_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'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 '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'
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'
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            8

# Given Formula = C13 H20 B1 Br1 F4 N2 
# Dc =      1.37 Fooo =   1504.00 Mu =     34.13 M =    371.02
# Found Formula = C16 H22 B1 Br1 F4 N2 
# Dc =      1.51 FOOO =   1664.00 Mu =     34.74 M =    409.07

_chemical_formula_sum            'C16 H22 B Br F4 N2'
_chemical_formula_moiety         'C16 H22 Br N2, B F4'
_chemical_compound_source        .
_chemical_formula_weight         409.07


_cell_measurement_reflns_used    16388
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.29
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_max          0.34

_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    3.474

# Sheldrick geometric approximatio 0.34 0.37 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.20
_exptl_absorpt_correction_T_max  0.37
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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      100
_diffrn_reflns_number            29348
_reflns_number_total             3728
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0331
# Number of reflections with Friedels Law is 3728 
# Theoretical number of reflections is about 7532 


_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_max         76.156
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        73.110
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -36
_reflns_limit_h_max              35
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.62
_oxford_diffrn_Wilson_scale      0.39

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

_refine_diff_density_min         -0.80
_refine_diff_density_max         0.98


# 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     0
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3713
_oxford_refine_ls_R_factor_ref   0.0442
_refine_ls_wR_factor_ref         0.1089
_refine_ls_goodness_of_fit_ref   1.0044
_refine_ls_shift/su_max          0.0007224
_refine_ls_shift/su_mean         0.0000234


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3713
_refine_ls_R_factor_all          0.0442
_refine_ls_wR_factor_all         0.1089

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3582
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_gt          0.1078


_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 +13.43P] 
 ,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 0.7500 0.2500 0.5000 0.0307 1.0000 Uani S . . . . .
N11 N 0.74558(8) 0.0184(3) 0.44649(14) 0.0296 1.0000 Uani . . . . . .
C12 C 0.78566(9) -0.0659(3) 0.44896(18) 0.0315 1.0000 Uani . . . . . .
C13 C 0.78316(10) -0.2089(3) 0.40320(19) 0.0325 1.0000 Uani . . . . . .
C14 C 0.73998(10) -0.2658(3) 0.35421(18) 0.0314 1.0000 Uani . . . . . .
C15 C 0.69970(9) -0.1790(3) 0.35602(17) 0.0317 1.0000 Uani . . . . . .
C16 C 0.70260(9) -0.0378(3) 0.40304(17) 0.0302 1.0000 Uani . . . . . .
C17 C 0.83178(11) 0.0002(4) 0.5015(2) 0.0450 1.0000 Uani . . . . . .
C18 C 0.73700(11) -0.4168(4) 0.3007(2) 0.0444 1.0000 Uani . . . . . .
C19 C 0.65931(10) 0.0568(4) 0.4073(2) 0.0413 1.0000 Uani . . . . . .
Br2 Br 0.50548(2) 0.50644(9) 0.48415(4) 0.0239 0.5000 Uani . . . 1 -1 .
N21 N 0.53931(19) 0.4795(8) 0.3740(4) 0.0237 0.5000 Uani . . . 1 -1 .
C22 C 0.5515(2) 0.6086(9) 0.3333(6) 0.0205 0.5000 Uani . . . 1 -1 .
C23 C 0.5748(2) 0.5945(8) 0.2640(5) 0.0234 0.5000 Uani . . . 1 -1 .
C24 C 0.5859(3) 0.4436(9) 0.2329(7) 0.0271 0.5000 Uani . . . 1 -1 .
C25 C 0.5708(3) 0.3139(9) 0.2774(6) 0.0279 0.5000 Uani . . . 1 -1 .
C26 C 0.5479(3) 0.3322(9) 0.3477(7) 0.0262 0.5000 Uani . . . 1 -1 .
C27 C 0.5396(3) 0.7705(8) 0.3642(5) 0.0285 0.5000 Uani . . . 1 -1 .
C28 C 0.6118(3) 0.4277(9) 0.1584(6) 0.0365 0.5000 Uani . . . 1 -1 .
C29 C 0.5327(3) 0.1943(10) 0.3932(6) 0.0417 0.5000 Uani . . . 1 -1 .
N31 N 0.47113(19) 0.5308(7) 0.5944(4) 0.0216 0.5000 Uani . . . 1 -1 .
C32 C 0.4587(3) 0.4029(9) 0.6355(5) 0.0231 0.5000 Uani . . . 1 -1 .
C33 C 0.4353(3) 0.4173(9) 0.7036(6) 0.0276 0.5000 Uani . . . 1 -1 .
C34 C 0.4230(3) 0.5682(11) 0.7327(6) 0.0307 0.5000 Uani . . . 1 -1 .
C35 C 0.4379(3) 0.6944(11) 0.6879(7) 0.0307 0.5000 Uani . . . 1 -1 .
C36 C 0.4610(3) 0.6782(10) 0.6190(6) 0.0275 0.5000 Uani . . . 1 -1 .
C37 C 0.4730(3) 0.2439(9) 0.6078(5) 0.0386 0.5000 Uani . . . 1 -1 .
C38 C 0.3957(3) 0.5859(10) 0.8066(6) 0.0353 0.5000 Uani . . . 1 -1 .
C39 C 0.4762(3) 0.8172(9) 0.5718(6) 0.0434 0.5000 Uani . . . 1 -1 .
B1 B 0.61163(14) 0.0330(5) 0.6419(2) 0.0444 1.0000 Uani . . . . . .
F11 F 0.62431(12) 0.1796(3) 0.61628(18) 0.0847 1.0000 Uani . . . . . .
F12 F 0.58081(8) 0.0501(3) 0.6987(2) 0.0792 1.0000 Uani . . . . . .
F13 F 0.59295(14) -0.0580(3) 0.56722(16) 0.1165 1.0000 Uani . . . . . .
F14 F 0.65043(7) -0.0470(3) 0.69095(18) 0.0692 1.0000 Uani . . . . . .
H131 H 0.8101 -0.2665 0.4054 0.0389 1.0000 Uiso R . . . . .
H151 H 0.6698 -0.2143 0.3254 0.0382 1.0000 Uiso R . . . . .
H171 H 0.8568 -0.0753 0.5040 0.0667 1.0000 Uiso R . . . . .
H172 H 0.8394 0.0956 0.4751 0.0668 1.0000 Uiso R . . . . .
H173 H 0.8310 0.0235 0.5637 0.0667 1.0000 Uiso R . . . . .
H181 H 0.7099 -0.4755 0.3066 0.0684 1.0000 Uiso R . . . . .
H182 H 0.7356 -0.3894 0.2388 0.0679 1.0000 Uiso R . . . . .
H183 H 0.7646 -0.4790 0.3251 0.0681 1.0000 Uiso R . . . . .
H191 H 0.6582 0.0780 0.4691 0.0608 1.0000 Uiso R . . . . .
H192 H 0.6592 0.1560 0.3771 0.0613 1.0000 Uiso R . . . . .
H193 H 0.6315 -0.0006 0.3796 0.0615 1.0000 Uiso R . . . . .
H231 H 0.5834 0.6837 0.2365 0.0280 0.5000 Uiso R . . 1 -1 .
H251 H 0.5762 0.2128 0.2591 0.0327 0.5000 Uiso R . . 1 -1 .
H271 H 0.5498 0.8490 0.3273 0.0428 0.5000 Uiso R . . 1 -1 .
H272 H 0.5556 0.7859 0.4265 0.0429 0.5000 Uiso R . . 1 -1 .
H273 H 0.5063 0.7786 0.3586 0.0428 0.5000 Uiso R . . 1 -1 .
H281 H 0.5992 0.3404 0.1206 0.0553 0.5000 Uiso R . . 1 -1 .
H282 H 0.6448 0.4112 0.1837 0.0548 0.5000 Uiso R . . 1 -1 .
H283 H 0.6081 0.5203 0.1216 0.0553 0.5000 Uiso R . . 1 -1 .
H291 H 0.4994 0.1998 0.3894 0.0616 0.5000 Uiso R . . 1 -1 .
H292 H 0.5490 0.1913 0.4559 0.0619 0.5000 Uiso R . . 1 -1 .
H293 H 0.5393 0.0993 0.3641 0.0620 0.5000 Uiso R . . 1 -1 .
H331 H 0.4270 0.3287 0.7321 0.0330 0.5000 Uiso R . . 1 -1 .
H351 H 0.4320 0.7952 0.7068 0.0368 0.5000 Uiso R . . 1 -1 .
H371 H 0.4645 0.1668 0.6478 0.0579 0.5000 Uiso R . . 1 -1 .
H372 H 0.5063 0.2420 0.6129 0.0578 0.5000 Uiso R . . 1 -1 .
H373 H 0.4567 0.2219 0.5460 0.0579 0.5000 Uiso R . . 1 -1 .
H381 H 0.4140 0.6457 0.8561 0.0530 0.5000 Uiso R . . 1 -1 .
H382 H 0.3891 0.4857 0.8295 0.0530 0.5000 Uiso R . . 1 -1 .
H383 H 0.3662 0.6388 0.7841 0.0529 0.5000 Uiso R . . 1 -1 .
H391 H 0.4620 0.8125 0.5077 0.0649 0.5000 Uiso R . . 1 -1 .
H392 H 0.5099 0.8170 0.5815 0.0648 0.5000 Uiso R . . 1 -1 .
H393 H 0.4663 0.9114 0.5967 0.0649 0.5000 Uiso R . . 1 -1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.773(12)
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 . N11 4_656 2.115(2) yes
Br1 . N11 . 2.115(2) yes
N11 . C12 . 1.357(3) yes
N11 . C16 . 1.357(3) yes
C12 . C13 . 1.388(4) yes
C12 . C17 . 1.501(4) yes
C13 . C14 . 1.389(4) yes
C13 . H131 . 0.916 no
C14 . C15 . 1.385(4) yes
C14 . C18 . 1.504(4) yes
C15 . C16 . 1.383(4) yes
C15 . H151 . 0.934 no
C16 . C19 . 1.502(4) yes
C17 . H171 . 0.962 no
C17 . H172 . 0.948 no
C17 . H173 . 0.961 no
C18 . H181 . 0.950 no
C18 . H182 . 0.951 no
C18 . H183 . 0.959 no
C19 . H191 . 0.954 no
C19 . H192 . 0.956 no
C19 . H193 . 0.954 no
Br2 . N21 . 2.116(6) yes
Br2 . N31 . 2.125(6) yes
N21 . C22 . 1.339(10) yes
N21 . C26 . 1.349(10) yes
C22 . C23 . 1.368(10) yes
C22 . C27 . 1.513(10) yes
C23 . C24 . 1.423(11) yes
C23 . H231 . 0.922 no
C24 . C25 . 1.407(11) yes
C24 . C28 . 1.485(11) yes
C25 . C26 . 1.377(11) yes
C25 . H251 . 0.924 no
C26 . C29 . 1.472(11) yes
C27 . H271 . 0.953 no
C27 . H272 . 0.958 no
C27 . H273 . 0.953 no
C28 . H281 . 0.955 no
C28 . H282 . 0.958 no
C28 . H283 . 0.954 no
C29 . H291 . 0.955 no
C29 . H292 . 0.956 no
C29 . H293 . 0.957 no
N31 . C32 . 1.337(9) yes
N31 . C36 . 1.354(11) yes
C32 . C33 . 1.355(10) yes
C32 . C37 . 1.495(11) yes
C33 . C34 . 1.422(13) yes
C33 . H331 . 0.922 no
C34 . C35 . 1.385(12) yes
C34 . C38 . 1.507(10) yes
C35 . C36 . 1.359(11) yes
C35 . H351 . 0.929 no
C36 . C39 . 1.492(10) yes
C37 . H371 . 0.957 no
C37 . H372 . 0.951 no
C37 . H373 . 0.961 no
C38 . H381 . 0.956 no
C38 . H382 . 0.952 no
C38 . H383 . 0.960 no
C39 . H391 . 0.960 no
C39 . H392 . 0.955 no
C39 . H393 . 0.954 no
B1 . F11 . 1.376(4) yes
B1 . F12 . 1.374(5) yes
B1 . F13 . 1.370(4) yes
B1 . F14 . 1.378(5) 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
N11 4_656 Br1 . N11 . 179.99 yes
Br1 . N11 . C12 . 119.97(18) yes
Br1 . N11 . C16 . 118.68(18) yes
C12 . N11 . C16 . 121.1(2) yes
N11 . C12 . C13 . 119.8(2) yes
N11 . C12 . C17 . 118.3(2) yes
C13 . C12 . C17 . 121.9(2) yes
C12 . C13 . C14 . 120.5(3) yes
C12 . C13 . H131 . 119.9 no
C14 . C13 . H131 . 119.6 no
C13 . C14 . C15 . 117.9(2) yes
C13 . C14 . C18 . 121.1(3) yes
C15 . C14 . C18 . 121.0(3) yes
C14 . C15 . C16 . 121.0(2) yes
C14 . C15 . H151 . 120.8 no
C16 . C15 . H151 . 118.3 no
C15 . C16 . N11 . 119.6(2) yes
C15 . C16 . C19 . 121.8(2) yes
N11 . C16 . C19 . 118.6(2) yes
C12 . C17 . H171 . 110.4 no
C12 . C17 . H172 . 111.1 no
H171 . C17 . H172 . 109.9 no
C12 . C17 . H173 . 112.2 no
H171 . C17 . H173 . 106.3 no
H172 . C17 . H173 . 106.8 no
C14 . C18 . H181 . 110.3 no
C14 . C18 . H182 . 107.5 no
H181 . C18 . H182 . 111.3 no
C14 . C18 . H183 . 108.6 no
H181 . C18 . H183 . 108.0 no
H182 . C18 . H183 . 111.1 no
C16 . C19 . H191 . 110.6 no
C16 . C19 . H192 . 111.4 no
H191 . C19 . H192 . 107.5 no
C16 . C19 . H193 . 110.0 no
H191 . C19 . H193 . 108.2 no
H192 . C19 . H193 . 109.2 no
N21 . Br2 . N31 . 179.3(3) yes
Br2 . N21 . C22 . 119.0(5) yes
Br2 . N21 . C26 . 118.5(6) yes
C22 . N21 . C26 . 122.5(7) yes
N21 . C22 . C23 . 120.1(6) yes
N21 . C22 . C27 . 120.0(8) yes
C23 . C22 . C27 . 119.9(7) yes
C22 . C23 . C24 . 121.0(7) yes
C22 . C23 . H231 . 119.8 no
C24 . C23 . H231 . 119.2 no
C23 . C24 . C25 . 115.4(9) yes
C23 . C24 . C28 . 121.2(8) yes
C25 . C24 . C28 . 123.4(7) yes
C24 . C25 . C26 . 122.1(8) yes
C24 . C25 . H251 . 119.5 no
C26 . C25 . H251 . 118.4 no
C25 . C26 . N21 . 118.8(8) yes
C25 . C26 . C29 . 120.9(7) yes
N21 . C26 . C29 . 120.3(9) yes
C22 . C27 . H271 . 109.5 no
C22 . C27 . H272 . 109.4 no
H271 . C27 . H272 . 109.3 no
C22 . C27 . H273 . 109.5 no
H271 . C27 . H273 . 109.7 no
H272 . C27 . H273 . 109.5 no
C24 . C28 . H281 . 109.2 no
C24 . C28 . H282 . 110.0 no
H281 . C28 . H282 . 109.9 no
C24 . C28 . H283 . 110.7 no
H281 . C28 . H283 . 108.2 no
H282 . C28 . H283 . 108.9 no
C26 . C29 . H291 . 109.7 no
C26 . C29 . H292 . 110.3 no
H291 . C29 . H292 . 109.4 no
C26 . C29 . H293 . 110.1 no
H291 . C29 . H293 . 108.5 no
H292 . C29 . H293 . 108.9 no
Br2 . N31 . C32 . 120.2(5) yes
Br2 . N31 . C36 . 118.1(5) yes
C32 . N31 . C36 . 121.7(6) yes
N31 . C32 . C33 . 120.5(7) yes
N31 . C32 . C37 . 118.9(7) yes
C33 . C32 . C37 . 120.5(7) yes
C32 . C33 . C34 . 121.0(7) yes
C32 . C33 . H331 . 120.2 no
C34 . C33 . H331 . 118.8 no
C33 . C34 . C35 . 114.8(8) yes
C33 . C34 . C38 . 121.6(8) yes
C35 . C34 . C38 . 123.6(8) yes
C34 . C35 . C36 . 123.5(8) yes
C34 . C35 . H351 . 117.6 no
C36 . C35 . H351 . 118.9 no
C35 . C36 . N31 . 118.4(7) yes
C35 . C36 . C39 . 122.0(7) yes
N31 . C36 . C39 . 119.6(7) yes
C32 . C37 . H371 . 108.4 no
C32 . C37 . H372 . 109.3 no
H371 . C37 . H372 . 109.5 no
C32 . C37 . H373 . 109.8 no
H371 . C37 . H373 . 109.6 no
H372 . C37 . H373 . 110.1 no
C34 . C38 . H381 . 109.7 no
C34 . C38 . H382 . 111.1 no
H381 . C38 . H382 . 108.3 no
C34 . C38 . H383 . 111.1 no
H381 . C38 . H383 . 108.7 no
H382 . C38 . H383 . 107.9 no
C36 . C39 . H391 . 109.8 no
C36 . C39 . H392 . 109.0 no
H391 . C39 . H392 . 110.5 no
C36 . C39 . H393 . 109.1 no
H391 . C39 . H393 . 109.3 no
H392 . C39 . H393 . 109.2 no
F11 . B1 . F12 . 109.2(3) yes
F11 . B1 . F13 . 111.1(3) yes
F12 . B1 . F13 . 112.1(3) yes
F11 . B1 . F14 . 111.0(3) yes
F12 . B1 . F14 . 106.6(3) yes
F13 . B1 . F14 . 106.7(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C28 2_666 H382 . C23 2_666 122 0.76 2.05 2.534(9) yes


####################################################################### 
# 
# 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_BrColl2ClO4-II-100K
_database_code_depnum_ccdc_archive 'CCDC 1853994'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 067YK14-100K
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
On initial refinement, displacement ellipsoids for one half IColl2 
cation were decidedly prolate.  This included the central 
iodine, so the cation was moved to a general position close to the 
inversion centre, with the occupancy fixed to a half.  Despite this 
disorder restraints were not necessary and the structure was refined 
freely.
;

_cell_length_a                   28.8168(10)
_cell_length_b                   8.5588(2)
_cell_length_c                   15.2931(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.549(3)
_cell_angle_gamma                90
_cell_volume                     3681.7(2)

_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'
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'
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'
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            8

# Given Formula = C16 H22 Br1 Cl1 N2 O4 
# Dc =      1.52 Fooo =   1728.00 Mu =     45.75 M =    421.72
# Found Formula = C16 H22 Br1 Cl1 N2 O4 
# Dc =      1.52 FOOO =   1728.00 Mu =     45.75 M =    421.72

_chemical_formula_sum            'C16 H22 Br Cl N2 O4'
_chemical_formula_moiety         'C16 H22 Br N2, Cl O4'
_chemical_compound_source        .
_chemical_formula_weight         421.72


_cell_measurement_reflns_used    8906
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.35

_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    4.575

# Sheldrick geometric approximatio 0.50 0.69 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_T_max  0.69
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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            19843
_reflns_number_total             3823
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0385
# Number of reflections with Friedels Law is 3823 
# Theoretical number of reflections is about 7712 


_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         76.248
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        74.723
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -36
_reflns_limit_h_max              35
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -1.16
_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_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3807
_oxford_refine_ls_R_factor_ref   0.0567
_refine_ls_wR_factor_ref         0.1503
_refine_ls_goodness_of_fit_ref   0.9978
_refine_ls_shift/su_max          0.0005115
_refine_ls_shift/su_mean         0.0000134


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3808
_refine_ls_R_factor_all          0.0567
_refine_ls_wR_factor_all         0.1504

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3460
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_gt          0.1443


_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) + ( 0.09P)² +14.78P] 
 ,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 0.7500 0.2500 0.5000 0.0376 1.0000 Uani S . . . . .
N11 N 0.74534(11) 0.0206(3) 0.44656(19) 0.0365 1.0000 Uani . . . . . .
C12 C 0.78513(12) -0.0640(4) 0.4481(2) 0.0371 1.0000 Uani . . . . . .
C13 C 0.78216(12) -0.2057(4) 0.4035(2) 0.0381 1.0000 Uani . . . . . .
C14 C 0.73857(13) -0.2623(4) 0.3572(2) 0.0387 1.0000 Uani . . . . . .
C15 C 0.69824(13) -0.1748(4) 0.3600(2) 0.0399 1.0000 Uani . . . . . .
C16 C 0.70163(13) -0.0341(4) 0.4051(2) 0.0377 1.0000 Uani . . . . . .
C17 C 0.83178(14) 0.0012(5) 0.4986(3) 0.0496 1.0000 Uani . . . . . .
C18 C 0.73493(16) -0.4132(5) 0.3047(3) 0.0542 1.0000 Uani . . . . . .
C19 C 0.65868(14) 0.0618(5) 0.4087(3) 0.0519 1.0000 Uani . . . . . .
Br2 Br 0.50411(4) 0.50632(15) 0.48490(6) 0.0288 0.5000 Uani . . . 1 -1 .
N21 N 0.5380(3) 0.4804(12) 0.3754(6) 0.0292 0.5000 Uani . . . 1 -1 .
C22 C 0.5507(4) 0.6071(13) 0.3359(9) 0.0254 0.5000 Uani . . . 1 -1 .
C23 C 0.5743(4) 0.5945(11) 0.2677(7) 0.0280 0.5000 Uani . . . 1 -1 .
C24 C 0.5857(4) 0.4464(14) 0.2383(9) 0.0298 0.5000 Uani . . . 1 -1 .
C25 C 0.5705(5) 0.3153(17) 0.2798(9) 0.0351 0.5000 Uani . . . 1 -1 .
C26 C 0.5465(4) 0.3360(14) 0.3472(9) 0.0320 0.5000 Uani . . . 1 -1 .
C27 C 0.5382(4) 0.7680(12) 0.3675(7) 0.0335 0.5000 Uani . . . 1 -1 .
C28 C 0.6120(6) 0.4289(17) 0.1655(9) 0.0449 0.5000 Uani . . . 1 -1 .
C29 C 0.5307(4) 0.1999(14) 0.3948(8) 0.0445 0.5000 Uani . . . 1 -1 .
N31 N 0.4702(3) 0.5292(11) 0.5946(5) 0.0260 0.5000 Uani . . . 1 -1 .
C32 C 0.4586(4) 0.4022(13) 0.6354(7) 0.0273 0.5000 Uani . . . 1 -1 .
C33 C 0.4351(4) 0.4181(12) 0.7037(8) 0.0304 0.5000 Uani . . . 1 -1 .
C34 C 0.4236(4) 0.5652(16) 0.7334(8) 0.0332 0.5000 Uani . . . 1 -1 .
C35 C 0.4373(5) 0.6902(17) 0.6910(10) 0.0359 0.5000 Uani . . . 1 -1 .
C36 C 0.4600(4) 0.6775(15) 0.6201(8) 0.0317 0.5000 Uani . . . 1 -1 .
C37 C 0.4723(5) 0.2453(13) 0.6063(8) 0.0449 0.5000 Uani . . . 1 -1 .
C38 C 0.3966(5) 0.5806(17) 0.8064(9) 0.0426 0.5000 Uani . . . 1 -1 .
C39 C 0.4752(5) 0.8175(13) 0.5723(9) 0.0513 0.5000 Uani . . . 1 -1 .
Cl1 Cl 0.61195(4) 0.03241(12) 0.64337(6) 0.0506 1.0000 Uani . . . . . .
O11 O 0.6246(2) 0.1832(5) 0.6187(3) 0.1119 1.0000 Uani . . . . . .
O12 O 0.57987(14) 0.0473(4) 0.7012(3) 0.0820 1.0000 Uani . . . . . .
O13 O 0.5935(2) -0.0613(5) 0.5671(2) 0.1193 1.0000 Uani . . . . . .
O14 O 0.65207(13) -0.0502(5) 0.6946(3) 0.0835 1.0000 Uani . . . . . .
H131 H 0.8094 -0.2631 0.4049 0.0460 1.0000 Uiso R . . . . .
H151 H 0.6680 -0.2091 0.3313 0.0480 1.0000 Uiso R . . . . .
H171 H 0.8575 -0.0719 0.5003 0.0737 1.0000 Uiso R . . . . .
H172 H 0.8380 0.0987 0.4721 0.0739 1.0000 Uiso R . . . . .
H173 H 0.8297 0.0242 0.5601 0.0737 1.0000 Uiso R . . . . .
H181 H 0.7039 -0.4590 0.2969 0.0813 1.0000 Uiso R . . . . .
H182 H 0.7408 -0.3915 0.2463 0.0813 1.0000 Uiso R . . . . .
H183 H 0.7580 -0.4879 0.3349 0.0813 1.0000 Uiso R . . . . .
H191 H 0.6581 0.0865 0.4690 0.0771 1.0000 Uiso R . . . . .
H192 H 0.6590 0.1564 0.3767 0.0776 1.0000 Uiso R . . . . .
H193 H 0.6308 0.0038 0.3817 0.0776 1.0000 Uiso R . . . . .
H231 H 0.5827 0.6835 0.2407 0.0339 0.5000 Uiso R . . 1 -1 .
H251 H 0.5765 0.2153 0.2614 0.0421 0.5000 Uiso R . . 1 -1 .
H271 H 0.5490 0.8474 0.3324 0.0499 0.5000 Uiso R . . 1 -1 .
H272 H 0.5532 0.7818 0.4297 0.0499 0.5000 Uiso R . . 1 -1 .
H273 H 0.5044 0.7757 0.3600 0.0498 0.5000 Uiso R . . 1 -1 .
H281 H 0.5966 0.3520 0.1231 0.0671 0.5000 Uiso R . . 1 -1 .
H282 H 0.6442 0.3969 0.1906 0.0668 0.5000 Uiso R . . 1 -1 .
H283 H 0.6124 0.5269 0.1360 0.0667 0.5000 Uiso R . . 1 -1 .
H291 H 0.4969 0.2035 0.3886 0.0667 0.5000 Uiso R . . 1 -1 .
H292 H 0.5459 0.2028 0.4572 0.0670 0.5000 Uiso R . . 1 -1 .
H293 H 0.5387 0.1037 0.3698 0.0669 0.5000 Uiso R . . 1 -1 .
H331 H 0.4263 0.3302 0.7311 0.0361 0.5000 Uiso R . . 1 -1 .
H351 H 0.4315 0.7889 0.7104 0.0430 0.5000 Uiso R . . 1 -1 .
H371 H 0.4645 0.1686 0.6461 0.0670 0.5000 Uiso R . . 1 -1 .
H372 H 0.5059 0.2428 0.6095 0.0669 0.5000 Uiso R . . 1 -1 .
H373 H 0.4550 0.2244 0.5461 0.0669 0.5000 Uiso R . . 1 -1 .
H381 H 0.4124 0.6511 0.8520 0.0641 0.5000 Uiso R . . 1 -1 .
H382 H 0.3938 0.4817 0.8337 0.0639 0.5000 Uiso R . . 1 -1 .
H383 H 0.3651 0.6193 0.7833 0.0639 0.5000 Uiso R . . 1 -1 .
H391 H 0.4594 0.8148 0.5100 0.0769 0.5000 Uiso R . . 1 -1 .
H392 H 0.5090 0.8146 0.5786 0.0769 0.5000 Uiso R . . 1 -1 .
H393 H 0.4666 0.9115 0.5988 0.0768 0.5000 Uiso R . . 1 -1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.664(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
Br1 . N11 4_656 2.120(3) yes
Br1 . N11 . 2.120(3) yes
N11 . C12 . 1.352(4) yes
N11 . C16 . 1.364(5) yes
C12 . C13 . 1.385(5) yes
C12 . C17 . 1.505(5) yes
C13 . C14 . 1.389(5) yes
C13 . H131 . 0.921 no
C14 . C15 . 1.391(5) yes
C14 . C18 . 1.512(5) yes
C15 . C16 . 1.381(5) yes
C15 . H151 . 0.933 no
C16 . C19 . 1.496(5) yes
C17 . H171 . 0.966 no
C17 . H172 . 0.961 no
C17 . H173 . 0.975 no
C18 . H181 . 0.959 no
C18 . H182 . 0.963 no
C18 . H183 . 0.965 no
C19 . H191 . 0.949 no
C19 . H192 . 0.948 no
C19 . H193 . 0.959 no
Br2 . N21 . 2.125(8) yes
Br2 . N31 . 2.127(8) yes
N21 . C22 . 1.332(14) yes
N21 . C26 . 1.349(17) yes
C22 . C23 . 1.368(12) yes
C22 . C27 . 1.527(16) yes
C23 . C24 . 1.408(16) yes
C23 . H231 . 0.923 no
C24 . C25 . 1.404(17) yes
C24 . C28 . 1.485(12) yes
C25 . C26 . 1.372(14) yes
C25 . H251 . 0.929 no
C26 . C29 . 1.496(14) yes
C27 . H271 . 0.959 no
C27 . H272 . 0.963 no
C27 . H273 . 0.959 no
C28 . H281 . 0.961 no
C28 . H282 . 0.962 no
C28 . H283 . 0.953 no
C29 . H291 . 0.959 no
C29 . H292 . 0.959 no
C29 . H293 . 0.957 no
N31 . C32 . 1.331(13) yes
N31 . C36 . 1.378(17) yes
C32 . C33 . 1.370(13) yes
C32 . C37 . 1.495(16) yes
C33 . C34 . 1.403(19) yes
C33 . H331 . 0.924 no
C34 . C35 . 1.354(18) yes
C34 . C38 . 1.498(13) yes
C35 . C36 . 1.387(13) yes
C35 . H351 . 0.923 no
C36 . C39 . 1.517(14) yes
C37 . H371 . 0.954 no
C37 . H372 . 0.958 no
C37 . H373 . 0.964 no
C38 . H381 . 0.959 no
C38 . H382 . 0.955 no
C38 . H383 . 0.959 no
C39 . H391 . 0.962 no
C39 . H392 . 0.958 no
C39 . H393 . 0.957 no
Cl1 . O11 . 1.415(4) yes
Cl1 . O12 . 1.417(4) yes
Cl1 . O13 . 1.420(4) yes
Cl1 . O14 . 1.434(4) 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
N11 4_656 Br1 . N11 . 179.99 yes
Br1 . N11 . C12 . 120.5(2) yes
Br1 . N11 . C16 . 118.1(2) yes
C12 . N11 . C16 . 121.2(3) yes
N11 . C12 . C13 . 119.9(3) yes
N11 . C12 . C17 . 118.0(3) yes
C13 . C12 . C17 . 122.0(3) yes
C12 . C13 . C14 . 120.6(3) yes
C12 . C13 . H131 . 119.6 no
C14 . C13 . H131 . 119.8 no
C13 . C14 . C15 . 117.8(3) yes
C13 . C14 . C18 . 121.3(3) yes
C15 . C14 . C18 . 120.9(3) yes
C14 . C15 . C16 . 121.1(3) yes
C14 . C15 . H151 . 121.1 no
C16 . C15 . H151 . 117.8 no
C15 . C16 . N11 . 119.3(3) yes
C15 . C16 . C19 . 121.9(3) yes
N11 . C16 . C19 . 118.8(3) yes
C12 . C17 . H171 . 111.6 no
C12 . C17 . H172 . 109.4 no
H171 . C17 . H172 . 111.2 no
C12 . C17 . H173 . 109.6 no
H171 . C17 . H173 . 108.1 no
H172 . C17 . H173 . 106.7 no
C14 . C18 . H181 . 111.7 no
C14 . C18 . H182 . 108.7 no
H181 . C18 . H182 . 108.1 no
C14 . C18 . H183 . 110.6 no
H181 . C18 . H183 . 108.5 no
H182 . C18 . H183 . 109.2 no
C16 . C19 . H191 . 110.3 no
C16 . C19 . H192 . 110.4 no
H191 . C19 . H192 . 108.4 no
C16 . C19 . H193 . 108.8 no
H191 . C19 . H193 . 110.1 no
H192 . C19 . H193 . 108.8 no
N21 . Br2 . N31 . 179.3(5) yes
Br2 . N21 . C22 . 119.4(7) yes
Br2 . N21 . C26 . 119.7(8) yes
C22 . N21 . C26 . 120.9(10) yes
N21 . C22 . C23 . 120.9(9) yes
N21 . C22 . C27 . 118.9(11) yes
C23 . C22 . C27 . 120.2(10) yes
C22 . C23 . C24 . 120.2(10) yes
C22 . C23 . H231 . 119.9 no
C24 . C23 . H231 . 119.9 no
C23 . C24 . C25 . 117.3(11) yes
C23 . C24 . C28 . 121.5(12) yes
C25 . C24 . C28 . 121.2(10) yes
C24 . C25 . C26 . 119.6(12) yes
C24 . C25 . H251 . 120.2 no
C26 . C25 . H251 . 120.2 no
C25 . C26 . N21 . 121.0(12) yes
C25 . C26 . C29 . 121.5(11) yes
N21 . C26 . C29 . 117.5(12) yes
C22 . C27 . H271 . 109.5 no
C22 . C27 . H272 . 109.7 no
H271 . C27 . H272 . 109.6 no
C22 . C27 . H273 . 109.1 no
H271 . C27 . H273 . 109.2 no
H272 . C27 . H273 . 109.7 no
C24 . C28 . H281 . 109.8 no
C24 . C28 . H282 . 109.4 no
H281 . C28 . H282 . 109.8 no
C24 . C28 . H283 . 109.0 no
H281 . C28 . H283 . 109.6 no
H282 . C28 . H283 . 109.3 no
C26 . C29 . H291 . 109.7 no
C26 . C29 . H292 . 110.1 no
H291 . C29 . H292 . 109.4 no
C26 . C29 . H293 . 110.5 no
H291 . C29 . H293 . 108.4 no
H292 . C29 . H293 . 108.8 no
Br2 . N31 . C32 . 120.0(7) yes
Br2 . N31 . C36 . 118.0(7) yes
C32 . N31 . C36 . 122.0(9) yes
N31 . C32 . C33 . 119.5(10) yes
N31 . C32 . C37 . 119.0(9) yes
C33 . C32 . C37 . 121.5(10) yes
C32 . C33 . C34 . 121.8(10) yes
C32 . C33 . H331 . 119.7 no
C34 . C33 . H331 . 118.5 no
C33 . C34 . C35 . 116.0(12) yes
C33 . C34 . C38 . 121.2(11) yes
C35 . C34 . C38 . 122.8(12) yes
C34 . C35 . C36 . 123.4(12) yes
C34 . C35 . H351 . 118.5 no
C36 . C35 . H351 . 118.1 no
C35 . C36 . N31 . 117.3(10) yes
C35 . C36 . C39 . 123.3(11) yes
N31 . C36 . C39 . 119.4(10) yes
C32 . C37 . H371 . 108.3 no
C32 . C37 . H372 . 109.6 no
H371 . C37 . H372 . 109.2 no
C32 . C37 . H373 . 109.6 no
H371 . C37 . H373 . 109.7 no
H372 . C37 . H373 . 110.5 no
C34 . C38 . H381 . 110.8 no
C34 . C38 . H382 . 110.8 no
H381 . C38 . H382 . 108.1 no
C34 . C38 . H383 . 111.0 no
H381 . C38 . H383 . 108.3 no
H382 . C38 . H383 . 107.7 no
C36 . C39 . H391 . 109.6 no
C36 . C39 . H392 . 108.9 no
H391 . C39 . H392 . 110.4 no
C36 . C39 . H393 . 109.4 no
H391 . C39 . H393 . 109.3 no
H392 . C39 . H393 . 109.2 no
O11 . Cl1 . O12 . 109.0(3) yes
O11 . Cl1 . O13 . 111.6(2) yes
O12 . Cl1 . O13 . 112.7(3) yes
O11 . Cl1 . O14 . 111.8(3) yes
O12 . Cl1 . O14 . 105.1(3) yes
O13 . Cl1 . O14 . 106.4(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C23 . H231 . O12 6_564 156 0.92 2.38 3.245(14) yes
C25 . H251 . O12 6_554 172 0.93 2.44 3.360(14) yes
C27 . H271 . O12 6_564 155 0.96 2.53 3.425(14) yes
C27 . H272 . O13 1_565 155 0.96 2.55 3.446(14) yes
C37 2_666 H272 . O13 1_565 148 0.85 2.55 3.306(14) yes
C28 . H283 . O11 6_564 158 0.95 2.53 3.432(14) yes
C37 . H373 . O13 2_656 153 0.96 2.42 3.306(14) yes


####################################################################### 
# 
# 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_BrColl2PF6-100K
_database_code_depnum_ccdc_archive 'CCDC 1853986'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 074lcm18
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   7.9058(3)
_cell_length_b                   8.2573(3)
_cell_length_c                   15.1037(6)
_cell_angle_alpha                98.632(3)
_cell_angle_beta                 98.087(3)
_cell_angle_gamma                100.308(3)
_cell_volume                     944.74(6)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
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'
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'
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'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 '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 = C16 H22 Br1 F6 N2 P1 
# Dc =      1.64 Fooo =    472.00 Mu =     43.33 M =    467.23
# Found Formula = C16 H22.00 Br1 F6 N2 P1 
# Dc =      1.64 FOOO =    472.00 Mu =     43.33 M =    467.23

_chemical_formula_sum            'C16 H22 Br F6 N2 P'
_chemical_formula_moiety         'C16 H22 Br N2, F6 P'
_chemical_compound_source        .
_chemical_formula_weight         467.23


_cell_measurement_reflns_used    5784
_cell_measurement_theta_min      6
_cell_measurement_theta_max      76
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            clear_plate_colourless
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             471.998
_exptl_absorpt_coefficient_mu    4.333

# Sheldrick geometric approximatio 0.42 0.68 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.68
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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            9313
_reflns_number_total             3891
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.0218
# Number of reflections with Friedels Law is 3891 
# Theoretical number of reflections is about 7944 


_diffrn_reflns_theta_min         5.536
_diffrn_reflns_theta_max         76.527
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        73.466
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.70
_refine_diff_density_max         0.42


# 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>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3891
_oxford_refine_ls_R_factor_ref   0.0283
_refine_ls_wR_factor_ref         0.0747
_refine_ls_goodness_of_fit_ref   1.0387
_refine_ls_shift/su_max          0.0007781
_refine_ls_shift/su_mean         0.0000206


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3891
_refine_ls_R_factor_all          0.0283
_refine_ls_wR_factor_all         0.0747

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3832
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_gt          0.0744


_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) + ( 0.04P)² + 0.89P] 
 ,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 0.48025(2) 0.50967(2) 0.218970(11) 0.0142 1.0000 Uani . . . . . .
N11 N 0.3554(2) 0.52486(19) 0.08490(10) 0.0149 1.0000 Uani . . . . . .
C12 C 0.2596(2) 0.3838(2) 0.02962(12) 0.0166 1.0000 Uani . . . . . .
C13 C 0.1660(2) 0.3935(2) -0.05347(13) 0.0182 1.0000 Uani . . . . . .
C14 C 0.1685(2) 0.5472(2) -0.08099(12) 0.0173 1.0000 Uani . . . . . .
C15 C 0.2700(2) 0.6891(2) -0.02284(13) 0.0178 1.0000 Uani . . . . . .
C16 C 0.3635(2) 0.6759(2) 0.05986(12) 0.0162 1.0000 Uani . . . . . .
C17 C 0.2570(3) 0.2188(2) 0.06015(13) 0.0217 1.0000 Uani . . . . . .
C18 C 0.0664(3) 0.5577(3) -0.17067(13) 0.0216 1.0000 Uani . . . . . .
C19 C 0.4739(3) 0.8265(2) 0.12345(13) 0.0207 1.0000 Uani . . . . . .
N21 N 0.5981(2) 0.49217(19) 0.34875(10) 0.0144 1.0000 Uani . . . . . .
C22 C 0.6412(2) 0.6300(2) 0.41533(12) 0.0164 1.0000 Uani . . . . . .
C23 C 0.7263(2) 0.6192(2) 0.50010(13) 0.0183 1.0000 Uani . . . . . .
C24 C 0.7681(2) 0.4691(2) 0.51788(13) 0.0181 1.0000 Uani . . . . . .
C25 C 0.7189(2) 0.3303(2) 0.44804(13) 0.0175 1.0000 Uani . . . . . .
C26 C 0.6338(2) 0.3428(2) 0.36356(13) 0.0158 1.0000 Uani . . . . . .
C27 C 0.5980(3) 0.7915(2) 0.39510(13) 0.0206 1.0000 Uani . . . . . .
C28 C 0.8634(3) 0.4583(3) 0.60917(13) 0.0224 1.0000 Uani . . . . . .
C29 C 0.5812(3) 0.1949(2) 0.28739(13) 0.0194 1.0000 Uani . . . . . .
P1 P 0.04316(6) -0.00886(6) 0.27690(3) 0.0190 1.0000 Uani . . . . . .
F11 F -0.05439(18) 0.07894(17) 0.35023(10) 0.0329 1.0000 Uani . . . . . .
F12 F -0.10235(18) 0.01331(18) 0.19617(10) 0.0344 1.0000 Uani . . . . . .
F13 F 0.15622(16) 0.17121(15) 0.27285(9) 0.0273 1.0000 Uani . . . . . .
F14 F 0.18934(19) -0.02958(18) 0.35667(10) 0.0381 1.0000 Uani . . . . . .
F15 F -0.07114(18) -0.18783(16) 0.27985(11) 0.0346 1.0000 Uani . . . . . .
F16 F 0.14071(18) -0.09500(19) 0.20269(11) 0.0393 1.0000 Uani . . . . . .
H171 H 0.1911 0.1310 0.0133 0.0333 1.0000 Uiso R . . . . .
H173 H 0.2064 0.2181 0.1137 0.0327 1.0000 Uiso R . . . . .
H172 H 0.3753 0.2009 0.0743 0.0324 1.0000 Uiso R . . . . .
H131 H 0.1001 0.2963 -0.0918 0.0225 1.0000 Uiso R . . . . .
H151 H 0.2757 0.7938 -0.0390 0.0213 1.0000 Uiso R . . . . .
H193 H 0.5912 0.8106 0.1369 0.0300 1.0000 Uiso R . . . . .
H192 H 0.4275 0.8460 0.1779 0.0297 1.0000 Uiso R . . . . .
H191 H 0.4738 0.9218 0.0950 0.0312 1.0000 Uiso R . . . . .
H181 H 0.1215 0.5102 -0.2178 0.0328 1.0000 Uiso R . . . . .
H182 H 0.0663 0.6722 -0.1752 0.0321 1.0000 Uiso R . . . . .
H183 H -0.0502 0.4975 -0.1777 0.0317 1.0000 Uiso R . . . . .
H271 H 0.6307 0.8731 0.4487 0.0315 1.0000 Uiso R . . . . .
H273 H 0.4749 0.7781 0.3746 0.0305 1.0000 Uiso R . . . . .
H272 H 0.6615 0.8274 0.3503 0.0309 1.0000 Uiso R . . . . .
H231 H 0.7573 0.7149 0.5464 0.0223 1.0000 Uiso R . . . . .
H281 H 0.8952 0.3525 0.6097 0.0360 1.0000 Uiso R . . . . .
H282 H 0.9679 0.5433 0.6261 0.0356 1.0000 Uiso R . . . . .
H283 H 0.7911 0.4746 0.6537 0.0358 1.0000 Uiso R . . . . .
H251 H 0.7473 0.2289 0.4573 0.0206 1.0000 Uiso R . . . . .
H291 H 0.6402 0.2157 0.2388 0.0292 1.0000 Uiso R . . . . .
H292 H 0.4580 0.1732 0.2663 0.0287 1.0000 Uiso R . . . . .
H293 H 0.6126 0.0988 0.3073 0.0297 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.17(11)
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 . N11 . 2.1560(15) yes
Br1 . N21 . 2.0857(15) yes
N11 . C12 . 1.358(2) yes
N11 . C16 . 1.350(2) yes
C12 . C13 . 1.385(3) yes
C12 . C17 . 1.500(3) yes
C13 . C14 . 1.392(3) yes
C13 . H131 . 0.936 no
C14 . C15 . 1.394(3) yes
C14 . C18 . 1.499(3) yes
C15 . C16 . 1.389(3) yes
C15 . H151 . 0.928 no
C16 . C19 . 1.500(2) yes
C17 . H171 . 0.952 no
C17 . H173 . 0.952 no
C17 . H172 . 0.972 no
C18 . H181 . 0.957 no
C18 . H182 . 0.958 no
C18 . H183 . 0.949 no
C19 . H193 . 0.958 no
C19 . H192 . 0.950 no
C19 . H191 . 0.951 no
N21 . C22 . 1.358(2) yes
N21 . C26 . 1.357(2) yes
C22 . C23 . 1.383(3) yes
C23 . C24 . 1.392(3) yes
C23 . H231 . 0.944 no
C24 . C25 . 1.393(3) yes
C25 . C26 . 1.384(3) yes
C25 . H251 . 0.930 no
C27 . C22 . 1.498(3) yes
C27 . H271 . 0.945 no
C27 . H273 . 0.960 no
C27 . H272 . 0.949 no
C28 . C24 . 1.498(3) yes
C28 . H281 . 0.952 no
C28 . H282 . 0.958 no
C28 . H283 . 0.952 no
C29 . C26 . 1.500(2) yes
C29 . H291 . 0.944 no
C29 . H292 . 0.957 no
C29 . H293 . 0.950 no
P1 . F11 . 1.5958(13) yes
P1 . F12 . 1.6098(14) yes
P1 . F13 . 1.6065(13) yes
P1 . F14 . 1.5991(14) yes
P1 . F15 . 1.5986(13) yes
P1 . F16 . 1.5991(14) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N11 . Br1 . N21 . 179.18(6) yes
Br1 . N11 . C12 . 119.33(12) yes
Br1 . N11 . C16 . 119.42(12) yes
C12 . N11 . C16 . 121.08(16) yes
N11 . C12 . C13 . 120.04(17) yes
N11 . C12 . C17 . 118.93(16) yes
C13 . C12 . C17 . 121.03(17) yes
C12 . C13 . C14 . 120.60(18) yes
C12 . C13 . H131 . 120.2 no
C14 . C13 . H131 . 119.2 no
C13 . C14 . C15 . 117.67(17) yes
C13 . C14 . C18 . 120.57(18) yes
C15 . C14 . C18 . 121.76(17) yes
C14 . C15 . C16 . 120.63(17) yes
C14 . C15 . H151 . 120.2 no
C16 . C15 . H151 . 119.1 no
C15 . C16 . N11 . 119.96(17) yes
C15 . C16 . C19 . 121.61(17) yes
N11 . C16 . C19 . 118.42(16) yes
C12 . C17 . H171 . 109.6 no
C12 . C17 . H173 . 109.9 no
H171 . C17 . H173 . 109.7 no
C12 . C17 . H172 . 110.2 no
H171 . C17 . H172 . 109.4 no
H173 . C17 . H172 . 108.1 no
C14 . C18 . H181 . 108.2 no
C14 . C18 . H182 . 110.2 no
H181 . C18 . H182 . 108.8 no
C14 . C18 . H183 . 110.5 no
H181 . C18 . H183 . 109.4 no
H182 . C18 . H183 . 109.6 no
C16 . C19 . H193 . 109.8 no
C16 . C19 . H192 . 110.4 no
H193 . C19 . H192 . 110.3 no
C16 . C19 . H191 . 108.9 no
H193 . C19 . H191 . 109.1 no
H192 . C19 . H191 . 108.3 no
Br1 . N21 . C22 . 119.73(12) yes
Br1 . N21 . C26 . 118.57(12) yes
C22 . N21 . C26 . 121.67(16) yes
C27 . C22 . N21 . 119.31(16) yes
C27 . C22 . C23 . 121.29(17) yes
N21 . C22 . C23 . 119.40(17) yes
C22 . C23 . C24 . 120.87(17) yes
C22 . C23 . H231 . 119.7 no
C24 . C23 . H231 . 119.4 no
C28 . C24 . C23 . 120.84(18) yes
C28 . C24 . C25 . 121.39(18) yes
C23 . C24 . C25 . 117.77(17) yes
C24 . C25 . C26 . 120.78(17) yes
C24 . C25 . H251 . 119.9 no
C26 . C25 . H251 . 119.3 no
C29 . C26 . C25 . 121.44(17) yes
C29 . C26 . N21 . 119.06(16) yes
C25 . C26 . N21 . 119.50(17) yes
C22 . C27 . H271 . 109.0 no
C22 . C27 . H273 . 110.6 no
H271 . C27 . H273 . 108.5 no
C22 . C27 . H272 . 109.2 no
H271 . C27 . H272 . 109.0 no
H273 . C27 . H272 . 110.5 no
C24 . C28 . H281 . 111.9 no
C24 . C28 . H282 . 110.4 no
H281 . C28 . H282 . 108.1 no
C24 . C28 . H283 . 109.6 no
H281 . C28 . H283 . 108.4 no
H282 . C28 . H283 . 108.4 no
C26 . C29 . H291 . 110.0 no
C26 . C29 . H292 . 110.3 no
H291 . C29 . H292 . 109.3 no
C26 . C29 . H293 . 110.2 no
H291 . C29 . H293 . 107.6 no
H292 . C29 . H293 . 109.5 no
F11 . P1 . F12 . 90.15(8) yes
F11 . P1 . F13 . 89.47(7) yes
F12 . P1 . F13 . 89.72(7) yes
F11 . P1 . F14 . 90.15(8) yes
F12 . P1 . F14 . 179.36(8) yes
F13 . P1 . F14 . 89.72(7) yes
F11 . P1 . F15 . 90.57(8) yes
F12 . P1 . F15 . 89.54(8) yes
F13 . P1 . F15 . 179.26(8) yes
F14 . P1 . F15 . 91.02(8) yes
F11 . P1 . F16 . 179.27(8) yes
F12 . P1 . F16 . 89.35(8) yes
F13 . P1 . F16 . 90.00(8) yes
F14 . P1 . F16 . 90.35(9) yes
F15 . P1 . F16 . 89.95(8) yes


####################################################################### 
# 
# 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_BrColl2ClO4-I-300K
_database_code_depnum_ccdc_archive 'CCDC 1853989'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-20
_audit_creation_method           CRYSTALS_ver_14.61_build_6156

_oxford_structure_analysis_title 126lcm18
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   27.3108(5)
_cell_length_b                   11.0568(1)
_cell_length_c                   23.5758(4)
_cell_angle_alpha                90
_cell_angle_beta                 127.217(3)
_cell_angle_gamma                90
_cell_volume                     5669.4(3)

_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
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'
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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            12

# Given Formula = C16 H22 Br1 Cl1 N2 O4 
# Dc =      1.48 Fooo =   2592.00 Mu =     44.57 M =    421.72
# Found Formula = C16 H22 Br1 Cl1 N2 O4 
# Dc =      1.48 FOOO =   2592.00 Mu =     44.57 M =    421.72

_chemical_formula_sum            'C16 H22 Br1 Cl1 N2 O4'
_chemical_formula_moiety         'C16 H22 Br1 N2, Cl O4'
_chemical_compound_source        .
_chemical_formula_weight         421.72


_cell_measurement_reflns_used    15897
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_max          0.34

_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2592
_exptl_absorpt_coefficient_mu    4.457

# Sheldrick geometric approximatio 0.38 0.67 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.28
_exptl_absorpt_correction_T_max  0.67
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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      300
_diffrn_reflns_number            34084
_reflns_number_total             5906
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0470
# Number of reflections with Friedels Law is 5906 
# Theoretical number of reflections is about 11855 


_diffrn_reflns_theta_min         3.943
_diffrn_reflns_theta_max         76.118
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        76.118
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -34
_reflns_limit_h_max              27
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   4.57
_oxford_diffrn_Wilson_scale      0.49

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

_refine_diff_density_min         -0.45
_refine_diff_density_max         0.43


# 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         5906
_refine_ls_number_restraints     0
_refine_ls_number_parameters     327
_oxford_refine_ls_R_factor_ref   0.0372
_refine_ls_wR_factor_ref         0.0941
_refine_ls_goodness_of_fit_ref   0.9990
_refine_ls_shift/su_max          0.0016640
_refine_ls_shift/su_mean         0.0000573


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5906
_refine_ls_R_factor_all          0.0372
_refine_ls_wR_factor_all         0.0941

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5337
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_gt          0.0904

# 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 + 2.92P] 
 ,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 0.5000 0.0000 0.5000 0.0513 1.0000 Uani S . . . . .
N11 N 0.57344(7) 0.10967(16) 0.58125(8) 0.0506 1.0000 Uani . . . . . .
C12 C 0.57950(9) 0.2237(2) 0.56540(11) 0.0548 1.0000 Uani . . . . . .
C13 C 0.63051(10) 0.2910(2) 0.61554(12) 0.0596 1.0000 Uani . . . . . .
C14 C 0.67500(10) 0.2451(2) 0.68295(12) 0.0597 1.0000 Uani . . . . . .
C15 C 0.66605(10) 0.1293(2) 0.69756(11) 0.0603 1.0000 Uani . . . . . .
C16 C 0.61540(10) 0.0627(2) 0.64699(11) 0.0549 1.0000 Uani . . . . . .
C17 C 0.52958(11) 0.2740(2) 0.49340(13) 0.0692 1.0000 Uani . . . . . .
C18 C 0.73041(12) 0.3179(3) 0.73841(15) 0.0798 1.0000 Uani . . . . . .
C19 C 0.60390(13) -0.0617(2) 0.66271(13) 0.0722 1.0000 Uani . . . . . .
Br2 Br 0.797343(10) 0.04941(2) 0.645187(11) 0.0589 1.0000 Uani . . . . . .
N21 N 0.72842(8) 0.16494(18) 0.56597(10) 0.0587 1.0000 Uani . . . . . .
C22 C 0.67534(11) 0.1162(2) 0.50895(13) 0.0696 1.0000 Uani . . . . . .
C23 C 0.63165(12) 0.1906(3) 0.45434(14) 0.0714 1.0000 Uani . . . . . .
C24 C 0.64075(11) 0.3137(2) 0.45595(13) 0.0657 1.0000 Uani . . . . . .
C25 C 0.69537(12) 0.3591(2) 0.51495(14) 0.0663 1.0000 Uani . . . . . .
C26 C 0.73884(11) 0.2853(2) 0.56986(12) 0.0603 1.0000 Uani . . . . . .
C27 C 0.66596(16) -0.0166(3) 0.5073(2) 0.1144 1.0000 Uani . . . . . .
C28 C 0.59284(14) 0.3935(3) 0.39590(16) 0.0835 1.0000 Uani . . . . . .
C29 C 0.79737(13) 0.3358(3) 0.63467(15) 0.0802 1.0000 Uani . . . . . .
N31 N 0.87053(8) -0.06687(18) 0.72366(10) 0.0570 1.0000 Uani . . . . . .
C32 C 0.91218(11) -0.0253(2) 0.79080(12) 0.0617 1.0000 Uani . . . . . .
C33 C 0.96185(11) -0.0953(3) 0.83986(12) 0.0661 1.0000 Uani . . . . . .
C34 C 0.97057(10) -0.2085(3) 0.82234(13) 0.0652 1.0000 Uani . . . . . .
C35 C 0.92680(11) -0.2486(2) 0.75329(13) 0.0660 1.0000 Uani . . . . . .
C36 C 0.87681(10) -0.1782(2) 0.70465(12) 0.0616 1.0000 Uani . . . . . .
C37 C 0.90232(14) 0.0975(3) 0.80954(15) 0.0868 1.0000 Uani . . . . . .
C38 C 1.02536(13) -0.2854(3) 0.87576(16) 0.0858 1.0000 Uani . . . . . .
C39 C 0.82838(13) -0.2223(3) 0.63011(15) 0.0824 1.0000 Uani . . . . . .
Cl1 Cl 0.65410(3) 0.64028(5) 0.56560(3) 0.0634 1.0000 Uani . . . . . .
O11 O 0.64043(14) 0.7519(2) 0.58276(15) 0.1093 1.0000 Uani . . . . . .
O12 O 0.60044(10) 0.5662(2) 0.52651(13) 0.0936 1.0000 Uani . . . . . .
O13 O 0.67384(12) 0.6623(2) 0.52265(13) 0.0963 1.0000 Uani . . . . . .
O14 O 0.70082(12) 0.5765(2) 0.62811(12) 0.1039 1.0000 Uani . . . . . .
Cl2 Cl 0.5000 0.09892(10) 0.2500 0.0884 1.0000 Uani S T . . . .
H231 H 0.5953 0.1558 0.4159 0.0854 1.0000 Uiso R . . . . .
H251 H 0.7037 0.4400 0.5178 0.0782 1.0000 Uiso R . . . . .
H271 H 0.6688 -0.0402 0.5476 0.1705 1.0000 Uiso R . . . . .
H272 H 0.6970 -0.0583 0.5082 0.1705 1.0000 Uiso R . . . . .
H273 H 0.6270 -0.0374 0.4658 0.1708 1.0000 Uiso R . . . . .
H281 H 0.6006 0.4748 0.4094 0.1256 1.0000 Uiso R . . . . .
H282 H 0.5927 0.3826 0.3556 0.1247 1.0000 Uiso R . . . . .
H283 H 0.5543 0.3711 0.3829 0.1249 1.0000 Uiso R . . . . .
H291 H 0.8007 0.3127 0.6757 0.1195 1.0000 Uiso R . . . . .
H292 H 0.8317 0.3037 0.6385 0.1196 1.0000 Uiso R . . . . .
H293 H 0.7978 0.4219 0.6326 0.1202 1.0000 Uiso R . . . . .
H331 H 0.9912 -0.0679 0.8867 0.0794 1.0000 Uiso R . . . . .
H351 H 0.9314 -0.3238 0.7396 0.0787 1.0000 Uiso R . . . . .
H371 H 0.8610 0.1030 0.7940 0.1297 1.0000 Uiso R . . . . .
H372 H 0.9097 0.1601 0.7872 0.1294 1.0000 Uiso R . . . . .
H373 H 0.9296 0.1055 0.8593 0.1296 1.0000 Uiso R . . . . .
H381 H 1.0283 -0.2956 0.9175 0.1290 1.0000 Uiso R . . . . .
H382 H 1.0617 -0.2488 0.8884 0.1291 1.0000 Uiso R . . . . .
H383 H 1.0227 -0.3633 0.8568 0.1291 1.0000 Uiso R . . . . .
H391 H 0.7893 -0.2208 0.6210 0.1224 1.0000 Uiso R . . . . .
H392 H 0.8257 -0.1737 0.5943 0.1226 1.0000 Uiso R . . . . .
H393 H 0.8368 -0.3040 0.6245 0.1226 1.0000 Uiso R . . . . .
H131 H 0.6341 0.3698 0.6030 0.0706 1.0000 Uiso R . . . . .
H151 H 0.6952 0.0958 0.7429 0.0720 1.0000 Uiso R . . . . .
H171 H 0.5414 0.3562 0.4928 0.1043 1.0000 Uiso R . . . . .
H172 H 0.5253 0.2265 0.4555 0.1030 1.0000 Uiso R . . . . .
H173 H 0.4908 0.2733 0.4859 0.1029 1.0000 Uiso R . . . . .
H181 H 0.7296 0.3320 0.7770 0.1207 1.0000 Uiso R . . . . .
H182 H 0.7310 0.3936 0.7197 0.1196 1.0000 Uiso R . . . . .
H183 H 0.7670 0.2755 0.7550 0.1199 1.0000 Uiso R . . . . .
H191 H 0.5646 -0.0646 0.6536 0.1074 1.0000 Uiso R . . . . .
H192 H 0.6044 -0.1199 0.6322 0.1079 1.0000 Uiso R . . . . .
H193 H 0.6353 -0.0804 0.7115 0.1074 1.0000 Uiso R . . . . .
O21 O 0.4834(2) 0.1684(6) 0.2823(3) 0.2340 1.0000 Uani . . . . . .
O22 O 0.4490(2) 0.0271(3) 0.20049(18) 0.1818 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.497(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
Br1 . N11 2_656 2.1248(17) yes
Br1 . N11 . 2.1248(17) yes
N11 . C12 . 1.353(3) yes
N11 . C16 . 1.355(2) yes
C12 . C13 . 1.379(3) yes
C12 . C17 . 1.500(3) yes
C13 . C14 . 1.387(3) yes
C13 . H131 . 0.943 no
C14 . C15 . 1.385(4) yes
C14 . C18 . 1.501(3) yes
C15 . C16 . 1.372(3) yes
C15 . H151 . 0.939 no
C16 . C19 . 1.506(3) yes
C17 . H171 . 0.968 no
C17 . H172 . 0.981 no
C17 . H173 . 0.962 no
C18 . H181 . 0.936 no
C18 . H182 . 0.951 no
C18 . H183 . 0.948 no
C19 . H191 . 0.960 no
C19 . H192 . 0.972 no
C19 . H193 . 0.953 no
Br2 . N21 . 2.1000(19) yes
Br2 . N31 . 2.1443(19) yes
N21 . C22 . 1.357(3) yes
N21 . C26 . 1.352(3) yes
C22 . C23 . 1.379(4) yes
C22 . C27 . 1.486(4) yes
C23 . C24 . 1.380(4) yes
C23 . H231 . 0.930 no
C24 . C25 . 1.379(4) yes
C24 . C28 . 1.502(4) yes
C25 . C26 . 1.376(4) yes
C25 . H251 . 0.915 no
C26 . C29 . 1.499(3) yes
C27 . H271 . 0.944 no
C27 . H272 . 0.952 no
C27 . H273 . 0.939 no
C28 . H281 . 0.934 no
C28 . H282 . 0.956 no
C28 . H283 . 0.935 no
C29 . H291 . 0.952 no
C29 . H292 . 0.955 no
C29 . H293 . 0.954 no
N31 . C32 . 1.354(3) yes
N31 . C36 . 1.356(3) yes
C32 . C33 . 1.371(4) yes
C32 . C37 . 1.501(4) yes
C33 . C34 . 1.383(4) yes
C33 . H331 . 0.941 no
C34 . C35 . 1.386(3) yes
C34 . C38 . 1.506(4) yes
C35 . C36 . 1.375(3) yes
C35 . H351 . 0.927 no
C36 . C39 . 1.505(3) yes
C37 . H371 . 0.954 no
C37 . H372 . 0.962 no
C37 . H373 . 0.938 no
C38 . H381 . 0.946 no
C38 . H382 . 0.939 no
C38 . H383 . 0.952 no
C39 . H391 . 0.951 no
C39 . H392 . 0.966 no
C39 . H393 . 0.961 no
Cl1 . O11 . 1.417(2) yes
Cl1 . O12 . 1.426(2) yes
Cl1 . O13 . 1.427(2) yes
Cl1 . O14 . 1.422(2) yes
Cl2 . O22 6_655 1.402(3) yes
Cl2 . O21 6_655 1.339(4) yes
Cl2 . O21 . 1.339(4) yes
Cl2 . O22 . 1.402(3) 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
N11 2_656 Br1 . N11 . 179.995 yes
Br1 . N11 . C12 . 119.28(13) yes
Br1 . N11 . C16 . 119.77(15) yes
C12 . N11 . C16 . 120.85(19) yes
N11 . C12 . C13 . 119.69(19) yes
N11 . C12 . C17 . 118.6(2) yes
C13 . C12 . C17 . 121.7(2) yes
C12 . C13 . C14 . 121.0(2) yes
C12 . C13 . H131 . 118.2 no
C14 . C13 . H131 . 120.8 no
C13 . C14 . C15 . 117.3(2) yes
C13 . C14 . C18 . 121.6(2) yes
C15 . C14 . C18 . 121.0(2) yes
C14 . C15 . C16 . 121.1(2) yes
C14 . C15 . H151 . 119.4 no
C16 . C15 . H151 . 119.5 no
C15 . C16 . N11 . 119.9(2) yes
C15 . C16 . C19 . 121.81(19) yes
N11 . C16 . C19 . 118.3(2) yes
C12 . C17 . H171 . 106.4 no
C12 . C17 . H172 . 111.0 no
H171 . C17 . H172 . 110.2 no
C12 . C17 . H173 . 110.6 no
H171 . C17 . H173 . 110.3 no
H172 . C17 . H173 . 108.4 no
C14 . C18 . H181 . 109.4 no
C14 . C18 . H182 . 111.0 no
H181 . C18 . H182 . 108.6 no
C14 . C18 . H183 . 110.5 no
H181 . C18 . H183 . 108.7 no
H182 . C18 . H183 . 108.6 no
C16 . C19 . H191 . 110.3 no
C16 . C19 . H192 . 108.9 no
H191 . C19 . H192 . 109.1 no
C16 . C19 . H193 . 109.0 no
H191 . C19 . H193 . 109.3 no
H192 . C19 . H193 . 110.2 no
N21 . Br2 . N31 . 176.76(7) yes
Br2 . N21 . C22 . 119.01(17) yes
Br2 . N21 . C26 . 119.97(15) yes
C22 . N21 . C26 . 120.9(2) yes
N21 . C22 . C23 . 119.4(2) yes
N21 . C22 . C27 . 118.9(2) yes
C23 . C22 . C27 . 121.8(2) yes
C22 . C23 . C24 . 121.6(2) yes
C22 . C23 . H231 . 118.3 no
C24 . C23 . H231 . 120.2 no
C23 . C24 . C25 . 117.0(2) yes
C23 . C24 . C28 . 120.9(3) yes
C25 . C24 . C28 . 122.1(3) yes
C24 . C25 . C26 . 121.6(2) yes
C24 . C25 . H251 . 120.0 no
C26 . C25 . H251 . 118.4 no
C25 . C26 . N21 . 119.6(2) yes
C25 . C26 . C29 . 121.3(2) yes
N21 . C26 . C29 . 119.1(2) yes
C22 . C27 . H271 . 109.8 no
C22 . C27 . H272 . 110.0 no
H271 . C27 . H272 . 108.2 no
C22 . C27 . H273 . 109.8 no
H271 . C27 . H273 . 109.4 no
H272 . C27 . H273 . 109.7 no
C24 . C28 . H281 . 110.8 no
C24 . C28 . H282 . 109.9 no
H281 . C28 . H282 . 108.9 no
C24 . C28 . H283 . 108.7 no
H281 . C28 . H283 . 110.2 no
H282 . C28 . H283 . 108.3 no
C26 . C29 . H291 . 108.9 no
C26 . C29 . H292 . 109.8 no
H291 . C29 . H292 . 108.7 no
C26 . C29 . H293 . 111.0 no
H291 . C29 . H293 . 108.8 no
H292 . C29 . H293 . 109.6 no
Br2 . N31 . C32 . 119.37(17) yes
Br2 . N31 . C36 . 119.83(15) yes
C32 . N31 . C36 . 120.7(2) yes
N31 . C32 . C33 . 119.8(2) yes
N31 . C32 . C37 . 118.5(2) yes
C33 . C32 . C37 . 121.6(2) yes
C32 . C33 . C34 . 121.4(2) yes
C32 . C33 . H331 . 121.0 no
C34 . C33 . H331 . 117.6 no
C33 . C34 . C35 . 117.3(2) yes
C33 . C34 . C38 . 121.6(2) yes
C35 . C34 . C38 . 121.1(3) yes
C34 . C35 . C36 . 120.9(2) yes
C34 . C35 . H351 . 119.6 no
C36 . C35 . H351 . 119.5 no
C35 . C36 . N31 . 119.9(2) yes
C35 . C36 . C39 . 121.2(2) yes
N31 . C36 . C39 . 118.9(2) yes
C32 . C37 . H371 . 109.0 no
C32 . C37 . H372 . 110.7 no
H371 . C37 . H372 . 109.6 no
C32 . C37 . H373 . 107.7 no
H371 . C37 . H373 . 109.7 no
H372 . C37 . H373 . 110.1 no
C34 . C38 . H381 . 110.7 no
C34 . C38 . H382 . 110.3 no
H381 . C38 . H382 . 108.4 no
C34 . C38 . H383 . 111.3 no
H381 . C38 . H383 . 108.4 no
H382 . C38 . H383 . 107.7 no
C36 . C39 . H391 . 109.4 no
C36 . C39 . H392 . 112.8 no
H391 . C39 . H392 . 108.1 no
C36 . C39 . H393 . 110.6 no
H391 . C39 . H393 . 108.4 no
H392 . C39 . H393 . 107.5 no
O11 . Cl1 . O12 . 109.85(17) yes
O11 . Cl1 . O13 . 109.38(16) yes
O12 . Cl1 . O13 . 108.72(16) yes
O11 . Cl1 . O14 . 111.22(16) yes
O12 . Cl1 . O14 . 108.18(15) yes
O13 . Cl1 . O14 . 109.44(17) yes
O22 6_655 Cl2 . O21 6_655 106.9(3) yes
O22 6_655 Cl2 . O21 . 111.0(3) yes
O21 6_655 Cl2 . O21 . 110.0(6) yes
O22 6_655 Cl2 . O22 . 111.0(3) yes
O21 6_655 Cl2 . O22 . 111.0(3) yes
O21 . Cl2 . O22 . 106.9(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C35 . H351 . O22 7_545 177 0.93 2.58 3.509(4) yes
C19 . H192 . O11 1_545 161 0.97 2.39 3.327(4) yes


####################################################################### 
# 
# 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_IColl2ClO4-I-100K
_database_code_depnum_ccdc_archive 'CCDC 1853988'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 139lcm18-100K
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
On initial refinement, displacement ellipsoids for the perchlorate ion 
associated with Cl2 were decidedly prolate.  This included the central 
chloride, so the perchlorate moved to a general position close to the 
inversion centre, with the occupancy fixed to a half.  Because of this 
disorder, same distance, vibrational and thermal similarity restraints 
were required to maintian a sensible model for the anion.
;

_cell_length_a                   27.2651(14)
_cell_length_b                   10.9468(3)
_cell_length_c                   23.2069(12)
_cell_angle_alpha                90
_cell_angle_beta                 126.137(8)
_cell_angle_gamma                90
_cell_volume                     5593.9(7)

_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
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'
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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            12

# Given Formula = C17.33 H23.83 Cl1.08 I1.08 N2.17 O4.33 
# Dc =      1.81 Fooo =   3042.00 Mu =    162.57 M =    507.78
# Found Formula = C16 H22 Cl1 I1 N2 O4 
# Dc =      1.67 FOOO =   2808.00 Mu =    150.07 M =    468.72

_chemical_formula_sum            'C16 H22 Cl I N2 O4'
_chemical_formula_moiety         'C16 H22 I N2, Cl O4'
_chemical_compound_source        .
_chemical_formula_weight         468.72


_cell_measurement_reflns_used    17154
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.11
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2808
_exptl_absorpt_coefficient_mu    15.007

# Sheldrick geometric approximatio 0.07 0.19 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.19
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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      100
_diffrn_reflns_number            34815
_reflns_number_total             5833
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0387
# Number of reflections with Friedels Law is 5833 
# Theoretical number of reflections is about 11696 


_diffrn_reflns_theta_min         4.004
_diffrn_reflns_theta_max         76.107
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.107
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -34
_reflns_limit_h_max              27
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   2.13
_oxford_diffrn_Wilson_scale      0.78

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

_refine_diff_density_min         -1.52
_refine_diff_density_max         1.63


# 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     44
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5829
_oxford_refine_ls_R_factor_ref   0.0395
_refine_ls_wR_factor_ref         0.1082
_refine_ls_goodness_of_fit_ref   0.9847
_refine_ls_shift/su_max          0.0021835
_refine_ls_shift/su_mean         0.0000506


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5831
_refine_ls_R_factor_all          0.0395
_refine_ls_wR_factor_all         0.1083

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5507
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_gt          0.1057


_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 +42.71P] 
 ,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 0.5000 0.0000 0.5000 0.0221 1.0000 Uani S . . . . .
N11 N 0.57702(13) 0.1203(3) 0.58717(15) 0.0236 1.0000 Uani . . . . . .
C12 C 0.58435(16) 0.2351(4) 0.57086(19) 0.0253 1.0000 Uani . . . . . .
C13 C 0.63577(17) 0.3021(4) 0.6198(2) 0.0265 1.0000 Uani . . . . . .
C14 C 0.67970(16) 0.2540(4) 0.6870(2) 0.0269 1.0000 Uani . . . . . .
C15 C 0.66954(17) 0.1386(4) 0.70312(19) 0.0268 1.0000 Uani . . . . . .
C16 C 0.61812(17) 0.0727(4) 0.6531(2) 0.0257 1.0000 Uani . . . . . .
C17 C 0.53469(18) 0.2886(4) 0.4998(2) 0.0325 1.0000 Uani . . . . . .
C18 C 0.73562(18) 0.3257(4) 0.7414(2) 0.0359 1.0000 Uani . . . . . .
C19 C 0.6054(2) -0.0503(4) 0.6704(2) 0.0335 1.0000 Uani . . . . . .
I2 I 0.793801(11) 0.05543(2) 0.643843(12) 0.0278 1.0000 Uani . . . . . .
N21 N 0.72039(16) 0.1799(3) 0.55781(18) 0.0311 1.0000 Uani . . . . . .
C22 C 0.6680(2) 0.1298(4) 0.5015(2) 0.0376 1.0000 Uani . . . . . .
C23 C 0.6244(2) 0.2029(4) 0.4470(2) 0.0389 1.0000 Uani . . . . . .
C24 C 0.6327(2) 0.3276(4) 0.4468(2) 0.0352 1.0000 Uani . . . . . .
C25 C 0.6868(2) 0.3762(4) 0.5047(2) 0.0338 1.0000 Uani . . . . . .
C26 C 0.73003(19) 0.3020(4) 0.5599(2) 0.0314 1.0000 Uani . . . . . .
C27 C 0.6590(3) -0.0060(5) 0.5005(3) 0.0566 1.0000 Uani . . . . . .
C28 C 0.5848(2) 0.4062(5) 0.3866(3) 0.0456 1.0000 Uani . . . . . .
C29 C 0.7877(2) 0.3558(4) 0.6228(3) 0.0421 1.0000 Uani . . . . . .
N31 N 0.87084(15) -0.0708(3) 0.72676(17) 0.0282 1.0000 Uani . . . . . .
C32 C 0.91238(19) -0.0284(4) 0.7944(2) 0.0314 1.0000 Uani . . . . . .
C33 C 0.96236(18) -0.0978(4) 0.8427(2) 0.0321 1.0000 Uani . . . . . .
C34 C 0.97246(17) -0.2110(4) 0.8244(2) 0.0319 1.0000 Uani . . . . . .
C35 C 0.92923(18) -0.2529(4) 0.7550(2) 0.0305 1.0000 Uani . . . . . .
C36 C 0.87870(17) -0.1824(4) 0.7072(2) 0.0305 1.0000 Uani . . . . . .
C37 C 0.9020(2) 0.0942(5) 0.8149(2) 0.0424 1.0000 Uani . . . . . .
C38 C 1.02758(19) -0.2853(5) 0.8765(2) 0.0394 1.0000 Uani . . . . . .
C39 C 0.83125(19) -0.2289(4) 0.6331(2) 0.0384 1.0000 Uani . . . . . .
Cl1 Cl 0.65260(4) 0.65251(8) 0.56382(5) 0.0284 1.0000 Uani . . . . . .
O11 O 0.63702(17) 0.7638(3) 0.58204(19) 0.0473 1.0000 Uani . . . . . .
O12 O 0.59958(14) 0.5762(3) 0.52384(17) 0.0393 1.0000 Uani . . . . . .
O13 O 0.67388(15) 0.6801(3) 0.52131(17) 0.0396 1.0000 Uani . . . . . .
O14 O 0.69943(14) 0.5885(3) 0.62781(16) 0.0414 1.0000 Uani . . . . . .
Cl2 Cl 0.5097(3) 0.1044(2) 0.2559(5) 0.0598 0.5000 Uani D U . 1 -1 .
O21 O 0.4887(5) 0.1548(11) 0.2930(6) 0.0829 0.5000 Uani D U . 1 -1 .
O22 O 0.4645(6) 0.0305(13) 0.2002(8) 0.1246 0.5000 Uani D U . 1 -1 .
O23 O 0.5256(7) 0.1995(8) 0.2293(7) 0.0851 0.5000 Uani D U . 1 -1 .
O24 O 0.5618(5) 0.0321(10) 0.3023(7) 0.0699 0.5000 Uani D U . 1 -1 .
H231 H 0.5882 0.1672 0.4092 0.0474 1.0000 Uiso R . . . . .
H251 H 0.6940 0.4595 0.5069 0.0409 1.0000 Uiso R . . . . .
H271 H 0.6597 -0.0281 0.5408 0.0848 1.0000 Uiso R . . . . .
H272 H 0.6908 -0.0493 0.5035 0.0848 1.0000 Uiso R . . . . .
H273 H 0.6206 -0.0278 0.4570 0.0848 1.0000 Uiso R . . . . .
H281 H 0.5912 0.4896 0.4002 0.0680 1.0000 Uiso R . . . . .
H282 H 0.5859 0.3977 0.3464 0.0681 1.0000 Uiso R . . . . .
H283 H 0.5456 0.3821 0.3728 0.0680 1.0000 Uiso R . . . . .
H291 H 0.7891 0.3411 0.6649 0.0632 1.0000 Uiso R . . . . .
H292 H 0.8226 0.3218 0.6285 0.0628 1.0000 Uiso R . . . . .
H293 H 0.7877 0.4412 0.6159 0.0632 1.0000 Uiso R . . . . .
H331 H 0.9905 -0.0685 0.8884 0.0392 1.0000 Uiso R . . . . .
H351 H 0.9347 -0.3279 0.7409 0.0368 1.0000 Uiso R . . . . .
H371 H 0.8615 0.0974 0.8020 0.0637 1.0000 Uiso R . . . . .
H372 H 0.9077 0.1571 0.7893 0.0635 1.0000 Uiso R . . . . .
H373 H 0.9313 0.1051 0.8657 0.0641 1.0000 Uiso R . . . . .
H381 H 1.0295 -0.2959 0.9183 0.0589 1.0000 Uiso R . . . . .
H382 H 1.0631 -0.2445 0.8879 0.0590 1.0000 Uiso R . . . . .
H383 H 1.0249 -0.3635 0.8571 0.0592 1.0000 Uiso R . . . . .
H391 H 0.7916 -0.2251 0.6233 0.0575 1.0000 Uiso R . . . . .
H392 H 0.8305 -0.1816 0.5974 0.0579 1.0000 Uiso R . . . . .
H393 H 0.8398 -0.3116 0.6289 0.0576 1.0000 Uiso R . . . . .
H131 H 0.6409 0.3793 0.6084 0.0318 1.0000 Uiso R . . . . .
H151 H 0.6977 0.1055 0.7483 0.0322 1.0000 Uiso R . . . . .
H171 H 0.5438 0.3726 0.4979 0.0489 1.0000 Uiso R . . . . .
H172 H 0.5306 0.2433 0.4623 0.0488 1.0000 Uiso R . . . . .
H173 H 0.4972 0.2844 0.4948 0.0488 1.0000 Uiso R . . . . .
H181 H 0.7383 0.3412 0.7840 0.0541 1.0000 Uiso R . . . . .
H182 H 0.7360 0.4019 0.7220 0.0537 1.0000 Uiso R . . . . .
H183 H 0.7707 0.2821 0.7546 0.0542 1.0000 Uiso R . . . . .
H191 H 0.5665 -0.0551 0.6631 0.0495 1.0000 Uiso R . . . . .
H192 H 0.6062 -0.1113 0.6418 0.0502 1.0000 Uiso R . . . . .
H193 H 0.6363 -0.0699 0.7200 0.0501 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.184(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 . N11 2_656 2.286(3) yes
I1 . N11 . 2.286(3) yes
N11 . C12 . 1.361(5) yes
N11 . C16 . 1.358(5) yes
C12 . C13 . 1.384(5) yes
C12 . C17 . 1.503(5) yes
C13 . C14 . 1.393(5) yes
C13 . H131 . 0.921 no
C14 . C15 . 1.391(6) yes
C14 . C18 . 1.505(5) yes
C15 . C16 . 1.383(5) yes
C15 . H151 . 0.933 no
C16 . C19 . 1.503(6) yes
C17 . H171 . 0.960 no
C17 . H172 . 0.950 no
C17 . H173 . 0.959 no
C18 . H181 . 0.961 no
C18 . H182 . 0.950 no
C18 . H183 . 0.944 no
C19 . H191 . 0.972 no
C19 . H192 . 0.951 no
C19 . H193 . 0.968 no
I2 . N21 . 2.266(3) yes
I2 . N31 . 2.293(3) yes
N21 . C22 . 1.358(6) yes
N21 . C26 . 1.358(6) yes
C22 . C23 . 1.372(6) yes
C22 . C27 . 1.505(7) yes
C23 . C24 . 1.384(7) yes
C23 . H231 . 0.935 no
C24 . C25 . 1.389(6) yes
C24 . C28 . 1.498(6) yes
C25 . C26 . 1.381(6) yes
C25 . H251 . 0.927 no
C26 . C29 . 1.498(6) yes
C27 . H271 . 0.955 no
C27 . H272 . 0.955 no
C27 . H273 . 0.962 no
C28 . H281 . 0.948 no
C28 . H282 . 0.956 no
C28 . H283 . 0.955 no
C29 . H291 . 0.968 no
C29 . H292 . 0.955 no
C29 . H293 . 0.949 no
N31 . C32 . 1.366(5) yes
N31 . C36 . 1.363(6) yes
C32 . C33 . 1.375(6) yes
C32 . C37 . 1.505(6) yes
C33 . C34 . 1.389(6) yes
C33 . H331 . 0.925 no
C34 . C35 . 1.397(6) yes
C34 . C38 . 1.496(6) yes
C35 . C36 . 1.386(6) yes
C35 . H351 . 0.928 no
C36 . C39 . 1.507(6) yes
C37 . H371 . 0.958 no
C37 . H372 . 0.979 no
C37 . H373 . 0.966 no
C38 . H381 . 0.947 no
C38 . H382 . 0.951 no
C38 . H383 . 0.950 no
C39 . H391 . 0.966 no
C39 . H392 . 0.965 no
C39 . H393 . 0.953 no
Cl1 . O11 . 1.434(3) yes
Cl1 . O12 . 1.438(3) yes
Cl1 . O13 . 1.441(3) yes
Cl1 . O14 . 1.446(3) yes
Cl2 . O21 . 1.398(8) yes
Cl2 . O22 . 1.402(6) yes
Cl2 . O23 . 1.404(7) yes
Cl2 . O24 . 1.415(7) 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
N11 2_656 I1 . N11 . 179.99 yes
I1 . N11 . C12 . 119.7(2) yes
I1 . N11 . C16 . 119.5(3) yes
C12 . N11 . C16 . 120.6(3) yes
N11 . C12 . C13 . 120.3(3) yes
N11 . C12 . C17 . 118.6(3) yes
C13 . C12 . C17 . 121.0(4) yes
C12 . C13 . C14 . 120.3(4) yes
C12 . C13 . H131 . 120.2 no
C14 . C13 . H131 . 119.5 no
C13 . C14 . C15 . 117.9(3) yes
C13 . C14 . C18 . 121.3(4) yes
C15 . C14 . C18 . 120.8(4) yes
C14 . C15 . C16 . 120.8(3) yes
C14 . C15 . H151 . 119.5 no
C16 . C15 . H151 . 119.7 no
C15 . C16 . N11 . 120.0(4) yes
C15 . C16 . C19 . 121.4(3) yes
N11 . C16 . C19 . 118.5(3) yes
C12 . C17 . H171 . 109.5 no
C12 . C17 . H172 . 110.2 no
H171 . C17 . H172 . 110.5 no
C12 . C17 . H173 . 108.7 no
H171 . C17 . H173 . 109.0 no
H172 . C17 . H173 . 108.8 no
C14 . C18 . H181 . 112.3 no
C14 . C18 . H182 . 110.4 no
H181 . C18 . H182 . 108.4 no
C14 . C18 . H183 . 109.9 no
H181 . C18 . H183 . 107.9 no
H182 . C18 . H183 . 107.8 no
C16 . C19 . H191 . 113.7 no
C16 . C19 . H192 . 109.8 no
H191 . C19 . H192 . 108.2 no
C16 . C19 . H193 . 109.9 no
H191 . C19 . H193 . 106.8 no
H192 . C19 . H193 . 108.2 no
N21 . I2 . N31 . 176.18(12) yes
I2 . N21 . C22 . 119.0(3) yes
I2 . N21 . C26 . 120.6(3) yes
C22 . N21 . C26 . 120.2(4) yes
N21 . C22 . C23 . 120.0(4) yes
N21 . C22 . C27 . 118.9(4) yes
C23 . C22 . C27 . 121.1(4) yes
C22 . C23 . C24 . 121.6(4) yes
C22 . C23 . H231 . 118.9 no
C24 . C23 . H231 . 119.5 no
C23 . C24 . C25 . 117.2(4) yes
C23 . C24 . C28 . 121.0(4) yes
C25 . C24 . C28 . 121.8(4) yes
C24 . C25 . C26 . 120.7(4) yes
C24 . C25 . H251 . 120.0 no
C26 . C25 . H251 . 119.3 no
C25 . C26 . N21 . 120.3(4) yes
C25 . C26 . C29 . 120.3(4) yes
N21 . C26 . C29 . 119.4(4) yes
C22 . C27 . H271 . 109.1 no
C22 . C27 . H272 . 110.8 no
H271 . C27 . H272 . 108.2 no
C22 . C27 . H273 . 109.2 no
H271 . C27 . H273 . 110.3 no
H272 . C27 . H273 . 109.4 no
C24 . C28 . H281 . 110.8 no
C24 . C28 . H282 . 110.1 no
H281 . C28 . H282 . 108.2 no
C24 . C28 . H283 . 110.0 no
H281 . C28 . H283 . 109.1 no
H282 . C28 . H283 . 108.6 no
C26 . C29 . H291 . 108.3 no
C26 . C29 . H292 . 111.6 no
H291 . C29 . H292 . 110.7 no
C26 . C29 . H293 . 109.1 no
H291 . C29 . H293 . 109.3 no
H292 . C29 . H293 . 107.9 no
I2 . N31 . C32 . 119.2(3) yes
I2 . N31 . C36 . 120.5(3) yes
C32 . N31 . C36 . 120.0(3) yes
N31 . C32 . C33 . 120.0(4) yes
N31 . C32 . C37 . 118.9(4) yes
C33 . C32 . C37 . 121.1(4) yes
C32 . C33 . C34 . 121.5(4) yes
C32 . C33 . H331 . 119.7 no
C34 . C33 . H331 . 118.8 no
C33 . C34 . C35 . 117.4(4) yes
C33 . C34 . C38 . 121.5(4) yes
C35 . C34 . C38 . 121.0(4) yes
C34 . C35 . C36 . 120.3(4) yes
C34 . C35 . H351 . 119.6 no
C36 . C35 . H351 . 120.1 no
C35 . C36 . N31 . 120.7(4) yes
C35 . C36 . C39 . 120.3(4) yes
N31 . C36 . C39 . 119.0(4) yes
C32 . C37 . H371 . 109.3 no
C32 . C37 . H372 . 108.0 no
H371 . C37 . H372 . 110.5 no
C32 . C37 . H373 . 108.7 no
H371 . C37 . H373 . 110.3 no
H372 . C37 . H373 . 109.9 no
C34 . C38 . H381 . 108.5 no
C34 . C38 . H382 . 110.0 no
H381 . C38 . H382 . 109.9 no
C34 . C38 . H383 . 110.4 no
H381 . C38 . H383 . 108.4 no
H382 . C38 . H383 . 109.7 no
C36 . C39 . H391 . 109.9 no
C36 . C39 . H392 . 111.6 no
H391 . C39 . H392 . 108.7 no
C36 . C39 . H393 . 109.9 no
H391 . C39 . H393 . 108.9 no
H392 . C39 . H393 . 107.9 no
O11 . Cl1 . O12 . 108.9(2) yes
O11 . Cl1 . O13 . 109.5(2) yes
O12 . Cl1 . O13 . 109.7(2) yes
O11 . Cl1 . O14 . 110.2(2) yes
O12 . Cl1 . O14 . 108.90(19) yes
O13 . Cl1 . O14 . 109.7(2) yes
O21 . Cl2 . O22 . 109.8(7) yes
O23 . Cl2 . O21 . 108.9(5) yes
O23 . Cl2 . O22 . 110.7(7) yes
O24 . Cl2 . O21 . 110.2(6) yes
O24 . Cl2 . O22 . 108.8(5) yes
O23 . Cl2 . O24 . 108.5(6) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C23 . H231 . O24 . 133 0.93 2.60 3.305(7) yes
C23 . H231 . O21 . 158 0.93 2.45 3.338(7) yes
C23 . H231 . O22 6_655 148 0.93 2.54 3.367(7) yes
C25 . H251 . O13 . 153 0.93 2.54 3.391(7) yes
C35 . H351 . O24 4_646 174 0.93 2.47 3.399(7) yes
C38 . H383 . O22 4_646 163 0.95 2.38 3.298(7) yes
C15 . H151 . O14 8_646 156 0.93 2.58 3.453(7) yes
C17 . H171 . O12 . 163 0.96 2.56 3.491(7) yes
C19 . H191 . O21 2_656 144 0.97 2.51 3.344(7) yes
C19 . H192 . O11 1_545 163 0.95 2.42 3.342(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 .
-6 2 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_BrColl2PF6-300K
_database_code_depnum_ccdc_archive 'CCDC 1853985'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 011lcm17
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   8.0237(2)
_cell_length_b                   8.3951(2)
_cell_length_c                   15.2556(4)
_cell_angle_alpha                99.420(2)
_cell_angle_beta                 98.926(2)
_cell_angle_gamma                97.070(2)
_cell_volume                     989.79(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
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'
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'
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'
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'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 '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 = C16 H22 Br1 F6 N2 P1 
# Dc =      1.57 Fooo =    472.00 Mu =     41.36 M =    467.23
# Found Formula = C16 H22.00 Br1 F6 N2 P1 
# Dc =      1.57 FOOO =    472.00 Mu =     41.36 M =    467.23

_chemical_formula_sum            'C16 H22 Br F6 N2 P'
_chemical_formula_moiety         'C16 H22 Br N2, F6 P'
_chemical_compound_source        .
_chemical_formula_weight         467.23


_cell_measurement_reflns_used    9248
_cell_measurement_theta_min      5
_cell_measurement_theta_max      75
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             471.998
_exptl_absorpt_coefficient_mu    4.136

# Sheldrick geometric approximatio 0.61 0.69 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.69
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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      300
_diffrn_reflns_number            15137
_reflns_number_total             3961
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.0321
# Number of reflections with Friedels Law is 3961 
# Theoretical number of reflections is about 8174 


_diffrn_reflns_theta_min         5.404
_diffrn_reflns_theta_max         75.169
_diffrn_measured_fraction_theta_max 0.970

_diffrn_reflns_theta_full        71.000
_diffrn_measured_fraction_theta_full 0.992


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   3.96
_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         -0.36
_refine_diff_density_max         0.76


# 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     0
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3953
_oxford_refine_ls_R_factor_ref   0.0412
_refine_ls_wR_factor_ref         0.1062
_refine_ls_goodness_of_fit_ref   0.8915
_refine_ls_shift/su_max          0.0006844
_refine_ls_shift/su_mean         0.0000290


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3953
_refine_ls_R_factor_all          0.0412
_refine_ls_wR_factor_all         0.1062

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3625
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_gt          0.1029


_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 + 0.88P] 
 ,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 0.47882(3) 0.51736(3) 0.222944(16) 0.0488 1.0000 Uani . . . . . .
N11 N 0.3557(3) 0.5333(3) 0.08953(14) 0.0483 1.0000 Uani . . . . . .
C12 C 0.2700(4) 0.3972(3) 0.03300(18) 0.0524 1.0000 Uani . . . . . .
C13 C 0.1811(4) 0.4088(4) -0.04988(19) 0.0570 1.0000 Uani . . . . . .
C14 C 0.1765(4) 0.5572(4) -0.07667(18) 0.0552 1.0000 Uani . . . . . .
C15 C 0.2672(4) 0.6942(4) -0.0174(2) 0.0578 1.0000 Uani . . . . . .
C16 C 0.3573(4) 0.6811(3) 0.06551(19) 0.0521 1.0000 Uani . . . . . .
C17 C 0.2755(5) 0.2356(4) 0.0620(2) 0.0712 1.0000 Uani . . . . . .
C18 C 0.0785(5) 0.5687(5) -0.1670(2) 0.0728 1.0000 Uani . . . . . .
C19 C 0.4569(5) 0.8284(4) 0.1295(2) 0.0680 1.0000 Uani . . . . . .
N21 N 0.5980(3) 0.4985(3) 0.35269(14) 0.0465 1.0000 Uani . . . . . .
C22 C 0.6429(4) 0.6348(3) 0.41792(18) 0.0524 1.0000 Uani . . . . . .
C23 C 0.7290(4) 0.6230(4) 0.50151(19) 0.0579 1.0000 Uani . . . . . .
C24 C 0.7710(4) 0.4759(4) 0.52023(18) 0.0571 1.0000 Uani . . . . . .
C25 C 0.7209(4) 0.3398(4) 0.4520(2) 0.0568 1.0000 Uani . . . . . .
C26 C 0.6339(3) 0.3520(3) 0.36812(18) 0.0496 1.0000 Uani . . . . . .
C27 C 0.5981(5) 0.7944(4) 0.3974(2) 0.0687 1.0000 Uani . . . . . .
C28 C 0.8675(5) 0.4649(5) 0.6107(2) 0.0764 1.0000 Uani . . . . . .
C29 C 0.5770(5) 0.2047(4) 0.2950(2) 0.0670 1.0000 Uani . . . . . .
P1 P 0.03741(10) -0.02113(10) 0.27307(6) 0.0686 1.0000 Uani . . . . . .
F11 F -0.0442(4) 0.0840(5) 0.3425(3) 0.1491 1.0000 Uani . . . . . .
F12 F -0.1100(5) -0.0009(5) 0.1955(3) 0.1605 1.0000 Uani . . . . . .
F13 F 0.1461(4) 0.1421(4) 0.2635(3) 0.1369 1.0000 Uani . . . . . .
F14 F 0.1831(5) -0.0357(5) 0.3489(3) 0.1697 1.0000 Uani . . . . . .
F15 F -0.0792(5) -0.1795(4) 0.2780(3) 0.1567 1.0000 Uani . . . . . .
F16 F 0.1154(5) -0.1257(7) 0.2042(4) 0.2296 1.0000 Uani . . . . . .
H173 H 0.2105 0.1510 0.0153 0.1069 1.0000 Uiso R . . . . .
H171 H 0.2269 0.2360 0.1157 0.1062 1.0000 Uiso R . . . . .
H172 H 0.3916 0.2151 0.0748 0.1065 1.0000 Uiso R . . . . .
H131 H 0.1246 0.3136 -0.0887 0.0684 1.0000 Uiso R . . . . .
H151 H 0.2674 0.7970 -0.0340 0.0691 1.0000 Uiso R . . . . .
H193 H 0.5729 0.8110 0.1447 0.1019 1.0000 Uiso R . . . . .
H192 H 0.4080 0.8419 0.1830 0.1016 1.0000 Uiso R . . . . .
H191 H 0.4510 0.9221 0.1023 0.1023 1.0000 Uiso R . . . . .
H182 H 0.1388 0.5290 -0.2134 0.1093 1.0000 Uiso R . . . . .
H183 H 0.0675 0.6803 -0.1685 0.1090 1.0000 Uiso R . . . . .
H181 H -0.0345 0.5050 -0.1772 0.1090 1.0000 Uiso R . . . . .
H271 H 0.6362 0.8751 0.4499 0.1028 1.0000 Uiso R . . . . .
H231 H 0.7583 0.7163 0.5466 0.0694 1.0000 Uiso R . . . . .
H251 H 0.7465 0.2381 0.4621 0.0674 1.0000 Uiso R . . . . .
H272 H 0.4778 0.7884 0.3796 0.1026 1.0000 Uiso R . . . . .
H273 H 0.6535 0.8219 0.3498 0.1026 1.0000 Uiso R . . . . .
H283 H 0.8932 0.3577 0.6117 0.1155 1.0000 Uiso R . . . . .
H282 H 0.9717 0.5383 0.6256 0.1154 1.0000 Uiso R . . . . .
H281 H 0.8017 0.4932 0.6560 0.1153 1.0000 Uiso R . . . . .
H292 H 0.6251 0.2232 0.2437 0.0997 1.0000 Uiso R . . . . .
H293 H 0.4560 0.1879 0.2779 0.0997 1.0000 Uiso R . . . . .
H291 H 0.6129 0.1116 0.3154 0.1002 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.9(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 . N11 . 2.153(2) yes
Br1 . N21 . 2.100(2) yes
N11 . C12 . 1.350(3) yes
N11 . C16 . 1.350(4) yes
C12 . C13 . 1.376(4) yes
C12 . C17 . 1.498(4) yes
C13 . C14 . 1.376(4) yes
C13 . H131 . 0.931 no
C14 . C15 . 1.385(4) yes
C14 . C18 . 1.501(4) yes
C15 . C16 . 1.384(4) yes
C15 . H151 . 0.938 no
C16 . C19 . 1.497(4) yes
C17 . H173 . 0.956 no
C17 . H171 . 0.960 no
C17 . H172 . 0.964 no
C18 . H182 . 0.956 no
C18 . H183 . 0.955 no
C18 . H181 . 0.971 no
C19 . H193 . 0.958 no
C19 . H192 . 0.955 no
C19 . H191 . 0.950 no
N21 . C22 . 1.358(3) yes
N21 . C26 . 1.346(4) yes
C22 . C23 . 1.378(4) yes
C22 . C27 . 1.497(4) yes
C23 . C24 . 1.382(4) yes
C23 . H231 . 0.933 no
C24 . C25 . 1.385(4) yes
C24 . C28 . 1.497(4) yes
C25 . C26 . 1.385(4) yes
C25 . H251 . 0.933 no
C26 . C29 . 1.495(4) yes
C27 . H271 . 0.943 no
C27 . H272 . 0.954 no
C27 . H273 . 0.952 no
C28 . H283 . 0.950 no
C28 . H282 . 0.948 no
C28 . H281 . 0.951 no
C29 . H292 . 0.951 no
C29 . H293 . 0.952 no
C29 . H291 . 0.948 no
P1 . F11 . 1.543(3) yes
P1 . F12 . 1.584(4) yes
P1 . F13 . 1.572(3) yes
P1 . F14 . 1.544(3) yes
P1 . F15 . 1.548(3) yes
P1 . F16 . 1.518(3) 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
N11 . Br1 . N21 . 179.25(8) yes
Br1 . N11 . C12 . 119.79(18) yes
Br1 . N11 . C16 . 119.24(17) yes
C12 . N11 . C16 . 120.9(2) yes
N11 . C12 . C13 . 119.9(3) yes
N11 . C12 . C17 . 118.8(2) yes
C13 . C12 . C17 . 121.4(3) yes
C12 . C13 . C14 . 121.4(3) yes
C12 . C13 . H131 . 118.9 no
C14 . C13 . H131 . 119.7 no
C13 . C14 . C15 . 117.3(3) yes
C13 . C14 . C18 . 121.0(3) yes
C15 . C14 . C18 . 121.7(3) yes
C14 . C15 . C16 . 120.9(3) yes
C14 . C15 . H151 . 119.3 no
C16 . C15 . H151 . 119.8 no
C15 . C16 . N11 . 119.7(3) yes
C15 . C16 . C19 . 121.2(3) yes
N11 . C16 . C19 . 119.1(2) yes
C12 . C17 . H173 . 109.4 no
C12 . C17 . H171 . 109.5 no
H173 . C17 . H171 . 108.9 no
C12 . C17 . H172 . 110.6 no
H173 . C17 . H172 . 109.7 no
H171 . C17 . H172 . 108.6 no
C14 . C18 . H182 . 109.5 no
C14 . C18 . H183 . 109.3 no
H182 . C18 . H183 . 109.1 no
C14 . C18 . H181 . 110.2 no
H182 . C18 . H181 . 109.8 no
H183 . C18 . H181 . 109.0 no
C16 . C19 . H193 . 109.1 no
C16 . C19 . H192 . 108.2 no
H193 . C19 . H192 . 109.2 no
C16 . C19 . H191 . 109.5 no
H193 . C19 . H191 . 110.9 no
H192 . C19 . H191 . 110.0 no
Br1 . N21 . C22 . 119.44(18) yes
Br1 . N21 . C26 . 118.94(17) yes
C22 . N21 . C26 . 121.6(2) yes
N21 . C22 . C23 . 119.1(3) yes
N21 . C22 . C27 . 119.3(2) yes
C23 . C22 . C27 . 121.5(3) yes
C22 . C23 . C24 . 121.5(3) yes
C22 . C23 . H231 . 119.1 no
C24 . C23 . H231 . 119.4 no
C23 . C24 . C25 . 117.4(2) yes
C23 . C24 . C28 . 121.1(3) yes
C25 . C24 . C28 . 121.6(3) yes
C24 . C25 . C26 . 121.0(3) yes
C24 . C25 . H251 . 119.9 no
C26 . C25 . H251 . 119.1 no
C25 . C26 . N21 . 119.5(2) yes
C25 . C26 . C29 . 121.0(3) yes
N21 . C26 . C29 . 119.5(2) yes
C22 . C27 . H272 . 111.2 no
C22 . C27 . H273 . 109.1 no
H272 . C27 . H273 . 109.2 no
C22 . C27 . H271 . 108.4 no
H272 . C27 . H271 . 109.1 no
H273 . C27 . H271 . 109.9 no
C24 . C28 . H281 . 109.8 no
C24 . C28 . H283 . 111.0 no
H281 . C28 . H283 . 109.1 no
C24 . C28 . H282 . 111.1 no
H281 . C28 . H282 . 107.6 no
H283 . C28 . H282 . 108.1 no
C26 . C29 . H293 . 110.0 no
C26 . C29 . H292 . 108.6 no
H293 . C29 . H292 . 108.1 no
C26 . C29 . H291 . 109.8 no
H293 . C29 . H291 . 109.9 no
H292 . C29 . H291 . 110.4 no
F11 . P1 . F12 . 89.3(2) yes
F11 . P1 . F13 . 87.1(2) yes
F12 . P1 . F13 . 91.0(2) yes
F11 . P1 . F14 . 90.1(3) yes
F12 . P1 . F14 . 178.4(2) yes
F13 . P1 . F14 . 87.5(2) yes
F11 . P1 . F15 . 92.5(2) yes
F12 . P1 . F15 . 85.3(2) yes
F13 . P1 . F15 . 176.3(2) yes
F14 . P1 . F15 . 96.2(2) yes
F11 . P1 . F16 . 179.26(19) yes
F12 . P1 . F16 . 90.1(3) yes
F13 . P1 . F16 . 93.5(3) yes
F14 . P1 . F16 . 90.4(3) yes
F15 . P1 . F16 . 86.9(3) 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
5 -1 14 x .
-2 0 4 x .
-1 -4 5 x .
-1 3 6 x .
3 -5 1 x .
-5 3 15 x .
1 -4 3 x .
-1 1 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_BrColl2ClO4-II-300K
_database_code_depnum_ccdc_archive 'CCDC 1853993'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 067YK14-300K
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
On initial refinement, displacement ellipsoids for the perchlorate ion 
associated were decidedly prolate.  Because of this disorder, same 
distance, vibrational and thermal similarity restraints were required 
to maintian a sensible model for the anion.
;

_cell_length_a                   28.8059(14)
_cell_length_b                   8.5296(3)
_cell_length_c                   15.8383(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.565(4)
_cell_angle_gamma                90
_cell_volume                     3837.4(3)

_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'
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'
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'
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            8

# Given Formula = C16 H22 Br1 Cl1 N2 O4 
# Dc =      1.46 Fooo =   1728.00 Mu =     43.89 M =    421.72
# Found Formula = C16 H22 Br1 Cl1 N2 O4.00 
# Dc =      1.46 FOOO =   1728.00 Mu =     43.89 M =    421.72

_chemical_formula_sum            'C16 H22 Br Cl N2 O4'
_chemical_formula_moiety         'C16 H22 Br N2, Cl O4'
_chemical_compound_source        .
_chemical_formula_weight         421.72


_cell_measurement_reflns_used    7301
_cell_measurement_theta_min      5
_cell_measurement_theta_max      75
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.35

_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    4.389

# Sheldrick geometric approximatio 0.52 0.70 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.70
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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      300
_diffrn_reflns_number            20990
_reflns_number_total             3997
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0391
# Number of reflections with Friedels Law is 3997 
# Theoretical number of reflections is about 8093 


_diffrn_reflns_theta_min         3.111
_diffrn_reflns_theta_max         76.785
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        75.249
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -36
_reflns_limit_h_max              35
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   5.62
_oxford_diffrn_Wilson_scale      0.34

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

_refine_diff_density_min         -0.54
_refine_diff_density_max         0.44


# 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     88
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3981
_oxford_refine_ls_R_factor_ref   0.0516
_refine_ls_wR_factor_ref         0.1367
_refine_ls_goodness_of_fit_ref   0.9997
_refine_ls_shift/su_max          0.0003745
_refine_ls_shift/su_mean         0.0000223


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3982
_refine_ls_R_factor_all          0.0517
_refine_ls_wR_factor_all         0.1369

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3385
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_gt          0.1257


_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) + ( 0.08P)² + 3.16P] 
 ,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 0.7500 0.2500 0.5000 0.0704 1.0000 Uani S . . . . .
N11 N 0.74665(10) 0.0241(3) 0.44328(17) 0.0693 1.0000 Uani . . . . . .
C12 C 0.78563(12) -0.0654(4) 0.4481(2) 0.0717 1.0000 Uani . . . . . .
C13 C 0.78357(14) -0.2066(5) 0.4053(2) 0.0794 1.0000 Uani . . . . . .
C14 C 0.74273(15) -0.2574(4) 0.3570(2) 0.0816 1.0000 Uani . . . . . .
C15 C 0.70309(15) -0.1655(5) 0.3547(2) 0.0844 1.0000 Uani . . . . . .
C16 C 0.70495(13) -0.0250(5) 0.3982(2) 0.0784 1.0000 Uani . . . . . .
C17 C 0.83030(14) -0.0063(5) 0.5000(3) 0.0928 1.0000 Uani . . . . . .
C18 C 0.7406(2) -0.4089(6) 0.3067(4) 0.1217 1.0000 Uani . . . . . .
C19 C 0.66232(15) 0.0771(7) 0.3960(3) 0.1093 1.0000 Uani . . . . . .
Br2 Br 0.5000 0.5000 0.5000 0.0731 1.0000 Uani S . . . . .
N21 N 0.53308(10) 0.4737(3) 0.3911(2) 0.0732 1.0000 Uani . . . . . .
C22 C 0.54837(13) 0.6011(4) 0.3536(3) 0.0792 1.0000 Uani . . . . . .
C23 C 0.57214(14) 0.5846(5) 0.2865(3) 0.0871 1.0000 Uani . . . . . .
C24 C 0.58105(13) 0.4375(5) 0.2554(3) 0.0855 1.0000 Uani . . . . . .
C25 C 0.56426(14) 0.3103(4) 0.2942(3) 0.0848 1.0000 Uani . . . . . .
C26 C 0.54011(13) 0.3283(4) 0.3613(2) 0.0775 1.0000 Uani . . . . . .
C27 C 0.5389(2) 0.7607(4) 0.3870(4) 0.1133 1.0000 Uani . . . . . .
C28 C 0.60817(19) 0.4190(7) 0.1831(3) 0.1139 1.0000 Uani . . . . . .
C29 C 0.5211(2) 0.1903(4) 0.4021(3) 0.1104 1.0000 Uani . . . . . .
Cl1 Cl 0.61146(4) 0.06374(14) 0.62998(7) 0.0965 1.0000 Uani D U . . . .
O11 O 0.6079(6) 0.2087(8) 0.5972(8) 0.2196 0.560(11) Uani D U P 1 1 .
O12 O 0.5841(4) 0.0540(11) 0.6943(6) 0.1578 0.560(11) Uani D U P 1 1 .
O13 O 0.5945(5) -0.0462(10) 0.5672(5) 0.1721 0.560(11) Uani D U P 1 1 .
O14 O 0.6557(3) 0.020(2) 0.6652(8) 0.2832 0.560(11) Uani D U P 1 1 .
O111 O 0.5747(4) 0.1613(17) 0.5975(10) 0.2141 0.440(11) Uani D U P 1 2 .
O112 O 0.6082(7) 0.0138(17) 0.7091(5) 0.2438 0.440(11) Uani D U P 1 2 .
O113 O 0.6162(5) -0.0534(14) 0.5743(8) 0.1763 0.440(11) Uani D U P 1 2 .
O114 O 0.6518(4) 0.1607(13) 0.6379(8) 0.1681 0.440(11) Uani D U P 1 2 .
H131 H 0.8102 -0.2663 0.4093 0.0950 1.0000 Uiso R . . . . .
H151 H 0.6743 -0.1981 0.3222 0.1010 1.0000 Uiso R . . . . .
H171 H 0.8550 -0.0797 0.4972 0.1388 1.0000 Uiso R . . . . .
H172 H 0.8381 0.0918 0.4758 0.1392 1.0000 Uiso R . . . . .
H173 H 0.8274 0.0098 0.5588 0.1384 1.0000 Uiso R . . . . .
H181 H 0.7102 -0.4555 0.3058 0.1831 1.0000 Uiso R . . . . .
H182 H 0.7449 -0.3829 0.2496 0.1828 1.0000 Uiso R . . . . .
H183 H 0.7654 -0.4808 0.3321 0.1828 1.0000 Uiso R . . . . .
H191 H 0.6611 0.1090 0.4536 0.1639 1.0000 Uiso R . . . . .
H192 H 0.6653 0.1692 0.3630 0.1639 1.0000 Uiso R . . . . .
H193 H 0.6348 0.0208 0.3725 0.1639 1.0000 Uiso R . . . . .
H231 H 0.5819 0.6744 0.2626 0.1046 1.0000 Uiso R . . . . .
H251 H 0.5690 0.2091 0.2746 0.1014 1.0000 Uiso R . . . . .
H271 H 0.5529 0.8404 0.3567 0.1698 1.0000 Uiso R . . . . .
H272 H 0.5527 0.7686 0.4464 0.1695 1.0000 Uiso R . . . . .
H273 H 0.5059 0.7774 0.3797 0.1695 1.0000 Uiso R . . . . .
H281 H 0.5897 0.3579 0.1398 0.1710 1.0000 Uiso R . . . . .
H282 H 0.6362 0.3646 0.2057 0.1704 1.0000 Uiso R . . . . .
H283 H 0.6149 0.5225 0.1632 0.1708 1.0000 Uiso R . . . . .
H291 H 0.4878 0.2012 0.4043 0.1659 1.0000 Uiso R . . . . .
H292 H 0.5390 0.1790 0.4581 0.1659 1.0000 Uiso R . . . . .
H293 H 0.5262 0.0985 0.3703 0.1653 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.826(16)
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 . N11 4_656 2.121(3) yes
Br1 . N11 . 2.121(3) yes
N11 . C12 . 1.350(4) yes
N11 . C16 . 1.358(5) yes
C12 . C13 . 1.378(5) yes
C12 . C17 . 1.494(6) yes
C13 . C14 . 1.363(6) yes
C13 . H131 . 0.913 no
C14 . C15 . 1.380(5) yes
C14 . C18 . 1.514(6) yes
C15 . C16 . 1.379(5) yes
C15 . H151 . 0.943 no
C16 . C19 . 1.501(5) yes
C17 . H171 . 0.954 no
C17 . H172 . 0.963 no
C17 . H173 . 0.958 no
C18 . H181 . 0.961 no
C18 . H182 . 0.958 no
C18 . H183 . 0.976 no
C19 . H191 . 0.958 no
C19 . H192 . 0.955 no
C19 . H193 . 0.949 no
Br2 . N21 2_666 2.117(3) yes
Br2 . N21 . 2.117(3) yes
N21 . C22 . 1.347(5) yes
N21 . C26 . 1.354(4) yes
C22 . C23 . 1.363(6) yes
C22 . C27 . 1.502(5) yes
C23 . C24 . 1.387(6) yes
C23 . H231 . 0.919 no
C24 . C25 . 1.373(6) yes
C24 . C28 . 1.498(6) yes
C25 . C26 . 1.373(6) yes
C25 . H251 . 0.934 no
C26 . C29 . 1.490(6) yes
C27 . H271 . 0.959 no
C27 . H272 . 0.961 no
C27 . H273 . 0.948 no
C28 . H281 . 0.949 no
C28 . H282 . 0.949 no
C28 . H283 . 0.968 no
C29 . H291 . 0.970 no
C29 . H292 . 0.954 no
C29 . H293 . 0.956 no
Cl1 . O11 . 1.338(6) yes
Cl1 . O12 . 1.391(6) yes
Cl1 . O13 . 1.395(6) yes
Cl1 . O14 . 1.356(6) yes
Cl1 . O111 . 1.377(7) yes
Cl1 . O112 . 1.342(7) yes
Cl1 . O113 . 1.355(6) yes
Cl1 . O114 . 1.415(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
N11 4_656 Br1 . N11 . 179.99 yes
Br1 . N11 . C12 . 120.7(2) yes
Br1 . N11 . C16 . 118.5(2) yes
C12 . N11 . C16 . 120.7(3) yes
N11 . C12 . C13 . 119.9(3) yes
N11 . C12 . C17 . 118.2(3) yes
C13 . C12 . C17 . 121.8(3) yes
C12 . C13 . C14 . 121.1(3) yes
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 119.8 no
C13 . C14 . C15 . 117.9(4) yes
C13 . C14 . C18 . 121.5(4) yes
C15 . C14 . C18 . 120.7(4) yes
C14 . C15 . C16 . 121.1(4) yes
C14 . C15 . H151 . 119.8 no
C16 . C15 . H151 . 119.1 no
C15 . C16 . N11 . 119.3(3) yes
C15 . C16 . C19 . 121.9(4) yes
N11 . C16 . C19 . 118.8(4) yes
C12 . C17 . H171 . 109.5 no
C12 . C17 . H172 . 108.1 no
H171 . C17 . H172 . 109.1 no
C12 . C17 . H173 . 112.2 no
H171 . C17 . H173 . 108.9 no
H172 . C17 . H173 . 109.0 no
C14 . C18 . H181 . 108.5 no
C14 . C18 . H182 . 107.4 no
H181 . C18 . H182 . 110.0 no
C14 . C18 . H183 . 110.9 no
H181 . C18 . H183 . 110.4 no
H182 . C18 . H183 . 109.6 no
C16 . C19 . H191 . 107.5 no
C16 . C19 . H192 . 110.1 no
H191 . C19 . H192 . 107.9 no
C16 . C19 . H193 . 110.1 no
H191 . C19 . H193 . 110.9 no
H192 . C19 . H193 . 110.3 no
N21 2_666 Br2 . N21 . 179.99 yes
Br2 . N21 . C22 . 119.9(2) yes
Br2 . N21 . C26 . 119.6(3) yes
C22 . N21 . C26 . 120.5(3) yes
N21 . C22 . C23 . 120.2(3) yes
N21 . C22 . C27 . 118.9(4) yes
C23 . C22 . C27 . 120.8(4) yes
C22 . C23 . C24 . 121.1(4) yes
C22 . C23 . H231 . 117.5 no
C24 . C23 . H231 . 121.4 no
C23 . C24 . C25 . 117.1(4) yes
C23 . C24 . C28 . 121.2(4) yes
C25 . C24 . C28 . 121.7(4) yes
C24 . C25 . C26 . 121.3(3) yes
C24 . C25 . H251 . 120.0 no
C26 . C25 . H251 . 118.7 no
C25 . C26 . N21 . 119.7(4) yes
C25 . C26 . C29 . 121.2(3) yes
N21 . C26 . C29 . 119.1(4) yes
C22 . C27 . H271 . 110.5 no
C22 . C27 . H272 . 109.8 no
H271 . C27 . H272 . 107.4 no
C22 . C27 . H273 . 109.3 no
H271 . C27 . H273 . 109.2 no
H272 . C27 . H273 . 110.7 no
C24 . C28 . H281 . 108.0 no
C24 . C28 . H282 . 106.4 no
H281 . C28 . H282 . 110.1 no
C24 . C28 . H283 . 108.1 no
H281 . C28 . H283 . 112.6 no
H282 . C28 . H283 . 111.5 no
C26 . C29 . H291 . 112.1 no
C26 . C29 . H292 . 107.6 no
H291 . C29 . H292 . 111.2 no
C26 . C29 . H293 . 108.6 no
H291 . C29 . H293 . 109.6 no
H292 . C29 . H293 . 107.5 no
O11 . Cl1 . O12 . 108.8(5) yes
O11 . Cl1 . O13 . 110.5(6) yes
O12 . Cl1 . O13 . 107.9(6) yes
O11 . Cl1 . O14 . 115.0(7) yes
O12 . Cl1 . O14 . 106.9(6) yes
O13 . Cl1 . O14 . 107.6(6) yes
O111 . Cl1 . O112 . 111.8(7) yes
O111 . Cl1 . O113 . 110.9(6) yes
O112 . Cl1 . O113 . 113.9(7) yes
O111 . Cl1 . O114 . 104.4(6) yes
O112 . Cl1 . O114 . 106.7(6) yes
O113 . Cl1 . O114 . 108.6(7) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 . H131 . O113 4_646 177 0.91 2.60 3.511(6) yes
C18 . H183 . O14 4_646 139 0.98 2.29 3.094(6) yes
C19 . H193 . O112 6_554 123 0.95 2.59 3.202(6) yes
C23 . H231 . O12 6_564 163 0.92 2.56 3.452(6) yes
C25 . H251 . O112 6_554 159 0.93 2.52 3.409(6) yes
C27 . H273 . O111 2_666 164 0.95 2.46 3.387(6) yes
C28 . H283 . O11 6_564 164 0.97 2.51 3.454(6) yes
C29 . H292 . O111 . 174 0.95 2.28 3.230(6) yes


####################################################################### 
# 
# 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_IColl2ClO4-II-100K
_database_code_depnum_ccdc_archive 'CCDC 1853992'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-06-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 100lcm18
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   29.0825(6)
_cell_length_b                   8.5757(2)
_cell_length_c                   15.4139(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.602(2)
_cell_angle_gamma                90
_cell_volume                     3751.66(14)

_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
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'
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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C16 H22 Cl1 I1 N2 O4 
# Dc =      1.66 Fooo =   1872.00 Mu =    149.17 M =    468.72
# Found Formula = C16 H22.00 Cl1 I1 N2 O4 
# Dc =      1.66 FOOO =   1871.99 Mu =    149.17 M =    468.72

_chemical_formula_sum            'C16 H22 Cl I N2 O4'
_chemical_formula_moiety         'C16 H22 I N2, Cl O4'
_chemical_compound_source        .
_chemical_formula_weight         468.72


_cell_measurement_reflns_used    6392
_cell_measurement_theta_min      5
_cell_measurement_theta_max      75
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.041
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_max          0.211

_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1871.992
_exptl_absorpt_coefficient_mu    14.917

# Sheldrick geometric approximatio 0.09 0.54 
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
; 
 Gaussian Integration (Busing and Levy, 1957) 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 4 0.0600
0 1 -5 0.0800
-1 1 0 0.0800
1 -1 -1 0.0800
1 0 0 0.0010
-1 0 0 0.0400
0 0 1 0.0800

_exptl_absorpt_correction_T_min  0.136
_exptl_absorpt_correction_T_max  0.748
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Refined from known structure'
_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            12365
_reflns_number_total             3878
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.0447
# Number of reflections with Friedels Law is 3878 
# Theoretical number of reflections is about 7868 


_diffrn_reflns_theta_min         5.389
_diffrn_reflns_theta_max         76.341
_diffrn_measured_fraction_theta_max 0.986

_diffrn_reflns_theta_full        74.051
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -36
_reflns_limit_h_max              35
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.67
_refine_diff_density_max         1.21


# 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     0
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3869
_oxford_refine_ls_R_factor_ref   0.0395
_refine_ls_wR_factor_ref         0.1035
_refine_ls_goodness_of_fit_ref   1.0089
_refine_ls_shift/su_max          0.0002682
_refine_ls_shift/su_mean         0.0000228


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3870
_refine_ls_R_factor_all          0.0396
_refine_ls_wR_factor_all         0.1036

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3455
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_gt          0.0991


_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 + 7.68P] 
 ,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 0.7500 0.2500 0.5000 0.0367 1.0000 Uani S . . . . .
N11 N 0.74490(12) 0.0040(3) 0.4430(2) 0.0383 1.0000 Uani . . . . . .
C12 C 0.78439(13) -0.0821(4) 0.4463(2) 0.0372 1.0000 Uani . . . . . .
C13 C 0.78199(13) -0.2215(5) 0.4010(3) 0.0395 1.0000 Uani . . . . . .
C14 C 0.73925(14) -0.2758(5) 0.3503(3) 0.0414 1.0000 Uani . . . . . .
C15 C 0.69932(14) -0.1869(5) 0.3509(3) 0.0425 1.0000 Uani . . . . . .
C16 C 0.70256(14) -0.0490(5) 0.3983(3) 0.0427 1.0000 Uani . . . . . .
C17 C 0.83064(14) -0.0210(5) 0.4990(3) 0.0457 1.0000 Uani . . . . . .
C18 C 0.73570(17) -0.4223(6) 0.2959(3) 0.0543 1.0000 Uani . . . . . .
C19 C 0.65898(16) 0.0457(7) 0.3998(4) 0.0610 1.0000 Uani . . . . . .
I2 I 0.5000 0.5000 0.5000 0.0367 1.0000 Uani S . . . . .
N21 N 0.53526(11) 0.4679(4) 0.3828(2) 0.0391 1.0000 Uani . . . . . .
C22 C 0.54934(12) 0.5931(4) 0.3423(3) 0.0395 1.0000 Uani . . . . . .
C23 C 0.57378(13) 0.5751(4) 0.2754(3) 0.0413 1.0000 Uani . . . . . .
C24 C 0.58448(12) 0.4261(5) 0.2486(3) 0.0440 1.0000 Uani . . . . . .
C25 C 0.56795(14) 0.3002(5) 0.2891(3) 0.0465 1.0000 Uani . . . . . .
C26 C 0.54346(14) 0.3212(4) 0.3557(3) 0.0439 1.0000 Uani . . . . . .
C27 C 0.53766(17) 0.7531(4) 0.3702(3) 0.0492 1.0000 Uani . . . . . .
C28 C 0.61263(15) 0.4045(5) 0.1792(3) 0.0528 1.0000 Uani . . . . . .
C29 C 0.5255(2) 0.1849(5) 0.3988(4) 0.0630 1.0000 Uani . . . . . .
Cl1 Cl 0.61060(4) 0.04983(12) 0.63223(7) 0.0492 1.0000 Uani . . . . . .
O11 O 0.6197(3) 0.1980(6) 0.6039(4) 0.1299 1.0000 Uani . . . . . .
O12 O 0.57960(16) 0.0623(4) 0.6918(4) 0.0847 1.0000 Uani . . . . . .
O13 O 0.5926(2) -0.0515(5) 0.5598(3) 0.0939 1.0000 Uani . . . . . .
O14 O 0.65184(16) -0.0230(6) 0.6826(4) 0.1134 1.0000 Uani . . . . . .
H131 H 0.8096 -0.2790 0.4042 0.0468 1.0000 Uiso R . . . . .
H151 H 0.6698 -0.2205 0.3179 0.0505 1.0000 Uiso R . . . . .
H171 H 0.8551 -0.0972 0.4996 0.0685 1.0000 Uiso R . . . . .
H172 H 0.8391 0.0738 0.4737 0.0686 1.0000 Uiso R . . . . .
H173 H 0.8285 -0.0009 0.5583 0.0686 1.0000 Uiso R . . . . .
H181 H 0.7086 -0.4822 0.2993 0.0811 1.0000 Uiso R . . . . .
H182 H 0.7333 -0.3939 0.2358 0.0813 1.0000 Uiso R . . . . .
H183 H 0.7631 -0.4851 0.3134 0.0812 1.0000 Uiso R . . . . .
H191 H 0.6565 0.0668 0.4602 0.0908 1.0000 Uiso R . . . . .
H192 H 0.6601 0.1438 0.3691 0.0904 1.0000 Uiso R . . . . .
H193 H 0.6319 -0.0110 0.3695 0.0910 1.0000 Uiso R . . . . .
H231 H 0.5829 0.6623 0.2474 0.0503 1.0000 Uiso R . . . . .
H251 H 0.5732 0.1995 0.2710 0.0559 1.0000 Uiso R . . . . .
H271 H 0.5465 0.8273 0.3306 0.0738 1.0000 Uiso R . . . . .
H272 H 0.5551 0.7735 0.4307 0.0735 1.0000 Uiso R . . . . .
H273 H 0.5047 0.7615 0.3671 0.0738 1.0000 Uiso R . . . . .
H281 H 0.5972 0.3299 0.1357 0.0789 1.0000 Uiso R . . . . .
H282 H 0.6439 0.3688 0.2070 0.0787 1.0000 Uiso R . . . . .
H283 H 0.6149 0.5026 0.1509 0.0791 1.0000 Uiso R . . . . .
H291 H 0.4923 0.1944 0.3972 0.0948 1.0000 Uiso R . . . . .
H292 H 0.5424 0.1777 0.4607 0.0950 1.0000 Uiso R . . . . .
H293 H 0.5309 0.0922 0.3679 0.0949 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.611(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 . N11 4_656 2.278(3) yes
I1 . N11 . 2.278(3) yes
N11 . C12 . 1.357(5) yes
N11 . C16 . 1.352(5) yes
C12 . C13 . 1.379(5) yes
C12 . C17 . 1.505(5) yes
C13 . C14 . 1.396(6) yes
C13 . H131 . 0.934 no
C14 . C15 . 1.391(6) yes
C14 . C18 . 1.501(6) yes
C15 . C16 . 1.383(6) yes
C15 . H151 . 0.941 no
C16 . C19 . 1.509(5) yes
C17 . H171 . 0.964 no
C17 . H172 . 0.957 no
C17 . H173 . 0.945 no
C18 . H181 . 0.951 no
C18 . H182 . 0.946 no
C18 . H183 . 0.951 no
C19 . H191 . 0.966 no
C19 . H192 . 0.968 no
C19 . H193 . 0.956 no
I2 . N21 2_666 2.280(3) yes
I2 . N21 . 2.280(3) yes
N21 . C22 . 1.350(5) yes
N21 . C26 . 1.362(5) yes
C22 . C23 . 1.382(6) yes
C22 . C27 . 1.499(5) yes
C23 . C24 . 1.400(5) yes
C23 . H231 . 0.930 no
C24 . C25 . 1.385(6) yes
C24 . C28 . 1.493(6) yes
C25 . C26 . 1.383(6) yes
C25 . H251 . 0.930 no
C26 . C29 . 1.494(6) yes
C27 . H271 . 0.955 no
C27 . H272 . 0.975 no
C27 . H273 . 0.953 no
C28 . H281 . 0.964 no
C28 . H282 . 0.968 no
C28 . H283 . 0.957 no
C29 . H291 . 0.965 no
C29 . H292 . 0.975 no
C29 . H293 . 0.957 no
Cl1 . O11 . 1.388(5) yes
Cl1 . O12 . 1.424(4) yes
Cl1 . O13 . 1.421(4) yes
Cl1 . O14 . 1.423(5) 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
N11 4_656 I1 . N11 . 179.99 yes
I1 . N11 . C12 . 120.4(3) yes
I1 . N11 . C16 . 118.9(3) yes
C12 . N11 . C16 . 120.4(3) yes
N11 . C12 . C13 . 120.2(3) yes
N11 . C12 . C17 . 118.7(3) yes
C13 . C12 . C17 . 121.0(3) yes
C12 . C13 . C14 . 120.9(4) yes
C12 . C13 . H131 . 118.9 no
C14 . C13 . H131 . 120.2 no
C13 . C14 . C15 . 117.1(4) yes
C13 . C14 . C18 . 122.4(4) yes
C15 . C14 . C18 . 120.4(4) yes
C14 . C15 . C16 . 120.8(4) yes
C14 . C15 . H151 . 119.5 no
C16 . C15 . H151 . 119.7 no
C15 . C16 . N11 . 120.4(4) yes
C15 . C16 . C19 . 120.5(4) yes
N11 . C16 . C19 . 119.1(4) yes
C12 . C17 . H171 . 109.9 no
C12 . C17 . H172 . 110.8 no
H171 . C17 . H172 . 108.9 no
C12 . C17 . H173 . 110.2 no
H171 . C17 . H173 . 108.6 no
H172 . C17 . H173 . 108.5 no
C14 . C18 . H181 . 112.3 no
C14 . C18 . H182 . 108.2 no
H181 . C18 . H182 . 107.9 no
C14 . C18 . H183 . 111.4 no
H181 . C18 . H183 . 109.3 no
H182 . C18 . H183 . 107.6 no
C16 . C19 . H191 . 110.8 no
C16 . C19 . H192 . 110.0 no
H191 . C19 . H192 . 109.0 no
C16 . C19 . H193 . 108.8 no
H191 . C19 . H193 . 109.8 no
H192 . C19 . H193 . 108.3 no
N21 2_666 I2 . N21 . 179.99 yes
I2 . N21 . C22 . 120.3(2) yes
I2 . N21 . C26 . 119.6(3) yes
C22 . N21 . C26 . 120.1(4) yes
N21 . C22 . C23 . 120.9(3) yes
N21 . C22 . C27 . 119.0(4) yes
C23 . C22 . C27 . 120.1(4) yes
C22 . C23 . C24 . 120.4(4) yes
C22 . C23 . H231 . 120.1 no
C24 . C23 . H231 . 119.5 no
C23 . C24 . C25 . 117.2(4) yes
C23 . C24 . C28 . 121.2(4) yes
C25 . C24 . C28 . 121.7(4) yes
C24 . C25 . C26 . 121.3(4) yes
C24 . C25 . H251 . 119.5 no
C26 . C25 . H251 . 119.2 no
C25 . C26 . N21 . 120.1(4) yes
C25 . C26 . C29 . 121.0(4) yes
N21 . C26 . C29 . 119.0(4) yes
C22 . C27 . H271 . 108.4 no
C22 . C27 . H272 . 109.6 no
H271 . C27 . H272 . 109.7 no
C22 . C27 . H273 . 110.1 no
H271 . C27 . H273 . 109.1 no
H272 . C27 . H273 . 109.9 no
C24 . C28 . H281 . 109.5 no
C24 . C28 . H282 . 109.4 no
H281 . C28 . H282 . 110.5 no
C24 . C28 . H283 . 108.6 no
H281 . C28 . H283 . 109.6 no
H282 . C28 . H283 . 109.2 no
C26 . C29 . H291 . 111.6 no
C26 . C29 . H292 . 109.6 no
H291 . C29 . H292 . 108.4 no
C26 . C29 . H293 . 108.6 no
H291 . C29 . H293 . 109.2 no
H292 . C29 . H293 . 109.4 no
O11 . Cl1 . O12 . 109.0(3) yes
O11 . Cl1 . O13 . 112.1(3) yes
O12 . Cl1 . O13 . 112.1(3) yes
O11 . Cl1 . O14 . 112.2(4) yes
O12 . Cl1 . O14 . 104.9(4) yes
O13 . Cl1 . O14 . 106.4(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 . H131 . O14 4_646 142 0.93 2.57 3.353(6) yes
C18 . H183 . O14 4_646 140 0.95 2.46 3.249(6) yes
C23 . H231 . O12 6_564 157 0.93 2.51 3.384(6) yes
C25 . H251 . O12 6_554 169 0.93 2.58 3.500(6) yes
C27 . H272 . O13 1_565 154 0.98 2.54 3.444(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
-3 1 1 x .
8 0 2 x .
6 0 2 x .
4 0 2 x .
-1 1 4 x .
-4 0 2 x .
1 1 1 x .
-23 7 8 x .
