#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:36:15 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257509 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/53/7705386.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_7705386
loop_
_publ_author_name
'Hammoud, Joanna'
'Abou-Khalil, Fatima'
'Roisnel, Thierry'
'Dorcet, Vincent'
'Bour, Christophe'
'Gandon, Vincent'
'Lebœuf, David'
'Carpentier, Jean-François'
'Sarazin, Yann'
_publ_section_title
;
 Alkaline-earth complexes with macrocyclic-functionalised bis(phenolate)s
 and bis(fluoroalkoxide)s.
;
_journal_issue                   37
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13017
_journal_page_last               13028
_journal_paper_doi               10.1039/d0dt02573a
_journal_volume                  49
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H30 F12 N2 O6'
_chemical_formula_sum            'C20 H30 F12 N2 O6'
_chemical_formula_weight         622.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2020-06-12 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                114.820(8)
_cell_angle_beta                 95.801(7)
_cell_angle_gamma                99.354(8)
_cell_formula_units_Z            1
_cell_length_a                   5.5168(9)
_cell_length_b                   10.777(2)
_cell_length_c                   12.424(3)
_cell_measurement_reflns_used    2810
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4666
_cell_measurement_theta_min      3.3346
_cell_measurement_wavelength     0.71073
_cell_volume                     649.6(2)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2018)'
_computing_structure_refinement  'SHELXL-2017_1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1527
_diffrn_reflns_av_unetI/netI     0.1062
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14190
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.335
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       stick
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1366
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0842P)²+0.0783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1770
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1684
_reflns_number_total             2845
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0dt02573a2.cif
_cod_data_source_block           JH014
_cod_depositor_comments
'Adding full bibliography for 7705378--7705389.cif.'
_cod_database_code               7705386
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.2312(5) 0.7818(3) 0.2249(3) 0.0157(7) Uani 1 1 d . . . . .
O2 O 0.0238(4) 0.6903(2) 0.2263(2) 0.0242(6) Uani 1 1 d . . . . .
H2 H 0.092(7) 0.635(4) 0.244(3) 0.029 Uiso 1 1 d . U . . .
C3 C 0.2262(6) 0.9287(3) 0.3159(3) 0.0255(8) Uani 1 1 d . . . . .
F4 F 0.4170(4) 1.0255(2) 0.3218(2) 0.0414(6) Uani 1 1 d . . . . .
F5 F 0.0154(4) 0.96769(19) 0.29372(18) 0.0351(5) Uani 1 1 d . . . . .
F6 F 0.2405(4) 0.9365(2) 0.42711(16) 0.0379(6) Uani 1 1 d . . . . .
C7 C 0.2080(7) 0.7696(4) 0.0973(3) 0.0336(9) Uani 1 1 d . . . . .
F8 F -0.0015(4) 0.7996(3) 0.06213(18) 0.0553(7) Uani 1 1 d . . . . .
F9 F 0.3983(5) 0.8539(3) 0.0863(2) 0.0588(7) Uani 1 1 d . . . . .
F10 F 0.2061(4) 0.6392(2) 0.01918(16) 0.0487(7) Uani 1 1 d . . . . .
C11 C 0.4790(5) 0.7414(3) 0.2602(3) 0.0182(7) Uani 1 1 d . . . . .
H11A H 0.572971 0.717489 0.193161 0.022 Uiso 1 1 calc R U . . .
H11B H 0.586589 0.821358 0.332660 0.022 Uiso 1 1 calc R U . . .
N12 N 0.4099(4) 0.6216(2) 0.2847(2) 0.0155(6) Uani 1 1 d . . . . .
C13 C 0.4462(6) 0.4887(3) 0.1917(3) 0.0202(7) Uani 1 1 d . . . . .
H13A H 0.627656 0.493987 0.193974 0.024 Uiso 1 1 calc R U . . .
H13B H 0.370402 0.476088 0.111077 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3324(5) 0.3641(3) 0.2092(3) 0.0189(7) Uani 1 1 d . . . . .
H14A H 0.341609 0.276573 0.139628 0.023 Uiso 1 1 calc R U . . .
H14B H 0.425794 0.367583 0.283190 0.023 Uiso 1 1 calc R U . . .
O15 O 0.0780(4) 0.3652(2) 0.21976(17) 0.0184(5) Uani 1 1 d . . . . .
C16 C -0.0465(6) 0.2494(3) 0.2361(3) 0.0206(7) Uani 1 1 d . . . . .
H16A H 0.033098 0.169427 0.198772 0.025 Uiso 1 1 calc R U . . .
H16B H -0.223111 0.220143 0.194184 0.025 Uiso 1 1 calc R U . . .
C17 C 0.4854(5) 0.6484(3) 0.4106(2) 0.0175(7) Uani 1 1 d . . . . .
H17A H 0.394873 0.568334 0.421239 0.021 Uiso 1 1 calc R U . . .
H17B H 0.430372 0.732907 0.463251 0.021 Uiso 1 1 calc R U . . .
C18 C 0.7616(5) 0.6698(3) 0.4539(3) 0.0190(7) Uani 1 1 d . . . . .
H18A H 0.823255 0.586736 0.403506 0.023 Uiso 1 1 calc R U . . .
H18B H 0.857455 0.753266 0.449832 0.023 Uiso 1 1 calc R U . . .
O19 O 0.7882(4) 0.6894(2) 0.57543(17) 0.0210(5) Uani 1 1 d . . . . .
C20 C 1.0386(6) 0.7159(3) 0.6327(3) 0.0192(7) Uani 1 1 d . . . . .
H20A H 1.141595 0.795427 0.625552 0.023 Uiso 1 1 calc R U . . .
H20B H 1.107983 0.632197 0.593057 0.023 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
O2 C1 C3 107.4(2) . . ?
O2 C1 C7 107.4(3) . . ?
C3 C1 C7 111.2(3) . . ?
O2 C1 C11 110.2(2) . . ?
C3 C1 C11 110.2(2) . . ?
C7 C1 C11 110.3(2) . . ?
C1 O2 H2 101(2) . . ?
F4 C3 F5 107.5(3) . . ?
F4 C3 F6 106.6(3) . . ?
F5 C3 F6 106.0(2) . . ?
F4 C3 C1 112.6(3) . . ?
F5 C3 C1 113.2(3) . . ?
F6 C3 C1 110.4(3) . . ?
F10 C7 F9 107.2(3) . . ?
F10 C7 F8 107.2(3) . . ?
F9 C7 F8 107.4(3) . . ?
F10 C7 C1 110.0(3) . . ?
F9 C7 C1 112.2(3) . . ?
F8 C7 C1 112.6(3) . . ?
N12 C11 C1 107.9(2) . . ?
N12 C11 H11A 110.1 . . ?
C1 C11 H11A 110.1 . . ?
N12 C11 H11B 110.1 . . ?
C1 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C11 N12 C17 115.3(2) . . ?
C11 N12 C13 114.3(2) . . ?
C17 N12 C13 116.1(2) . . ?
N12 C13 C14 112.5(2) . . ?
N12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
O15 C14 C13 109.2(2) . . ?
O15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C14 O15 C16 113.1(2) . . ?
O15 C16 C20 112.5(2) . 2_666 ?
O15 C16 H16A 109.1 . . ?
C20 C16 H16A 109.1 2_666 . ?
O15 C16 H16B 109.1 . . ?
C20 C16 H16B 109.1 2_666 . ?
H16A C16 H16B 107.8 . . ?
N12 C17 C18 116.1(2) . . ?
N12 C17 H17A 108.3 . . ?
C18 C17 H17A 108.3 . . ?
N12 C17 H17B 108.3 . . ?
C18 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
O19 C18 C17 106.0(2) . . ?
O19 C18 H18A 110.5 . . ?
C17 C18 H18A 110.5 . . ?
O19 C18 H18B 110.5 . . ?
C17 C18 H18B 110.5 . . ?
H18A C18 H18B 108.7 . . ?
C20 O19 C18 114.0(2) . . ?
O19 C20 C16 109.2(2) . 2_666 ?
O19 C20 H20A 109.8 . . ?
C16 C20 H20A 109.8 2_666 . ?
O19 C20 H20B 109.8 . . ?
C16 C20 H20B 109.8 2_666 . ?
H20A C20 H20B 108.3 . . ?
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
C1 O2 1.391(4) . ?
C1 C3 1.518(4) . ?
C1 C7 1.525(4) . ?
C1 C11 1.576(4) . ?
O2 H2 0.84(4) . ?
C3 F4 1.328(4) . ?
C3 F5 1.340(3) . ?
C3 F6 1.341(4) . ?
C7 F10 1.329(4) . ?
C7 F9 1.330(4) . ?
C7 F8 1.330(4) . ?
C11 N12 1.448(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 C17 1.467(3) . ?
N12 C13 1.476(4) . ?
C13 C14 1.498(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O15 1.424(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
O15 C16 1.426(4) . ?
C16 C20 1.506(4) 2_666 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.510(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O19 1.423(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
O19 C20 1.414(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
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
C14 H14B O19 0.99 2.44 3.076(4) 121.7 2_666 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C3 F4 -179.8(2) . . . . ?
C7 C1 C3 F4 -62.5(3) . . . . ?
C11 C1 C3 F4 60.2(3) . . . . ?
O2 C1 C3 F5 -57.6(3) . . . . ?
C7 C1 C3 F5 59.8(4) . . . . ?
C11 C1 C3 F5 -177.6(2) . . . . ?
O2 C1 C3 F6 61.1(3) . . . . ?
C7 C1 C3 F6 178.5(3) . . . . ?
C11 C1 C3 F6 -58.9(3) . . . . ?
O2 C1 C7 F10 -61.0(3) . . . . ?
C3 C1 C7 F10 -178.3(3) . . . . ?
C11 C1 C7 F10 59.1(4) . . . . ?
O2 C1 C7 F9 179.8(3) . . . . ?
C3 C1 C7 F9 62.5(3) . . . . ?
C11 C1 C7 F9 -60.1(3) . . . . ?
O2 C1 C7 F8 58.5(4) . . . . ?
C3 C1 C7 F8 -58.9(4) . . . . ?
C11 C1 C7 F8 178.6(3) . . . . ?
O2 C1 C11 N12 -0.8(3) . . . . ?
C3 C1 C11 N12 117.6(3) . . . . ?
C7 C1 C11 N12 -119.2(3) . . . . ?
C1 C11 N12 C17 -113.4(3) . . . . ?
C1 C11 N12 C13 108.3(3) . . . . ?
C11 N12 C13 C14 -170.1(2) . . . . ?
C17 N12 C13 C14 51.9(3) . . . . ?
N12 C13 C14 O15 52.3(3) . . . . ?
C13 C14 O15 C16 179.7(2) . . . . ?
C14 O15 C16 C20 93.8(3) . . . 2_666 ?
C11 N12 C17 C18 -71.7(3) . . . . ?
C13 N12 C17 C18 65.9(3) . . . . ?
N12 C17 C18 O19 -178.3(2) . . . . ?
C17 C18 O19 C20 -178.0(2) . . . . ?
C18 O19 C20 C16 173.8(3) . . . 2_666 ?
