#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:10:23 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/97/7239703.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7239703
loop_
_publ_author_name
'Flores, Linda'
'López Duarte, Ismael'
'Gómez-Lor, Berta'
'Gutierrez-Puebla, Enrique'
'Hennrich, Gunther'
_publ_section_title
;
 Supramolecular synthesis with N-hetero-tolanes: liquid crystals and
 hydrogen-bonded and halogen-bonded co-crystals
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              416
_journal_page_last               419
_journal_paper_doi               10.1039/C9CE01551E
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C3 F2 I, C18 H19 N'
_chemical_formula_sum            'C21 H19 F2 I N'
_chemical_formula_weight         450.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc20x58d
_audit_creation_date             2019-11-14
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-19 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.417(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6232(19)
_cell_length_b                   5.4878(6)
_cell_length_c                   20.948(2)
_cell_measurement_reflns_used    1646
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      47.52
_cell_measurement_theta_min      2.64
_cell_volume                     1922.2(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_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)'
_diffrn_ambient_temperature      250.0
_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_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_standards_number         0
_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_crystal_density_diffrn    1.556
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_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_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0685
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1684
_reflns_number_total             3274
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01551e2.cif
_cod_data_source_block           eg_lf_diiodox2_0m_a
_cod_depositor_comments
;Adding full bibliography for 7239700--7239703.cif.

 Adding full bibliography for 7239700--7239703.cif.
;
_cod_database_code               7239703
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.503
_shelx_estimated_absorpt_t_min   0.350
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
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_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'
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
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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 .
