# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

####################################################################### 
# 
# 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_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 1979343'
loop_
_audit_author_name
_audit_author_address
'Santiago Uriel'
;University of Zaragoza
Spain
;
_audit_update_record             
;
2020-01-22 deposited with the CCDC.	2021-01-14 downloaded from the CCDC.
;
_audit_creation_date             
;
'Wed Mar 30 11:05:50 2011'
;
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H34 Br I2 N'
_chemical_formula_weight         658.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/m

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

_cell_length_a                   7.8843(4)
_cell_length_b                   14.5796(6)
_cell_length_c                   11.5600(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.065(3)
_cell_angle_gamma                90.00
_cell_volume                     1318.73(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1826
_cell_measurement_theta_min      2.9134
_cell_measurement_theta_max      26.5748

_exptl_crystal_description       Platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    3.908
_exptl_absorpt_correction_T_min  0.87254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5627
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2803
_reflns_number_gt                2080
_reflns_threshold_expression     >2sigma(I)


_computing_structure_solution    'SHELXTL Bruker'
_computing_structure_refinement  'SHELXTL Bruker'
_computing_molecular_graphics    'SHELXTL Bruker'
_computing_publication_material  'SHELXTL Bruker'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0298P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2803
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.35521(5) 0.00915(3) 0.15925(4) 0.03110(16) Uani 1 1 d . . .
Br1 Br 0.0000 0.0000 0.0000 0.0448(3) Uani 1 2 d S . .
N1 N 1.1479(11) 0.2500 0.8693(7) 0.040(2) Uani 1 2 d S . .
C1 C 1.2208(11) 0.1664(5) 0.8203(8) 0.0411(19) Uani 1 1 d . . .
H1A H 1.202(8) 0.166(4) 0.742(6) 0.03(2) Uiso 1 1 d . . .
H1B H 1.341(8) 0.168(3) 0.842(6) 0.030(18) Uiso 1 1 d . . .
H1C H 1.175(9) 0.113(5) 0.857(7) 0.07(2) Uiso 1 1 d . . .
C2 C 1.1854(18) 0.2500 0.9954(10) 0.070(4) Uani 1 2 d S . .
H2A H 1.1376 0.1961 1.0263 0.105 Uiso 0.50 1 calc PR . .
H2B H 1.1366 0.3036 1.0264 0.105 Uiso 0.50 1 calc PR . .
H2C H 1.3070 0.2503 1.0168 0.105 Uiso 1 2 calc SR . .
C3 C 0.9540(14) 0.2500 0.8364(11) 0.048(3) Uani 1 2 d S . .
H3 H 0.922(7) 0.191(3) 0.887(6) 0.037(18) Uiso 1 1 d . . .
C4 C 0.8903(15) 0.2500 0.7031(11) 0.063(4) Uani 1 2 d S . .
H4A H 0.9336 0.1961 0.6672 0.075 Uiso 0.50 1 calc PR . .
H4B H 0.9336 0.3039 0.6672 0.075 Uiso 0.50 1 calc PR . .
C5 C 0.6894(17) 0.2500 0.6821(11) 0.060(3) Uani 1 2 d S . .
H5 H 0.642(11) 0.190(5) 0.743(8) 0.12(3) Uiso 1 1 d . . .
C6 C 0.6145(15) 0.2500 0.5535(10) 0.044(3) Uani 1 2 d S . .
H6 H 0.668(8) 0.194(4) 0.519(6) 0.035(18) Uiso 1 1 d . . .
C7 C 0.4196(17) 0.2500 0.5413(10) 0.048(3) Uani 1 2 d S . .
H7 H 0.385(8) 0.203(4) 0.586(6) 0.04(2) Uiso 1 1 d . . .
C8 C 0.3353(15) 0.2500 0.4171(10) 0.045(3) Uani 1 2 d S . .
H8 H 0.382(9) 0.198(4) 0.387(7) 0.06(2) Uiso 1 1 d . . .
C9 C 0.1380(14) 0.2500 0.4097(9) 0.039(2) Uani 1 2 d S . .
H9 H 0.104(7) 0.192(3) 0.459(5) 0.030(16) Uiso 1 1 d . . .
C10 C 0.0483(14) 0.2500 0.2880(10) 0.044(3) Uani 1 2 d S . .
H10 H 0.088(8) 0.193(4) 0.257(6) 0.040(19) Uiso 1 1 d . . .
C11 C -0.1441(15) 0.2500 0.2801(11) 0.048(3) Uani 1 2 d S . .
H11 H -0.175(7) 0.196(3) 0.328(5) 0.021(15) Uiso 1 1 d . . .
C12 C -0.2449(15) 0.2500 0.1556(12) 0.071(4) Uani 1 2 d S . .
H12A H -0.3654 0.2500 0.1613 0.107 Uiso 1 2 calc SR . .
H12B H -0.2158 0.1962 0.1143 0.107 Uiso 0.50 1 calc PR . .
H12C H -0.2158 0.3038 0.1143 0.107 Uiso 0.50 1 calc PR . .
C13 C 0.5687(8) 0.0124(4) 0.2741(6) 0.0334(16) Uani 1 1 d . . .
C14 C 0.6936(7) 0.0106(3) 0.3440(6) 0.0234(13) Uani 1 1 d . . .
C15 C 0.8502(7) 0.0056(3) 0.4234(6) 0.0261(14) Uani 1 1 d . . .
C16 C 0.8437(7) 0.0011(3) 0.5434(6) 0.0278(14) Uani 1 1 d . . .
H16 H 0.7387 0.0013 0.5723 0.033 Uiso 1 1 calc R . .
C17 C 0.9921(8) -0.0036(3) 0.6188(6) 0.0304(14) Uani 1 1 d . . .
H17 H 0.9872 -0.0054 0.6987 0.036 Uiso 1 1 calc R . .

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 0.0210(2) 0.0416(3) 0.0292(3) -0.0005(2) -0.00313(17) 0.00322(17)
Br1 0.0309(5) 0.0490(6) 0.0492(7) 0.0203(5) -0.0167(5) -0.0173(4)
N1 0.057(6) 0.027(4) 0.043(6) 0.000 0.032(5) 0.000
C1 0.051(5) 0.029(4) 0.048(6) 0.002(4) 0.024(4) 0.004(4)
C2 0.145(13) 0.032(6) 0.037(7) 0.000 0.028(8) 0.000
C3 0.062(8) 0.030(6) 0.057(8) 0.000 0.032(6) 0.000
C4 0.088(10) 0.050(7) 0.058(9) 0.000 0.038(7) 0.000
C5 0.072(9) 0.068(8) 0.044(8) 0.000 0.028(7) 0.000
C6 0.059(7) 0.041(7) 0.034(6) 0.000 0.014(5) 0.000
C7 0.073(8) 0.042(7) 0.031(7) 0.000 0.019(6) 0.000
C8 0.055(7) 0.048(7) 0.037(7) 0.000 0.026(6) 0.000
C9 0.062(7) 0.028(6) 0.032(6) 0.000 0.021(5) 0.000
C10 0.056(7) 0.029(6) 0.051(8) 0.000 0.026(6) 0.000
C11 0.067(8) 0.032(6) 0.052(8) 0.000 0.033(6) 0.000
C12 0.063(9) 0.077(9) 0.076(11) 0.000 0.021(8) 0.000
C13 0.023(3) 0.036(4) 0.040(4) -0.013(3) -0.001(3) 0.003(3)
C14 0.020(3) 0.016(3) 0.032(4) 0.000(3) -0.002(3) 0.001(2)
C15 0.021(3) 0.020(3) 0.036(4) -0.002(3) -0.003(3) -0.006(2)
C16 0.018(3) 0.033(3) 0.032(4) -0.001(3) 0.000(3) 0.005(2)
C17 0.032(3) 0.030(3) 0.028(3) 0.004(3) 0.001(3) 0.003(3)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C13 2.012(6) . ?
N1 C2 1.450(13) . ?
N1 C1 1.489(8) 4_565 ?
N1 C1 1.489(8) . ?
N1 C3 1.529(14) . ?
C3 C4 1.561(16) . ?
C4 C5 1.573(16) . ?
C5 C6 1.531(16) . ?
C6 C7 1.526(16) . ?
C7 C8 1.506(16) . ?
C8 C9 1.548(14) . ?
C9 C10 1.494(15) . ?
C10 C11 1.509(15) . ?
C11 C12 1.557(17) . ?
C13 C14 1.195(8) . ?
C14 C15 1.447(8) . ?
C15 C17 1.391(8) 3_756 ?
C15 C16 1.396(9) . ?
C16 C17 1.372(8) . ?
C17 C15 1.391(8) 3_756 ?

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_3
_geom_angle_publ_flag
C2 N1 C1 110.0(6) . 4_565 ?
C2 N1 C1 110.0(6) . . ?
C1 N1 C1 109.9(8) 4_565 . ?
C2 N1 C3 108.9(9) . . ?
C1 N1 C3 109.0(6) 4_565 . ?
C1 N1 C3 109.0(6) . . ?
N1 C3 C4 115.8(9) . . ?
C3 C4 C5 110.4(9) . . ?
C6 C5 C4 114.3(10) . . ?
C7 C6 C5 110.7(9) . . ?
C8 C7 C6 114.2(9) . . ?
C7 C8 C9 112.1(9) . . ?
C10 C9 C8 114.1(8) . . ?
C9 C10 C11 114.4(9) . . ?
C10 C11 C12 116.8(9) . . ?
C14 C13 I1 177.1(6) . . ?
C13 C14 C15 176.6(7) . . ?
C17 C15 C16 119.4(6) 3_756 . ?
C17 C15 C14 120.5(6) 3_756 . ?
C16 C15 C14 120.0(6) . . ?
C17 C16 C15 120.0(6) . . ?
C16 C17 C15 120.5(6) . 3_756 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.134
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.143
####################################################################### 
# 
# 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_xcalibur_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1979344'
loop_
_audit_author_name
_audit_author_address
'Santiago Uriel'
;University of Zaragoza
Spain
;
_audit_update_record             
;
2020-01-22 deposited with the CCDC.	2021-01-14 downloaded from the CCDC.
;
_audit_creation_date             
;
'Tue Nov 16 14:59:35 2010'
;
_audit_creation_method           
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H40 Br I2 N'
_chemical_formula_weight         700.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

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

_cell_length_a                   17.9505(8)
_cell_length_b                   8.6914(4)
_cell_length_c                   18.8483(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.616(4)
_cell_angle_gamma                90.00
_cell_volume                     2940.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1428
_cell_measurement_theta_min      3.1134
_cell_measurement_theta_max      25.3768

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    3.510
_exptl_absorpt_correction_T_min  0.9070
_exptl_absorpt_correction_T_max  1.0908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42018
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         24.71
_reflns_number_total             5007
_reflns_number_gt                3703
_reflns_threshold_expression     >2sigma(I)


_computing_structure_solution    'SHELXTL Bruker'
_computing_structure_refinement  'SHELXTL Bruker'
_computing_molecular_graphics    'SHELXTL Bruker'
_computing_publication_material  'SHELXTL Bruker'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0958P)²+11.4863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5007
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.84284(3) 0.12303(7) 0.27589(3) 0.0531(2) Uani 1 1 d . . .
N1 N 0.7657(4) -0.6939(9) -0.0103(4) 0.0567(19) Uani 1 1 d . . .
Br1 Br 0.74057(6) -1.21142(12) -0.08285(5) 0.0635(3) Uani 1 1 d . . .
C1 C 0.8990(5) 0.0774(12) 0.1861(5) 0.059(2) Uani 1 1 d . . .
I2 I 0.63920(3) -1.32051(8) -0.21928(3) 0.0573(2) Uani 1 1 d . . .
C2 C 0.9306(5) 0.0513(11) 0.1318(4) 0.052(2) Uani 1 1 d . . .
C3 C 0.9674(5) 0.0251(11) 0.0650(4) 0.053(2) Uani 1 1 d . . .
C4 C 0.9313(5) -0.0678(12) 0.0136(4) 0.054(2) Uani 1 1 d . . .
H4 H 0.8850 -0.1115 0.0227 0.065 Uiso 1 1 calc R . .
C5 C 0.9660(5) -0.0920(12) -0.0501(4) 0.056(2) Uani 1 1 d . . .
H5 H 0.9434 -0.1555 -0.0838 0.068 Uiso 1 1 calc R . .
C6 C 0.5867(5) -1.3931(12) -0.3088(5) 0.059(2) Uani 1 1 d . . .
C7 C 0.5579(5) -1.4323(11) -0.3626(5) 0.053(2) Uani 1 1 d . . .
C8 C 0.5285(4) -1.4697(11) -0.4320(5) 0.051(2) Uani 1 1 d . . .
C9 C 0.5560(5) -1.5905(11) -0.4715(5) 0.055(2) Uani 1 1 d . . .
H9 H 0.5939 -1.6513 -0.4525 0.066 Uiso 1 1 calc R . .
C10 C 0.4718(5) -1.3763(11) -0.4601(5) 0.056(2) Uani 1 1 d . . .
H10 H 0.4530 -1.2943 -0.4341 0.067 Uiso 1 1 calc R . .
C11 C 0.7551(5) -0.5596(12) 0.0377(6) 0.065(3) Uani 1 1 d . . .
H11A H 0.7025 -0.5532 0.0489 0.078 Uiso 1 1 calc R . .
H11B H 0.7677 -0.4672 0.0116 0.078 Uiso 1 1 calc R . .
C12 C 0.7980(6) -0.5577(14) 0.1061(6) 0.079(3) Uani 1 1 d . . .
H12A H 0.8509 -0.5664 0.0967 0.095 Uiso 1 1 calc R . .
H12B H 0.7835 -0.6445 0.1351 0.095 Uiso 1 1 calc R . .
C13 C 0.7823(8) -0.4061(19) 0.1456(9) 0.107(5) Uani 1 1 d . . .
C14 C 0.8258(11) -0.383(3) 0.2104(10) 0.111(9) Uani 0.71(3) 1 d P . .
C14A C 0.818(2) -0.293(5) 0.137(2) 0.068(14) Uiso 0.29(3) 1 d P . .
C15 C 0.7496(5) -0.8432(11) 0.0274(5) 0.055(2) Uani 1 1 d . . .
H15A H 0.7823 -0.8504 0.0686 0.066 Uiso 1 1 calc R . .
H15B H 0.7620 -0.9274 -0.0041 0.066 Uiso 1 1 calc R . .
C16 C 0.6703(6) -0.8653(12) 0.0517(6) 0.072(3) Uani 1 1 d . . .
H16A H 0.6373 -0.8743 0.0108 0.086 Uiso 1 1 calc R . .
H16B H 0.6548 -0.7766 0.0791 0.086 Uiso 1 1 calc R . .
C17 C 0.6648(7) -1.0118(15) 0.0976(6) 0.083(3) Uani 1 1 d . . .
H17A H 0.6808 -1.1001 0.0703 0.100 Uiso 1 1 calc R . .
H17B H 0.6975 -1.0022 0.1387 0.100 Uiso 1 1 calc R . .
C18 C 0.5846(8) -1.0359(17) 0.1218(8) 0.110(5) Uani 1 1 d . . .
C19 C 0.7127(6) -0.6717(13) -0.0747(6) 0.071(3) Uani 1 1 d . . .
H19A H 0.6618 -0.6728 -0.0580 0.085 Uiso 1 1 calc R . .
H19B H 0.7218 -0.5711 -0.0951 0.085 Uiso 1 1 calc R . .
C20 C 0.7202(7) -0.7912(15) -0.1325(6) 0.084(4) Uani 1 1 d . . .
H20A H 0.7139 -0.8919 -0.1111 0.101 Uiso 1 1 calc R . .
H20B H 0.7706 -0.7863 -0.1503 0.101 Uiso 1 1 calc R . .
C21 C 0.6658(8) -0.7791(17) -0.1966(8) 0.099(4) Uani 1 1 d . . .
C22 C 0.589(2) -0.833(13) -0.164(2) 0.08(2) Uani 0.61(19) 1 d P . .
C22A C 0.598(4) -0.759(14) -0.165(4) 0.095(17) Uani 0.39(19) 1 d P . .
C23 C 0.8466(6) -0.7028(12) -0.0353(6) 0.065(3) Uani 1 1 d . . .
H23A H 0.8784 -0.7228 0.0057 0.078 Uiso 1 1 calc R . .
H23B H 0.8511 -0.7899 -0.0671 0.078 Uiso 1 1 calc R . .
C24 C 0.8755(6) -0.5614(14) -0.0727(7) 0.084(3) Uani 1 1 d . . .
H24A H 0.8807 -0.4768 -0.0394 0.101 Uiso 1 1 calc R . .
H24B H 0.8412 -0.5306 -0.1101 0.101 Uiso 1 1 calc R . .
C25 C 0.9536(8) -0.6034(18) -0.1048(9) 0.105(5) Uani 1 1 d . . .
C26 C 0.9817(10) -0.479(2) -0.1434(13) 0.087(9) Uani 0.58(3) 1 d P . .
C26A C 0.9502(19) -0.695(5) -0.161(2) 0.121(17) Uani 0.42(3) 1 d P . .

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 0.0595(4) 0.0596(4) 0.0404(3) -0.0034(3) 0.0041(2) 0.0070(3)
N1 0.044(4) 0.061(5) 0.065(5) 0.001(4) -0.005(3) 0.011(4)
Br1 0.0837(7) 0.0538(6) 0.0530(5) 0.0018(4) -0.0041(5) -0.0069(5)
C1 0.061(6) 0.074(7) 0.041(5) -0.006(5) 0.003(4) 0.008(5)
I2 0.0533(4) 0.0652(4) 0.0535(4) 0.0118(3) 0.0065(3) 0.0006(3)
C2 0.051(5) 0.065(6) 0.041(5) -0.006(4) -0.009(4) 0.004(4)
C3 0.067(6) 0.061(6) 0.030(4) -0.004(4) -0.008(4) 0.028(5)
C4 0.044(5) 0.074(6) 0.043(5) -0.009(4) -0.005(4) 0.014(4)
C5 0.053(5) 0.072(7) 0.044(5) -0.017(4) -0.010(4) 0.017(5)
C6 0.042(5) 0.070(7) 0.064(6) 0.012(5) 0.006(4) 0.004(4)
C7 0.046(5) 0.059(6) 0.054(5) 0.017(5) 0.004(4) -0.001(4)
C8 0.038(4) 0.055(6) 0.058(5) 0.014(4) 0.003(4) -0.006(4)
C9 0.041(5) 0.056(6) 0.066(6) 0.015(5) -0.001(4) 0.001(4)
C10 0.043(5) 0.050(6) 0.075(6) 0.005(5) 0.002(4) 0.000(4)
C11 0.044(5) 0.059(6) 0.093(7) -0.015(6) 0.003(5) 0.006(4)
C12 0.063(6) 0.081(8) 0.093(8) -0.028(7) -0.008(6) 0.009(6)
C13 0.090(9) 0.105(11) 0.127(12) -0.056(9) 0.005(8) -0.002(8)
C14 0.093(14) 0.17(2) 0.073(12) -0.033(13) -0.014(10) -0.001(14)
C15 0.052(5) 0.059(6) 0.054(5) -0.004(4) 0.002(4) 0.016(4)
C16 0.071(7) 0.057(7) 0.087(7) -0.020(6) 0.003(6) 0.003(5)
C17 0.101(9) 0.085(9) 0.063(6) 0.002(6) 0.014(6) -0.014(7)
C18 0.112(11) 0.097(10) 0.121(11) -0.013(9) 0.052(9) -0.030(9)
C19 0.062(6) 0.064(7) 0.087(8) 0.017(6) -0.010(5) 0.013(5)
C20 0.101(9) 0.084(9) 0.067(7) -0.003(6) -0.027(6) -0.002(7)
C21 0.105(10) 0.097(11) 0.096(9) 0.006(8) 0.003(8) 0.017(8)
C22 0.059(16) 0.09(4) 0.098(18) -0.01(2) -0.005(12) 0.008(17)
C22A 0.11(4) 0.05(4) 0.12(3) 0.01(3) 0.06(3) -0.02(3)
C23 0.064(6) 0.064(7) 0.068(6) -0.004(5) 0.011(5) 0.016(5)
C24 0.070(7) 0.070(8) 0.112(9) 0.007(7) 0.016(6) 0.011(6)
C25 0.084(9) 0.091(10) 0.140(13) 0.027(10) 0.046(9) 0.024(8)
C26 0.051(11) 0.073(15) 0.14(2) 0.007(13) 0.000(11) 0.012(9)
C26A 0.09(2) 0.15(4) 0.13(3) -0.04(3) 0.03(2) 0.04(2)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.020(9) . ?
N1 C11 1.491(12) . ?
N1 C15 1.509(12) . ?
N1 C23 1.533(12) . ?
N1 C19 1.547(12) . ?
C1 C2 1.196(12) . ?
I2 C6 2.024(11) . ?
C2 C3 1.445(12) . ?
C3 C5 1.363(13) 3_755 ?
C3 C4 1.413(13) . ?
C4 C5 1.375(12) . ?
C5 C3 1.363(13) 3_755 ?
C6 C7 1.184(13) . ?
C7 C8 1.442(13) . ?
C8 C9 1.381(13) . ?
C8 C10 1.402(12) . ?
C9 C10 1.407(13) 3_624 ?
C10 C9 1.407(13) 3_624 ?
C11 C12 1.494(14) . ?
C12 C13 1.542(17) . ?
C13 C14A 1.18(4) . ?
C13 C14 1.45(2) . ?
C14 C14A 1.59(4) . ?
C15 C16 1.512(14) . ?
C16 C17 1.543(16) . ?
C17 C18 1.529(17) . ?
C19 C20 1.511(16) . ?
C20 C21 1.550(18) . ?
C21 C22A 1.36(6) . ?
C21 C22 1.58(8) . ?
C22 C22A 0.66(4) . ?
C23 C24 1.512(15) . ?
C24 C25 1.576(16) . ?
C25 C26A 1.32(4) . ?
C25 C26 1.40(2) . ?
C26 C26A 1.99(5) . ?

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_3
_geom_angle_publ_flag
C11 N1 C15 111.2(7) . . ?
C11 N1 C23 110.8(7) . . ?
C15 N1 C23 106.8(7) . . ?
C11 N1 C19 107.3(7) . . ?
C15 N1 C19 110.9(7) . . ?
C23 N1 C19 110.0(8) . . ?
C2 C1 I1 178.2(8) . . ?
C1 C2 C3 177.7(10) . . ?
C5 C3 C4 120.0(8) 3_755 . ?
C5 C3 C2 121.4(8) 3_755 . ?
C4 C3 C2 118.5(9) . . ?
C5 C4 C3 118.5(9) . . ?
C3 C5 C4 121.4(9) 3_755 . ?
C7 C6 I2 177.5(8) . . ?
C6 C7 C8 173.8(9) . . ?
C9 C8 C10 119.9(8) . . ?
C9 C8 C7 122.1(8) . . ?
C10 C8 C7 118.0(9) . . ?
C8 C9 C10 121.6(8) . 3_624 ?
C8 C10 C9 118.4(9) . 3_624 ?
N1 C11 C12 117.6(8) . . ?
C11 C12 C13 109.3(10) . . ?
C14A C13 C14 73(2) . . ?
C14A C13 C12 123(2) . . ?
C14 C13 C12 115.0(15) . . ?
C13 C14 C14A 45.5(15) . . ?
C13 C14A C14 61(2) . . ?
N1 C15 C16 116.0(8) . . ?
C15 C16 C17 109.9(9) . . ?
C18 C17 C16 110.3(11) . . ?
C20 C19 N1 114.9(8) . . ?
C19 C20 C21 117.1(11) . . ?
C22A C21 C20 103(4) . . ?
C22A C21 C22 25(2) . . ?
C20 C21 C22 103.0(18) . . ?
C22A C22 C21 59(9) . . ?
C22 C22A C21 96(10) . . ?
C24 C23 N1 115.7(8) . . ?
C23 C24 C25 107.6(9) . . ?
C26A C25 C26 94(2) . . ?
C26A C25 C24 114(2) . . ?
C26 C25 C24 110.3(12) . . ?
C25 C26 C26A 41.4(14) . . ?
C25 C26A C26 44.6(16) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.212
_refine_diff_density_min         -1.475
_refine_diff_density_rms         0.148
####################################################################### 
# 
# 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_xcalibur_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1979345'
loop_
_audit_author_name
_audit_author_address
'Santiago Uriel'
;University of Zaragoza
Spain
;
_audit_update_record             
;
2020-01-22 deposited with the CCDC.	2021-01-14 downloaded from the CCDC.
;
_audit_creation_date             
;
'Wed Jan 26 15:03:01 2011'
;
_audit_creation_method           
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H32 Br I2 N'
_chemical_formula_weight         644.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/n

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

_cell_length_a                   9.9332(4)
_cell_length_b                   8.8016(4)
_cell_length_c                   14.5701(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.374(4)
_cell_angle_gamma                90.00
_cell_volume                     1260.25(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1248
_cell_measurement_theta_min      3.0132
_cell_measurement_theta_max      27.3768

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    4.087
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_T_max  1.0308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6307
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_sigmaI/netI    0.1427
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.68
_reflns_number_total             2394
_reflns_number_gt                1351
_reflns_threshold_expression     >2sigma(I)


_computing_structure_solution    'SHELXTL Bruker'
_computing_structure_refinement  'SHELXTL Bruker'
_computing_molecular_graphics    'SHELXTL Bruker'
_computing_publication_material  'SHELXTL Bruker'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0165P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2394
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   0.795
_refine_ls_restrained_S_all      0.795
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.99922(5) -0.28569(6) 0.15516(3) 0.02913(15) Uani 1 1 d . . .
N1 N 1.2500 0.1549(9) 0.2500 0.029(2) Uani 1 2 d S . .
Br1 Br 0.7500 -0.15794(12) 0.2500 0.0278(3) Uani 1 2 d S . .
C1 C 1.1639(7) -0.3655(8) 0.1034(5) 0.033(2) Uani 1 1 d . . .
C2 C 1.2635(7) -0.4074(8) 0.0722(5) 0.0266(18) Uani 1 1 d . . .
C3 C 1.3842(7) -0.4551(8) 0.0359(4) 0.0217(17) Uani 1 1 d . . .
C4 C 1.3739(6) -0.5466(8) -0.0426(4) 0.0268(19) Uani 1 1 d . . .
H4 H 1.2887 -0.5775 -0.0716 0.032 Uiso 1 1 calc R . .
C5 C 1.5128(7) -0.4088(8) 0.0774(4) 0.0284(18) Uani 1 1 d . . .
H5 H 1.5212 -0.3467 0.1296 0.034 Uiso 1 1 calc R . .
C6 C 1.1272(6) 0.2589(7) 0.2247(4) 0.0319(19) Uani 1 1 d . . .
H6A H 1.1188 0.3239 0.2773 0.038 Uiso 1 1 calc R . .
H6B H 1.1436 0.3238 0.1737 0.038 Uiso 1 1 calc R . .
C7 C 0.9943(6) 0.1765(8) 0.1974(5) 0.041(2) Uani 1 1 d . . .
H7A H 0.9741 0.1152 0.2490 0.049 Uiso 1 1 calc R . .
H7B H 1.0019 0.1092 0.1456 0.049 Uiso 1 1 calc R . .
C8 C 0.8801(7) 0.2888(9) 0.1701(5) 0.048(2) Uani 1 1 d . . .
H8A H 0.7972 0.2347 0.1496 0.072 Uiso 1 1 calc R . .
H8B H 0.9020 0.3523 0.1207 0.072 Uiso 1 1 calc R . .
H8C H 0.8686 0.3508 0.2226 0.072 Uiso 1 1 calc R . .
C9 C 1.2716(7) 0.0536(8) 0.1712(4) 0.0313(19) Uani 1 1 d . . .
H9A H 1.1918 -0.0103 0.1567 0.038 Uiso 1 1 calc R . .
H9B H 1.3479 -0.0127 0.1922 0.038 Uiso 1 1 calc R . .
C10 C 1.2985(8) 0.1294(8) 0.0823(4) 0.038(2) Uani 1 1 d . . .
H10A H 1.3828 0.1864 0.0935 0.045 Uiso 1 1 calc R . .
H10B H 1.2253 0.1996 0.0609 0.045 Uiso 1 1 calc R . .
C11 C 1.3080(9) 0.0085(9) 0.0089(5) 0.058(3) Uani 1 1 d . . .
H11A H 1.3232 0.0563 -0.0479 0.088 Uiso 1 1 calc R . .
H11B H 1.2246 -0.0482 -0.0014 0.088 Uiso 1 1 calc R . .
H11C H 1.3822 -0.0589 0.0298 0.088 Uiso 1 1 calc R . .

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 0.0245(2) 0.0301(3) 0.0342(3) -0.0030(3) 0.00919(19) -0.0021(3)
N1 0.038(5) 0.024(6) 0.024(5) 0.000 0.001(4) 0.000
Br1 0.0228(5) 0.0374(8) 0.0251(6) 0.000 0.0104(5) 0.000
C1 0.035(5) 0.024(5) 0.040(5) 0.001(4) 0.005(4) 0.002(4)
C2 0.027(4) 0.022(5) 0.029(5) 0.004(3) -0.003(4) -0.005(4)
C3 0.027(4) 0.014(4) 0.025(4) 0.003(3) 0.007(3) -0.001(3)
C4 0.021(4) 0.024(5) 0.032(5) 0.000(3) -0.008(3) -0.001(3)
C5 0.029(4) 0.031(5) 0.027(4) -0.012(3) 0.011(3) -0.001(4)
C6 0.042(4) 0.018(5) 0.034(4) 0.003(3) -0.001(4) -0.003(4)
C7 0.032(4) 0.033(6) 0.053(5) 0.002(4) -0.007(4) 0.002(4)
C8 0.048(5) 0.042(5) 0.053(5) 0.000(5) 0.004(4) -0.006(5)
C9 0.034(4) 0.032(5) 0.029(5) -0.010(4) 0.006(3) 0.001(4)
C10 0.053(5) 0.035(6) 0.025(5) 0.000(4) 0.006(4) 0.001(4)
C11 0.098(8) 0.056(7) 0.026(5) 0.011(4) 0.024(5) -0.004(5)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.024(8) . ?
N1 C9 1.494(7) 2_755 ?
N1 C9 1.494(7) . ?
N1 C6 1.527(7) 2_755 ?
N1 C6 1.527(7) . ?
C1 C2 1.205(9) . ?
C2 C3 1.441(9) . ?
C3 C4 1.390(8) . ?
C3 C5 1.392(8) . ?
C4 C5 1.358(9) 3_845 ?
C5 C4 1.358(9) 3_845 ?
C6 C7 1.508(8) . ?
C7 C8 1.514(9) . ?
C9 C10 1.514(9) . ?
C10 C11 1.521(9) . ?

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_3
_geom_angle_publ_flag
C9 N1 C9 106.7(8) 2_755 . ?
C9 N1 C6 111.8(3) 2_755 2_755 ?
C9 N1 C6 110.1(4) . 2_755 ?
C9 N1 C6 110.1(4) 2_755 . ?
C9 N1 C6 111.8(3) . . ?
C6 N1 C6 106.3(7) 2_755 . ?
C2 C1 I1 177.5(7) . . ?
C1 C2 C3 178.8(8) . . ?
C4 C3 C5 118.7(6) . . ?
C4 C3 C2 120.4(6) . . ?
C5 C3 C2 121.0(6) . . ?
C5 C4 C3 120.6(6) 3_845 . ?
C4 C5 C3 120.7(6) 3_845 . ?
C7 C6 N1 114.4(5) . . ?
C6 C7 C8 110.4(6) . . ?
N1 C9 C10 117.2(6) . . ?
C9 C10 C11 109.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.147
####################################################################### 
# 
# 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_xcalibur_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1979346'
loop_
_audit_author_name
_audit_author_address
'Santiago Uriel'
;University of Zaragoza
Spain
;
_audit_update_record             
;
2020-01-22 deposited with the CCDC.	2021-01-14 downloaded from the CCDC.
;
_audit_creation_date             
;
'Wed Mar 30 11:05:50 2011'
;
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H4 I2'
_chemical_formula_weight         377.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   4.1533(3)
_cell_length_b                   17.1541(16)
_cell_length_c                   7.0511(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.332(7)
_cell_angle_gamma                90.00
_cell_volume                     500.19(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    515
_cell_measurement_theta_min      2.8956
_cell_measurement_theta_max      28.7525

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    6.229
_exptl_absorpt_correction_T_min  0.93045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1610
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         24.71
_reflns_number_total             848
_reflns_number_gt                613
_reflns_threshold_expression     >2sigma(I)


_computing_structure_solution    'SHELXTL Bruker'
_computing_structure_refinement  'SHELXTL Bruker'
_computing_molecular_graphics    'SHELXTL Bruker'
_computing_publication_material  'SHELXTL Bruker'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0136P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         848
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.08318(14) 0.27991(4) 0.60251(9) 0.0277(2) Uani 1 1 d . . .
C1 C -0.107(2) 0.3562(6) 0.4133(13) 0.022(2) Uani 1 1 d . . .
C2 C -0.223(2) 0.3992(6) 0.2931(14) 0.024(2) Uani 1 1 d . . .
C3 C -0.363(2) 0.4521(6) 0.1439(13) 0.023(2) Uani 1 1 d . . .
C4 C -0.318(2) 0.4356(7) -0.0450(14) 0.028(3) Uani 1 1 d . . .
H4 H -0.209(18) 0.385(6) -0.089(12) 0.03(3) Uiso 1 1 d . . .
C5 C -0.547(3) 0.5155(7) 0.1881(15) 0.027(3) Uani 1 1 d . . .
H5 H -0.594(17) 0.526(5) 0.287(11) 0.01(2) Uiso 1 1 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 0.0290(4) 0.0314(4) 0.0223(4) 0.0040(4) 0.0005(3) 0.0069(4)
C1 0.031(5) 0.022(6) 0.015(5) 0.000(5) 0.003(4) 0.004(5)
C2 0.029(6) 0.020(7) 0.024(6) -0.013(5) 0.009(5) -0.006(5)
C3 0.027(6) 0.016(6) 0.025(6) -0.006(5) -0.001(5) -0.002(5)
C4 0.037(6) 0.022(7) 0.024(6) 0.001(5) 0.001(5) 0.008(5)
C5 0.038(6) 0.030(7) 0.016(5) 0.003(5) 0.011(6) 0.001(5)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 1.980(10) . ?
C1 C2 1.191(13) . ?
C2 C3 1.468(13) . ?
C3 C5 1.382(14) . ?
C3 C4 1.392(13) . ?
C4 C5 1.389(14) 3_465 ?
C5 C4 1.389(14) 3_465 ?

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_3
_geom_angle_publ_flag
C2 C1 I1 176.8(9) . . ?
C1 C2 C3 179.3(11) . . ?
C5 C3 C4 120.2(9) . . ?
C5 C3 C2 121.1(9) . . ?
C4 C3 C2 118.7(9) . . ?
C5 C4 C3 119.4(10) 3_465 . ?
C3 C5 C4 120.4(10) . 3_465 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.219
