#------------------------------------------------------------------------------
#$Date: 2019-10-10 04:06:14 +0300 (Thu, 10 Oct 2019) $
#$Revision: 219233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/13/7701340.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_7701340
loop_
_publ_author_name
'Kodrin, Ivan'
'Borovina, Mladen'
'Šmital, Luka'
'Valdés-Martínez, Jesús'
'Aakeröy, Christer B'
'Đaković, Marijana'
_publ_section_title
;
 Exploring and predicting intermolecular binding preferences in
 crystalline Cu(ii) coordination complexes.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/c9dt03346g
_journal_year                    2019
_chemical_formula_moiety         'C24 H24 Cu F6 N4 O6'
_chemical_formula_sum            'C24 H24 Cu F6 N4 O6'
_chemical_formula_weight         642.01
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-23 deposited with the CCDC.    2019-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9094(2)
_cell_length_b                   8.9094(2)
_cell_length_c                   33.9781(12)
_cell_measurement_reflns_used    2917
_cell_measurement_temperature    200
_cell_measurement_theta_max      31.2020
_cell_measurement_theta_min      3.7740
_cell_volume                     2697.09(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            7762
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1308
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1086 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0413
_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)+(0.0505P)²+0.5448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3223
_reflns_number_total             3587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03346g2.cif
_cod_data_source_block           2b
_cod_original_cell_volume        2697.09(15)
_cod_database_code               7701340
_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   0.827
_shelx_estimated_absorpt_t_min   0.715
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3
 0.81 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C8(H8), C9(H9), C3(H3A)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C5(H5A,H5B,H5C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.55359(4) 0.44641(4) 0.250000 0.02777(15) Uani 1 2 d S T P
O1 O 0.4031(3) 0.2892(3) 0.24169(7) 0.0362(5) Uani 1 1 d . . .
O3 O 0.4756(3) 1.1375(3) 0.33591(8) 0.0425(7) Uani 1 1 d D . .
F3 F 0.3304(3) -0.0912(3) 0.23440(8) 0.0644(8) Uani 1 1 d . . .
O2 O 0.6946(3) 0.3252(3) 0.20829(9) 0.0497(7) Uani 1 1 d . . .
N1 N 0.4192(3) 0.5420(3) 0.29641(8) 0.0308(6) Uani 1 1 d . . .
F1 F 0.2135(3) 0.0820(3) 0.26419(8) 0.0689(8) Uani 1 1 d . . .
F2 F 0.2121(4) 0.0721(4) 0.20115(9) 0.0818(10) Uani 1 1 d . . .
N2 N 0.4740(4) 0.9828(3) 0.32806(9) 0.0369(7) Uani 1 1 d . . .
C6 C 0.4288(4) 0.6873(4) 0.30532(9) 0.0300(7) Uani 1 1 d . . .
H6 H 0.495098 0.748034 0.290276 0.036 Uiso 1 1 calc R . .
C7 C 0.3474(4) 0.7554(4) 0.33532(9) 0.0292(6) Uani 1 1 d . . .
C10 C 0.3262(4) 0.4564(4) 0.31751(9) 0.0338(7) Uani 1 1 d . . .
H10 H 0.317798 0.352982 0.311109 0.041 Uiso 1 1 calc R . .
C11 C 0.3582(4) 0.9184(4) 0.34271(9) 0.0310(7) Uani 1 1 d . . .
C8 C 0.2524(4) 0.6631(4) 0.35726(9) 0.0354(7) Uani 1 1 d . . .
H8 H 0.195162 0.703737 0.378316 0.042 Uiso 1 1 calc R . .
C2 C 0.4317(4) 0.1557(4) 0.23091(9) 0.0328(7) Uani 1 1 d . . .
C9 C 0.2420(5) 0.5120(4) 0.34811(10) 0.0380(8) Uani 1 1 d . . .
H9 H 0.177692 0.447778 0.362744 0.046 Uiso 1 1 calc R . .
C4 C 0.6880(5) 0.1857(5) 0.20475(11) 0.0419(8) Uani 1 1 d . . .
C3 C 0.5620(5) 0.0978(4) 0.21592(11) 0.0394(8) Uani 1 1 d . . .
H3A H 0.568579 -0.007986 0.212790 0.047 Uiso 1 1 calc R . .
C1 C 0.2954(4) 0.0545(5) 0.23302(10) 0.0409(8) Uani 1 1 d . . .
C12 C 0.2356(5) 0.9943(5) 0.36510(12) 0.0461(9) Uani 1 1 d . . .
H12A H 0.241757 0.965802 0.392913 0.069 Uiso 1 1 calc GR . .
H12B H 0.138133 0.963405 0.354447 0.069 Uiso 1 1 calc GR . .
H12C H 0.246356 1.103321 0.362638 0.069 Uiso 1 1 calc GR . .
C5 C 0.8185(5) 0.1054(6) 0.18635(16) 0.0639(13) Uani 1 1 d . . .
H5A H 0.829437 0.137656 0.158928 0.096 Uiso 1 1 calc GR . .
H5B H 0.800693 -0.003126 0.187191 0.096 Uiso 1 1 calc GR . .
H5C H 0.910370 0.129146 0.200916 0.096 Uiso 1 1 calc GR . .
H3 H 0.532(5) 1.167(6) 0.3191(11) 0.067(17) Uiso 1 1 d 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'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 O1 177.50(15) . 8_665
O1 Cu1 O2 91.18(10) 8_665 .
O1 Cu1 O2 86.92(11) 8_665 8_665
O1 Cu1 O2 86.92(11) . .
O1 Cu1 O2 91.18(10) . 8_665
O1 Cu1 N1 91.21(10) . 8_665
O1 Cu1 N1 90.46(10) . .
O1 Cu1 N1 91.22(10) 8_665 .
O1 Cu1 N1 90.46(10) 8_665 8_665
O2 Cu1 O2 81.46(14) . 8_665
N1 Cu1 O2 91.57(10) . 8_665
N1 Cu1 O2 91.57(10) 8_665 .
N1 Cu1 O2 172.49(10) . .
N1 Cu1 O2 172.49(10) 8_665 8_665
N1 Cu1 N1 95.52(14) 8_665 .
C2 O1 Cu1 125.0(2) . .
C4 O2 Cu1 121.9(3) . .
C6 N1 Cu1 121.0(2) . .
C6 N1 C10 118.2(3) . .
C10 N1 Cu1 120.8(2) . .
C11 N2 O3 111.9(3) . .
N1 C6 C7 123.9(3) . .
C6 C7 C11 121.3(3) . .
C6 C7 C8 116.8(3) . .
C8 C7 C11 121.9(3) . .
N1 C10 C9 122.6(3) . .
N2 C11 C7 115.2(3) . .
N2 C11 C12 125.8(3) . .
C7 C11 C12 118.9(3) . .
C9 C8 C7 119.5(3) . .
O1 C2 C3 129.1(3) . .
O1 C2 C1 112.5(3) . .
C3 C2 C1 118.2(3) . .
C10 C9 C8 118.9(3) . .
O2 C4 C3 124.0(4) . .
O2 C4 C5 118.6(4) . .
C3 C4 C5 117.4(4) . .
C2 C3 C4 124.2(4) . .
F3 C1 C2 113.1(3) . .
F1 C1 F3 106.5(3) . .
F1 C1 F2 109.1(4) . .
F1 C1 C2 112.0(3) . .
F2 C1 F3 106.0(3) . .
F2 C1 C2 110.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.959(2) .
Cu1 O1 1.959(2) 8_665
Cu1 O2 2.180(3) .
Cu1 O2 2.180(3) 8_665
Cu1 N1 2.155(3) 8_665
Cu1 N1 2.155(3) .
O1 C2 1.270(4) .
O3 N2 1.404(4) .
F3 C1 1.336(5) .
O2 C4 1.249(5) .
N1 C6 1.332(4) .
N1 C10 1.335(4) .
F1 C1 1.309(4) .
F2 C1 1.322(4) .
N2 C11 1.281(5) .
C6 C7 1.390(5) .
C7 C11 1.477(5) .
C7 C8 1.396(5) .
C10 C9 1.374(5) .
C11 C12 1.493(5) .
C8 C9 1.385(5) .
C2 C3 1.369(6) .
C2 C1 1.514(5) .
C4 C3 1.421(6) .
C4 C5 1.501(6) .
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
O3 H3 O2 0.806(13) 2.00(3) 2.764(4) 158(6) 8_675 yes
