#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:06:00 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261636 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/17/7241799.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_7241799
loop_
_publ_author_name
'Chahine, Ali Y.'
'Turner, David R.'
'Batten, Stuart R.'
_publ_section_title
;
 Crystal engineering of coordination polymers using flexible
 tetracarboxylate linkers with embedded cyclohexyldiamine cores
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              569
_journal_page_last               590
_journal_paper_doi               10.1039/D0CE01620A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C46 H46 N2 O8'
_chemical_formula_sum            'C46 H46 N2 O8'
_chemical_formula_weight         754.85
_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_creation_date             2019-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-06 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                97.309(2)
_cell_angle_beta                 100.270(2)
_cell_angle_gamma                113.335(3)
_cell_formula_units_Z            1
_cell_length_a                   7.6700(2)
_cell_length_b                   8.6982(3)
_cell_length_c                   16.1026(3)
_cell_measurement_reflns_used    4038
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      76.6956
_cell_measurement_theta_min      5.6773
_cell_volume                     947.06(5)
_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      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10604
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.696
_diffrn_reflns_theta_min         5.677
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.88134
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0460
_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)+(0.0645P)²+0.1894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3038
_reflns_number_total             3815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01620a2.cif
_cod_data_source_block           L2
_cod_depositor_comments
'Adding full bibliography for 7241796--7241816.cif.'
_cod_database_code               7241799
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 O3-H3 = O1-H1
 0.82 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3A)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.42827(18) 0.94751(16) 0.30759(9) 0.0403(3) Uani 1 1 d D . . . .
O2 O 0.69019(18) 1.08400(15) 0.42051(8) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.49415(17) 0.76261(15) 0.50507(8) 0.0346(3) Uani 1 1 d D . . . .
O4 O 0.7610(2) 0.91400(18) 0.61352(9) 0.0467(4) Uani 1 1 d . . . . .
N1 N 0.93662(19) 0.23739(16) 0.12183(8) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.8293(2) -0.1445(2) -0.05907(11) 0.0278(3) Uani 1 1 d . . . . .
H1A H 0.800483 -0.229966 -0.024016 0.033 Uiso 1 1 calc R . . . .
H1B H 0.734029 -0.194159 -0.114692 0.033 Uiso 1 1 calc R . . . .
C2 C 0.8119(2) 0.01403(19) -0.01438(11) 0.0280(4) Uani 1 1 d . . . . .
H2A H 0.831827 0.096391 -0.051164 0.034 Uiso 1 1 calc R . . . .
H2B H 0.681449 -0.019560 -0.005216 0.034 Uiso 1 1 calc R . . . .
C3 C 0.9642(2) 0.09649(19) 0.07222(10) 0.0244(3) Uani 1 1 d . . . . .
H3A H 0.940339 0.007529 0.106085 0.029 Uiso 1 1 calc R . . . .
C4 C 0.9908(2) 0.38923(19) 0.08379(10) 0.0278(3) Uani 1 1 d . . . . .
H4A H 0.947186 0.352508 0.021268 0.033 Uiso 1 1 calc R . . . .
H4B H 1.132542 0.452210 0.099200 0.033 Uiso 1 1 calc R . . . .
C5 C 0.9025(2) 0.50694(19) 0.11382(10) 0.0250(3) Uani 1 1 d . . . . .
C6 C 1.0164(2) 0.65814(19) 0.17594(11) 0.0280(3) Uani 1 1 d . . . . .
H6 H 1.151163 0.693554 0.193864 0.034 Uiso 1 1 calc R . . . .
C7 C 0.9331(2) 0.75654(19) 0.21143(11) 0.0279(3) Uani 1 1 d . . . . .
H7 H 1.011639 0.855492 0.253969 0.034 Uiso 1 1 calc R . . . .
C8 C 0.7320(2) 0.70869(19) 0.18400(10) 0.0261(3) Uani 1 1 d . . . . .
C9 C 0.6201(2) 0.5639(2) 0.11711(10) 0.0274(3) Uani 1 1 d . . . . .
H9 H 0.487749 0.534439 0.095075 0.033 Uiso 1 1 calc R . . . .
C10 C 0.7038(2) 0.46370(19) 0.08318(10) 0.0267(3) Uani 1 1 d . . . . .
H10 H 0.626401 0.366483 0.039459 0.032 Uiso 1 1 calc R . . . .
C11 C 0.6359(2) 0.7989(2) 0.22713(11) 0.0286(3) Uani 1 1 d . . . . .
H11 H 0.510123 0.779147 0.198272 0.034 Uiso 1 1 calc R . . . .
C12 C 0.7136(2) 0.9072(2) 0.30441(11) 0.0298(4) Uani 1 1 d . . . . .
H12 H 0.842404 0.934456 0.332528 0.036 Uiso 1 1 calc R . . . .
C13 C 0.6052(2) 0.9851(2) 0.34707(11) 0.0300(4) Uani 1 1 d . . . . .
C14 C 1.0372(2) 0.2802(2) 0.21366(10) 0.0294(4) Uani 1 1 d . . . . .
H14A H 1.172966 0.360423 0.221647 0.035 Uiso 1 1 calc R . . . .
H14B H 1.036512 0.176819 0.230470 0.035 Uiso 1 1 calc R . . . .
C15 C 0.9464(2) 0.3582(2) 0.27294(10) 0.0272(3) Uani 1 1 d . . . . .
C16 C 1.0651(3) 0.4849(2) 0.34690(11) 0.0317(4) Uani 1 1 d . . . . .
H16 H 1.199605 0.517517 0.360766 0.038 Uiso 1 1 calc R . . . .
H1 H 0.376(3) 0.998(3) 0.3361(13) 0.038 Uiso 1 1 d DR . . . .
H3 H 0.440(3) 0.819(2) 0.5308(13) 0.038 Uiso 1 1 d DR . . . .
C17 C 0.9865(2) 0.5629(2) 0.40007(10) 0.0316(4) Uani 1 1 d . . . . .
H17 H 1.068370 0.646732 0.449196 0.038 Uiso 1 1 calc R . . . .
C18 C 0.7849(2) 0.5165(2) 0.38030(10) 0.0277(3) Uani 1 1 d . . . . .
C19 C 0.6658(2) 0.3856(2) 0.30779(10) 0.0283(3) Uani 1 1 d . . . . .
H19 H 0.530920 0.351105 0.294452 0.034 Uiso 1 1 calc R . . . .
C20 C 0.7447(2) 0.3062(2) 0.25528(10) 0.0281(3) Uani 1 1 d . . . . .
H20 H 0.662364 0.217716 0.208021 0.034 Uiso 1 1 calc R . . . .
C21 C 0.6948(2) 0.6026(2) 0.43009(10) 0.0290(4) Uani 1 1 d . . . . .
H21 H 0.559913 0.564323 0.410563 0.035 Uiso 1 1 calc R . . . .
C22 C 0.7841(3) 0.7300(2) 0.50039(11) 0.0322(4) Uani 1 1 d . . . . .
H22 H 0.918382 0.770369 0.523297 0.039 Uiso 1 1 calc R . . . .
C23 C 0.6744(2) 0.8076(2) 0.54221(11) 0.0312(4) Uani 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 0.0181 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'
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
C13 O1 H1 112.3(15) . . ?
C23 O3 H3 114.1(15) . . ?
C4 N1 C3 112.39(11) . . ?
C14 N1 C3 111.84(12) . . ?
C14 N1 C4 111.92(12) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C3 C1 H1A 109.5 2_755 . ?
C3 C1 H1B 109.5 2_755 . ?
C3 C1 C2 110.89(12) 2_755 . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.22(13) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
N1 C3 C1 115.24(12) . 2_755 ?
N1 C3 C2 111.68(12) . . ?
N1 C3 H3A 106.4 . . ?
C1 C3 H3A 106.4 2_755 . ?
C2 C3 C1 110.19(12) . 2_755 ?
C2 C3 H3A 106.4 . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
N1 C4 C5 112.52(12) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C6 C5 C4 120.63(14) . . ?
C6 C5 C10 118.24(13) . . ?
C10 C5 C4 121.07(13) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.21(15) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.55(14) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 118.15(13) . . ?
C7 C8 C11 121.73(14) . . ?
C9 C8 C11 119.99(14) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.88(14) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.69(13) . . ?
C9 C10 H10 119.7 . . ?
C8 C11 H11 117.2 . . ?
C12 C11 C8 125.55(16) . . ?
C12 C11 H11 117.2 . . ?
C11 C12 H12 118.5 . . ?
C11 C12 C13 123.08(16) . . ?
C13 C12 H12 118.5 . . ?
O1 C13 C12 117.97(14) . . ?
O2 C13 O1 123.60(14) . . ?
O2 C13 C12 118.42(15) . . ?
N1 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
N1 C14 C15 113.92(13) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C16 C15 C14 120.21(14) . . ?
C20 C15 C14 121.34(14) . . ?
C20 C15 C16 118.45(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.30(15) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.35(15) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C21 123.00(14) . . ?
C19 C18 C17 118.16(14) . . ?
C19 C18 C21 118.81(15) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.30(15) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.34(14) . . ?
C19 C20 H20 119.8 . . ?
C18 C21 H21 116.3 . . ?
C22 C21 C18 127.41(16) . . ?
C22 C21 H21 116.3 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.23(16) . . ?
C23 C22 H22 119.4 . . ?
O3 C23 C22 118.53(14) . . ?
O4 C23 O3 122.87(14) . . ?
O4 C23 C22 118.59(15) . . ?
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
O1 C13 1.281(2) . ?
O1 H1 0.843(15) . ?
O2 C13 1.259(2) . ?
O3 H3 0.871(15) . ?
O3 C23 1.281(2) . ?
O4 C23 1.260(2) . ?
N1 C3 1.4836(16) . ?
N1 C4 1.468(2) . ?
N1 C14 1.465(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.5377(18) . ?
C1 C3 1.532(2) 2_755 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.524(2) . ?
C3 H3A 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5104(19) . ?
C5 C6 1.392(2) . ?
C5 C10 1.392(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.397(2) . ?
C8 C9 1.397(2) . ?
C8 C11 1.464(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.335(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.468(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5180(19) . ?
C15 C16 1.395(2) . ?
C15 C20 1.391(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(2) . ?
C18 C19 1.397(2) . ?
C18 C21 1.462(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.335(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.467(2) . ?
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
N1 C4 C5 C6 103.21(17) . . . . ?
N1 C4 C5 C10 -73.89(19) . . . . ?
N1 C14 C15 C16 -144.75(16) . . . . ?
N1 C14 C15 C20 35.2(2) . . . . ?
C1 C2 C3 N1 -173.28(12) . . . . ?
C1 C2 C3 C1 57.30(19) . . . 2_755 ?
C3 N1 C4 C5 160.77(13) . . . . ?
C3 N1 C14 C15 -153.76(13) . . . . ?
C3 C1 C2 C3 -57.71(19) 2_755 . . . ?
C4 N1 C3 C1 55.53(18) . . . 2_755 ?
C4 N1 C3 C2 -71.20(16) . . . . ?
C4 N1 C14 C15 79.11(17) . . . . ?
C4 C5 C6 C7 -172.25(15) . . . . ?
C4 C5 C10 C9 173.74(15) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C6 C5 C10 C9 -3.4(2) . . . . ?
C6 C7 C8 C9 -3.0(2) . . . . ?
C6 C7 C8 C11 172.85(15) . . . . ?
C7 C8 C9 C10 4.5(2) . . . . ?
C7 C8 C11 C12 -14.5(3) . . . . ?
C8 C9 C10 C5 -1.3(2) . . . . ?
C8 C11 C12 C13 -175.78(15) . . . . ?
C9 C8 C11 C12 161.26(17) . . . . ?
C10 C5 C6 C7 4.9(2) . . . . ?
C11 C8 C9 C10 -171.44(15) . . . . ?
C11 C12 C13 O1 -0.4(3) . . . . ?
C11 C12 C13 O2 179.06(17) . . . . ?
C14 N1 C3 C1 -71.35(18) . . . 2_755 ?
C14 N1 C3 C2 161.92(13) . . . . ?
C14 N1 C4 C5 -72.39(16) . . . . ?
C14 C15 C16 C17 177.31(16) . . . . ?
C14 C15 C20 C19 -176.52(15) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C15 C20 C19 3.4(3) . . . . ?
C16 C17 C18 C19 2.4(3) . . . . ?
C16 C17 C18 C21 -175.35(16) . . . . ?
C17 C18 C19 C20 -1.6(3) . . . . ?
C17 C18 C21 C22 -1.9(3) . . . . ?
C18 C19 C20 C15 -1.3(3) . . . . ?
C18 C21 C22 C23 178.16(16) . . . . ?
C19 C18 C21 C22 -179.62(18) . . . . ?
C20 C15 C16 C17 -2.6(3) . . . . ?
C21 C18 C19 C20 176.25(15) . . . . ?
C21 C22 C23 O3 -6.9(3) . . . . ?
C21 C22 C23 O4 172.33(18) . . . . ?
