# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1xHCl
_audit_block_doi                 10.5517/ccdc.csd.cc20x5bg
_database_code_depnum_ccdc_archive 'CCDC 1874115'
loop_
_audit_author_name
_audit_author_address
'Gunther Hennrich'
;universidad autonoma de madrid
Spain
;
_audit_update_record             
;
2019-11-19 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Cl), C9 H10 N0.5'
_chemical_formula_sum            'C18 H20 Cl N'
_chemical_formula_weight         285.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   4.7609(5)
_cell_length_b                   8.4720(10)
_cell_length_c                   23.813(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.392(7)
_cell_angle_gamma                90
_cell_volume                     959.66(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1684
_cell_measurement_temperature    250
_cell_measurement_theta_max      62.864
_cell_measurement_theta_min      3.716
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.353
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.4492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7809
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.281
_diffrn_reflns_theta_max         66.281
_diffrn_reflns_theta_min         1.857
_diffrn_ambient_temperature      250
_diffrn_detector                 'Bruker VANTEC 500 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            ' area detector'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker X8 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microsource X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1127
_reflns_number_total             1777
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1143P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.2033
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H00A(0.5) H00B(0.5) H00C(0.5) H00D(0.5) H00G(0.5) H00H(0.5)
 H00J(0.5) H00K(0.5) H00L(0.5) H00M(0.5) H00N(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00B(H00C,H00D), C00E(H00G,H00H), C00G(H00J,H00K)
3.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00E), C00D(H00F), C00F(H00I)
3.c Idealised Me refined as rotating group:
 C00H(H00L,H00M,H00N)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 1.5601(2) 0.250000 0.46011(5) 0.0692(4) Uani 1 2 d S T P . .
C003 C 0.5702(8) 0.250000 0.67794(19) 0.0563(11) Uani 1 2 d S T P . .
C004 C 0.4083(8) 0.250000 0.71442(19) 0.0562(11) Uani 1 2 d S T P . .
N005 N 1.1526(9) 0.250000 0.55296(19) 0.098(2) Uani 1 2 d S T P . .
H005 H 1.308(12) 0.250000 0.520(3) 0.117 Uiso 1 2 d RS T P . .
C006 C 0.7704(8) 0.250000 0.63475(18) 0.0532(11) Uani 1 2 d S T P . .
C007 C 0.2171(8) 0.250000 0.75906(19) 0.0555(11) Uani 1 2 d S T P . .
C008 C -0.1531(8) 0.250000 0.84686(19) 0.0637(13) Uani 1 2 d S T P . .
C009 C 0.8672(7) 0.3906(5) 0.61336(15) 0.0713(10) Uani 1 1 d . . . . .
H009 H 0.801794 0.486726 0.626389 0.086 Uiso 1 1 calc R . . . .
C00A C -0.3545(10) 0.250000 1.0031(2) 0.0662(13) Uani 1 2 d S T P . .
H00A H -0.474716 0.342473 1.001695 0.079 Uiso 0.5 1 calc R . . . .
H00B H -0.474717 0.157527 1.001695 0.079 Uiso 0.5 1 calc R . . . .
C00B C -0.1763(9) 0.250000 0.9524(2) 0.0723(14) Uani 1 2 d S T P . .
H00C H -0.055878 0.157598 0.953977 0.087 Uiso 0.5 1 calc R . . . .
H00D H -0.055878 0.342402 0.953977 0.087 Uiso 0.5 1 calc R . . . .
C00C C 0.1216(7) 0.3905(5) 0.78080(15) 0.0761(11) Uani 1 1 d . . . . .
H00E H 0.181320 0.485983 0.766186 0.091 Uiso 1 1 calc R . . . .
C00D C -0.0618(7) 0.3895(5) 0.82406(16) 0.0788(11) Uani 1 1 d . . . . .
H00F H -0.125213 0.484883 0.838156 0.095 Uiso 1 1 calc R . . . .
C00E C -0.3427(9) 0.250000 0.8966(2) 0.0768(16) Uani 1 2 d S T P . .
H00G H -0.462614 0.342562 0.894590 0.092 Uiso 0.5 1 calc R . . . .
H00H H -0.462614 0.157438 0.894590 0.092 Uiso 0.5 1 calc R . . . .
C00F C 1.0623(7) 0.3854(7) 0.57245(16) 0.0917(15) Uani 1 1 d . . . . .
H00I H 1.131780 0.479217 0.558270 0.110 Uiso 1 1 calc R . . . .
C00G C -0.1867(13) 0.250000 1.0573(2) 0.103(2) Uani 1 2 d S T P . .
H00J H -0.066118 0.342337 1.058346 0.123 Uiso 0.5 1 calc R . . . .
H00K H -0.066118 0.157663 1.058346 0.123 Uiso 0.5 1 calc R . . . .
C00H C -0.3573(14) 0.250000 1.1094(2) 0.104(2) Uani 1 2 d S T P . .
H00L H -0.444658 0.351241 1.113520 0.156 Uiso 0.5 1 calc GR . . A -1
H00M H -0.236046 0.228921 1.141786 0.156 Uiso 0.5 1 calc GR . . A -1
H00N H -0.499513 0.169837 1.106088 0.156 Uiso 0.5 1 calc GR . . A -1

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
Cl01 0.0648(7) 0.0797(8) 0.0649(8) 0.000 0.0235(6) 0.000
C003 0.040(2) 0.074(3) 0.054(3) 0.000 0.0058(19) 0.000
C004 0.036(2) 0.080(3) 0.053(3) 0.000 0.0024(19) 0.000
N005 0.046(2) 0.201(7) 0.048(3) 0.000 0.012(2) 0.000
C006 0.037(2) 0.078(3) 0.045(3) 0.000 0.0027(17) 0.000
C007 0.036(2) 0.082(3) 0.050(3) 0.000 0.0080(18) 0.000
C008 0.039(2) 0.101(4) 0.052(3) 0.000 0.0062(19) 0.000
C009 0.0575(19) 0.089(2) 0.069(2) 0.013(2) 0.0108(17) 0.0031(18)
C00A 0.063(3) 0.080(3) 0.056(3) 0.000 0.017(2) 0.000
C00B 0.055(3) 0.104(4) 0.060(3) 0.000 0.013(2) 0.000
C00C 0.079(2) 0.079(2) 0.072(3) 0.008(2) 0.0276(19) 0.0009(19)
C00D 0.073(2) 0.087(3) 0.079(3) -0.002(2) 0.030(2) 0.0121(19)
C00E 0.047(3) 0.123(5) 0.062(3) 0.000 0.015(2) 0.000
C00F 0.056(2) 0.151(5) 0.068(3) 0.038(3) 0.0058(19) -0.018(2)
C00G 0.086(4) 0.168(7) 0.055(4) 0.000 0.018(3) 0.000
C00H 0.112(5) 0.141(6) 0.060(4) 0.000 0.021(3) 0.000

_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
C003 C004 1.185(6) . ?
C003 C006 1.431(5) . ?
C004 C007 1.428(5) . ?
N005 H005 1.11(6) . ?
N005 C00F 1.316(5) . ?
N005 C00F 1.316(5) 4_565 ?
C006 C009 1.382(4) . ?
C006 C009 1.382(4) 4_565 ?
C007 C00C 1.382(4) . ?
C007 C00C 1.382(4) 4_565 ?
C008 C00D 1.379(4) 4_565 ?
C008 C00D 1.379(4) . ?
C008 C00E 1.519(6) . ?
C009 H009 0.9300 . ?
C009 C00F 1.375(5) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00B 1.505(6) . ?
C00A C00G 1.490(8) . ?
C00B H00C 0.9700 . ?
C00B H00D 0.9700 . ?
C00B C00E 1.517(7) . ?
C00C H00E 0.9300 . ?
C00C C00D 1.378(4) . ?
C00D H00F 0.9300 . ?
C00E H00G 0.9700 . ?
C00E H00H 0.9700 . ?
C00F H00I 0.9300 . ?
C00G H00J 0.9700 . ?
C00G H00K 0.9700 . ?
C00G C00H 1.511(7) . ?
C00H H00L 0.9600 . ?
C00H H00M 0.9600 . ?
C00H H00N 0.9600 . ?

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
C004 C003 C006 178.8(5) . . ?
C003 C004 C007 179.0(5) . . ?
C00F N005 H005 119.4(2) 4_565 . ?
C00F N005 H005 119.4(2) . . ?
C00F N005 C00F 121.3(5) . 4_565 ?
C009 C006 C003 120.5(2) 4_565 . ?
C009 C006 C003 120.5(2) . . ?
C009 C006 C009 119.0(4) . 4_565 ?
C00C C007 C004 120.6(2) . . ?
C00C C007 C004 120.6(2) 4_565 . ?
C00C C007 C00C 118.8(4) 4_565 . ?
C00D C008 C00D 118.1(4) 4_565 . ?
C00D C008 C00E 121.0(2) 4_565 . ?
C00D C008 C00E 121.0(2) . . ?
C006 C009 H009 120.7 . . ?
C00F C009 C006 118.6(4) . . ?
C00F C009 H009 120.7 . . ?
H00A C00A H00B 107.7 . . ?
C00B C00A H00A 108.9 . . ?
C00B C00A H00B 108.9 . . ?
C00G C00A H00A 108.9 . . ?
C00G C00A H00B 108.9 . . ?
C00G C00A C00B 113.3(4) . . ?
C00A C00B H00C 108.7 . . ?
C00A C00B H00D 108.7 . . ?
C00A C00B C00E 114.3(4) . . ?
H00C C00B H00D 107.6 . . ?
C00E C00B H00C 108.7 . . ?
C00E C00B H00D 108.7 . . ?
C007 C00C H00E 119.9 . . ?
C00D C00C C007 120.2(3) . . ?
C00D C00C H00E 119.9 . . ?
C008 C00D H00F 119.4 . . ?
C00C C00D C008 121.3(4) . . ?
C00C C00D H00F 119.4 . . ?
C008 C00E H00G 109.2 . . ?
C008 C00E H00H 109.2 . . ?
C00B C00E C008 112.1(4) . . ?
C00B C00E H00G 109.2 . . ?
C00B C00E H00H 109.2 . . ?
H00G C00E H00H 107.9 . . ?
N005 C00F C009 121.2(4) . . ?
N005 C00F H00I 119.4 . . ?
C009 C00F H00I 119.4 . . ?
C00A C00G H00J 108.5 . . ?
C00A C00G H00K 108.5 . . ?
C00A C00G C00H 115.1(5) . . ?
H00J C00G H00K 107.5 . . ?
C00H C00G H00J 108.5 . . ?
C00H C00G H00K 108.5 . . ?
C00G C00H H00L 109.5 . . ?
C00G C00H H00M 109.5 . . ?
C00G C00H H00N 109.5 . . ?
H00L C00H H00M 109.5 . . ?
H00L C00H H00N 109.5 . . ?
H00M C00H H00N 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N005 H005 Cl01 1.11(6) 1.89(6) 3.002(4) 177(5) . yes

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.285 0.250 0.290 95.1 27.1 ?
2 -0.041 0.750 0.710 95.1 26.5 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1xTerph
_audit_block_doi                 10.5517/ccdc.csd.cc20x57c
_database_code_depnum_ccdc_archive 'CCDC 1874112'
loop_
_audit_author_name
_audit_author_address
'Gunther Hennrich'
;universidad autonoma de madrid
Spain
;
_audit_update_record             
;
2019-11-19 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 O2, C18 H19 N'
_chemical_formula_sum            'C22 H22 N O2'
_chemical_formula_weight         332.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9346(6)
_cell_length_b                   11.9374(14)
_cell_length_c                   13.4258(15)
_cell_angle_alpha                73.485(9)
_cell_angle_beta                 85.966(8)
_cell_angle_gamma                82.697(8)
_cell_volume                     903.91(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1284
_cell_measurement_temperature    250
_cell_measurement_theta_max      65.49
_cell_measurement_theta_min      3.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0996 before and 0.0605 after correction.
The Ratio of minimum to maximum transmission is 0.6677.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6768
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        58.908
_diffrn_reflns_theta_max         58.908
_diffrn_reflns_theta_min         3.436
_diffrn_ambient_temperature      250
_diffrn_detector                 'Bruker VANTEC 500 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            ' area detector'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker X8 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microsource X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1583
_reflns_number_total             2530
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1615
_refine_ls_R_factor_gt           0.1032
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2683
_refine_ls_wR_factor_ref         0.3299
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00M(H00G,H00H), C00N(H00J,H00M), C00O(H00N,H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00A(H00S), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00I(H00I), C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00P(H00P,H00Q,H00R)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.3987(6) 0.1295(4) 0.6214(3) 0.0474(13) Uani 1 1 d . . . . .
O002 O 0.1053(7) 0.2630(3) 0.5641(3) 0.0432(12) Uani 1 1 d . . . . .
H002 H 0.170(11) 0.341(6) 0.583(5) 0.065 Uiso 1 1 d R . . . .
N003 N 0.3440(7) 0.4121(4) 0.6180(3) 0.0359(13) Uani 1 1 d . . . . .
C004 C 0.9023(9) 0.7984(5) 0.7737(4) 0.0307(14) Uani 1 1 d . . . . .
C005 C 0.2178(9) 0.1578(5) 0.5795(4) 0.0271(13) Uani 1 1 d . . . . .
C006 C 0.1033(9) 0.0765(5) 0.5395(4) 0.0320(14) Uani 1 1 d . . . . .
C007 C 0.9058(9) 0.9898(5) 0.7952(4) 0.0310(14) Uani 1 1 d . . . . .
H007 H 0.837170 1.066411 0.785438 0.037 Uiso 1 1 calc R . . . .
C008 C 1.1126(8) 0.9550(5) 0.8459(4) 0.0293(13) Uani 1 1 d . . . . .
C009 C 0.2154(9) -0.0335(5) 0.5377(4) 0.0327(14) Uani 1 1 d . . . . .
H009 H 0.360907 -0.055787 0.563108 0.039 Uiso 1 1 calc R . . . .
C00A C 0.1159(9) -0.1081(5) 0.4996(4) 0.0301(14) Uani 1 1 d . . . . .
H00S H 0.193576 -0.180813 0.499333 0.036 Uiso 1 1 calc R . . . .
C00B C 0.5855(9) 0.5617(5) 0.6825(4) 0.0291(14) Uani 1 1 d . . . . .
C00C C 0.3716(10) 0.5976(5) 0.6409(4) 0.0393(15) Uani 1 1 d . . . . .
H00C H 0.304286 0.673816 0.634843 0.047 Uiso 1 1 calc R . . . .
C00D C 0.8036(9) 0.9128(5) 0.7598(4) 0.0340(14) Uani 1 1 d . . . . .
H00D H 0.666713 0.937531 0.726256 0.041 Uiso 1 1 calc R . . . .
C00E C 1.2080(9) 0.8420(5) 0.8579(4) 0.0316(14) Uani 1 1 d . . . . .
H00E H 1.345559 0.817508 0.890933 0.038 Uiso 1 1 calc R . . . .
C00F C 0.5483(10) 0.3752(5) 0.6579(4) 0.0387(15) Uani 1 1 d . . . . .
H00F H 0.607643 0.297601 0.664530 0.046 Uiso 1 1 calc R . . . .
C00G C 1.2658(10) 1.2279(5) 0.9223(4) 0.0408(15) Uani 1 1 d . . . . .
H00A H 1.273337 1.187969 0.995960 0.049 Uiso 1 1 calc R . . . .
H00B H 1.419672 1.225805 0.892742 0.049 Uiso 1 1 calc R . . . .
C00H C 0.7933(9) 0.7143(5) 0.7399(4) 0.0329(14) Uani 1 1 d . . . . .
C00I C 0.2610(10) 0.5226(5) 0.6091(4) 0.0361(15) Uani 1 1 d . . . . .
H00I H 0.120170 0.549771 0.579614 0.043 Uiso 1 1 calc R . . . .
C00J C 0.7060(10) 0.6420(5) 0.7133(4) 0.0370(15) Uani 1 1 d . . . . .
C00K C 1.1083(9) 0.7625(5) 0.8229(4) 0.0392(15) Uani 1 1 d . . . . .
H00K H 1.177849 0.686079 0.832071 0.047 Uiso 1 1 calc R . . . .
C00L C 0.6752(10) 0.4458(5) 0.6897(4) 0.0391(15) Uani 1 1 d . . . . .
H00L H 0.818805 0.417164 0.715660 0.047 Uiso 1 1 calc R . . . .
C00M C 1.1285(9) 1.1619(5) 0.8720(4) 0.0344(14) Uani 1 1 d . . . . .
H00G H 0.974446 1.163306 0.901349 0.041 Uiso 1 1 calc R . . . .
H00H H 1.121752 1.200749 0.798095 0.041 Uiso 1 1 calc R . . . .
C00N C 1.1706(11) 1.3541(5) 0.9089(4) 0.0427(16) Uani 1 1 d . . . . .
H00J H 1.016012 1.356746 0.937640 0.051 Uiso 1 1 calc R . . . .
H00M H 1.165614 1.394884 0.835306 0.051 Uiso 1 1 calc R . . . .
C00O C 1.2293(10) 1.0380(6) 0.8879(5) 0.0442(16) Uani 1 1 d . . . . .
H00N H 1.242406 1.003060 0.962213 0.053 Uiso 1 1 calc R . . . .
H00O H 1.382687 1.039559 0.857783 0.053 Uiso 1 1 calc R . . . .
C00P C 1.3113(13) 1.4178(5) 0.9621(5) 0.062(2) Uani 1 1 d . . . . .
H00P H 1.463032 1.418047 0.932091 0.092 Uiso 1 1 calc GR . . . .
H00Q H 1.316353 1.377939 1.035033 0.092 Uiso 1 1 calc GR . . . .
H00R H 1.243032 1.497254 0.952562 0.092 Uiso 1 1 calc GR . . . .

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
O001 0.024(2) 0.065(3) 0.066(3) -0.035(2) -0.014(2) -0.008(2)
O002 0.043(2) 0.030(2) 0.066(3) -0.027(2) -0.022(2) 0.0005(19)
N003 0.027(3) 0.047(3) 0.038(3) -0.016(2) -0.001(2) -0.009(2)
C004 0.030(3) 0.038(4) 0.028(3) -0.014(2) 0.004(2) -0.011(3)
C005 0.024(3) 0.029(3) 0.033(3) -0.014(2) -0.004(2) -0.004(2)
C006 0.029(3) 0.039(4) 0.028(3) -0.007(2) 0.002(2) -0.009(3)
C007 0.026(3) 0.029(3) 0.043(3) -0.015(3) 0.001(3) -0.006(2)
C008 0.025(3) 0.035(3) 0.031(3) -0.013(2) 0.005(2) -0.009(2)
C009 0.023(3) 0.038(3) 0.043(3) -0.020(3) -0.011(2) -0.005(3)
C00A 0.027(3) 0.027(3) 0.038(3) -0.012(2) -0.005(2) 0.002(2)
C00B 0.036(3) 0.030(3) 0.028(3) -0.017(2) 0.000(2) -0.009(3)
C00C 0.044(4) 0.034(3) 0.044(4) -0.019(3) -0.011(3) 0.003(3)
C00D 0.022(3) 0.050(4) 0.033(3) -0.013(3) -0.005(2) -0.011(3)
C00E 0.024(3) 0.029(3) 0.049(3) -0.020(3) -0.013(3) -0.002(2)
C00F 0.040(4) 0.033(4) 0.046(4) -0.016(3) -0.004(3) -0.006(3)
C00G 0.044(4) 0.042(4) 0.043(3) -0.018(3) -0.006(3) -0.015(3)
C00H 0.038(3) 0.038(4) 0.029(3) -0.016(3) -0.003(2) -0.013(3)
C00I 0.035(3) 0.034(4) 0.040(3) -0.012(3) -0.011(3) 0.003(3)
C00J 0.044(4) 0.033(3) 0.042(3) -0.018(3) 0.001(3) -0.014(3)
C00K 0.037(3) 0.040(4) 0.042(3) -0.014(3) -0.006(3) -0.001(3)
C00L 0.033(3) 0.036(4) 0.056(4) -0.023(3) -0.010(3) -0.003(3)
C00M 0.038(3) 0.028(3) 0.042(3) -0.013(3) -0.008(3) -0.008(3)
C00N 0.052(4) 0.042(4) 0.037(3) -0.011(3) -0.008(3) -0.013(3)
C00O 0.031(3) 0.057(4) 0.051(4) -0.024(3) 0.001(3) -0.012(3)
C00P 0.102(6) 0.024(4) 0.070(5) -0.019(3) -0.019(4) -0.027(4)

_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
O001 C005 1.211(6) . ?
O002 H002 1.15(7) . ?
O002 C005 1.313(6) . ?
N003 C00F 1.331(7) . ?
N003 C00I 1.323(7) . ?
C004 C00D 1.383(7) . ?
C004 C00H 1.448(7) . ?
C004 C00K 1.391(8) . ?
C005 C006 1.484(7) . ?
C006 C009 1.400(8) . ?
C006 C00A 1.403(7) 2_556 ?
C007 H007 0.9300 . ?
C007 C008 1.404(7) . ?
C007 C00D 1.366(7) . ?
C008 C00E 1.365(7) . ?
C008 C00O 1.526(8) . ?
C009 H009 0.9300 . ?
C009 C00A 1.357(7) . ?
C00A H00S 0.9300 . ?
C00B C00C 1.390(8) . ?
C00B C00J 1.428(7) . ?
C00B C00L 1.396(7) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.349(8) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00K 1.381(7) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.368(8) . ?
C00G H00A 0.9700 . ?
C00G H00B 0.9700 . ?
C00G C00M 1.511(7) . ?
C00G C00N 1.505(8) . ?
C00H C00J 1.207(7) . ?
C00I H00I 0.9300 . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00G 0.9700 . ?
C00M H00H 0.9700 . ?
C00M C00O 1.484(8) . ?
C00N H00J 0.9700 . ?
C00N H00M 0.9700 . ?
C00N C00P 1.529(8) . ?
C00O H00N 0.9700 . ?
C00O H00O 0.9700 . ?
C00P H00P 0.9600 . ?
C00P H00Q 0.9600 . ?
C00P H00R 0.9600 . ?

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
C005 O002 H002 125(3) . . ?
C00I N003 C00F 117.9(5) . . ?
C00D C004 C00H 121.3(5) . . ?
C00D C004 C00K 119.4(5) . . ?
C00K C004 C00H 119.3(5) . . ?
O001 C005 O002 123.5(5) . . ?
O001 C005 C006 122.9(5) . . ?
O002 C005 C006 113.6(4) . . ?
C009 C006 C005 120.3(5) . . ?
C009 C006 C00A 118.2(5) . 2_556 ?
C00A C006 C005 121.5(5) 2_556 . ?
C008 C007 H007 119.5 . . ?
C00D C007 H007 119.5 . . ?
C00D C007 C008 121.1(5) . . ?
C007 C008 C00O 122.4(5) . . ?
C00E C008 C007 117.5(5) . . ?
C00E C008 C00O 120.0(5) . . ?
C006 C009 H009 119.3 . . ?
C00A C009 C006 121.3(5) . . ?
C00A C009 H009 119.3 . . ?
C006 C00A H00S 119.8 2_556 . ?
C009 C00A C006 120.5(5) . 2_556 ?
C009 C00A H00S 119.8 . . ?
C00C C00B C00J 120.6(5) . . ?
C00C C00B C00L 116.5(5) . . ?
C00L C00B C00J 122.8(5) . . ?
C00B C00C H00C 119.8 . . ?
C00I C00C C00B 120.5(5) . . ?
C00I C00C H00C 119.8 . . ?
C004 C00D H00D 119.8 . . ?
C007 C00D C004 120.4(5) . . ?
C007 C00D H00D 119.8 . . ?
C008 C00E H00E 118.7 . . ?
C008 C00E C00K 122.5(5) . . ?
C00K C00E H00E 118.7 . . ?
N003 C00F H00F 118.4 . . ?
N003 C00F C00L 123.2(5) . . ?
C00L C00F H00F 118.4 . . ?
H00A C00G H00B 107.7 . . ?
C00M C00G H00A 108.8 . . ?
C00M C00G H00B 108.8 . . ?
C00N C00G H00A 108.8 . . ?
C00N C00G H00B 108.8 . . ?
C00N C00G C00M 113.8(5) . . ?
C00J C00H C004 178.4(6) . . ?
N003 C00I C00C 122.9(5) . . ?
N003 C00I H00I 118.6 . . ?
C00C C00I H00I 118.6 . . ?
C00H C00J C00B 175.4(6) . . ?
C004 C00K H00K 120.5 . . ?
C00E C00K C004 119.0(5) . . ?
C00E C00K H00K 120.5 . . ?
C00B C00L H00L 120.5 . . ?
C00F C00L C00B 118.9(5) . . ?
C00F C00L H00L 120.5 . . ?
C00G C00M H00G 109.3 . . ?
C00G C00M H00H 109.3 . . ?
H00G C00M H00H 108.0 . . ?
C00O C00M C00G 111.5(5) . . ?
C00O C00M H00G 109.3 . . ?
C00O C00M H00H 109.3 . . ?
C00G C00N H00J 109.1 . . ?
C00G C00N H00M 109.1 . . ?
C00G C00N C00P 112.4(5) . . ?
H00J C00N H00M 107.9 . . ?
C00P C00N H00J 109.1 . . ?
C00P C00N H00M 109.1 . . ?
C008 C00O H00N 107.4 . . ?
C008 C00O H00O 107.4 . . ?
C00M C00O C008 119.9(5) . . ?
C00M C00O H00N 107.4 . . ?
C00M C00O H00O 107.4 . . ?
H00N C00O H00O 106.9 . . ?
C00N C00P H00P 109.5 . . ?
C00N C00P H00Q 109.5 . . ?
C00N C00P H00R 109.5 . . ?
H00P C00P H00Q 109.5 . . ?
H00P C00P H00R 109.5 . . ?
H00Q C00P H00R 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O002 H002 N003 1.15(7) 1.59(7) 2.686(6) 158(5) . yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1xdiiodox1
_audit_block_doi                 10.5517/ccdc.csd.cc20x59f
_database_code_depnum_ccdc_archive 'CCDC 1874114'
loop_
_audit_author_name
_audit_author_address
'Gunther Hennrich'
;universidad autonoma de madrid
Spain
;
_audit_update_record             
;
2019-11-19 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 F2 I, C18 H19 N'
_chemical_formula_sum            'C21 H19 F2 I N'
_chemical_formula_weight         450.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.8479(3)
_cell_length_b                   8.0949(4)
_cell_length_c                   40.0427(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.972(3)
_cell_angle_gamma                90
_cell_volume                     1894.43(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4731
_cell_measurement_temperature    250
_cell_measurement_theta_max      65.58
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.412
_shelx_estimated_absorpt_T_min   0.222
_exptl_absorpt_coefficient_mu    13.465
_exptl_absorpt_correction_T_max  0.4681
_exptl_absorpt_correction_T_min  0.2739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1156
_diffrn_reflns_av_unetI/netI     0.1360
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            13174
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        65.075
_diffrn_reflns_theta_max         65.075
_diffrn_reflns_theta_min         2.208
_diffrn_ambient_temperature      250.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker X8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2668
_reflns_number_total             3002
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.075
_refine_diff_density_min         -1.937
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0901
_refine_ls_restrained_S_all      1.295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+13.6308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2172
_refine_ls_wR_factor_ref         0.2224
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C00B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00I(H00G,H00I), C00N(H00N,H00O), C00P(H00Q,H00R)
3.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00M(H00M), C00O(H00P)
3.c Idealised Me refined as rotating group:
 C00L(H00J,H00K,H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I 0.86637(15) 0.39404(10) 0.58184(2) 0.0343(3) Uani 1 1 d . . . . .
F002 F 1.3960(13) 0.6563(9) 0.48870(18) 0.0351(17) Uani 1 1 d . . . . .
F003 F 1.2991(13) 0.5701(9) 0.55070(18) 0.0390(18) Uani 1 1 d . . . . .
N004 N 0.686(2) 0.3438(14) 0.6472(3) 0.036(3) Uani 1 1 d . . . . .
C005 C 0.949(2) 0.4555(14) 0.5334(3) 0.024(2) Uani 1 1 d . . . . .
C006 C -0.160(2) 0.3438(14) 0.8504(3) 0.026(3) Uani 1 1 d . . . . .
C007 C 0.768(2) 0.2721(17) 0.6753(3) 0.035(3) Uani 1 1 d . . . . .
H007 H 0.912608 0.221805 0.675122 0.042 Uiso 1 1 calc R . . . .
C008 C 0.305(2) 0.3525(16) 0.7354(3) 0.035(3) Uani 1 1 d . . . . .
C009 C -0.670(2) 0.4186(17) 0.9330(4) 0.038(3) Uani 1 1 d . . . . .
H00A H -0.653883 0.301664 0.927244 0.045 Uiso 1 1 calc R . . . .
H00B H -0.770811 0.469635 0.915895 0.045 Uiso 1 1 calc R . . . .
C00A C -0.140(2) 0.4268(16) 0.7920(3) 0.035(3) Uani 1 1 d . . . . .
H00C H -0.205638 0.480817 0.773189 0.042 Uiso 1 1 calc R . . . .
C00B C 0.438(2) 0.3510(13) 0.7055(3) 0.027(3) Uani 1 1 d . U . . .
C00C C 1.199(2) 0.5773(13) 0.4941(3) 0.025(3) Uani 1 1 d . . . . .
C00D C 0.165(2) 0.2671(19) 0.8180(3) 0.036(3) Uani 1 1 d . . . . .
H00D H 0.309083 0.215696 0.816950 0.044 Uiso 1 1 calc R . . . .
C00E C 0.353(2) 0.4265(17) 0.6763(3) 0.036(3) Uani 1 1 d . . . . .
H00E H 0.211786 0.482480 0.675757 0.043 Uiso 1 1 calc R . . . .
C00F C 0.648(2) 0.2687(16) 0.7048(3) 0.034(3) Uani 1 1 d . . . . .
H00F H 0.707110 0.212640 0.723784 0.041 Uiso 1 1 calc R . . . .
C00G C 0.073(2) 0.3481(16) 0.7896(3) 0.035(3) Uani 1 1 d . . . . .
C00H C 0.485(3) 0.4157(17) 0.6477(3) 0.039(3) Uani 1 1 d . . . . .
H00H H 0.425270 0.462834 0.627771 0.047 Uiso 1 1 calc R . . . .
C00I C -0.442(2) 0.498(2) 0.9321(4) 0.043(4) Uani 1 1 d . . . . .
H00G H -0.337269 0.438235 0.947384 0.051 Uiso 1 1 calc R . . . .
H00I H -0.455536 0.611079 0.940569 0.051 Uiso 1 1 calc R . . . .
C00J C 0.200(2) 0.3515(19) 0.7597(4) 0.042(3) Uani 1 1 d . . . . .
C00K C 1.150(2) 0.5316(16) 0.5260(3) 0.028(3) Uani 1 1 d . . . . .
C00L C -0.782(3) 0.4308(19) 0.9661(4) 0.047(4) Uani 1 1 d . . . . .
H00J H -0.926318 0.371661 0.965071 0.070 Uiso 1 1 calc GR . . . .
H00K H -0.809554 0.545988 0.971353 0.070 Uiso 1 1 calc GR . . . .
H00L H -0.682429 0.382655 0.983407 0.070 Uiso 1 1 calc GR . . . .
C00M C -0.254(2) 0.4256(18) 0.8216(4) 0.040(3) Uani 1 1 d . . . . .
H00M H -0.396042 0.479676 0.822802 0.048 Uiso 1 1 calc R . . . .
C00N C -0.336(2) 0.5049(17) 0.8976(3) 0.037(3) Uani 1 1 d . . . . .
H00N H -0.439875 0.566197 0.882290 0.045 Uiso 1 1 calc R . . . .
H00O H -0.192187 0.566262 0.899471 0.045 Uiso 1 1 calc R . . . .
C00O C 0.047(2) 0.2616(17) 0.8478(3) 0.036(3) Uani 1 1 d . . . . .
H00P H 0.108780 0.201951 0.866130 0.044 Uiso 1 1 calc R . . . .
C00P C -0.291(3) 0.3386(19) 0.8827(3) 0.042(3) Uani 1 1 d . . . . .
H00Q H -0.437297 0.282686 0.878257 0.050 Uiso 1 1 calc R . . . .
H00R H -0.203176 0.272436 0.899131 0.050 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
I001 0.0408(5) 0.0346(5) 0.0278(5) 0.0028(3) 0.0034(3) -0.0004(4)
F002 0.031(4) 0.036(4) 0.038(4) 0.003(3) 0.000(3) -0.012(3)
F003 0.040(4) 0.041(5) 0.035(4) -0.004(3) -0.005(3) -0.006(4)
N004 0.046(7) 0.032(6) 0.028(6) 0.008(4) 0.002(5) -0.008(5)
C005 0.032(7) 0.014(6) 0.025(6) 0.004(4) 0.000(5) 0.004(5)
C006 0.025(6) 0.014(6) 0.040(7) -0.003(4) 0.000(5) -0.001(5)
C007 0.028(7) 0.030(8) 0.048(8) 0.004(5) 0.011(6) 0.000(6)
C008 0.037(7) 0.024(7) 0.045(8) -0.002(5) 0.001(6) -0.008(6)
C009 0.025(7) 0.025(8) 0.063(9) -0.006(6) 0.004(6) 0.001(6)
C00A 0.039(8) 0.030(8) 0.035(7) 0.004(5) 0.001(5) -0.012(6)
C00B 0.029(6) 0.006(6) 0.047(8) -0.002(4) 0.000(5) -0.010(5)
C00C 0.035(7) 0.005(6) 0.034(7) -0.001(4) 0.003(5) 0.003(5)
C00D 0.021(6) 0.057(10) 0.031(7) -0.001(6) 0.003(5) 0.000(6)
C00E 0.030(7) 0.034(8) 0.043(8) 0.007(5) 0.001(6) -0.001(6)
C00F 0.037(7) 0.024(7) 0.042(8) 0.007(5) 0.001(6) 0.003(6)
C00G 0.043(8) 0.026(7) 0.036(7) 0.004(5) 0.016(6) -0.002(6)
C00H 0.042(8) 0.035(8) 0.039(8) 0.010(6) 0.001(6) -0.008(7)
C00I 0.024(7) 0.050(10) 0.053(9) -0.016(7) -0.004(6) 0.015(7)
C00J 0.034(8) 0.054(10) 0.039(8) 0.004(6) 0.009(6) -0.006(7)
C00K 0.025(6) 0.037(7) 0.022(6) -0.008(5) -0.004(5) -0.002(6)
C00L 0.037(8) 0.040(10) 0.064(10) 0.000(7) 0.011(7) 0.003(7)
C00M 0.033(7) 0.041(9) 0.046(9) 0.009(6) 0.003(6) 0.011(7)
C00N 0.036(7) 0.031(8) 0.045(8) -0.008(6) 0.007(6) -0.001(6)
C00O 0.027(7) 0.039(8) 0.043(8) 0.005(6) 0.000(5) 0.003(6)
C00P 0.044(8) 0.045(9) 0.036(8) 0.002(6) 0.009(6) -0.001(7)

_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
I001 C005 2.077(11) . ?
F002 C00C 1.341(15) . ?
F003 C00K 1.333(14) . ?
N004 C007 1.341(17) . ?
N004 C00H 1.315(19) . ?
C005 C00C 1.401(17) 3_766 ?
C005 C00K 1.371(18) . ?
C006 C00M 1.423(18) . ?
C006 C00O 1.392(19) . ?
C006 C00P 1.523(18) . ?
C007 H007 0.9400 . ?
C007 C00F 1.395(19) . ?
C008 C00B 1.449(19) . ?
C008 C00J 1.17(2) . ?
C009 H00A 0.9800 . ?
C009 H00B 0.9800 . ?
C009 C00I 1.48(2) . ?
C009 C00L 1.50(2) . ?
C00A H00C 0.9400 . ?
C00A C00G 1.40(2) . ?
C00A C00M 1.38(2) . ?
C00B C00E 1.396(18) . ?
C00B C00F 1.399(19) . ?
C00C C00K 1.368(18) . ?
C00D H00D 0.9400 . ?
C00D C00G 1.405(19) . ?
C00D C00O 1.399(19) . ?
C00E H00E 0.9400 . ?
C00E C00H 1.40(2) . ?
C00F H00F 0.9400 . ?
C00G C00J 1.431(19) . ?
C00H H00H 0.9400 . ?
C00I H00G 0.9800 . ?
C00I H00I 0.9800 . ?
C00I C00N 1.54(2) . ?
C00L H00J 0.9700 . ?
C00L H00K 0.9700 . ?
C00L H00L 0.9700 . ?
C00M H00M 0.9400 . ?
C00N H00N 0.9800 . ?
C00N H00O 0.9800 . ?
C00N C00P 1.50(2) . ?
C00O H00P 0.9400 . ?
C00P H00Q 0.9800 . ?
C00P H00R 0.9800 . ?

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
C00H N004 C007 118.2(12) . . ?
C00C C005 I001 122.2(9) 3_766 . ?
C00K C005 I001 122.5(8) . . ?
C00K C005 C00C 115.3(11) . 3_766 ?
C00M C006 C00P 120.6(12) . . ?
C00O C006 C00M 118.3(12) . . ?
C00O C006 C00P 121.0(12) . . ?
N004 C007 H007 118.5 . . ?
N004 C007 C00F 123.1(13) . . ?
C00F C007 H007 118.5 . . ?
C00J C008 C00B 178.7(16) . . ?
H00A C009 H00B 107.6 . . ?
C00I C009 H00A 108.7 . . ?
C00I C009 H00B 108.7 . . ?
C00I C009 C00L 114.4(12) . . ?
C00L C009 H00A 108.7 . . ?
C00L C009 H00B 108.7 . . ?
C00G C00A H00C 119.6 . . ?
C00M C00A H00C 119.6 . . ?
C00M C00A C00G 120.7(12) . . ?
C00E C00B C008 120.1(12) . . ?
C00E C00B C00F 118.8(12) . . ?
C00F C00B C008 121.1(12) . . ?
F002 C00C C005 118.2(10) . 3_766 ?
F002 C00C C00K 119.3(10) . . ?
C00K C00C C005 122.5(12) . 3_766 ?
C00G C00D H00D 119.4 . . ?
C00O C00D H00D 119.4 . . ?
C00O C00D C00G 121.2(12) . . ?
C00B C00E H00E 121.1 . . ?
C00B C00E C00H 117.7(13) . . ?
C00H C00E H00E 121.1 . . ?
C007 C00F C00B 118.3(12) . . ?
C007 C00F H00F 120.9 . . ?
C00B C00F H00F 120.9 . . ?
C00A C00G C00D 118.3(12) . . ?
C00A C00G C00J 122.5(13) . . ?
C00D C00G C00J 119.2(13) . . ?
N004 C00H C00E 123.9(12) . . ?
N004 C00H H00H 118.0 . . ?
C00E C00H H00H 118.0 . . ?
C009 C00I H00G 108.4 . . ?
C009 C00I H00I 108.4 . . ?
C009 C00I C00N 115.4(12) . . ?
H00G C00I H00I 107.5 . . ?
C00N C00I H00G 108.4 . . ?
C00N C00I H00I 108.4 . . ?
C008 C00J C00G 179.3(17) . . ?
F003 C00K C005 119.3(11) . . ?
F003 C00K C00C 118.5(11) . . ?
C00C C00K C005 122.2(11) . . ?
C009 C00L H00J 109.5 . . ?
C009 C00L H00K 109.5 . . ?
C009 C00L H00L 109.5 . . ?
H00J C00L H00K 109.5 . . ?
H00J C00L H00L 109.5 . . ?
H00K C00L H00L 109.5 . . ?
C006 C00M H00M 119.5 . . ?
C00A C00M C006 121.0(13) . . ?
C00A C00M H00M 119.5 . . ?
C00I C00N H00N 108.7 . . ?
C00I C00N H00O 108.7 . . ?
H00N C00N H00O 107.6 . . ?
C00P C00N C00I 114.1(12) . . ?
C00P C00N H00N 108.7 . . ?
C00P C00N H00O 108.7 . . ?
C006 C00O C00D 120.4(12) . . ?
C006 C00O H00P 119.8 . . ?
C00D C00O H00P 119.8 . . ?
C006 C00P H00Q 108.6 . . ?
C006 C00P H00R 108.6 . . ?
C00N C00P C006 114.5(12) . . ?
C00N C00P H00Q 108.6 . . ?
C00N C00P H00R 108.6 . . ?
H00Q C00P H00R 107.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_eg_lf_diiodox2_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc20x58d
_database_code_depnum_ccdc_archive 'CCDC 1874113'
loop_
_audit_author_name
_audit_author_address
'Gunther Hennrich'
;universidad autonoma de madrid
Spain
;
_audit_update_record             
;
2019-11-19 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 F2 I, C18 H19 N'
_chemical_formula_sum            'C21 H19 F2 I N'
_chemical_formula_weight         450.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.6232(19)
_cell_length_b                   5.4878(6)
_cell_length_c                   20.948(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.417(7)
_cell_angle_gamma                90
_cell_volume                     1922.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1646
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      47.52
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.503
_shelx_estimated_absorpt_T_min   0.350
_exptl_absorpt_coefficient_mu    13.270
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_correction_T_min  0.4760
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1266 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.6348.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1275
_diffrn_reflns_av_unetI/netI     0.1458
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11949
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         2.643
_diffrn_ambient_temperature      250.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1684
_reflns_number_total             3274
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.173
_refine_ls_extinction_coef       0.00044(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1734
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00G(H00C,H00D), C00K(H00E,H00G), C00N(H00I,H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00F(H00F), C00H(H00H), C00J(H00J), C00L(H00L),
 C00M(H00M), C00P(H00Q)
2.c Idealised Me refined as rotating group:
 C00O(H00N,H00O,H00P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I 0.90547(5) 0.39286(15) 0.36675(4) 0.0503(3) Uani 1 1 d . . . . .
F002 F 0.8941(4) 0.3299(14) 0.5162(3) 0.060(2) Uani 1 1 d . . . . .
F003 F 0.9647(4) 0.0321(14) 0.6162(3) 0.067(2) Uani 1 1 d . . . . .
N004 N 0.8473(6) 0.738(2) 0.2546(5) 0.054(3) Uani 1 1 d . . . . .
C005 C 0.6762(8) 0.672(2) 0.2959(6) 0.051(3) Uani 1 1 d . . . . .
C006 C 0.5444(7) 0.644(2) 0.3129(6) 0.050(3) Uani 1 1 d . . . . .
H006 H 0.530473 0.796770 0.292179 0.059 Uiso 1 1 calc R . . . .
C007 C 0.6185(7) 0.547(2) 0.3217(5) 0.045(3) Uani 1 1 d . . . . .
C008 C 0.7244(7) 0.762(3) 0.2763(6) 0.054(4) Uani 1 1 d . . . . .
C009 C 0.8846(9) 1.024(3) 0.1827(6) 0.059(4) Uani 1 1 d . . . . .
H009 H 0.921924 1.070568 0.161257 0.071 Uiso 1 1 calc R . . . .
C00A C 0.4105(7) 0.293(2) 0.4355(6) 0.056(4) Uani 1 1 d . . . . .
H00A H 0.395115 0.454693 0.416141 0.067 Uiso 1 1 calc R . . . .
H00B H 0.450600 0.314686 0.479813 0.067 Uiso 1 1 calc R . . . .
C00B C 0.5107(8) 0.300(2) 0.3700(6) 0.051(3) Uani 1 1 d . . . . .
C00C C 0.9823(6) 0.012(2) 0.5585(5) 0.039(3) Uani 1 1 d . . . . .
C00D C 0.7797(7) 0.872(2) 0.2448(6) 0.045(3) Uani 1 1 d . . . . .
C00E C 0.9463(7) 0.164(2) 0.5073(6) 0.047(3) Uani 1 1 d . . . . .
C00F C 0.8169(9) 1.156(3) 0.1745(7) 0.065(4) Uani 1 1 d . . . . .
H00F H 0.806089 1.296340 0.147314 0.079 Uiso 1 1 calc R . . . .
C00G C 0.3374(7) 0.170(3) 0.4449(7) 0.061(4) Uani 1 1 d . . . . .
H00C H 0.296662 0.153357 0.400745 0.073 Uiso 1 1 calc R . . . .
H00D H 0.352406 0.006018 0.462766 0.073 Uiso 1 1 calc R . . . .
C00H C 0.6417(8) 0.331(2) 0.3567(6) 0.058(4) Uani 1 1 d . . . . .
H00H H 0.693255 0.266798 0.363870 0.069 Uiso 1 1 calc R . . . .
C00I C 0.9608(6) 0.161(2) 0.4463(5) 0.044(3) Uani 1 1 d . . . . .
C00J C 0.5868(9) 0.211(3) 0.3808(6) 0.059(4) Uani 1 1 d . . . . .
H00J H 0.602001 0.064974 0.405033 0.070 Uiso 1 1 calc R . . . .
C00K C 0.3019(8) 0.301(3) 0.4902(7) 0.067(4) Uani 1 1 d . . . . .
H00E H 0.284321 0.462471 0.471322 0.080 Uiso 1 1 calc R . . . .
H00G H 0.343014 0.324172 0.533867 0.080 Uiso 1 1 calc R . . . .
C00L C 0.7644(8) 1.079(3) 0.2072(7) 0.069(4) Uani 1 1 d . . . . .
H00L H 0.717916 1.169468 0.203397 0.083 Uiso 1 1 calc R . . . .
C00M C 0.8969(9) 0.822(3) 0.2230(7) 0.066(4) Uani 1 1 d . . . . .
H00M H 0.944523 0.735173 0.228922 0.079 Uiso 1 1 calc R . . . .
C00N C 0.4484(8) 0.153(3) 0.3909(6) 0.060(4) Uani 1 1 d . . . . .
H00I H 0.406136 0.101218 0.350240 0.072 Uiso 1 1 calc R . . . .
H00K H 0.473932 0.006395 0.414722 0.072 Uiso 1 1 calc R . . . .
C00O C 0.2302(8) 0.166(3) 0.5009(7) 0.077(5) Uani 1 1 d . . . . .
H00N H 0.183985 0.182311 0.461004 0.116 Uiso 1 1 calc GR . . . .
H00O H 0.218217 0.236064 0.539189 0.116 Uiso 1 1 calc GR . . . .
H00P H 0.243296 -0.005067 0.509432 0.116 Uiso 1 1 calc GR . . . .
C00P C 0.4907(8) 0.515(2) 0.3349(6) 0.052(3) Uani 1 1 d . . . . .
H00Q H 0.438400 0.575834 0.325645 0.063 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
I001 0.0476(5) 0.0537(6) 0.0459(5) 0.0068(5) 0.0096(3) 0.0030(5)
F002 0.071(5) 0.062(5) 0.055(4) 0.011(4) 0.031(4) 0.023(4)
F003 0.084(5) 0.069(6) 0.054(4) 0.008(4) 0.032(4) 0.022(4)
N004 0.049(6) 0.060(8) 0.059(7) 0.020(6) 0.027(5) 0.020(6)
C005 0.054(8) 0.044(9) 0.050(7) -0.015(6) 0.007(7) -0.009(7)
C006 0.044(7) 0.043(9) 0.058(7) 0.012(7) 0.011(6) 0.004(7)
C007 0.047(8) 0.052(10) 0.036(6) -0.008(6) 0.013(6) 0.001(7)
C008 0.036(7) 0.076(11) 0.042(7) 0.003(7) 0.002(6) 0.004(7)
C009 0.074(10) 0.069(11) 0.035(7) 0.004(7) 0.019(7) -0.019(8)
C00A 0.060(8) 0.053(9) 0.052(8) -0.001(7) 0.013(7) -0.025(7)
C00B 0.070(10) 0.047(8) 0.045(7) -0.002(7) 0.028(7) -0.004(7)
C00C 0.035(6) 0.057(8) 0.019(6) 0.005(5) 0.003(5) 0.009(6)
C00D 0.039(7) 0.037(8) 0.049(7) 0.002(6) 0.000(5) -0.004(7)
C00E 0.043(7) 0.040(9) 0.056(8) -0.021(6) 0.013(6) 0.014(6)
C00F 0.062(9) 0.051(10) 0.077(10) 0.019(8) 0.012(8) -0.006(8)
C00G 0.053(8) 0.057(10) 0.070(9) -0.002(7) 0.013(7) -0.018(7)
C00H 0.066(9) 0.051(10) 0.061(8) -0.004(7) 0.026(7) -0.006(8)
C00I 0.039(7) 0.049(9) 0.043(7) -0.007(6) 0.014(5) 0.001(6)
C00J 0.076(10) 0.048(9) 0.053(8) 0.005(7) 0.021(7) -0.001(8)
C00K 0.080(10) 0.048(9) 0.073(9) -0.001(7) 0.026(8) 0.006(8)
C00L 0.054(8) 0.078(12) 0.060(8) 0.010(9) -0.004(7) 0.014(9)
C00M 0.071(10) 0.063(11) 0.063(9) 0.002(8) 0.018(8) 0.006(8)
C00N 0.064(8) 0.064(10) 0.047(7) -0.010(7) 0.013(6) -0.010(8)
C00O 0.058(9) 0.104(14) 0.085(10) 0.000(9) 0.043(8) 0.003(9)
C00P 0.048(8) 0.054(9) 0.051(8) -0.003(7) 0.009(6) 0.008(7)

_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
I001 C00I 2.080(12) . ?
F002 C00E 1.348(12) . ?
F003 C00C 1.345(11) . ?
N004 C00D 1.361(14) . ?
N004 C00M 1.334(16) . ?
C005 C007 1.465(18) . ?
C005 C008 1.162(16) . ?
C006 H006 0.9400 . ?
C006 C007 1.368(16) . ?
C006 C00P 1.372(17) . ?
C007 C00H 1.387(17) . ?
C008 C00D 1.469(18) . ?
C009 H009 0.9400 . ?
C009 C00F 1.360(18) . ?
C009 C00M 1.369(18) . ?
C00A H00A 0.9800 . ?
C00A H00B 0.9800 . ?
C00A C00G 1.519(16) . ?
C00A C00N 1.516(16) . ?
C00B C00J 1.377(17) . ?
C00B C00N 1.533(17) . ?
C00B C00P 1.378(17) . ?
C00C C00E 1.351(15) . ?
C00C C00I 1.405(15) 3_756 ?
C00D C00L 1.359(18) . ?
C00E C00I 1.379(15) . ?
C00F H00F 0.9400 . ?
C00F C00L 1.380(18) . ?
C00G H00C 0.9800 . ?
C00G H00D 0.9800 . ?
C00G C00K 1.477(17) . ?
C00H H00H 0.9400 . ?
C00H C00J 1.391(17) . ?
C00J H00J 0.9400 . ?
C00K H00E 0.9800 . ?
C00K H00G 0.9800 . ?
C00K C00O 1.541(18) . ?
C00L H00L 0.9400 . ?
C00M H00M 0.9400 . ?
C00N H00I 0.9800 . ?
C00N H00K 0.9800 . ?
C00O H00N 0.9700 . ?
C00O H00O 0.9700 . ?
C00O H00P 0.9700 . ?
C00P H00Q 0.9400 . ?

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
C00M N004 C00D 114.7(11) . . ?
C008 C005 C007 176.7(15) . . ?
C007 C006 H006 120.5 . . ?
C007 C006 C00P 119.0(12) . . ?
C00P C006 H006 120.5 . . ?
C006 C007 C005 120.8(12) . . ?
C006 C007 C00H 121.0(12) . . ?
C00H C007 C005 118.2(11) . . ?
C005 C008 C00D 174.3(13) . . ?
C00F C009 H009 121.0 . . ?
C00F C009 C00M 118.0(13) . . ?
C00M C009 H009 121.0 . . ?
H00A C00A H00B 107.6 . . ?
C00G C00A H00A 108.7 . . ?
C00G C00A H00B 108.7 . . ?
C00N C00A H00A 108.7 . . ?
C00N C00A H00B 108.7 . . ?
C00N C00A C00G 114.4(11) . . ?
C00J C00B C00N 121.0(12) . . ?
C00J C00B C00P 117.7(12) . . ?
C00P C00B C00N 121.1(13) . . ?
F003 C00C C00E 118.6(10) . . ?
F003 C00C C00I 119.6(9) . 3_756 ?
C00E C00C C00I 121.8(10) . 3_756 ?
N004 C00D C008 112.6(11) . . ?
C00L C00D N004 122.8(12) . . ?
C00L C00D C008 124.5(12) . . ?
F002 C00E C00C 118.6(10) . . ?
F002 C00E C00I 118.1(11) . . ?
C00C C00E C00I 123.3(10) . . ?
C009 C00F H00F 120.9 . . ?
C009 C00F C00L 118.3(13) . . ?
C00L C00F H00F 120.9 . . ?
C00A C00G H00C 108.6 . . ?
C00A C00G H00D 108.6 . . ?
H00C C00G H00D 107.6 . . ?
C00K C00G C00A 114.7(12) . . ?
C00K C00G H00C 108.6 . . ?
C00K C00G H00D 108.6 . . ?
C007 C00H H00H 120.9 . . ?
C007 C00H C00J 118.3(13) . . ?
C00J C00H H00H 120.9 . . ?
C00C C00I I001 121.3(8) 3_756 . ?
C00E C00I I001 123.8(9) . . ?
C00E C00I C00C 114.9(10) . 3_756 ?
C00B C00J C00H 121.7(13) . . ?
C00B C00J H00J 119.1 . . ?
C00H C00J H00J 119.1 . . ?
C00G C00K H00E 108.9 . . ?
C00G C00K H00G 108.9 . . ?
C00G C00K C00O 113.2(12) . . ?
H00E C00K H00G 107.7 . . ?
C00O C00K H00E 108.9 . . ?
C00O C00K H00G 108.9 . . ?
C00D C00L C00F 120.2(13) . . ?
C00D C00L H00L 119.9 . . ?
C00F C00L H00L 119.9 . . ?
N004 C00M C009 126.0(14) . . ?
N004 C00M H00M 117.0 . . ?
C009 C00M H00M 117.0 . . ?
C00A C00N C00B 114.0(11) . . ?
C00A C00N H00I 108.8 . . ?
C00A C00N H00K 108.8 . . ?
C00B C00N H00I 108.8 . . ?
C00B C00N H00K 108.8 . . ?
H00I C00N H00K 107.6 . . ?
C00K C00O H00N 109.5 . . ?
C00K C00O H00O 109.5 . . ?
C00K C00O H00P 109.5 . . ?
H00N C00O H00O 109.5 . . ?
H00N C00O H00P 109.5 . . ?
H00O C00O H00P 109.5 . . ?
C006 C00P C00B 122.2(12) . . ?
C006 C00P H00Q 118.9 . . ?
C00B C00P H00Q 118.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
