#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/06/1520620.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_1520620
loop_
_publ_author_name
'Engle, Keary M.'
'Pfeifer, Lukas'
'Pidgeon, George W.'
'Giuffredi, Guy T.'
'Thompson, Amber L.'
'Paton, Robert S.'
'Brown, John M.'
'Gouverneur, Véronique'
_publ_section_title
;
 Coordination diversity in hydrogen-bonded homoleptic fluoride--alcohol
 complexes modulates reactivity
;
_journal_issue                   9
_journal_name_full               'Chem. Sci.'
_journal_page_first              5293
_journal_paper_doi               10.1039/C5SC01812A
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C16 H36 N, 2(C5 H12 O3), F'
_chemical_formula_sum            'C26 H60 F N O6'
_chemical_formula_weight         501.76
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             13-03-18
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-05-19 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9133(1)
_cell_length_b                   17.3454(3)
_cell_length_c                   18.3631(3)
_cell_measurement_reflns_used    4020
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     3157.54(8)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            46870
_diffrn_reflns_theta_full        26.942
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         5.200
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.055
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9619
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.0005402
_refine_ls_shift/su_mean         0.0000480
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 1.18P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1057
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1057
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                2751
_reflns_number_total             3597
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.82
_oxford_diffrn_Wilson_scale      4.34
_oxford_refine_ls_r_factor_ref   0.0623
_oxford_refine_ls_scale          0.4964(9)
_oxford_reflns_number_all        3597
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 063ggke01
_cod_data_source_file            c5sc01812a2.cif
_cod_data_source_block           2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520618--1520631.cif.
;
_cod_original_sg_symbol_H-M      'P b c n '
_cod_original_formula_sum        'C26 H60 F1 N1 O6'
_cod_database_code               1520620
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE O   (  11,X'S) H   ( 111,X'S) 
RIDE O   (  12,X'S) H   ( 121,X'S) 
RIDE O   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  25,X'S) H   ( 252,X'S) H   ( 253,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) 
RIDE C   (  28,X'S) H   ( 282,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 293,X'S) H   ( 292,X'S) H   ( 291,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,-z+1/2
-x+1/2,-y+1/2,z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z
-x,y,-z+1/2
x,-y,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 0.5000 0.27953(8) 0.7500 0.0484 1.0000 Uani S T
O11 O 0.40012(9) 0.24409(6) 0.62274(5) 0.0429 1.0000 Uani . .
O12 O 0.65488(9) 0.36391(6) 0.66504(5) 0.0439 1.0000 Uani . .
O13 O 0.65601(9) 0.28057(7) 0.44334(5) 0.0482 1.0000 Uani . .
C14 C 0.51408(13) 0.25017(8) 0.57553(7) 0.0332 1.0000 Uani . .
C15 C 0.54159(12) 0.33180(8) 0.54877(6) 0.0308 1.0000 Uani . .
C16 C 0.55852(14) 0.38750(8) 0.61275(7) 0.0388 1.0000 Uani . .
C17 C 0.67155(13) 0.33030(9) 0.50427(7) 0.0397 1.0000 Uani . .
C18 C 0.42407(15) 0.36007(10) 0.50219(8) 0.0467 1.0000 Uani . .
N21 N 0.0000 0.27575(8) 0.7500 0.0241 1.0000 Uani S T
C22 C 0.01982(11) 0.32476(7) 0.81779(6) 0.0266 1.0000 Uani . .
C23 C -0.08660(12) 0.38576(7) 0.83215(6) 0.0301 1.0000 Uani . .
C24 C -0.05989(13) 0.42255(7) 0.90624(7) 0.0341 1.0000 Uani . .
C25 C -0.14602(16) 0.49324(8) 0.92037(8) 0.0440 1.0000 Uani . .
C26 C -0.12487(11) 0.22620(7) 0.76156(6) 0.0269 1.0000 Uani . .
C27 C -0.15489(12) 0.16644(7) 0.70371(7) 0.0323 1.0000 Uani . .
C28 C -0.27869(15) 0.12033(8) 0.72610(8) 0.0414 1.0000 Uani . .
C29 C -0.31618(18) 0.05819(9) 0.67198(9) 0.0546 1.0000 Uani . .
H111 H 0.4253 0.2553 0.6660 0.0641 1.0000 Uiso R .
H121 H 0.6118 0.3375 0.6967 0.0666 1.0000 Uiso R .
H131 H 0.7313 0.2742 0.4240 0.0718 1.0000 Uiso R .
H141 H 0.4945 0.2170 0.5324 0.0380 1.0000 Uiso R .
H142 H 0.5942 0.2301 0.6003 0.0408 1.0000 Uiso R .
H161 H 0.5907 0.4370 0.5930 0.0480 1.0000 Uiso R .
H162 H 0.4698 0.3945 0.6368 0.0465 1.0000 Uiso R .
H171 H 0.7453 0.3133 0.5354 0.0465 1.0000 Uiso R .
H172 H 0.6895 0.3825 0.4877 0.0488 1.0000 Uiso R .
H181 H 0.4369 0.4126 0.4860 0.0709 1.0000 Uiso R .
H182 H 0.3376 0.3570 0.5307 0.0683 1.0000 Uiso R .
H183 H 0.4180 0.3298 0.4580 0.0689 1.0000 Uiso R .
H221 H 0.0207 0.2877 0.8579 0.0313 1.0000 Uiso R .
H222 H 0.1080 0.3490 0.8134 0.0313 1.0000 Uiso R .
H231 H -0.1745 0.3624 0.8325 0.0358 1.0000 Uiso R .
H232 H -0.0839 0.4259 0.7938 0.0353 1.0000 Uiso R .
H241 H -0.0765 0.3843 0.9433 0.0423 1.0000 Uiso R .
H242 H 0.0356 0.4364 0.9084 0.0403 1.0000 Uiso R .
H251 H -0.1224 0.5335 0.8863 0.0639 1.0000 Uiso R .
H252 H -0.1315 0.5117 0.9704 0.0659 1.0000 Uiso R .
H253 H -0.2424 0.4810 0.9134 0.0649 1.0000 Uiso R .
H261 H -0.1147 0.2008 0.8090 0.0327 1.0000 Uiso R .
H262 H -0.2017 0.2616 0.7648 0.0306 1.0000 Uiso R .
H271 H -0.0794 0.1334 0.6975 0.0398 1.0000 Uiso R .
H272 H -0.1722 0.1914 0.6568 0.0398 1.0000 Uiso R .
H281 H -0.3556 0.1564 0.7307 0.0512 1.0000 Uiso R .
H282 H -0.2622 0.0955 0.7725 0.0530 1.0000 Uiso R .
H291 H -0.3313 0.0803 0.6221 0.0824 1.0000 Uiso R .
H292 H -0.2423 0.0196 0.6680 0.0828 1.0000 Uiso R .
H293 H -0.4022 0.0311 0.6863 0.0810 1.0000 Uiso R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 . O11 H111 . 108.4 no
C16 . O12 H121 . 106.2 no
C17 . O13 H131 . 108.6 no
O11 . C14 C15 . 113.96(10) yes
O11 . C14 H141 . 106.6 no
C15 . C14 H141 . 108.3 no
O11 . C14 H142 . 109.5 no
C15 . C14 H142 . 109.6 no
H141 . C14 H142 . 108.7 no
C14 . C15 C16 . 111.03(10) yes
C14 . C15 C17 . 107.94(11) yes
C16 . C15 C17 . 109.23(10) yes
C14 . C15 C18 . 110.04(11) yes
C16 . C15 C18 . 108.13(11) yes
C17 . C15 C18 . 110.48(11) yes
C15 . C16 O12 . 114.36(11) yes
C15 . C16 H161 . 107.7 no
O12 . C16 H161 . 106.4 no
C15 . C16 H162 . 108.7 no
O12 . C16 H162 . 109.4 no
H161 . C16 H162 . 110.2 no
C15 . C17 O13 . 109.91(10) yes
C15 . C17 H171 . 109.0 no
O13 . C17 H171 . 111.1 no
C15 . C17 H172 . 107.9 no
O13 . C17 H172 . 109.8 no
H171 . C17 H172 . 109.2 no
C15 . C18 H181 . 112.0 no
C15 . C18 H182 . 110.0 no
H181 . C18 H182 . 108.7 no
C15 . C18 H183 . 110.1 no
H181 . C18 H183 . 105.2 no
H182 . C18 H183 . 110.8 no
C26 7_556 N21 C22 7_556 107.86(6) yes
C26 7_556 N21 C22 . 108.96(6) yes
C22 7_556 N21 C22 . 112.00(12) yes
C26 7_556 N21 C26 . 111.23(12) yes
C22 7_556 N21 C26 . 108.96(6) yes
C22 . N21 C26 . 107.86(6) yes
N21 . C22 C23 . 116.25(9) yes
N21 . C22 H221 . 104.4 no
C23 . C22 H221 . 109.5 no
N21 . C22 H222 . 106.9 no
C23 . C22 H222 . 109.7 no
H221 . C22 H222 . 109.8 no
C22 . C23 C24 . 109.02(10) yes
C22 . C23 H231 . 109.7 no
C24 . C23 H231 . 109.1 no
C22 . C23 H232 . 110.3 no
C24 . C23 H232 . 109.6 no
H231 . C23 H232 . 109.0 no
C23 . C24 C25 . 113.14(11) yes
C23 . C24 H241 . 108.2 no
C25 . C24 H241 . 109.8 no
C23 . C24 H242 . 107.8 no
C25 . C24 H242 . 109.9 no
H241 . C24 H242 . 107.8 no
C24 . C25 H251 . 109.7 no
C24 . C25 H252 . 109.9 no
H251 . C25 H252 . 109.5 no
C24 . C25 H253 . 110.4 no
H251 . C25 H253 . 107.9 no
H252 . C25 H253 . 109.4 no
N21 . C26 C27 . 116.66(9) yes
N21 . C26 H261 . 107.1 no
C27 . C26 H261 . 109.6 no
N21 . C26 H262 . 106.7 no
C27 . C26 H262 . 108.6 no
H261 . C26 H262 . 107.9 no
C26 . C27 C28 . 109.20(10) yes
C26 . C27 H271 . 110.1 no
C28 . C27 H271 . 110.5 no
C26 . C27 H272 . 110.4 no
C28 . C27 H272 . 109.2 no
H271 . C27 H272 . 107.4 no
C27 . C28 C29 . 113.29(12) yes
C27 . C28 H281 . 108.2 no
C29 . C28 H281 . 108.5 no
C27 . C28 H282 . 109.6 no
C29 . C28 H282 . 107.6 no
H281 . C28 H282 . 109.6 no
C28 . C29 H291 . 111.3 no
C28 . C29 H292 . 110.3 no
H291 . C29 H292 . 107.4 no
C28 . C29 H293 . 111.7 no
H291 . C29 H293 . 106.8 no
H292 . C29 H293 . 109.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C14 . 1.4279(15) yes
O11 H111 . 0.855 no
O12 C16 . 1.4148(16) yes
O12 H121 . 0.855 no
O13 C17 . 1.4211(16) yes
O13 H131 . 0.834 no
C14 C15 . 1.5233(18) yes
C14 H141 . 0.998 no
C14 H142 . 0.980 no
C15 C16 . 1.5304(17) yes
C15 C17 . 1.5258(17) yes
C15 C18 . 1.5263(17) yes
C16 H161 . 0.985 no
C16 H162 . 0.991 no
C17 H171 . 0.973 no
C17 H172 . 0.972 no
C18 H181 . 0.967 no
C18 H182 . 1.005 no
C18 H183 . 0.968 no
N21 C26 7_556 1.5219(13) yes
N21 C22 7_556 1.5202(13) yes
N21 C22 . 1.5202(13) yes
N21 C26 . 1.5219(13) yes
C22 C23 . 1.5172(16) yes
C22 H221 . 0.978 no
C22 H222 . 0.974 no
C23 C24 . 1.5260(16) yes
C23 H231 . 0.961 no
C23 H232 . 0.990 no
C24 C25 . 1.5165(18) yes
C24 H241 . 0.964 no
C24 H242 . 0.978 no
C25 H251 . 0.967 no
C25 H252 . 0.984 no
C25 H253 . 0.987 no
C26 C27 . 1.5137(16) yes
C26 H261 . 0.981 no
C26 H262 . 0.980 no
C27 C28 . 1.5215(17) yes
C27 H271 . 0.950 no
C27 H272 . 0.980 no
C28 C29 . 1.5124(19) yes
C28 H281 . 0.990 no
C28 H282 . 0.969 no
C29 H291 . 1.004 no
C29 H292 . 0.995 no
C29 H293 . 1.009 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O13 H131 O11 5_556 177.42 0.834 1.908 2.7408(19) yes
C22 H222 O12 7_656 155.96 0.974 2.397 3.3106(19) yes
C26 H261 O13 4_555 142.56 0.981 2.522 3.3544(19) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045668
