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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1531716'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.6168(4)
_cell_length_b                   11.1573(3)
_cell_length_c                   10.8342(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1404.24(8)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 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'
Cl 0.1484 0.1585 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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C3 H9 Cl1 I1 N1 
# Dc =      2.09 Fooo =    832.00 Mu =     48.24 M =    221.47
# Found Formula = C3 H9 Cl1 I1 N1 
# Dc =      2.09 FOOO =    832.00 Mu =     48.24 M =    221.47

_chemical_formula_sum            'C3 H9 Cl1 I1 N1'
_chemical_formula_moiety         'C3 H9 Cl1 I1 N1'
_chemical_compound_source        ?
_chemical_formula_weight         221.47


_cell_measurement_reflns_used    12025
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    298

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.180
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.240

_exptl_crystal_density_diffrn    2.095
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    4.824

# Sheldrick geometric approximatio 0.38 0.42 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_T_max  0.42
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      298
_diffrn_reflns_number            1607
_reflns_number_total             1607
_diffrn_reflns_av_R_equivalents  0.033
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1607 
# Theoretical number of reflections is about 3222 


_diffrn_reflns_theta_min         3.153
_diffrn_reflns_theta_max         27.489
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        27.489
_diffrn_measured_fraction_theta_full 0.999


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

_oxford_diffrn_Wilson_B_factor   2.80
_oxford_diffrn_Wilson_scale      10.04

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

_refine_diff_density_min         -0.81
_refine_diff_density_max         0.68


# 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         1601
_refine_ls_number_restraints     18
_refine_ls_number_parameters     85
_oxford_refine_ls_R_factor_ref   0.0333
_refine_ls_wR_factor_ref         0.0399
_refine_ls_goodness_of_fit_ref   0.9793
_refine_ls_shift/su_max          0.0004949
_refine_ls_shift/su_mean         0.0000236


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1601
_refine_ls_R_factor_all          0.0333
_refine_ls_wR_factor_all         0.0399

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1333
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_gt          0.0365

# 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    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 12.5 15.8 4.89 
;

# 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 0.40237(2) 0.36577(2) 0.60062(2) 0.0329 1.0000 Uani . . . . . .
Cl2 Cl 0.52611(10) 0.25519(12) 0.44140(11) 0.0527 1.0000 Uani . . . . . .
N3 N 0.2936(3) 0.4629(3) 0.7477(3) 0.0342 1.0000 Uani D . . . . .
C1 C 0.2333(4) 0.3715(5) 0.8233(4) 0.0470 1.0000 Uani D . . . . .
C2 C 0.3709(4) 0.5357(4) 0.8256(5) 0.0461 1.0000 Uani D . . . . .
C3 C 0.2082(4) 0.5404(5) 0.6854(5) 0.0549 1.0000 Uani D . . . . .
H11 H 0.185(4) 0.410(3) 0.894(5) 0.063(9) 1.0000 Uiso D . . . . .
H12 H 0.180(4) 0.320(3) 0.768(4) 0.064(9) 1.0000 Uiso D . . . . .
H13 H 0.294(4) 0.322(4) 0.865(4) 0.064(9) 1.0000 Uiso D . . . . .
H21 H 0.325(3) 0.580(4) 0.886(4) 0.065(9) 1.0000 Uiso D . . . . .
H22 H 0.425(4) 0.483(4) 0.868(4) 0.065(9) 1.0000 Uiso D . . . . .
H23 H 0.417(4) 0.597(4) 0.770(4) 0.065(9) 1.0000 Uiso D . . . . .
H31 H 0.157(4) 0.577(3) 0.751(4) 0.067(9) 1.0000 Uiso D . . . . .
H32 H 0.248(3) 0.605(4) 0.637(4) 0.067(9) 1.0000 Uiso D . . . . .
H33 H 0.166(3) 0.497(4) 0.632(4) 0.067(9) 1.0000 Uiso D . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.03185(12) 0.03428(12) 0.03266(12) 0.00051(11) 0.00045(11) -0.00169(11)
Cl2 0.0548(6) 0.0538(6) 0.0495(6) -0.0140(5) 0.0111(6) -0.0002(6)
N3 0.0312(16) 0.0346(17) 0.0368(17) 0.0025(16) 0.0030(15) 0.0018(15)
C1 0.041(2) 0.048(3) 0.053(3) 0.003(2) 0.014(2) -0.012(2)
C2 0.046(3) 0.046(3) 0.046(3) -0.009(2) 0.002(2) -0.006(2)
C3 0.050(3) 0.060(3) 0.055(3) 0.001(3) -0.004(2) 0.024(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.31166(17)
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 . Cl2 . 2.5621(12) yes
I1 . N3 . 2.304(3) yes
N3 . C1 . 1.485(5) yes
N3 . C2 . 1.476(5) yes
N3 . C3 . 1.478(5) yes
C1 . H11 . 1.04(5) no
C1 . H12 . 1.03(5) no
C1 . H13 . 1.00(5) no
C2 . H21 . 0.97(5) no
C2 . H22 . 0.98(5) no
C2 . H23 . 1.06(5) no
C3 . H31 . 1.01(5) no
C3 . H32 . 1.01(5) no
C3 . H33 . 0.90(5) 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
Cl2 . I1 . N3 . 178.58(9) yes
I1 . N3 . C1 . 108.5(3) yes
I1 . N3 . C2 . 108.7(3) yes
C1 . N3 . C2 . 110.5(3) yes
I1 . N3 . C3 . 109.1(3) yes
C1 . N3 . C3 . 109.7(4) yes
C2 . N3 . C3 . 110.3(3) yes
N3 . C1 . H11 . 111.8(19) no
N3 . C1 . H12 . 110.0(19) no
H11 . C1 . H12 . 109(2) no
N3 . C1 . H13 . 107.5(19) no
H11 . C1 . H13 . 106(2) no
H12 . C1 . H13 . 112(2) no
N3 . C2 . H21 . 109.2(20) no
N3 . C2 . H22 . 109.6(19) no
H21 . C2 . H22 . 110(2) no
N3 . C2 . H23 . 110.1(18) no
H21 . C2 . H23 . 109(2) no
H22 . C2 . H23 . 109(2) no
N3 . C3 . H31 . 108.2(20) no
N3 . C3 . H32 . 111(2) no
H31 . C3 . H32 . 110(2) no
N3 . C3 . H33 . 110(2) no
H31 . C3 . H33 . 110(2) no
H32 . C3 . H33 . 108(2) no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 08/12/13 at 01:36:12
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT I    (    1 ,X'S,U'S)  UNTIL C    (    3 ) 
CONT H    (   11 ,X'S,U[ISO])  UNTIL H    (   33 ) 
EQUIV H(11,U[ISO]) UNTIL H(13) 
EQUIV H(21,U[ISO]) UNTIL H(23) 
EQUIV H(31,U[ISO]) UNTIL H(33) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 08/12/13 at 01:36:12
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            3 H ON SP 3 
ANGLE 109.54, 3.0 = 
CONT N(3) TO C ( 1) TO H(11) 
CONT N(3) TO C ( 1) TO H(12) 
CONT N(3) TO C ( 1) TO H(13) 
ANGLE 0.0, 3.0 = MEAN H(11) TO C ( 1) TO H(12) 
CONT H(11) TO C ( 1) TO H(13) 
CONT H(12) TO C ( 1) TO H(13) 
REM            3 H ON SP 3 
ANGLE 109.54, 3.0 = 
CONT N(3) TO C ( 2) TO H(21) 
CONT N(3) TO C ( 2) TO H(22) 
CONT N(3) TO C ( 2) TO H(23) 
ANGLE 0.0, 3.0 = MEAN H(21) TO C ( 2) TO H(22) 
CONT H(21) TO C ( 2) TO H(23) 
CONT H(22) TO C ( 2) TO H(23) 
REM            3 H ON SP 3 
ANGLE 109.54, 3.0 = 
CONT N(3) TO C ( 3) TO H(31) 
CONT N(3) TO C ( 3) TO H(32) 
CONT N(3) TO C ( 3) TO H(33) 
ANGLE 0.0, 3.0 = MEAN H(31) TO C ( 3) TO H(32) 
CONT H(31) TO C ( 3) TO H(33) 
CONT H(32) TO C ( 3) TO H(33) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 2 3 x .
_chemical_name_systematic        'Trimethylamine Iodine Monochloride Complex'
_chemical_name_common            TMA_ICL
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1531709'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.5039(3)
_cell_length_b                   10.9570(3)
_cell_length_c                   10.6758(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1345.67(6)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 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'
Cl 0.1484 0.1585 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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C3 H9 Cl1 I1 N1 
# Dc =      2.19 Fooo =    832.00 Mu =     50.34 M =    221.47
# Found Formula = C3 H9 Cl1 I1 N1 
# Dc =      2.19 FOOO =    832.00 Mu =     50.34 M =    221.47

_chemical_formula_sum            'C3 H9 Cl1 I1 N1'
_chemical_formula_moiety         'C3 H9 Cl1 I1 N1'
_chemical_compound_source        ?
_chemical_formula_weight         221.47


_cell_measurement_reflns_used    10668
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    110

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.180
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.240

_exptl_crystal_density_diffrn    2.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    5.034

# Sheldrick geometric approximatio 0.37 0.40 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.30
_exptl_absorpt_correction_T_max  0.40
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      110
_diffrn_reflns_number            9192
_reflns_number_total             1539
_diffrn_reflns_av_R_equivalents  0.030
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1539 
# Theoretical number of reflections is about 3080 


_diffrn_reflns_theta_min         3.199
_diffrn_reflns_theta_max         27.464
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        27.464
_diffrn_measured_fraction_theta_full 0.999


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

_oxford_diffrn_Wilson_B_factor   0.79
_oxford_diffrn_Wilson_scale      12.16

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

_refine_diff_density_min         -0.79
_refine_diff_density_max         0.56


# 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         1539
_refine_ls_number_restraints     0
_refine_ls_number_parameters     85
_oxford_refine_ls_R_factor_ref   0.0237
_refine_ls_wR_factor_ref         0.0353
_refine_ls_goodness_of_fit_ref   1.0001
_refine_ls_shift/su_max          0.0007647
_refine_ls_shift/su_mean         0.0000320


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1539
_refine_ls_R_factor_all          0.0237
_refine_ls_wR_factor_all         0.0353

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1418

_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_gt          0.0341

# 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    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 14.2 18.1 6.17 
;

# 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 0.404991(16) 0.366499(17) 0.601730(18) 0.0095 1.0000 Uani . . . . . .
Cl2 Cl 0.53050(7) 0.25578(8) 0.43695(7) 0.0155 1.0000 Uani . . . . . .
N3 N 0.2952(2) 0.4625(2) 0.7523(2) 0.0101 1.0000 Uani . . . . . .
C1 C 0.2359(3) 0.3675(3) 0.8278(3) 0.0148 1.0000 Uani . . . . . .
C2 C 0.3732(3) 0.5367(3) 0.8318(3) 0.0150 1.0000 Uani . . . . . .
C3 C 0.2077(3) 0.5413(3) 0.6899(3) 0.0159 1.0000 Uani . . . . . .
H11 H 0.187(3) 0.404(3) 0.900(4) 0.019(6) 1.0000 Uiso . . . . . .
H12 H 0.182(3) 0.318(3) 0.768(4) 0.019(6) 1.0000 Uiso . . . . . .
H13 H 0.290(3) 0.313(4) 0.863(4) 0.019(6) 1.0000 Uiso . . . . . .
H21 H 0.329(4) 0.577(4) 0.894(4) 0.022(6) 1.0000 Uiso . . . . . .
H22 H 0.432(3) 0.485(4) 0.872(4) 0.022(6) 1.0000 Uiso . . . . . .
H23 H 0.419(3) 0.603(3) 0.778(4) 0.022(6) 1.0000 Uiso . . . . . .
H31 H 0.162(4) 0.580(3) 0.756(4) 0.023(6) 1.0000 Uiso . . . . . .
H32 H 0.243(4) 0.603(4) 0.646(4) 0.023(6) 1.0000 Uiso . . . . . .
H33 H 0.157(4) 0.491(4) 0.638(4) 0.023(6) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.00949(9) 0.00973(9) 0.00918(8) 0.00016(7) 0.00031(7) -0.00037(8)
Cl2 0.0166(3) 0.0157(3) 0.0141(4) -0.0039(3) 0.0032(3) -0.0001(3)
N3 0.0094(11) 0.0115(12) 0.0095(12) 0.0006(11) 0.0013(10) 0.0009(10)
C1 0.0144(15) 0.0134(14) 0.0165(15) 0.0033(14) 0.0045(13) -0.0008(13)
C2 0.0158(16) 0.0157(15) 0.0135(15) -0.0038(13) -0.0022(12) -0.0008(13)
C3 0.0170(15) 0.0130(15) 0.0178(16) 0.0011(13) -0.0015(13) 0.0071(13)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.28878(14)
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 . Cl2 . 2.5790(8) yes
I1 . N3 . 2.299(3) yes
N3 . C1 . 1.483(4) yes
N3 . C2 . 1.478(4) yes
N3 . C3 . 1.484(4) yes
C1 . H11 . 1.03(4) no
C1 . H12 . 1.04(4) no
C1 . H13 . 0.94(4) no
C2 . H21 . 0.95(4) no
C2 . H22 . 0.98(4) no
C2 . H23 . 1.07(4) no
C3 . H31 . 0.98(4) no
C3 . H32 . 0.92(4) no
C3 . H33 . 0.97(4) 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
Cl2 . I1 . N3 . 178.65(7) yes
I1 . N3 . C1 . 108.15(19) yes
I1 . N3 . C2 . 108.61(19) yes
C1 . N3 . C2 . 110.7(3) yes
I1 . N3 . C3 . 108.98(19) yes
C1 . N3 . C3 . 109.9(2) yes
C2 . N3 . C3 . 110.5(2) yes
N3 . C1 . H11 . 113(2) no
N3 . C1 . H12 . 108(2) no
H11 . C1 . H12 . 109(3) no
N3 . C1 . H13 . 111(2) no
H11 . C1 . H13 . 108(3) no
H12 . C1 . H13 . 108(3) no
N3 . C2 . H21 . 110(2) no
N3 . C2 . H22 . 110(2) no
H21 . C2 . H22 . 110(3) no
N3 . C2 . H23 . 111(2) no
H21 . C2 . H23 . 109(3) no
H22 . C2 . H23 . 107(3) no
N3 . C3 . H31 . 107(2) no
N3 . C3 . H32 . 111(3) no
H31 . C3 . H32 . 107(3) no
N3 . C3 . H33 . 109(2) no
H31 . C3 . H33 . 110(3) no
H32 . C3 . H33 . 113(3) no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 08/12/13 at 01:42:51
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT I    (    1 ,X'S,U'S)  UNTIL C    (    3 ) 
CONT H    (   11 ,X'S,U[ISO])  UNTIL H    (   33 ) 
EQUIV H(11,U[ISO]) UNTIL H(13) 
EQUIV H(21,U[ISO]) UNTIL H(23) 
EQUIV H(31,U[ISO]) UNTIL H(33) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 08/12/13 at 01:42:51
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_systematic        'Trimethylamine Iodine momochloride comples'
_chemical_name_common            TAMICl
####################################################################### 
# 
# 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_TMA-ICL-OUT_phase_1
_database_code_depnum_ccdc_archive 'CCDC 1531801'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_pd_block_id                     2013-11-23T04:03|TMA-ICL-OUT_phase1|r||

# Histograms for phase 1
loop_
_pd_block_diffractogram_id
2013-11-23T04:03|TMA-ICL-OUT_H_01|r|hrpd
2013-11-23T04:03|TMA-ICL-OUT_H_02|r|hrpd
2013-11-23T04:03|TMA-ICL-OUT_H_03|r|hrpd

#==============================================================================
# 7. CHEMICAL, STRUCTURAL AND CRYSTAL DATA

_pd_char_particle_morphology     ?
_pd_char_colour                  yellow
_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and
# natural products
_symmetry_space_group_name_Hall  ?

_exptl_crystal_F_000             ?
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_cell_measurement_temperature    110
_diffrn_ambient_temperature      110
_cell_special_details            
; ?
;

_geom_special_details            ?

# The following item identifies the program(s) used (if appropriate).
_computing_structure_solution    ?


# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: J Clews preparation of material
S J Coles preparation of manuscript
R. J. Darton NMR studies, preparation of Manuscript
M. B. Pitak X-Ray data collection, initial analysis, preparation of manuscript
R. H. Jones Grant application, preparation of material Neutron Data collection 
Analysis of Data (Neutron and XRD, preparation of Manuscript)
K. S. Knight Neutron Data collection and initial analysis, 
and preparation of manuscript. 
W. G. Marshall Grant application , preparation of manuscript
W. Miller  XRD and neutron data analysis
;


_vrf_DIFF002_TMA-ICL-OUT_phase_1 
;
PROBLEM: _diffrn_radiation_wavelength is missing
RESPONSE:  TOF experiment
;
# end Validation Reply Form


#==============================================================================

# 8. Phase information from GSAS

_pd_phase_name                   TMAICL482648
_cell_length_a                   11.4812(7)
_cell_length_b                   10.9618(6)
_cell_length_c                   10.6723(6)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1343.16(21)
_diffrn_measurement_device_type  'ISIS HRPD '
_diffrn_radiation_type           neutron
_pd_instr_location               'ISIS spallation source, England'
_pd_meas_scan_method             tof
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_pd_proc_ls_prof_R_factor        0.0113
_pd_proc_ls_prof_wR_factor       0.0135
_pd_proc_ls_prof_wR_expected     0.0063
_refine_ls_R_Fsqd_factor         0.08792
_refine_ls_shift/su_max          0.01
_refine_ls_goodness_of_fit_all   2.64
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +x,+y,+z
2 -x+1/2,+y+1/2,+z
3 +x,-y+1/2,+z+1/2
4 -x+1/2,-y,+z+1/2
-1 -x,-y,-z
-2 +x+1/2,-y+1/2,-z
-3 -x,+y+1/2,-z+1/2
-4 +x+1/2,+y,-z+1/2

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
_vrf_DIFF001_TMA-ICL-OUT_phase_2 
;
PROBLEM: _diffrn_radiation_type is missing
RESPONSE: TOF
;

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
I I1 0.4026(5) 0.3658(4) 0.6026(4) 1.0 Uiso 0.0197(14) 8
Cl Cl2 0.52932(26) 0.25636(22) 0.43800(27) 1.0 Uiso 0.0203(8) 8
N N3 0.29339(23) 0.46286(23) 0.75197(31) 1.0 Uiso 0.0038(5) 8
C C1 0.23415(34) 0.3695(4) 0.8279(4) 1.0 Uiso 0.0108(11) 8
C C2 0.37219(34) 0.5395(4) 0.8340(4) 1.0 Uiso 0.0108(11) 8
C C3 0.2046(4) 0.5392(4) 0.6898(4) 1.0 Uiso 0.0194(11) 8
D H11 0.1828(4) 0.4159(4) 0.9025(4) 1.0 Uiso 0.0309(14) 8
D H12 0.1793(4) 0.3170(4) 0.7674(4) 1.0 Uiso 0.0283(14) 8
D H13 0.3049(4) 0.30837(35) 0.8689(4) 1.0 Uiso 0.0214(11) 8
D H21 0.3221(4) 0.5899(4) 0.9011(4) 1.0 Uiso 0.0234(11) 8
D H22 0.4343(4) 0.4776(4) 0.87695(32) 1.0 Uiso 0.0171(12) 8
D H23 0.42092(35) 0.60405(31) 0.7699(4) 1.0 Uiso 0.0234(13) 8
D H31 0.1505(4) 0.5809(4) 0.7598(4) 1.0 Uiso 0.0339(14) 8
D H32 0.2554(4) 0.6099(5) 0.6320(4) 1.0 Uiso 0.0283(13) 8
D H33 0.1531(5) 0.4830(4) 0.6286(5) 1.0 Uiso 0.0354(13) 8

loop_
_atom_type_symbol
_atom_type_number_in_cell
I 8.0
Cl 8.0
N 8.0
C 24.0
D 72.0

# If you change Z, be sure to change all 3 of the following
_chemical_formula_sum            'C3 D9 Cl I N'
_chemical_formula_weight         230.52
_cell_formula_units_Z            8

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cl2 2.578(6) . 1_555 N
I1 N3 2.290(5) . 1_555 N
Cl2 I1 2.578(6) . 1_555 N
N3 I1 2.290(5) . 1_555 N
N3 C1 1.472(5) . 1_555 N
N3 C2 1.513(4) . 1_555 N
N3 C3 1.477(5) . 1_555 N
C1 N3 1.472(5) . 1_555 N
C1 H11 1.114(5) . 1_555 N
C1 H12 1.070(4) . 1_555 N
C1 H13 1.140(5) . 1_555 N
C2 N3 1.513(4) . 1_555 N
C2 H21 1.072(5) . 1_555 N
C2 H22 1.086(5) . 1_555 N
C2 H23 1.133(4) . 1_555 N
C3 N3 1.477(5) . 1_555 N
C3 H31 1.074(5) . 1_555 N
C3 H32 1.149(5) . 1_555 N
C3 H33 1.075(5) . 1_555 N
H11 C1 1.114(5) . 1_555 N
H11 H12 1.805(6) . 1_555 N
H11 H13 1.866(7) . 1_555 N
H12 C1 1.070(4) . 1_555 N
H12 H11 1.805(6) . 1_555 N
H12 H13 1.806(7) . 1_555 N
H13 C1 1.140(5) . 1_555 N
H13 H11 1.866(7) . 1_555 N
H13 H12 1.806(7) . 1_555 N
H21 C2 1.072(5) . 1_555 N
H21 H22 1.800(6) . 1_555 N
H21 H23 1.809(6) . 1_555 N
H22 C2 1.086(5) . 1_555 N
H22 H21 1.800(6) . 1_555 N
H22 H23 1.803(5) . 1_555 N
H23 C2 1.133(4) . 1_555 N
H23 H21 1.809(6) . 1_555 N
H23 H22 1.803(5) . 1_555 N
H31 C3 1.074(5) . 1_555 N
H31 H32 1.847(7) . 1_555 N
H31 H33 1.764(7) . 1_555 N
H32 C3 1.149(5) . 1_555 N
H32 H31 1.847(7) . 1_555 N
H32 H33 1.821(7) . 1_555 N
H33 C3 1.075(5) . 1_555 N
H33 H31 1.764(7) . 1_555 N
H33 H32 1.821(7) . 1_555 N

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 I1 N3 178.69(25) 1_555 . 1_555 N
I1 N3 C1 108.25(27) 1_555 . 1_555 N
I1 N3 C2 109.47(24) 1_555 . 1_555 N
I1 N3 C3 109.15(30) 1_555 . 1_555 N
C1 N3 C2 110.10(30) 1_555 . 1_555 N
C1 N3 C3 108.81(32) 1_555 . 1_555 N
C2 N3 C3 111.00(28) 1_555 . 1_555 N
N3 C1 H11 108.7(4) 1_555 . 1_555 N
N3 C1 H12 108.3(5) 1_555 . 1_555 N
N3 C1 H13 106.9(4) 1_555 . 1_555 N
H11 C1 H12 111.5(5) 1_555 . 1_555 N
H11 C1 H13 111.7(6) 1_555 . 1_555 N
H12 C1 H13 109.6(5) 1_555 . 1_555 N
N3 C2 H21 110.6(4) 1_555 . 1_555 N
N3 C2 H22 106.9(4) 1_555 . 1_555 N
N3 C2 H23 107.0(4) 1_555 . 1_555 N
H21 C2 H22 113.1(5) 1_555 . 1_555 N
H21 C2 H23 110.3(5) 1_555 . 1_555 N
H22 C2 H23 108.7(5) 1_555 . 1_555 N
N3 C3 H31 109.1(5) 1_555 . 1_555 N
N3 C3 H32 105.8(4) 1_555 . 1_555 N
N3 C3 H33 109.2(5) 1_555 . 1_555 N
H31 C3 H32 112.4(6) 1_555 . 1_555 N
H31 C3 H33 110.4(6) 1_555 . 1_555 N
H32 C3 H33 109.9(6) 1_555 . 1_555 N
_exptl_crystal_colour            Orange
