#------------------------------------------------------------------------------
#$Date: 2019-10-10 04:06:14 +0300 (Thu, 10 Oct 2019) $
#$Revision: 219233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/13/7701342.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_7701342
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         'C34 H22 Cu F12 N4 O6'
_chemical_formula_sum            'C34 H22 Cu F12 N4 O6'
_chemical_formula_weight         874.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-23
_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                105.030(4)
_cell_angle_beta                 97.391(4)
_cell_angle_gamma                93.535(4)
_cell_formula_units_Z            1
_cell_length_a                   9.0451(4)
_cell_length_b                   10.1886(5)
_cell_length_c                   10.3628(4)
_cell_measurement_reflns_used    3688
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.3240
_cell_measurement_theta_min      2.9510
_cell_volume                     910.16(7)
_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      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8348
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.835
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79392
_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    1.595
_exptl_crystal_description       block
_exptl_crystal_F_000             439
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0432
_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)+(0.0660P)²+0.1157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3731
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03346g2.cif
_cod_data_source_block           5a-I
_cod_database_code               7701342
_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   0.865
_shelx_estimated_absorpt_t_min   0.769
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O3-H3
 0.81 with sigma of 0.01
 C1-F2A = C1-F3B = C1-F1A = C1-F2B = C1-F1B = C1-F3A
 1.32 with sigma of 0.005
 F2A-F1A \\sim F2A-F3A \\sim F3B-F2B \\sim F3B-F1B \\sim F1A-F3A \\sim F2B-F1B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F1A, F2A, F3A, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2B, F1B, F3B, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F2A)=Sof(F3A)=Sof(F1A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C3(H3A), C13(H13), C17(H17), C14(H14),
 C15(H15), C16(H16)
;
_olex2_date_sample_data_collection 2019-07-22
_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
Cu1 Cu 0.500000 0.500000 0.500000 0.03656(12) Uani 1 2 d S T P . .
O1 O 0.70406(16) 0.58429(15) 0.49957(15) 0.0445(3) Uani 1 1 d . . . . .
O2 O 0.46739(17) 0.71291(15) 0.64053(14) 0.0482(4) Uani 1 1 d . . . . .
N1 N 0.58139(19) 0.42892(16) 0.65565(16) 0.0383(4) Uani 1 1 d . . . . .
O3 O 0.7678(3) 0.2674(2) 1.19762(19) 0.0754(6) Uani 1 1 d D . . . .
F6 F 0.3386(2) 0.94700(19) 0.6486(2) 0.0993(6) Uani 1 1 d . . . . .
F5 F 0.5469(3) 1.05722(17) 0.6583(3) 0.1102(7) Uani 1 1 d . . . . .
N2 N 0.6980(3) 0.3074(2) 1.08884(19) 0.0583(5) Uani 1 1 d . . . . .
C6 C 0.5044(2) 0.4217(2) 0.7577(2) 0.0422(4) Uani 1 1 d . . . . .
H6 H 0.408272 0.449566 0.754925 0.051 Uiso 1 1 calc R . . . .
C7 C 0.5613(2) 0.3754(2) 0.8647(2) 0.0433(5) Uani 1 1 d . . . . .
H7 H 0.503232 0.370380 0.931422 0.052 Uiso 1 1 calc R . . . .
C8 C 0.7064(2) 0.3357(2) 0.87385(19) 0.0392(4) Uani 1 1 d . . . . .
C9 C 0.7849(2) 0.3436(2) 0.7679(2) 0.0444(5) Uani 1 1 d . . . . .
H9 H 0.881948 0.318168 0.768906 0.053 Uiso 1 1 calc R . . . .
C12 C 0.9272(2) 0.2404(2) 0.9904(2) 0.0437(5) Uani 1 1 d . . . . .
C10 C 0.7197(2) 0.3887(2) 0.6628(2) 0.0447(5) Uani 1 1 d . . . . .
H10 H 0.773919 0.391436 0.592977 0.054 Uiso 1 1 calc R . . . .
C2 C 0.7467(2) 0.7089(2) 0.5227(2) 0.0454(5) Uani 1 1 d . . . . .
F4 F 0.4986(3) 0.9814(2) 0.8238(2) 0.1298(10) Uani 1 1 d . . . . .
C11 C 0.7765(2) 0.2918(2) 0.9915(2) 0.0434(5) Uani 1 1 d . . . . .
C4 C 0.5432(3) 0.8154(2) 0.6325(2) 0.0470(5) Uani 1 1 d . . . . .
C3 C 0.6772(3) 0.8213(2) 0.5790(3) 0.0557(6) Uani 1 1 d . . . . .
H3A H 0.721906 0.906878 0.581854 0.067 Uiso 1 1 calc R . . . .
F1B F 1.0124(10) 0.726(3) 0.5638(15) 0.155(7) Uani 0.367(17) 1 d D U . A 1
C13 C 0.9517(3) 0.1259(3) 0.8930(2) 0.0562(6) Uani 1 1 d . . . . .
H13 H 0.872094 0.078385 0.828495 0.067 Uiso 1 1 calc R . . . .
C17 C 1.0471(3) 0.3079(3) 1.0867(3) 0.0660(7) Uani 1 1 d . . . . .
H17 H 1.032685 0.383947 1.154477 0.079 Uiso 1 1 calc R . . . .
C5 C 0.4817(4) 0.9520(3) 0.6916(3) 0.0716(8) Uani 1 1 d . . . . .
F2B F 0.9125(16) 0.6381(15) 0.3673(14) 0.131(6) Uani 0.367(17) 1 d D U . A 1
C14 C 1.0927(4) 0.0809(3) 0.8900(3) 0.0729(8) Uani 1 1 d . . . . .
H14 H 1.107607 0.003071 0.824450 0.087 Uiso 1 1 calc R . . . .
F3B F 0.916(2) 0.8458(13) 0.441(2) 0.140(6) Uani 0.367(17) 1 d D U . A 1
C15 C 1.2098(4) 0.1515(4) 0.9838(4) 0.0818(9) Uani 1 1 d . . . . .
H15 H 1.305386 0.123180 0.980290 0.098 Uiso 1 1 calc R . . . .
C16 C 1.1879(4) 0.2633(4) 1.0828(4) 0.0830(9) Uani 1 1 d . . . . .
H16 H 1.267836 0.309415 1.147675 0.100 Uiso 1 1 calc R . . . .
C1 C 0.8976(3) 0.7328(3) 0.4774(3) 0.0756(8) Uani 1 1 d D U . . .
F2A F 0.8824(10) 0.7025(15) 0.3466(5) 0.152(4) Uani 0.633(17) 1 d D U . A 2
F3A F 0.9614(9) 0.8577(5) 0.5272(14) 0.141(4) Uani 0.633(17) 1 d D U . A 2
F1A F 0.9934(6) 0.6575(8) 0.5192(10) 0.117(3) Uani 0.633(17) 1 d D U . A 2
H3 H 0.705(4) 0.283(5) 1.249(4) 0.143(18) 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 180.0 . 2_666
O1 Cu1 O2 84.90(6) . .
O1 Cu1 O2 95.10(6) 2_666 .
O1 Cu1 O2 95.10(6) . 2_666
O1 Cu1 O2 84.90(6) 2_666 2_666
O1 Cu1 N1 90.44(6) . 2_666
O1 Cu1 N1 89.56(6) . .
O1 Cu1 N1 89.56(6) 2_666 2_666
O1 Cu1 N1 90.44(6) 2_666 .
O2 Cu1 O2 180.00(7) 2_666 .
N1 Cu1 O2 86.81(6) 2_666 .
N1 Cu1 O2 93.19(6) . .
N1 Cu1 O2 93.19(6) 2_666 2_666
N1 Cu1 O2 86.81(6) . 2_666
N1 Cu1 N1 180.00(9) 2_666 .
C2 O1 Cu1 127.74(13) . .
C4 O2 Cu1 118.65(13) . .
C6 N1 Cu1 123.27(14) . .
C10 N1 Cu1 119.64(13) . .
C10 N1 C6 117.07(17) . .
C11 N2 O3 112.46(19) . .
N1 C6 C7 123.06(18) . .
C6 C7 C8 120.08(18) . .
C7 C8 C9 116.35(18) . .
C7 C8 C11 122.24(17) . .
C9 C8 C11 121.38(18) . .
C10 C9 C8 120.32(18) . .
C13 C12 C11 121.1(2) . .
C13 C12 C17 118.3(2) . .
C17 C12 C11 120.6(2) . .
N1 C10 C9 123.10(18) . .
O1 C2 C3 129.7(2) . .
O1 C2 C1 112.5(2) . .
C3 C2 C1 117.9(2) . .
N2 C11 C8 114.02(19) . .
N2 C11 C12 126.29(19) . .
C8 C11 C12 119.65(17) . .
O2 C4 C3 128.1(2) . .
O2 C4 C5 114.9(2) . .
C3 C4 C5 117.0(2) . .
C2 C3 C4 124.2(2) . .
C12 C13 C14 121.0(3) . .
C16 C17 C12 120.6(3) . .
F6 C5 F5 106.0(3) . .
F6 C5 F4 107.3(3) . .
F6 C5 C4 111.2(2) . .
F5 C5 C4 113.6(2) . .
F4 C5 F5 107.7(3) . .
F4 C5 C4 110.7(2) . .
C15 C14 C13 119.5(3) . .
C16 C15 C14 120.6(3) . .
C15 C16 C17 120.0(3) . .
F1B C1 C2 114.2(6) . .
F1B C1 F2B 103.9(8) . .
F1B C1 F3B 109.0(8) . .
F2B C1 C2 111.2(6) . .
F3B C1 C2 114.7(6) . .
F3B C1 F2B 102.7(7) . .
F2A C1 C2 110.1(4) . .
F2A C1 F3A 109.0(5) . .
F2A C1 F1A 108.5(6) . .
F3A C1 C2 113.8(4) . .
F1A C1 C2 110.7(4) . .
F1A C1 F3A 104.4(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9882(14) .
Cu1 O1 1.9883(14) 2_666
Cu1 O2 2.3376(14) .
Cu1 O2 2.3376(14) 2_666
Cu1 N1 2.0085(16) 2_666
Cu1 N1 2.0085(16) .
O1 C2 1.255(3) .
O2 C4 1.241(3) .
N1 C6 1.354(2) .
N1 C10 1.339(3) .
O3 N2 1.386(2) .
F6 C5 1.307(4) .
F5 C5 1.336(4) .
N2 C11 1.289(3) .
C6 C7 1.368(3) .
C7 C8 1.396(3) .
C8 C9 1.399(3) .
C8 C11 1.486(3) .
C9 C10 1.369(3) .
C12 C11 1.491(3) .
C12 C13 1.381(3) .
C12 C17 1.385(3) .
C2 C3 1.373(3) .
C2 C1 1.525(3) .
F4 C5 1.310(4) .
C4 C3 1.400(3) .
C4 C5 1.537(3) .
F1B C1 1.299(5) .
C13 C14 1.384(4) .
C17 C16 1.380(4) .
F2B C1 1.317(5) .
C14 C15 1.365(5) .
F3B C1 1.309(4) .
C15 C16 1.365(5) .
C1 F2A 1.296(4) .
C1 F3A 1.308(4) .
C1 F1A 1.298(4) .
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 0.821(10) 2.047(13) 2.859(2) 170(5) 2_667 yes
