#------------------------------------------------------------------------------
#$Date: 2023-10-06 02:24:39 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286692 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/96/1569696.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_1569696
loop_
_publ_author_name
'Wang, Lei'
'Xie, Zhu-Lin'
'Li, Xin'
'Lynch, Vincent M.'
'Mulfort, Karen L.'
_publ_section_title
;
 Optical detection of alcohols with a Cu(I)HETPHEN complex by reversible
 aldehyde to hemiacetal conversion.
;
_journal_issue                   18
_journal_name_full               'The Analyst'
_journal_page_first              4274
_journal_page_last               4278
_journal_paper_doi               10.1039/d3an01005h
_journal_volume                  148
_journal_year                    2023
_chemical_formula_moiety         'C44 H36 Cu N4 O2, F6 P, C H2 Cl2'
_chemical_formula_sum            'C46.5 H38 Cl2 Cu F6 N4 O2 P'
_chemical_formula_weight         964.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-12-12 deposited with the CCDC.	2023-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5422(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.52666(16)
_cell_length_b                   18.9337(2)
_cell_length_c                   17.8755(3)
_cell_measurement_reflns_used    13243
_cell_measurement_temperature    100.02(13)
_cell_measurement_theta_max      72.6760
_cell_measurement_theta_min      3.6340
_cell_volume                     4388.60(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00   13.50    --  -41.59  38.00-150.00   99
  2  ω     54.00 178.00   1.00   52.00    --  107.09  15.00 -90.00  124
  3  ω    -87.00  -6.00   1.00   13.50    --  -41.59 125.00-150.00   81
  4  ω     24.00 100.00   1.00   52.00    --  107.09 -94.00 -30.00   76
  5  ω   -115.00 -13.00   1.00   13.50    --  -41.59 -57.00 150.00  102
  6  ω     97.00 178.00   1.00   52.00    --  107.09 125.00 -90.00   81
  7  ω     34.00 112.00   1.00   52.00    --  107.09-125.00-180.00   78
  8  ω     35.00 136.00   1.00   52.00    --  107.09 -61.00 150.00  101
  9  ω   -116.00 -17.00   1.00   13.50    --  -41.59 -38.00  30.00   99
 10  ω     79.00 178.00   1.00   52.00    --  107.09  30.00 150.00   99
 11  ω     54.00  87.00   1.00   52.00    --  107.09  15.00  30.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0411026000
_diffrn_orient_matrix_UB_12      0.0719697000
_diffrn_orient_matrix_UB_13      -0.0357484000
_diffrn_orient_matrix_UB_21      0.0913439000
_diffrn_orient_matrix_UB_22      0.0372643000
_diffrn_orient_matrix_UB_23      0.0582569000
_diffrn_orient_matrix_UB_31      0.0639868000
_diffrn_orient_matrix_UB_32      -0.0069491000
_diffrn_orient_matrix_UB_33      -0.0584233000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24952
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.316
_diffrn_reflns_theta_min         3.479
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.764
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       prism
_exptl_crystal_F_000             1972
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         8546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0632P)²+4.1244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7500
_reflns_number_total             8546
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3an01005h2.cif
_cod_data_source_block           lw-cu-cho
_cod_depositor_comments
'Adding full bibliography for 1569695--1569696.cif.'
_cod_original_cell_volume        4388.59(10)
_cod_original_formula_sum        'C46.50 H38 Cl2 Cu F6 N4 O2 P'
_cod_database_code               1569696
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C48H38N4F6PCl2O2Cu
_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.
;
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C17(H17), C24(H24),
 C26(H26), C31(H31), C32(H32), C35(H35), C36(H36), C39(H39), C40(H40), C43(H43),
  C44(H44)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2021-05-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.142
_oxdiff_exptl_absorpt_empirical_full_min 0.907
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.80827(2) 0.74720(2) 0.48352(2) 0.02007(10) Uani 1 1 d . . . . .
O1 O 0.29030(13) 0.63797(11) 0.41034(12) 0.0437(5) Uani 1 1 d . . . . .
O2 O 0.41511(15) 0.87350(11) 0.15767(10) 0.0405(4) Uani 1 1 d . . . . .
N1 N 0.84383(13) 0.81015(9) 0.58135(10) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.96077(13) 0.72880(9) 0.51630(10) 0.0196(3) Uani 1 1 d . . . . .
N3 N 0.67781(12) 0.68973(9) 0.46930(10) 0.0198(3) Uani 1 1 d . . . . .
N4 N 0.72347(13) 0.79202(10) 0.38280(10) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.78402(16) 0.85102(11) 0.61069(12) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.82608(18) 0.89616(12) 0.67475(14) 0.0287(5) Uani 1 1 d . . . . .
H2 H 0.782093 0.926204 0.693447 0.034 Uiso 1 1 calc R U . . .
C3 C 0.93036(18) 0.89666(12) 0.71000(13) 0.0293(5) Uani 1 1 d . . . . .
H3 H 0.958937 0.927029 0.753033 0.035 Uiso 1 1 calc R U . . .
C4 C 0.99464(17) 0.85182(12) 0.68187(12) 0.0245(4) Uani 1 1 d . . . . .
C5 C 1.10392(17) 0.84649(12) 0.71695(13) 0.0287(5) Uani 1 1 d . . . . .
H5 H 1.136107 0.874635 0.761176 0.034 Uiso 1 1 calc R U . . .
C6 C 1.16159(16) 0.80174(12) 0.68763(13) 0.0279(5) Uani 1 1 d . . . . .
H6 H 1.233369 0.797650 0.712815 0.034 Uiso 1 1 calc R U . . .
C7 C 1.11620(16) 0.76042(11) 0.61921(13) 0.0237(4) Uani 1 1 d . . . . .
C8 C 1.17357(16) 0.71452(12) 0.58539(14) 0.0280(5) Uani 1 1 d . . . . .
H8 H 1.245488 0.708492 0.608755 0.034 Uiso 1 1 calc R U . . .
C9 C 1.12452(16) 0.67871(13) 0.51851(14) 0.0278(5) Uani 1 1 d . . . . .
H9 H 1.162524 0.647721 0.495286 0.033 Uiso 1 1 calc R U . . .
C10 C 1.01754(15) 0.68781(11) 0.48403(12) 0.0219(4) Uani 1 1 d . . . . .
C11 C 0.94742(15) 0.81023(11) 0.61619(12) 0.0205(4) Uani 1 1 d . . . . .
C12 C 1.00938(15) 0.76503(11) 0.58299(12) 0.0199(4) Uani 1 1 d . . . . .
C13 C 0.66961(16) 0.84663(11) 0.57577(12) 0.0215(4) Uani 1 1 d . . . . .
C14 C 0.61456(16) 0.79475(11) 0.60317(12) 0.0222(4) Uani 1 1 d . . . . .
C15 C 0.50748(16) 0.79189(12) 0.57153(13) 0.0255(4) Uani 1 1 d . . . . .
H15 H 0.469519 0.756749 0.589442 0.031 Uiso 1 1 calc R U . . .
C16 C 0.45530(17) 0.83914(13) 0.51460(13) 0.0285(5) Uani 1 1 d . . . . .
C17 C 0.51119(18) 0.89010(13) 0.48888(13) 0.0301(5) Uani 1 1 d . . . . .
H17 H 0.475952 0.922538 0.449817 0.036 Uiso 1 1 calc R U . . .
C18 C 0.61843(18) 0.89503(12) 0.51905(13) 0.0267(5) Uani 1 1 d . . . . .
C19 C 0.66858(17) 0.74346(12) 0.66608(13) 0.0276(5) Uani 1 1 d . . . . .
H19A H 0.726901 0.721952 0.652243 0.041 Uiso 1 1 calc R U . . .
H19B H 0.620146 0.706491 0.671075 0.041 Uiso 1 1 calc R U . . .
H19C H 0.693806 0.768594 0.715810 0.041 Uiso 1 1 calc R U . . .
C20 C 0.33941(18) 0.83455(16) 0.48110(16) 0.0394(6) Uani 1 1 d . . . . .
H20A H 0.318713 0.784865 0.473304 0.059 Uiso 1 1 calc R U . . .
H20B H 0.318337 0.859368 0.430943 0.059 Uiso 1 1 calc R U . . .
H20C H 0.306123 0.856430 0.517344 0.059 Uiso 1 1 calc R U . . .
C21 C 0.6767(2) 0.95233(14) 0.49092(16) 0.0392(6) Uani 1 1 d . . . . .
H21A H 0.709947 0.983565 0.534549 0.059 Uiso 1 1 calc R U . . .
H21B H 0.628691 0.979756 0.449778 0.059 Uiso 1 1 calc R U . . .
H21C H 0.729374 0.930888 0.470154 0.059 Uiso 1 1 calc R U . . .
C22 C 0.96616(15) 0.65323(12) 0.40764(12) 0.0227(4) Uani 1 1 d . . . . .
C23 C 0.90123(16) 0.59475(12) 0.40339(13) 0.0242(4) Uani 1 1 d . . . . .
C24 C 0.85442(17) 0.56475(12) 0.33024(14) 0.0286(5) Uani 1 1 d . . . . .
H24 H 0.809207 0.525715 0.326780 0.034 Uiso 1 1 calc R U . . .
C25 C 0.87250(18) 0.59067(13) 0.26263(13) 0.0304(5) Uani 1 1 d . . . . .
C26 C 0.93814(18) 0.64802(14) 0.26855(13) 0.0311(5) Uani 1 1 d . . . . .
H26 H 0.951320 0.665886 0.222656 0.037 Uiso 1 1 calc R U . . .
C27 C 0.98546(16) 0.68026(12) 0.34026(13) 0.0269(5) Uani 1 1 d . . . . .
C28 C 0.88235(19) 0.56303(13) 0.47527(14) 0.0302(5) Uani 1 1 d . . . . .
H28A H 0.944941 0.538966 0.505925 0.045 Uiso 1 1 calc R U . . .
H28B H 0.825631 0.528946 0.459921 0.045 Uiso 1 1 calc R U . . .
H28C H 0.864180 0.600508 0.506797 0.045 Uiso 1 1 calc R U . . .
C29 C 0.8207(2) 0.55710(16) 0.18461(15) 0.0418(6) Uani 1 1 d . . . . .
H29A H 0.853363 0.511533 0.180901 0.063 Uiso 1 1 calc R U . . .
H29B H 0.827761 0.588213 0.142619 0.063 Uiso 1 1 calc R U . . .
H29C H 0.747416 0.549769 0.179716 0.063 Uiso 1 1 calc R U . . .
C30 C 1.0547(2) 0.74343(14) 0.34344(16) 0.0374(6) Uani 1 1 d . . . . .
H30A H 1.041339 0.778557 0.379642 0.056 Uiso 1 1 calc R U . . .
H30B H 1.040744 0.764257 0.291279 0.056 Uiso 1 1 calc R U . . .
H30C H 1.126978 0.728464 0.361480 0.056 Uiso 1 1 calc R U . . .
C31 C 0.65803(16) 0.63747(11) 0.51219(12) 0.0224(4) Uani 1 1 d . . . . .
H31 H 0.713716 0.616932 0.551015 0.027 Uiso 1 1 calc R U . . .
C32 C 0.55835(17) 0.61127(12) 0.50261(13) 0.0260(4) Uani 1 1 d . . . . .
H32 H 0.547752 0.572901 0.533695 0.031 Uiso 1 1 calc R U . . .
C33 C 0.47605(16) 0.64099(12) 0.44839(13) 0.0260(4) Uani 1 1 d . . . . .
C34 C 0.49391(15) 0.69687(12) 0.40101(12) 0.0233(4) Uani 1 1 d . . . . .
C35 C 0.41555(17) 0.73231(14) 0.34141(13) 0.0296(5) Uani 1 1 d . . . . .
H35 H 0.345325 0.719894 0.333780 0.036 Uiso 1 1 calc R U . . .
C36 C 0.43922(17) 0.78285(14) 0.29591(12) 0.0296(5) Uani 1 1 d . . . . .
H36 H 0.385288 0.804925 0.256949 0.035 Uiso 1 1 calc R U . . .
C37 C 0.54377(17) 0.80389(12) 0.30510(12) 0.0249(4) Uani 1 1 d . . . . .
C38 C 0.57570(18) 0.85290(13) 0.25639(12) 0.0290(5) Uani 1 1 d . . . . .
C39 C 0.67862(19) 0.86924(13) 0.27262(14) 0.0314(5) Uani 1 1 d . . . . .
H39 H 0.701299 0.901400 0.240183 0.038 Uiso 1 1 calc R U . . .
C40 C 0.75028(18) 0.83849(12) 0.33705(13) 0.0279(5) Uani 1 1 d . . . . .
H40 H 0.820767 0.851616 0.348176 0.033 Uiso 1 1 calc R U . . .
C41 C 0.59699(15) 0.71862(11) 0.41346(11) 0.0209(4) Uani 1 1 d . . . . .
C42 C 0.62198(16) 0.77334(12) 0.36619(12) 0.0215(4) Uani 1 1 d . . . . .
C43 C 0.37218(18) 0.61196(14) 0.44512(16) 0.0352(5) Uani 1 1 d . . . . .
H43 H 0.370276 0.569360 0.472760 0.042 Uiso 1 1 calc R U . . .
C44 C 0.5057(2) 0.88581(14) 0.18546(14) 0.0360(6) Uani 1 1 d . . . . .
H44 H 0.535255 0.919998 0.159368 0.043 Uiso 1 1 calc R U . . .
P1 P 0.40971(5) 0.57705(3) 0.67612(4) 0.03624(16) Uani 1 1 d . . . . .
F1 F 0.42561(19) 0.63355(9) 0.61400(13) 0.0667(6) Uani 1 1 d . . . . .
F2 F 0.39075(14) 0.52118(10) 0.73679(12) 0.0569(5) Uani 1 1 d . . . . .
F3 F 0.38113(12) 0.64025(9) 0.72462(9) 0.0415(4) Uani 1 1 d . . . . .
F4 F 0.29016(12) 0.57066(8) 0.62731(9) 0.0435(4) Uani 1 1 d . . . . .
F5 F 0.43997(19) 0.51437(10) 0.62791(15) 0.0734(6) Uani 1 1 d . . . . .
F6 F 0.52745(14) 0.58431(12) 0.72596(17) 0.0800(7) Uani 1 1 d . . . . .
Cl1 Cl 0.27748(5) 0.47811(4) 0.31422(4) 0.04242(16) Uani 1 1 d . . . . .
Cl2 Cl 0.08135(5) 0.50666(4) 0.19918(4) 0.04376(16) Uani 1 1 d . . . . .
C45 C 0.15897(19) 0.52477(15) 0.29470(15) 0.0372(6) Uani 1 1 d . . . . .
H45A H 0.121974 0.510625 0.332805 0.045 Uiso 1 1 calc R U . . .
H45B H 0.172798 0.576128 0.300522 0.045 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -1 -9 0.0401
2 3 10 0.0748
-7 1 9 0.0456
-1 -2 -10 0.0871
-1 12 1 0.0194
1 -12 -1 0.0194
-8 -2 -1 0.0954
7 2 4 0.0853
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
N2 Cu1 N1 83.13(7) . . ?
N2 Cu1 N3 136.79(7) . . ?
N2 Cu1 N4 127.37(7) . . ?
N3 Cu1 N1 113.72(7) . . ?
N4 Cu1 N1 116.69(7) . . ?
N4 Cu1 N3 82.00(7) . . ?
C1 N1 Cu1 130.61(14) . . ?
C1 N1 C11 118.76(18) . . ?
C11 N1 Cu1 110.52(13) . . ?
C10 N2 Cu1 130.19(14) . . ?
C10 N2 C12 118.37(17) . . ?
C12 N2 Cu1 111.44(13) . . ?
C31 N3 Cu1 129.83(14) . . ?
C31 N3 C41 118.05(18) . . ?
C41 N3 Cu1 111.30(14) . . ?
C40 N4 Cu1 130.08(15) . . ?
C40 N4 C42 118.30(19) . . ?
C42 N4 Cu1 111.39(14) . . ?
N1 C1 C2 121.45(19) . . ?
N1 C1 C13 118.41(18) . . ?
C2 C1 C13 120.11(19) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 123.4(2) . . ?
C3 C4 C11 117.1(2) . . ?
C11 C4 C5 119.4(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 123.2(2) . . ?
C12 C7 C6 119.5(2) . . ?
C12 C7 C8 117.3(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.34(19) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
N2 C10 C9 121.80(19) . . ?
N2 C10 C22 118.35(17) . . ?
C9 C10 C22 119.80(19) . . ?
N1 C11 C4 123.09(19) . . ?
N1 C11 C12 117.07(18) . . ?
C4 C11 C12 119.85(19) . . ?
N2 C12 C7 122.98(19) . . ?
N2 C12 C11 117.71(18) . . ?
C7 C12 C11 119.30(19) . . ?
C14 C13 C1 118.80(18) . . ?
C18 C13 C1 120.44(19) . . ?
C18 C13 C14 120.7(2) . . ?
C13 C14 C19 121.25(19) . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 C19 120.2(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C20 120.4(2) . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 C20 120.8(2) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 C17 118.8(2) . . ?
C13 C18 C21 121.1(2) . . ?
C17 C18 C21 120.1(2) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 121.09(19) . . ?
C27 C22 C10 118.3(2) . . ?
C27 C22 C23 120.6(2) . . ?
C22 C23 C28 121.7(2) . . ?
C24 C23 C22 118.7(2) . . ?
C24 C23 C28 119.6(2) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.6(2) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C29 120.3(2) . . ?
C26 C25 C24 118.5(2) . . ?
C26 C25 C29 121.2(2) . . ?
C25 C26 H26 119.1 . . ?
C25 C26 C27 121.8(2) . . ?
C27 C26 H26 119.1 . . ?
C22 C27 C30 121.5(2) . . ?
C26 C27 C22 118.7(2) . . ?
C26 C27 C30 119.8(2) . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N3 C31 H31 118.7 . . ?
N3 C31 C32 122.7(2) . . ?
C32 C31 H31 118.7 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0(2) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C34 119.1(2) . . ?
C32 C33 C43 116.2(2) . . ?
C34 C33 C43 124.7(2) . . ?
C33 C34 C35 125.2(2) . . ?
C41 C34 C33 116.92(19) . . ?
C41 C34 C35 117.9(2) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 C34 121.7(2) . . ?
C36 C35 H35 119.1 . . ?
C35 C36 H36 119.2 . . ?
C35 C36 C37 121.5(2) . . ?
C37 C36 H36 119.2 . . ?
C38 C37 C36 125.0(2) . . ?
C42 C37 C36 118.2(2) . . ?
C42 C37 C38 116.8(2) . . ?
C37 C38 C44 124.4(2) . . ?
C39 C38 C37 118.9(2) . . ?
C39 C38 C44 116.5(2) . . ?
C38 C39 H39 119.9 . . ?
C38 C39 C40 120.1(2) . . ?
C40 C39 H39 119.9 . . ?
N4 C40 C39 122.5(2) . . ?
N4 C40 H40 118.7 . . ?
C39 C40 H40 118.7 . . ?
N3 C41 C34 123.2(2) . . ?
N3 C41 C42 116.42(18) . . ?
C34 C41 C42 120.37(19) . . ?
N4 C42 C37 123.2(2) . . ?
N4 C42 C41 116.68(18) . . ?
C37 C42 C41 120.06(19) . . ?
O1 C43 C33 125.7(3) . . ?
O1 C43 H43 117.2 . . ?
C33 C43 H43 117.2 . . ?
O2 C44 C38 126.6(3) . . ?
O2 C44 H44 116.7 . . ?
C38 C44 H44 116.7 . . ?
F1 P1 F4 89.24(11) . . ?
F2 P1 F1 178.49(12) . . ?
F2 P1 F3 90.99(10) . . ?
F2 P1 F4 89.28(9) . . ?
F2 P1 F5 89.41(12) . . ?
F2 P1 F6 90.33(12) . . ?
F3 P1 F1 88.66(9) . . ?
F3 P1 F4 89.39(9) . . ?
F3 P1 F6 89.41(11) . . ?
F5 P1 F1 90.96(11) . . ?
F5 P1 F3 179.14(11) . . ?
F5 P1 F4 91.38(12) . . ?
F5 P1 F6 89.82(13) . . ?
F6 P1 F1 91.14(14) . . ?
F6 P1 F4 178.73(13) . . ?
Cl1 C45 H45A 109.6 . . ?
Cl1 C45 H45B 109.6 . . ?
Cl2 C45 Cl1 110.39(15) . . ?
Cl2 C45 H45A 109.6 . . ?
Cl2 C45 H45B 109.6 . . ?
H45A C45 H45B 108.1 . . ?
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 N1 2.0570(17) . ?
Cu1 N2 2.0079(17) . ?
Cu1 N3 2.0268(17) . ?
Cu1 N4 2.0252(18) . ?
O1 C43 1.210(3) . ?
O2 C44 1.207(3) . ?
N1 C1 1.330(3) . ?
N1 C11 1.362(3) . ?
N2 C10 1.333(3) . ?
N2 C12 1.370(3) . ?
N3 C31 1.325(3) . ?
N3 C41 1.367(3) . ?
N4 C40 1.320(3) . ?
N4 C42 1.366(3) . ?
C1 C2 1.412(3) . ?
C1 C13 1.497(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(3) . ?
C4 C5 1.435(3) . ?
C4 C11 1.407(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.354(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.434(3) . ?
C7 C8 1.411(3) . ?
C7 C12 1.408(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.413(3) . ?
C10 C22 1.495(3) . ?
C11 C12 1.439(3) . ?
C13 C14 1.403(3) . ?
C13 C18 1.395(3) . ?
C14 C15 1.398(3) . ?
C14 C19 1.508(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 C17 1.383(4) . ?
C16 C20 1.513(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(3) . ?
C18 C21 1.509(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.402(3) . ?
C22 C27 1.400(3) . ?
C23 C24 1.401(3) . ?
C23 C28 1.505(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(4) . ?
C25 C26 1.387(4) . ?
C25 C29 1.511(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.399(3) . ?
C27 C30 1.510(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31 0.9500 . ?
C31 C32 1.401(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.371(3) . ?
C33 C34 1.418(3) . ?
C33 C43 1.494(3) . ?
C34 C35 1.437(3) . ?
C34 C41 1.410(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.352(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.433(3) . ?
C37 C38 1.421(3) . ?
C37 C42 1.410(3) . ?
C38 C39 1.374(4) . ?
C38 C44 1.486(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.403(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.437(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
P1 F1 1.6000(18) . ?
P1 F2 1.5872(18) . ?
P1 F3 1.5887(17) . ?
P1 F4 1.6086(17) . ?
P1 F5 1.5871(19) . ?
P1 F6 1.594(2) . ?
Cl1 C45 1.776(3) . ?
Cl2 C45 1.765(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
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
Cu1 N1 C1 C2 -173.21(16) . . . . ?
Cu1 N1 C1 C13 8.7(3) . . . . ?
Cu1 N1 C11 C4 176.33(16) . . . . ?
Cu1 N1 C11 C12 -3.8(2) . . . . ?
Cu1 N2 C10 C9 -176.53(16) . . . . ?
Cu1 N2 C10 C22 6.0(3) . . . . ?
Cu1 N2 C12 C7 178.83(16) . . . . ?
Cu1 N2 C12 C11 -1.9(2) . . . . ?
Cu1 N3 C31 C32 168.40(15) . . . . ?
Cu1 N3 C41 C34 -168.78(16) . . . . ?
Cu1 N3 C41 C42 11.6(2) . . . . ?
Cu1 N4 C40 C39 -173.81(17) . . . . ?
Cu1 N4 C42 C37 171.70(16) . . . . ?
Cu1 N4 C42 C41 -9.7(2) . . . . ?
N1 C1 C2 C3 -2.4(3) . . . . ?
N1 C1 C13 C14 85.8(2) . . . . ?
N1 C1 C13 C18 -96.5(2) . . . . ?
N1 C11 C12 N2 4.0(3) . . . . ?
N1 C11 C12 C7 -176.75(18) . . . . ?
N2 C10 C22 C23 -75.3(3) . . . . ?
N2 C10 C22 C27 105.4(2) . . . . ?
N3 C31 C32 C33 -1.6(3) . . . . ?
N3 C41 C42 N4 -1.3(3) . . . . ?
N3 C41 C42 C37 177.33(18) . . . . ?
C1 N1 C11 C4 -0.2(3) . . . . ?
C1 N1 C11 C12 179.66(18) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C13 C14 C15 178.63(18) . . . . ?
C1 C13 C14 C19 -0.6(3) . . . . ?
C1 C13 C18 C17 -178.75(19) . . . . ?
C1 C13 C18 C21 0.6(3) . . . . ?
C2 C1 C13 C14 -92.3(3) . . . . ?
C2 C1 C13 C18 85.4(3) . . . . ?
C2 C3 C4 C5 -177.3(2) . . . . ?
C2 C3 C4 C11 2.3(3) . . . . ?
C3 C4 C5 C6 179.3(2) . . . . ?
C3 C4 C11 N1 -2.2(3) . . . . ?
C3 C4 C11 C12 177.92(19) . . . . ?
C4 C5 C6 C7 2.3(3) . . . . ?
C4 C11 C12 N2 -176.13(19) . . . . ?
C4 C11 C12 C7 3.2(3) . . . . ?
C5 C4 C11 N1 177.40(19) . . . . ?
C5 C4 C11 C12 -2.5(3) . . . . ?
C5 C6 C7 C8 178.3(2) . . . . ?
C5 C6 C7 C12 -1.7(3) . . . . ?
C6 C7 C8 C9 -177.9(2) . . . . ?
C6 C7 C12 N2 178.13(19) . . . . ?
C6 C7 C12 C11 -1.1(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C7 C12 N2 -1.8(3) . . . . ?
C8 C7 C12 C11 178.92(19) . . . . ?
C8 C9 C10 N2 -2.5(3) . . . . ?
C8 C9 C10 C22 175.0(2) . . . . ?
C9 C10 C22 C23 107.1(2) . . . . ?
C9 C10 C22 C27 -72.1(3) . . . . ?
C10 N2 C12 C7 -0.6(3) . . . . ?
C10 N2 C12 C11 178.70(18) . . . . ?
C10 C22 C23 C24 179.50(19) . . . . ?
C10 C22 C23 C28 -1.6(3) . . . . ?
C10 C22 C27 C26 179.68(19) . . . . ?
C10 C22 C27 C30 -1.0(3) . . . . ?
C11 N1 C1 C2 2.6(3) . . . . ?
C11 N1 C1 C13 -175.54(18) . . . . ?
C11 C4 C5 C6 -0.3(3) . . . . ?
C12 N2 C10 C9 2.7(3) . . . . ?
C12 N2 C10 C22 -174.78(18) . . . . ?
C12 C7 C8 C9 2.1(3) . . . . ?
C13 C1 C2 C3 175.7(2) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C13 C18 C17 -1.1(3) . . . . ?
C14 C13 C18 C21 178.2(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C14 C15 C16 C20 179.7(2) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C16 C17 C18 C21 -178.6(2) . . . . ?
C18 C13 C14 C15 1.0(3) . . . . ?
C18 C13 C14 C19 -178.2(2) . . . . ?
C19 C14 C15 C16 178.8(2) . . . . ?
C20 C16 C17 C18 -179.8(2) . . . . ?
C22 C23 C24 C25 1.3(3) . . . . ?
C23 C22 C27 C26 0.4(3) . . . . ?
C23 C22 C27 C30 179.7(2) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C23 C24 C25 C29 -180.0(2) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C22 0.5(3) . . . . ?
C25 C26 C27 C30 -178.8(2) . . . . ?
C27 C22 C23 C24 -1.2(3) . . . . ?
C27 C22 C23 C28 177.7(2) . . . . ?
C28 C23 C24 C25 -177.7(2) . . . . ?
C29 C25 C26 C27 179.1(2) . . . . ?
C31 N3 C41 C34 1.9(3) . . . . ?
C31 N3 C41 C42 -177.73(18) . . . . ?
C31 C32 C33 C34 1.8(3) . . . . ?
C31 C32 C33 C43 -177.0(2) . . . . ?
C32 C33 C34 C35 179.2(2) . . . . ?
C32 C33 C34 C41 -0.3(3) . . . . ?
C32 C33 C43 O1 168.0(3) . . . . ?
C33 C34 C35 C36 -176.6(2) . . . . ?
C33 C34 C41 N3 -1.6(3) . . . . ?
C33 C34 C41 C42 177.99(19) . . . . ?
C34 C33 C43 O1 -10.8(4) . . . . ?
C34 C35 C36 C37 -0.3(4) . . . . ?
C34 C41 C42 N4 179.06(18) . . . . ?
C34 C41 C42 C37 -2.3(3) . . . . ?
C35 C34 C41 N3 178.85(19) . . . . ?
C35 C34 C41 C42 -1.6(3) . . . . ?
C35 C36 C37 C38 175.4(2) . . . . ?
C35 C36 C37 C42 -3.6(3) . . . . ?
C36 C37 C38 C39 178.9(2) . . . . ?
C36 C37 C38 C44 -4.3(4) . . . . ?
C36 C37 C42 N4 -176.6(2) . . . . ?
C36 C37 C42 C41 4.8(3) . . . . ?
C37 C38 C39 C40 -0.9(3) . . . . ?
C37 C38 C44 O2 -3.7(4) . . . . ?
C38 C37 C42 N4 4.3(3) . . . . ?
C38 C37 C42 C41 -174.31(19) . . . . ?
C38 C39 C40 N4 1.9(4) . . . . ?
C39 C38 C44 O2 173.1(2) . . . . ?
C40 N4 C42 C37 -3.4(3) . . . . ?
C40 N4 C42 C41 175.25(19) . . . . ?
C41 N3 C31 C32 -0.2(3) . . . . ?
C41 C34 C35 C36 2.9(3) . . . . ?
C42 N4 C40 C39 0.2(3) . . . . ?
C42 C37 C38 C39 -2.0(3) . . . . ?
C42 C37 C38 C44 174.7(2) . . . . ?
C43 C33 C34 C35 -2.0(3) . . . . ?
C43 C33 C34 C41 178.4(2) . . . . ?
C44 C38 C39 C40 -177.9(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.1909 -0.8124 -9.0517 -0.0305 0.0993 0.9946
1.9848 2.5276 9.8387 -0.2514 0.8487 -0.4654
-6.9137 0.9390 9.4107 0.0153 -0.0483 -0.9987
-0.9451 -2.4931 -10.4662 0.2336 -0.7890 0.5683
-1.2787 12.1608 0.6607 0.9042 0.3748 -0.2049
1.2787 -12.1608 -0.6607 -0.9042 -0.3748 0.2049
-8.0299 -1.6190 -1.2178 0.2571 -0.8648 -0.4314
7.0000 1.9997 4.0000 -0.2868 0.9470 0.2003
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 0.000 0.000 0.500 210.7 45.8 ?
2 0.500 0.500 0.000 210.7 45.8 ?
