#------------------------------------------------------------------------------
#$Date: 2020-05-04 04:35:48 +0200 (lun 04 de may de 2020) $
#$Revision: 251456 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/46/4134677.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_4134677
loop_
_publ_author_name
'Nisbet, Matthew L.'
'Pendleton, Ian M.'
'Nolis, Gene M.'
'Griffith, Kent J.'
'Schrier, Joshua'
'Cabana, Jordi'
'Norquist, Alexander J.'
'Poeppelmeier, Kenneth R.'
_publ_section_title
;
 Machine-Learning-Assisted Synthesis of Polar Racemates.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7555
_journal_page_last               7566
_journal_paper_doi               10.1021/jacs.0c01239
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C20 H18 Cu N4 O, F6 Hf, 1.5(O)'
_chemical_formula_sum            'C20 H18 Cu F6 Hf N4 O2.5'
_chemical_formula_weight         710.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5550(7)
_cell_length_b                   14.8898(5)
_cell_length_c                   15.0487(5)
_cell_measurement_reflns_used    9724
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.135
_cell_measurement_theta_min      3.191
_cell_volume                     4605.8(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 V2017.3 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.04
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            199823
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.215
_diffrn_reflns_theta_min         1.689
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.504
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0883 before and 0.0666 after correction. The Ratio of minimum to maximum transmission is 0.8219. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_description       block
_exptl_crystal_F_000             2728
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.031
_refine_diff_density_max         1.016
_refine_diff_density_min         -1.339
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details
;
 Flack x determined using 7934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         21788
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.185
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0140P)²+3.0221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0520
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                19766
_reflns_number_total             21788
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c01239_si_005.cif
_cod_data_source_block           work
_cod_depositor_comments
'Adding full bibliography for 4134676--4134681.cif.'
_cod_original_formula_sum        'C20 H18 Cu F6 Hf N4 O2.50'
_cod_database_code               4134677
_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   0.848
_shelx_estimated_absorpt_t_min   0.720
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
  C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30),
 C31(H31), C32(H32), C33(H33), C34(H34), C37(H37), C38(H38), C39(H39), C40(H40)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.78936(2) 0.61878(2) 0.51117(3) 0.01714(6) Uani 1 1 d . . . . .
O1 O 0.78316(13) 0.76075(16) 0.5093(2) 0.0362(7) Uani 1 1 d . . . . .
H1A H 0.749065 0.777799 0.477963 0.054 Uiso 1 1 d GR . . . .
H1B H 0.816515 0.783668 0.480077 0.054 Uiso 1 1 d GR . . . .
N1 N 0.73678(15) 0.56535(18) 0.6144(2) 0.0175(5) Uani 1 1 d . . . . .
N2 N 0.85426(14) 0.63125(18) 0.60604(18) 0.0169(5) Uani 1 1 d . . . . .
N3 N 0.84472(14) 0.55005(18) 0.42161(18) 0.0164(5) Uani 1 1 d . . . . .
N4 N 0.72517(14) 0.6114(2) 0.41457(18) 0.0191(5) Uani 1 1 d . . . . .
C1 C 0.67807(18) 0.5275(2) 0.6119(3) 0.0223(6) Uani 1 1 d . . . . .
H1 H 0.655934 0.524576 0.556574 0.027 Uiso 1 1 calc R . . . .
C2 C 0.64783(19) 0.4923(2) 0.6867(3) 0.0259(7) Uani 1 1 d . . . . .
H2 H 0.606124 0.465146 0.682410 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6796(2) 0.4975(3) 0.7674(3) 0.0278(7) Uani 1 1 d . . . . .
H3 H 0.659769 0.475009 0.819841 0.033 Uiso 1 1 calc R . . . .
C4 C 0.74106(19) 0.5362(2) 0.7707(2) 0.0233(6) Uani 1 1 d . . . . .
H4 H 0.763798 0.540639 0.825495 0.028 Uiso 1 1 calc R . . . .
C5 C 0.76870(17) 0.5683(2) 0.6930(2) 0.0183(5) Uani 1 1 d . . . . .
C6 C 0.83436(16) 0.6090(2) 0.6883(2) 0.0168(5) Uani 1 1 d . . . . .
C7 C 0.87404(19) 0.6240(2) 0.7613(2) 0.0237(7) Uani 1 1 d . . . . .
H7 H 0.859760 0.608587 0.819418 0.028 Uiso 1 1 calc R . . . .
C8 C 0.9353(2) 0.6622(2) 0.7481(3) 0.0272(8) Uani 1 1 d . . . . .
H8 H 0.963111 0.673539 0.797279 0.033 Uiso 1 1 calc R . . . .
C9 C 0.95523(19) 0.6832(2) 0.6631(3) 0.0260(7) Uani 1 1 d . . . . .
H9 H 0.997197 0.707799 0.652757 0.031 Uiso 1 1 calc R . . . .
C10 C 0.91324(17) 0.6679(2) 0.5934(2) 0.0220(6) Uani 1 1 d . . . . .
H10 H 0.926317 0.683738 0.534942 0.026 Uiso 1 1 calc R . . . .
C11 C 0.90511(17) 0.5188(2) 0.4314(2) 0.0199(6) Uani 1 1 d . . . . .
H11 H 0.927353 0.530346 0.485525 0.024 Uiso 1 1 calc R . . . .
C12 C 0.93706(18) 0.4696(2) 0.3652(2) 0.0222(6) Uani 1 1 d . . . . .
H12 H 0.980174 0.448388 0.374035 0.027 Uiso 1 1 calc R . . . .
C13 C 0.90439(17) 0.4527(2) 0.2869(2) 0.0209(6) Uani 1 1 d . . . . .
H13 H 0.924762 0.419594 0.240630 0.025 Uiso 1 1 calc R . . . .
C14 C 0.84110(17) 0.4848(2) 0.2764(2) 0.0199(6) Uani 1 1 d . . . . .
H14 H 0.817759 0.473722 0.223021 0.024 Uiso 1 1 calc R . . . .
C15 C 0.81285(15) 0.5328(2) 0.3447(2) 0.0159(5) Uani 1 1 d . . . . .
C16 C 0.74650(16) 0.5712(2) 0.3393(2) 0.0163(5) Uani 1 1 d . . . . .
C17 C 0.70852(17) 0.5690(2) 0.2631(2) 0.0199(6) Uani 1 1 d . . . . .
H17 H 0.723935 0.540683 0.210537 0.024 Uiso 1 1 calc R . . . .
C18 C 0.64741(18) 0.6091(2) 0.2652(2) 0.0231(6) Uani 1 1 d . . . . .
H18 H 0.620361 0.608006 0.213980 0.028 Uiso 1 1 calc R . . . .
C19 C 0.62622(18) 0.6506(3) 0.3422(3) 0.0258(7) Uani 1 1 d . . . . .
H19 H 0.584773 0.678742 0.344518 0.031 Uiso 1 1 calc R . . . .
C20 C 0.66659(17) 0.6504(3) 0.4159(2) 0.0231(6) Uani 1 1 d . . . . .
H20 H 0.652223 0.678677 0.469005 0.028 Uiso 1 1 calc R . . . .
Cu2 Cu 0.78430(2) 0.23392(3) 0.50065(3) 0.02035(7) Uani 1 1 d . . . . .
O2 O 0.79611(13) 0.09737(18) 0.5202(3) 0.0420(9) Uani 1 1 d . . . . .
H2A H 0.761428 0.067989 0.554238 0.063 Uiso 1 1 d GR . . . .
H2B H 0.833078 0.081029 0.557714 0.063 Uiso 1 1 d GR . . . .
N5 N 0.73108(14) 0.2409(2) 0.6098(2) 0.0207(5) Uani 1 1 d . . . . .
N6 N 0.84800(14) 0.3046(2) 0.58193(19) 0.0197(5) Uani 1 1 d . . . . .
N7 N 0.83659(15) 0.22477(19) 0.39090(19) 0.0206(5) Uani 1 1 d . . . . .
N8 N 0.72145(14) 0.29458(18) 0.41441(19) 0.0176(5) Uani 1 1 d . . . . .
C21 C 0.67312(18) 0.1998(3) 0.6187(3) 0.0246(7) Uani 1 1 d . . . . .
H21 H 0.654974 0.168985 0.569311 0.029 Uiso 1 1 calc R . . . .
C22 C 0.63932(17) 0.2015(3) 0.6985(3) 0.0246(7) Uani 1 1 d . . . . .
H22 H 0.598542 0.171984 0.703813 0.029 Uiso 1 1 calc R . . . .
C23 C 0.66565(17) 0.2466(2) 0.7701(2) 0.0239(7) Uani 1 1 d . . . . .
H23 H 0.642517 0.250182 0.824662 0.029 Uiso 1 1 calc R . . . .
C24 C 0.72672(17) 0.2871(2) 0.7616(2) 0.0214(6) Uani 1 1 d . . . . .
H24 H 0.746248 0.317056 0.810495 0.026 Uiso 1 1 calc R . . . .
C25 C 0.75820(16) 0.2826(2) 0.6802(2) 0.0186(6) Uani 1 1 d . . . . .
C26 C 0.82354(16) 0.3206(2) 0.6640(2) 0.0180(5) Uani 1 1 d . . . . .
C27 C 0.85891(17) 0.3672(2) 0.7278(2) 0.0205(6) Uani 1 1 d . . . . .
H27 H 0.841363 0.376806 0.785398 0.025 Uiso 1 1 calc R . . . .
C28 C 0.92057(18) 0.3997(2) 0.7060(2) 0.0230(6) Uani 1 1 d . . . . .
H28 H 0.945528 0.431811 0.748577 0.028 Uiso 1 1 calc R . . . .
C29 C 0.94495(17) 0.3845(2) 0.6213(3) 0.0232(6) Uani 1 1 d . . . . .
H29 H 0.986510 0.406772 0.604652 0.028 Uiso 1 1 calc R . . . .
C30 C 0.90744(16) 0.3363(2) 0.5618(2) 0.0221(6) Uani 1 1 d . . . . .
H30 H 0.924414 0.325140 0.504130 0.027 Uiso 1 1 calc R . . . .
C31 C 0.89523(18) 0.1851(2) 0.3849(3) 0.0246(6) Uani 1 1 d . . . . .
H31 H 0.915641 0.164215 0.437645 0.030 Uiso 1 1 calc R . . . .
C32 C 0.92673(18) 0.1737(2) 0.3047(3) 0.0245(6) Uani 1 1 d . . . . .
H32 H 0.968395 0.146154 0.302422 0.029 Uiso 1 1 calc R . . . .
C33 C 0.89680(18) 0.2028(2) 0.2278(2) 0.0225(6) Uani 1 1 d . . . . .
H33 H 0.917335 0.194951 0.171743 0.027 Uiso 1 1 calc R . . . .
C34 C 0.83617(17) 0.2438(2) 0.2335(2) 0.0201(6) Uani 1 1 d . . . . .
H34 H 0.814930 0.264782 0.181467 0.024 Uiso 1 1 calc R . . . .
C35 C 0.80721(16) 0.2535(2) 0.3155(2) 0.0178(5) Uani 1 1 d . . . . .
C36 C 0.74230(16) 0.2945(2) 0.3290(2) 0.0162(5) Uani 1 1 d . . . . .
C37 C 0.70536(17) 0.3314(2) 0.2608(2) 0.0215(6) Uani 1 1 d . . . . .
H37 H 0.720635 0.330088 0.201229 0.026 Uiso 1 1 calc R . . . .
C38 C 0.64560(18) 0.3704(2) 0.2811(2) 0.0227(6) Uani 1 1 d . . . . .
H38 H 0.619096 0.395017 0.235508 0.027 Uiso 1 1 calc R . . . .
C39 C 0.62546(17) 0.3728(2) 0.3686(2) 0.0227(6) Uani 1 1 d . . . . .
H39 H 0.585542 0.400893 0.384170 0.027 Uiso 1 1 calc R . . . .
C40 C 0.66416(16) 0.3338(2) 0.4335(2) 0.0202(6) Uani 1 1 d . . . . .
H40 H 0.649734 0.334840 0.493497 0.024 Uiso 1 1 calc R . . . .
Hf1 Hf 0.63792(2) 0.94181(2) 0.50830(2) 0.01581(2) Uani 1 1 d . . . . .
F1 F 0.6113(2) 0.8331(2) 0.5694(2) 0.0627(10) Uani 1 1 d . . . . .
F2 F 0.69676(13) 0.8684(2) 0.42942(17) 0.0418(7) Uani 1 1 d . . . . .
F3 F 0.71461(13) 0.9580(3) 0.58850(18) 0.0536(10) Uani 1 1 d . . . . .
F4 F 0.6696(3) 1.0547(2) 0.45009(19) 0.0672(13) Uani 1 1 d . . . . .
F5 F 0.58357(14) 1.0173(2) 0.58601(18) 0.0431(7) Uani 1 1 d . . . . .
F6 F 0.56998(14) 0.93399(18) 0.41457(19) 0.0369(6) Uani 1 1 d . . . . .
Hf2 Hf 0.96123(2) 0.93395(2) 0.53250(2) 0.01829(3) Uani 1 1 d . . . . .
F7 F 0.9360(2) 0.9447(2) 0.4060(2) 0.0587(10) Uani 1 1 d . . . . .
F8 F 1.01157(13) 0.82369(14) 0.5059(2) 0.0432(6) Uani 1 1 d . . . . .
F9 F 1.03952(9) 1.01076(13) 0.51094(16) 0.0266(4) Uani 1 1 d . . . . .
F10 F 0.98490(14) 0.9233(2) 0.65966(17) 0.0385(6) Uani 1 1 d . . . . .
F11 F 0.91215(12) 1.04684(15) 0.5604(2) 0.0367(6) Uani 1 1 d . . . . .
F12 F 0.88030(12) 0.86322(16) 0.5583(2) 0.0372(6) Uani 1 1 d . . . . .
O3 O 0.98182(18) 0.7004(2) 0.3800(3) 0.0424(8) Uani 1 1 d . . . . .
O4 O 0.96053(18) 0.6840(3) 0.9547(2) 0.0509(10) Uani 1 1 d . . . . .
O5 O 0.54015(18) 0.3181(2) 0.5697(3) 0.0433(8) 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 0.0033 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'
Hf Hf -0.5830 6.1852 '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
N1 Cu1 O1 111.42(13) . . ?
N2 Cu1 O1 87.49(11) . . ?
N2 Cu1 N1 81.02(12) . . ?
N2 Cu1 N3 98.56(11) . . ?
N2 Cu1 N4 177.61(12) . . ?
N3 Cu1 O1 121.71(13) . . ?
N3 Cu1 N1 126.83(11) . . ?
N4 Cu1 O1 90.30(12) . . ?
N4 Cu1 N1 100.66(12) . . ?
N4 Cu1 N3 81.83(12) . . ?
Cu1 O1 H1A 110.0 . . ?
Cu1 O1 H1B 110.2 . . ?
H1A O1 H1B 103.9 . . ?
C1 N1 Cu1 128.2(3) . . ?
C1 N1 C5 118.6(3) . . ?
C5 N1 Cu1 113.2(2) . . ?
C6 N2 Cu1 116.1(2) . . ?
C10 N2 Cu1 123.3(2) . . ?
C10 N2 C6 120.3(3) . . ?
C11 N3 Cu1 128.4(2) . . ?
C11 N3 C15 118.6(3) . . ?
C15 N3 Cu1 112.9(2) . . ?
C16 N4 Cu1 115.2(2) . . ?
C20 N4 Cu1 124.7(2) . . ?
C20 N4 C16 119.8(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.8(4) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C6 114.5(3) . . ?
C4 C5 C6 123.7(3) . . ?
N2 C6 C5 114.9(3) . . ?
N2 C6 C7 120.7(3) . . ?
C7 C6 C5 124.4(3) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.9(3) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9 120.6 . . ?
N2 C10 C9 121.7(4) . . ?
N2 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
N3 C11 H11 118.6 . . ?
N3 C11 C12 122.7(3) . . ?
C12 C11 H11 118.6 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.3(3) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 122.1(3) . . ?
N3 C15 C16 114.8(3) . . ?
C14 C15 C16 123.1(3) . . ?
N4 C16 C15 115.0(3) . . ?
N4 C16 C17 121.3(3) . . ?
C17 C16 C15 123.7(3) . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.6(3) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.8(3) . . ?
C20 C19 H19 120.6 . . ?
N4 C20 C19 121.9(3) . . ?
N4 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
O2 Cu2 N6 109.87(13) . . ?
N5 Cu2 O2 89.92(15) . . ?
N5 Cu2 N6 80.36(12) . . ?
N5 Cu2 N8 98.91(12) . . ?
N7 Cu2 O2 89.27(14) . . ?
N7 Cu2 N5 178.90(13) . . ?
N7 Cu2 N6 100.62(12) . . ?
N7 Cu2 N8 80.98(12) . . ?
N8 Cu2 O2 126.83(13) . . ?
N8 Cu2 N6 123.30(11) . . ?
Cu2 O2 H2A 115.3 . . ?
Cu2 O2 H2B 114.7 . . ?
H2A O2 H2B 98.8 . . ?
C21 N5 Cu2 123.2(3) . . ?
C21 N5 C25 119.9(3) . . ?
C25 N5 Cu2 116.6(2) . . ?
C26 N6 Cu2 113.1(2) . . ?
C30 N6 Cu2 128.2(2) . . ?
C30 N6 C26 118.7(3) . . ?
C31 N7 Cu2 125.0(2) . . ?
C31 N7 C35 118.8(3) . . ?
C35 N7 Cu2 115.9(2) . . ?
C36 N8 Cu2 113.7(2) . . ?
C40 N8 Cu2 127.6(2) . . ?
C40 N8 C36 118.7(3) . . ?
N5 C21 H21 119.3 . . ?
N5 C21 C22 121.4(4) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.2(3) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.3(3) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 120.7 . . ?
C25 C24 C23 118.7(3) . . ?
C25 C24 H24 120.7 . . ?
N5 C25 C24 121.5(3) . . ?
N5 C25 C26 115.0(3) . . ?
C24 C25 C26 123.5(3) . . ?
N6 C26 C25 114.9(3) . . ?
N6 C26 C27 121.6(3) . . ?
C27 C26 C25 123.5(3) . . ?
C26 C27 H27 120.5 . . ?
C26 C27 C28 119.1(3) . . ?
C28 C27 H27 120.5 . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.2(3) . . ?
C29 C28 H28 120.4 . . ?
C28 C29 H29 120.7 . . ?
C30 C29 C28 118.6(3) . . ?
C30 C29 H29 120.7 . . ?
N6 C30 C29 122.9(3) . . ?
N6 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
N7 C31 H31 118.9 . . ?
N7 C31 C32 122.2(3) . . ?
C32 C31 H31 118.9 . . ?
C31 C32 H32 120.5 . . ?
C31 C32 C33 119.0(3) . . ?
C33 C32 H32 120.5 . . ?
C32 C33 H33 120.5 . . ?
C32 C33 C34 119.0(3) . . ?
C34 C33 H33 120.5 . . ?
C33 C34 H34 120.3 . . ?
C35 C34 C33 119.3(3) . . ?
C35 C34 H34 120.3 . . ?
N7 C35 C34 121.6(3) . . ?
N7 C35 C36 114.6(3) . . ?
C34 C35 C36 123.8(3) . . ?
N8 C36 C35 114.6(3) . . ?
N8 C36 C37 121.8(3) . . ?
C37 C36 C35 123.6(3) . . ?
C36 C37 H37 120.5 . . ?
C36 C37 C38 118.9(3) . . ?
C38 C37 H37 120.5 . . ?
C37 C38 H38 120.5 . . ?
C39 C38 C37 119.0(3) . . ?
C39 C38 H38 120.5 . . ?
C38 C39 H39 120.4 . . ?
C38 C39 C40 119.3(3) . . ?
C40 C39 H39 120.4 . . ?
N8 C40 C39 122.2(3) . . ?
N8 C40 H40 118.9 . . ?
C39 C40 H40 118.9 . . ?
F1 Hf1 F2 89.75(16) . . ?
F1 Hf1 F3 92.12(16) . . ?
F1 Hf1 F4 176.74(18) . . ?
F1 Hf1 F5 92.01(16) . . ?
F1 Hf1 F6 95.12(15) . . ?
F3 Hf1 F2 87.01(11) . . ?
F3 Hf1 F4 84.62(18) . . ?
F4 Hf1 F2 90.14(16) . . ?
F5 Hf1 F2 177.49(14) . . ?
F5 Hf1 F3 91.14(11) . . ?
F5 Hf1 F4 88.00(16) . . ?
F5 Hf1 F6 93.23(11) . . ?
F6 Hf1 F2 88.39(10) . . ?
F6 Hf1 F3 171.41(14) . . ?
F6 Hf1 F4 88.13(15) . . ?
F7 Hf2 F8 90.55(16) . . ?
F7 Hf2 F9 90.50(13) . . ?
F7 Hf2 F10 179.02(17) . . ?
F7 Hf2 F11 90.11(15) . . ?
F7 Hf2 F12 90.65(14) . . ?
F8 Hf2 F9 91.20(9) . . ?
F8 Hf2 F11 178.70(12) . . ?
F8 Hf2 F12 92.13(11) . . ?
F9 Hf2 F11 87.67(9) . . ?
F9 Hf2 F12 176.47(10) . . ?
F10 Hf2 F8 90.03(14) . . ?
F10 Hf2 F9 90.28(10) . . ?
F10 Hf2 F11 89.33(13) . . ?
F10 Hf2 F12 88.53(11) . . ?
F11 Hf2 F12 88.98(11) . . ?
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
Cu1 O1 2.118(2) . ?
Cu1 N1 2.053(3) . ?
Cu1 N2 1.963(3) . ?
Cu1 N3 2.039(3) . ?
Cu1 N4 1.966(3) . ?
O1 H1A 0.8820 . ?
O1 H1B 0.8830 . ?
N1 C1 1.332(5) . ?
N1 C5 1.353(4) . ?
N2 C6 1.346(4) . ?
N2 C10 1.343(5) . ?
N3 C11 1.334(4) . ?
N3 C15 1.354(4) . ?
N4 C16 1.354(4) . ?
N4 C20 1.336(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(5) . ?
C5 C6 1.481(5) . ?
C6 C7 1.386(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.396(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.400(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(5) . ?
C15 C16 1.481(5) . ?
C16 C17 1.388(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(5) . ?
C20 H20 0.9500 . ?
Cu2 O2 2.069(3) . ?
Cu2 N5 1.977(3) . ?
Cu2 N6 2.078(3) . ?
Cu2 N7 1.975(3) . ?
Cu2 N8 2.042(3) . ?
O2 H2A 0.9807 . ?
O2 H2B 0.9773 . ?
N5 C21 1.346(5) . ?
N5 C25 1.347(5) . ?
N6 C26 1.354(4) . ?
N6 C30 1.345(4) . ?
N7 C31 1.345(5) . ?
N7 C35 1.355(4) . ?
N8 C36 1.354(4) . ?
N8 C40 1.346(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.398(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(5) . ?
C25 C26 1.477(5) . ?
C26 C27 1.390(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.396(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.387(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.380(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.381(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.390(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.377(5) . ?
C35 C36 1.481(5) . ?
C36 C37 1.391(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.393(5) . ?
C38 H38 0.9500 . ?
C38 C39 1.380(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.388(5) . ?
C40 H40 0.9500 . ?
Hf1 F1 1.939(3) . ?
Hf1 F2 2.017(3) . ?
Hf1 F3 2.000(3) . ?
Hf1 F4 2.005(3) . ?
Hf1 F5 1.969(2) . ?
Hf1 F6 1.988(2) . ?
Hf2 F7 1.979(3) . ?
Hf2 F8 1.981(2) . ?
Hf2 F9 2.0007(18) . ?
Hf2 F10 1.981(3) . ?
Hf2 F11 2.005(2) . ?
Hf2 F12 2.007(2) . ?
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
O1 H1A F2 0.88 1.87 2.677(4) 150.7 . yes
O2 H2A F3 0.98 1.97 2.858(5) 149.7 1_545 yes
O2 H2B F11 0.98 1.70 2.573(4) 146.1 1_545 yes
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.011 0.126 0.746 20.0 9.9 ?
2 -0.011 0.874 0.246 20.0 11.9 ?
3 0.489 0.626 0.246 20.0 10.0 ?
4 0.511 0.374 0.746 20.0 11.8 ?
