#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:33:37 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258056 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/97/7239788.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_7239788
loop_
_publ_author_name
'Sharma, Vishal R.'
'Mehmood, Arshad'
'Janesko, Benjamin G.'
'Simanek, Eric E.'
_publ_section_title
;
 Efficient syntheses of macrocycles ranging from 22--28 atoms through
 spontaneous dimerization to yield bis-hydrazones
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3217
_journal_page_last               3220
_journal_paper_doi               10.1039/C9RA08056B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C22 H34 N16 O4, 2(C2 F3 O2), 2(H2 O)'
_chemical_formula_sum            'C26 H38 F6 N16 O10'
_chemical_formula_weight         848.72
_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   mixed
_audit_creation_date             2019-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-03 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.1840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5858(3)
_cell_length_b                   18.8852(6)
_cell_length_c                   10.9389(4)
_cell_measurement_reflns_used    5480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.98
_cell_volume                     1792.03(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.96
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12645
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_min         2.981
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0476 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.8361. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0473
_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)+(0.0471P)²+1.5900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3504
_reflns_number_total             4393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra08056b2.cif
_cod_data_source_block           1x1
_cod_depositor_comments
'Adding full bibliography for 7239788--7239792.cif.'
_cod_database_code               7239788
_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   0.979
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C4(H4A,H4B), C7(H7A,H7B), C9(H9A,H9B), C6(H6A,H6B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C8(H8A)
;
_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
O2 O 0.03218(13) 0.59040(7) 0.01005(12) 0.0182(3) Uani 1 1 d .
O3 O 0.52588(14) 0.58728(7) 0.46216(12) 0.0208(3) Uani 1 1 d .
O5 O 0.72551(16) 0.55685(8) -0.02954(14) 0.0240(3) Uani 1 1 d .
F3 F 0.56462(15) 0.72442(6) 0.63316(17) 0.0482(4) Uani 1 1 d .
O4 O 0.63239(15) 0.57354(7) 0.68697(13) 0.0235(3) Uani 1 1 d .
F2 F 0.34589(16) 0.68880(8) 0.48368(15) 0.0559(5) Uani 1 1 d .
F1 F 0.41325(18) 0.66388(7) 0.68863(17) 0.0522(4) Uani 1 1 d .
N1 N 0.72953(16) 0.48986(8) 0.41623(14) 0.0142(3) Uani 1 1 d .
N2 N 0.94508(15) 0.41634(7) 0.53281(14) 0.0141(3) Uani 1 1 d .
N6 N 0.66374(16) 0.51926(8) 0.19247(15) 0.0174(3) Uani 1 1 d .
N5 N 0.82071(15) 0.47324(7) 0.64588(14) 0.0143(3) Uani 1 1 d .
H5 H 0.738043 0.495917 0.640370 0.017 Uiso 1 1 calc R
O1 O 1.1008(2) 0.21338(7) 0.37106(15) 0.0370(4) Uani 1 1 d .
N8 N 0.26855(16) 0.60567(8) 0.18261(16) 0.0186(3) Uani 1 1 d .
N7 N 0.54211(16) 0.55669(8) 0.19746(15) 0.0172(3) Uani 1 1 d .
N3 N 0.85328(16) 0.43725(7) 0.29353(14) 0.0154(3) Uani 1 1 d .
N4 N 1.04609(16) 0.35705(8) 0.40441(14) 0.0165(3) Uani 1 1 d .
C1 C 0.83509(17) 0.45873(8) 0.53279(16) 0.0130(3) Uani 1 1 d .
C10 C 0.12260(18) 0.58288(8) 0.12990(17) 0.0140(3) Uani 1 1 d .
C3 C 0.75079(18) 0.48101(9) 0.30172(16) 0.0147(3) Uani 1 1 d .
C2 C 0.94492(18) 0.40427(8) 0.41061(17) 0.0142(3) Uani 1 1 d .
C12 C 0.54831(18) 0.60274(9) 0.57900(17) 0.0165(3) Uani 1 1 d .
C8 C 0.47142(19) 0.59938(9) 0.10139(18) 0.0194(4) Uani 1 1 d .
H8A H 0.506373 0.607190 0.033231 0.023 Uiso 1 1 calc R
C11 C 0.93692(18) 0.45290(9) 0.77817(16) 0.0148(3) Uani 1 1 d .
H11A H 0.994420 0.495887 0.824189 0.018 Uiso 1 1 calc R
H11B H 1.010998 0.420590 0.765444 0.018 Uiso 1 1 calc R
C4 C 1.0371(2) 0.33049(9) 0.27526(18) 0.0194(4) Uani 1 1 d .
H4A H 1.138476 0.335032 0.272301 0.023 Uiso 1 1 calc R
H4B H 0.960295 0.358004 0.199435 0.023 Uiso 1 1 calc R
C7 C 1.15127(19) 0.31597(9) 0.52037(18) 0.0179(3) Uani 1 1 d .
H7A H 1.144141 0.332425 0.603449 0.022 Uiso 1 1 calc R
H7B H 1.258659 0.322870 0.532193 0.022 Uiso 1 1 calc R
C9 C 0.3326(2) 0.63718(11) 0.0968(2) 0.0281(4) Uani 1 1 d .
H9A H 0.360654 0.686967 0.124812 0.034 Uiso 1 1 calc R
H9B H 0.252523 0.637537 0.002459 0.034 Uiso 1 1 calc R
C13 C 0.4667(2) 0.67064(10) 0.5951(2) 0.0241(4) Uani 1 1 d .
C6 C 1.1090(3) 0.23790(10) 0.4974(2) 0.0308(5) Uani 1 1 d .
H6A H 1.187031 0.209820 0.571394 0.037 Uiso 1 1 calc R
H6B H 1.008101 0.230391 0.500004 0.037 Uiso 1 1 calc R
C5 C 0.9895(3) 0.25328(10) 0.2639(2) 0.0289(4) Uani 1 1 d .
H5A H 0.888110 0.249312 0.267014 0.035 Uiso 1 1 calc R
H5B H 0.979232 0.234026 0.176266 0.035 Uiso 1 1 calc R
H5C H 0.679(3) 0.5581(14) -0.112(3) 0.042(7) Uiso 1 1 d .
H5D H 0.822(4) 0.5706(16) -0.018(3) 0.055(8) Uiso 1 1 d .
H1 H 0.661(3) 0.5171(13) 0.420(2) 0.030(6) Uiso 1 1 d .
H6 H 0.689(2) 0.5230(12) 0.123(2) 0.023(5) Uiso 1 1 d .
H8 H 0.324(2) 0.5995(11) 0.267(2) 0.019(5) Uiso 1 1 d .
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_3
C3 N1 C1 117.41(14) .
C1 N2 C2 115.78(14) .
C3 N6 N7 117.07(14) .
C1 N5 C11 122.20(13) .
C5 O1 C6 109.88(15) .
C10 N8 C9 120.43(16) .
C8 N7 N6 117.01(14) .
C3 N3 C2 115.22(14) .
C2 N4 C4 121.94(14) .
C2 N4 C7 123.76(14) .
C7 N4 C4 112.97(13) .
N2 C1 N1 121.97(15) .
N2 C1 N5 121.48(15) .
N5 C1 N1 116.55(14) .
O2 C10 N8 123.64(15) .
O2 C10 C11 117.72(14) 3_666
N8 C10 C11 118.63(15) 3_666
N6 C3 N1 118.27(15) .
N3 C3 N1 123.22(15) .
N3 C3 N6 118.50(15) .
N2 C2 N3 125.60(15) .
N4 C2 N2 117.69(14) .
N4 C2 N3 116.69(14) .
O3 C12 O4 129.46(16) .
O3 C12 C13 115.99(15) .
O4 C12 C13 114.47(15) .
N7 C8 C9 119.12(16) .
N5 C11 C10 115.77(13) 3_666
N4 C4 C5 107.47(14) .
N4 C7 C6 109.53(15) .
N8 C9 C8 113.52(15) .
F3 C13 F1 106.57(17) .
F3 C13 C12 110.22(14) .
F2 C13 F3 108.47(17) .
F2 C13 F1 105.15(17) .
F2 C13 C12 113.37(16) .
F1 C13 C12 112.70(16) .
O1 C6 C7 112.04(15) .
O1 C5 C4 110.39(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C10 1.234(2) .
O3 C12 1.237(2) .
F3 C13 1.324(2) .
O4 C12 1.240(2) .
F2 C13 1.320(2) .
F1 C13 1.331(2) .
N1 C1 1.377(2) .
N1 C3 1.362(2) .
N2 C1 1.324(2) .
N2 C2 1.355(2) .
N6 N7 1.384(2) .
N6 C3 1.341(2) .
N5 C1 1.330(2) .
N5 C11 1.453(2) .
O1 C6 1.428(2) .
O1 C5 1.420(3) .
N8 C10 1.337(2) .
N8 C9 1.450(2) .
N7 C8 1.268(2) .
N3 C3 1.316(2) .
N3 C2 1.357(2) .
N4 C2 1.340(2) .
N4 C4 1.467(2) .
N4 C7 1.463(2) .
C10 C11 1.511(2) 3_666
C12 C13 1.551(2) .
C8 C9 1.492(2) .
C4 C5 1.517(3) .
C7 C6 1.521(3) .
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
N5 H5 O4 0.88 1.97 2.7820(18) 153.2 . yes
C8 H8A O5 0.95 2.65 3.405(2) 137.0 . yes
C11 H11A O2 0.99 2.61 3.470(2) 145.0 1_656 yes
C11 H11A N3 0.99 2.64 3.210(2) 116.6 3_766 yes
C4 H4B O2 0.99 2.52 3.263(2) 131.8 3_665 yes
C7 H7B O3 0.99 2.65 3.528(2) 147.5 3_766 yes
C9 H9A F3 0.99 2.55 3.344(2) 137.6 4_575 yes
O5 H5C O4 0.82(3) 2.07(3) 2.8560(19) 161(3) 1_554 yes
O5 H5D O2 0.92(3) 1.94(3) 2.8544(18) 175(3) 1_655 yes
N1 H1 O3 0.85(2) 2.04(3) 2.8779(19) 170(2) . yes
N6 H6 O5 0.89(2) 1.96(2) 2.824(2) 165(2) . yes
N8 H8 O3 0.85(2) 2.20(2) 3.0227(19) 161.5(19) . yes
