# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2887
_database_code_depnum_ccdc_archive 'CCDC 2288950'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H18 B N'
_chemical_formula_sum            'C9 H18 B N'
_chemical_formula_weight         151.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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'
B B 0.0040 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3'
_space_group_name_Hall           'R 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   10.5689(15)
_cell_length_b                   10.5689(15)
_cell_length_c                   8.3975(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     812.3(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      5.0
_cell_measurement_theta_max      35.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.926
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2342
_diffrn_reflns_av_unetI/netI     0.1776
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.265
_diffrn_reflns_theta_max         38.333
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             749
_reflns_number_gt                427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.994

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.046(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 133 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.3(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         749
_refine_ls_number_parameters     36
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1861
_refine_ls_wR_factor_gt          0.1610
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_restrained_S_all      0.871
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.6667 0.3333 0.6259(9) 0.059(2) Uani 1 3 d S T P . .
H1 H 0.6088 0.3682 0.6620 0.089 Uiso 1 1 d R U . . .
B1 B 0.6667 0.3333 0.4306(14) 0.068(3) Uani 1 3 d S T P . .
C1 C 0.7011(8) 0.4964(7) 0.3775(11) 0.075(2) Uani 1 1 d . . . . .
H1A H 0.7076 0.5031 0.2599 0.090 Uiso 1 1 calc R U . . .
H1B H 0.6180 0.5089 0.4103 0.090 Uiso 1 1 calc R U . . .
C2 C 0.8406(6) 0.6208(7) 0.4471(7) 0.074(2) Uani 1 1 d . . . . .
H2 H 0.9301 0.6325 0.4076 0.089 Uiso 1 1 calc R U . . .
C3 C 0.8498(8) 0.7134(6) 0.5560(7) 0.0740(18) Uani 1 1 d . . . . .
H3A H 0.7634 0.7063 0.5993 0.089 Uiso 1 1 calc R U . . .
H3B H 0.9428 0.7878 0.5919 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 B1 1.640(14) . ?
N1 H1 0.9100 . ?
B1 C1 1.635(7) . ?
C1 C2 1.519(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.307(9) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9500 . ?
C3 H3B 0.9500 . ?

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
B1 N1 H1 109.5 . . ?
C1 B1 C1 112.8(4) 2_655 . ?
C1 B1 N1 105.8(5) . . ?
C2 C1 B1 114.6(5) . . ?
C2 C1 H1A 108.6 . . ?
B1 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
B1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 126.4(6) . . ?
C3 C2 H2 116.8 . . ?
C1 C2 H2 116.8 . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?

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
C1 B1 C1 C2 -60.0(12) 3_665 . . . ?
C1 B1 C1 C2 170.6(6) 2_655 . . . ?
N1 B1 C1 C2 55.3(6) . . . . ?
B1 C1 C2 C3 -109.6(8) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.034

_shelxl_version_number           2014/6


# start Validation Reply Form
_vrf_PLAT049_2887                
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9264 Check 
RESPONSE: This is the intrinsic feature of the crystal structure.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TABDABCO
_database_code_depnum_ccdc_archive 'CCDC 2288951'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-16 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-08-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H27 B N2'
_chemical_formula_sum            'C15 H27 B N2'
_chemical_formula_weight         246.19
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.6952(2)
_cell_length_b                   10.1193(2)
_cell_length_c                   17.1397(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1508.11(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5580
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.4330
_exptl_absorpt_correction_T_min  0.3775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.8718.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20204
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.993
_diffrn_reflns_theta_min         2.337
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3582
_reflns_number_total             4000
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.080
_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)+(0.0608P)²+0.2999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          ?
_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,H) groups
2. Restrained distances
 C14-C13 \\sim C14'-C13'
 with sigma of 0.02
 C13'-B1 \\sim C13-B1
 with sigma of 0.02
 C10'-B1 \\sim C10-B1
 with sigma of 0.02
 C11'-C10' \\sim C11-C10
 with sigma of 0.02
 C12'-C11' \\sim C12-C11
 with sigma of 0.02
 C14-C15 \\sim C14'-C15
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C13) = Uanis(C13')
Uanis(C14) = Uanis(C14')
Uanis(C10') = Uanis(C10)
Uanis(C11) = Uanis(C11')
Uanis(C12') = Uanis(C12)
4. Others
 Sof(H15C)=Sof(H15D)=Sof(C13')=Sof(H13C)=Sof(H13D)=Sof(C14')=Sof(H14')=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14)=FVAR(1)
 Sof(C10')=Sof(H10C)=Sof(H10D)=Sof(C11')=Sof(H11')=Sof(C12')=Sof(H12C)=
 Sof(H12D)=1-FVAR(2)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C10(H10A,H10B), C13(H13A,H13B), C10'(H10C,H10D), C13'(H13C,H13D)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C14(H14), C11'(H11'), C14'(H14')
5.c X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C15(H15A,H15B), C15(H15C,H15D), C12(H12A,H12B), C12'(H12C,H12D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.22329(19) 0.44719(15) 0.60177(9) 0.0218(3) Uani 1 1 d . . . . .
N2 N 0.0249(2) 0.30655(18) 0.52230(10) 0.0284(4) Uani 1 1 d . . . . .
C1 C 0.2394(3) 0.3024(2) 0.61826(13) 0.0303(5) Uani 1 1 d . . . . .
H1A H 0.2349 0.2870 0.6753 0.036 Uiso 1 1 calc R U . . .
H1B H 0.3404 0.2708 0.5991 0.036 Uiso 1 1 calc R U . . .
C2 C 0.1106(3) 0.2253(2) 0.57803(14) 0.0361(5) Uani 1 1 d . . . . .
H2A H 0.1554 0.1486 0.5503 0.043 Uiso 1 1 calc R U . . .
H2B H 0.0388 0.1911 0.6181 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2447(3) 0.4639(2) 0.51500(11) 0.0303(5) Uani 1 1 d . . . . .
H3A H 0.3530 0.4450 0.5009 0.036 Uiso 1 1 calc R U . . .
H3B H 0.2217 0.5563 0.5000 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1377(3) 0.3697(2) 0.47071(13) 0.0345(5) Uani 1 1 d . . . . .
H4A H 0.0827 0.4196 0.4296 0.041 Uiso 1 1 calc R U . . .
H4B H 0.2001 0.3006 0.4449 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0609(2) 0.4855(2) 0.61991(12) 0.0252(4) Uani 1 1 d . . . . .
H5A H 0.0482 0.5820 0.6127 0.030 Uiso 1 1 calc R U . . .
H5B H 0.0377 0.4643 0.6751 0.030 Uiso 1 1 calc R U . . .
C6 C -0.0514(3) 0.4119(3) 0.56657(16) 0.0417(6) Uani 1 1 d . . . . .
H6A H -0.1348 0.3730 0.5986 0.050 Uiso 1 1 calc R U . . .
H6B H -0.0986 0.4754 0.5297 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5186(2) 0.4695(2) 0.64429(13) 0.0310(5) Uani 1 1 d . . . . .
H7A H 0.5172 0.3823 0.6704 0.037 Uiso 1 1 calc R U . . .
H7B H 0.5391 0.4545 0.5882 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6461(2) 0.5506(2) 0.67785(12) 0.0287(4) Uani 1 1 d . . . . .
H8 H 0.6733 0.6284 0.6501 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7244(3) 0.5259(3) 0.74152(16) 0.0452(6) Uani 1 1 d . . . . .
H9A H 0.7019 0.4494 0.7715 0.054 Uiso 1 1 calc R U . . .
H9B H 0.8036 0.5844 0.7577 0.054 Uiso 1 1 calc R U . . .
C15 C 0.1434(3) 0.4032(3) 0.83080(13) 0.0413(6) Uani 1 1 d D . . . .
H15A H 0.0525 0.4546 0.8260 0.050 Uiso 0.774(3) 1 calc R U P A 1
H15B H 0.1432 0.3255 0.8619 0.050 Uiso 0.774(3) 1 calc R U P A 1
H15C H 0.1940 0.3203 0.8265 0.050 Uiso 0.226(3) 1 calc R U P A 2
H15D H 0.0524 0.4108 0.8611 0.050 Uiso 0.226(3) 1 calc R U P A 2
B1 B 0.3503(3) 0.5381(2) 0.65372(13) 0.0251(4) Uani 1 1 d D . . . .
C10 C 0.3661(3) 0.6885(3) 0.61117(16) 0.0263(5) Uani 0.768(3) 1 d D . P A 1
H10A H 0.4451 0.7386 0.6404 0.032 Uiso 0.768(3) 1 calc R U P A 1
H10B H 0.4069 0.6746 0.5579 0.032 Uiso 0.768(3) 1 calc R U P A 1
C11 C 0.2274(4) 0.7760(2) 0.60406(17) 0.0300(6) Uani 0.768(3) 1 d D . P A 1
H11 H 0.1706 0.7914 0.6505 0.036 Uiso 0.768(3) 1 calc R U P A 1
C12 C 0.1760(4) 0.8338(3) 0.5404(2) 0.0364(8) Uani 0.768(3) 1 d D . P A 1
H12A H 0.2284 0.8218 0.4923 0.044 Uiso 0.768(3) 1 calc R U P A 1
H12B H 0.0864 0.8874 0.5426 0.044 Uiso 0.768(3) 1 calc R U P A 1
C13 C 0.2916(3) 0.5604(3) 0.74217(14) 0.0245(5) Uani 0.774(3) 1 d D . P A 1
H13A H 0.3638 0.6219 0.7681 0.029 Uiso 0.774(3) 1 calc R U P A 1
H13B H 0.1903 0.6049 0.7399 0.029 Uiso 0.774(3) 1 calc R U P A 1
C14 C 0.2755(3) 0.4412(3) 0.79266(15) 0.0274(5) Uani 0.774(3) 1 d D . P A 1
H14 H 0.3638 0.3871 0.7991 0.033 Uiso 0.774(3) 1 calc R U P A 1
C10' C 0.3133(11) 0.6819(8) 0.6591(5) 0.0263(5) Uani 0.232(3) 1 d D . P A 2
H10C H 0.3787 0.7230 0.6997 0.032 Uiso 0.232(3) 1 calc R U P A 2
H10D H 0.2046 0.6925 0.6752 0.032 Uiso 0.232(3) 1 calc R U P A 2
C11' C 0.3382(12) 0.7522(9) 0.5829(5) 0.0300(6) Uani 0.232(3) 1 d D . P A 2
H11' H 0.4410 0.7492 0.5642 0.036 Uiso 0.232(3) 1 calc R U P A 2
C12' C 0.2415(15) 0.8177(13) 0.5374(8) 0.0364(8) Uani 0.232(3) 1 d D . P A 2
H12C H 0.1364 0.8255 0.5517 0.044 Uiso 0.232(3) 1 calc R U P A 2
H12D H 0.2773 0.8568 0.4904 0.044 Uiso 0.232(3) 1 calc R U P A 2
C13' C 0.3373(10) 0.4743(9) 0.7523(5) 0.0245(5) Uani 0.226(3) 1 d D . P A 2
H13C H 0.3536 0.3776 0.7497 0.029 Uiso 0.226(3) 1 calc R U P A 2
H13D H 0.4241 0.5119 0.7824 0.029 Uiso 0.226(3) 1 calc R U P A 2
C14' C 0.1943(11) 0.4979(9) 0.7980(5) 0.0274(5) Uani 0.226(3) 1 d D . P A 2
H14' H 0.1468 0.5822 0.8010 0.033 Uiso 0.226(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N1 C1 1.499(3) . ?
N1 C3 1.508(2) . ?
N1 C5 1.497(2) . ?
N1 B1 1.691(3) . ?
N2 C2 1.464(3) . ?
N2 C4 1.467(3) . ?
N2 C6 1.467(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.529(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.533(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.531(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.495(3) . ?
C7 B1 1.627(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.310(3) . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C15 H15C 0.9500 . ?
C15 H15D 0.9500 . ?
C15 C14 1.377(4) . ?
C15 C14' 1.195(9) . ?
B1 C10 1.694(4) . ?
B1 C13 1.616(3) . ?
B1 C10' 1.494(8) . ?
B1 C13' 1.812(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.501(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.316(5) . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.490(4) . ?
C14 H14 0.9500 . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C10' C11' 1.503(12) . ?
C11' H11' 0.9500 . ?
C11' C12' 1.324(14) . ?
C12' H12C 0.9500 . ?
C12' H12D 0.9500 . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C13' C14' 1.489(11) . ?
C14' H14' 0.9500 . ?

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
C1 N1 C3 106.50(15) . . ?
C1 N1 B1 111.81(15) . . ?
C3 N1 B1 112.17(15) . . ?
C5 N1 C1 107.59(16) . . ?
C5 N1 C3 107.00(16) . . ?
C5 N1 B1 111.47(14) . . ?
C2 N2 C4 107.30(18) . . ?
C2 N2 C6 107.50(18) . . ?
C6 N2 C4 107.33(19) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.19(17) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N2 C2 C1 112.37(17) . . ?
N2 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
N1 C3 C4 110.08(17) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
N2 C4 C3 112.23(17) . . ?
N2 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 C6 110.59(15) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
N2 C6 C5 111.95(18) . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C8 C7 B1 113.25(17) . . ?
B1 C7 H7A 108.9 . . ?
B1 C7 H7B 108.9 . . ?
C7 C8 H8 116.5 . . ?
C9 C8 C7 126.9(2) . . ?
C9 C8 H8 116.5 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
H15C C15 H15D 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
C14' C15 H15C 120.0 . . ?
C14' C15 H15D 120.0 . . ?
N1 B1 C10 108.36(16) . . ?
N1 B1 C13' 104.9(3) . . ?
C7 B1 N1 107.65(15) . . ?
C7 B1 C10 105.54(18) . . ?
C7 B1 C13' 89.9(3) . . ?
C13 B1 N1 111.31(17) . . ?
C13 B1 C7 115.92(19) . . ?
C13 B1 C10 107.70(18) . . ?
C10' B1 N1 114.9(4) . . ?
C10' B1 C7 128.0(4) . . ?
C10' B1 C13' 106.0(5) . . ?
B1 C10 H10A 107.3 . . ?
B1 C10 H10B 107.3 . . ?
H10A C10 H10B 106.9 . . ?
C11 C10 B1 120.0(2) . . ?
C11 C10 H10A 107.3 . . ?
C11 C10 H10B 107.3 . . ?
C10 C11 H11 116.5 . . ?
C12 C11 C10 127.0(3) . . ?
C12 C11 H11 116.5 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
B1 C13 H13A 107.9 . . ?
B1 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
C14 C13 B1 117.5(2) . . ?
C14 C13 H13A 107.9 . . ?
C14 C13 H13B 107.9 . . ?
C15 C14 C13 125.5(2) . . ?
C15 C14 H14 117.3 . . ?
C13 C14 H14 117.3 . . ?
B1 C10' H10C 109.2 . . ?
B1 C10' H10D 109.2 . . ?
B1 C10' C11' 112.1(7) . . ?
H10C C10' H10D 107.9 . . ?
C11' C10' H10C 109.2 . . ?
C11' C10' H10D 109.2 . . ?
C10' C11' H11' 114.5 . . ?
C12' C11' C10' 131.1(11) . . ?
C12' C11' H11' 114.5 . . ?
C11' C12' H12C 120.0 . . ?
C11' C12' H12D 120.0 . . ?
H12C C12' H12D 120.0 . . ?
B1 C13' H13C 107.5 . . ?
B1 C13' H13D 107.5 . . ?
H13C C13' H13D 107.0 . . ?
C14' C13' B1 119.1(6) . . ?
C14' C13' H13C 107.5 . . ?
C14' C13' H13D 107.5 . . ?
C15 C14' C13' 115.4(8) . . ?
C15 C14' H14' 122.3 . . ?
C13' C14' H14' 122.3 . . ?

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 C1 C2 N2 11.4(3) . . . . ?
N1 C3 C4 N2 10.2(3) . . . . ?
N1 C5 C6 N2 10.5(3) . . . . ?
N1 B1 C10 C11 60.5(3) . . . . ?
N1 B1 C13 C14 63.9(3) . . . . ?
N1 B1 C10' C11' -71.7(7) . . . . ?
N1 B1 C13' C14' -68.7(7) . . . . ?
C1 N1 C3 C4 51.9(2) . . . . ?
C1 N1 C5 C6 -62.7(2) . . . . ?
C1 N1 B1 C7 47.8(2) . . . . ?
C1 N1 B1 C10 161.46(17) . . . . ?
C1 N1 B1 C13 -80.3(2) . . . . ?
C1 N1 B1 C10' -162.9(4) . . . . ?
C1 N1 B1 C13' -46.9(3) . . . . ?
C2 N2 C4 C3 -63.4(2) . . . . ?
C2 N2 C6 C5 51.3(3) . . . . ?
C3 N1 C1 C2 -64.0(2) . . . . ?
C3 N1 C5 C6 51.5(2) . . . . ?
C3 N1 B1 C7 -71.8(2) . . . . ?
C3 N1 B1 C10 41.9(2) . . . . ?
C3 N1 B1 C13 160.14(19) . . . . ?
C3 N1 B1 C10' 77.6(4) . . . . ?
C3 N1 B1 C13' -166.5(3) . . . . ?
C4 N2 C2 C1 51.2(2) . . . . ?
C4 N2 C6 C5 -63.9(3) . . . . ?
C5 N1 C1 C2 50.5(2) . . . . ?
C5 N1 C3 C4 -62.9(2) . . . . ?
C5 N1 B1 C7 168.24(17) . . . . ?
C5 N1 B1 C10 -78.1(2) . . . . ?
C5 N1 B1 C13 40.2(2) . . . . ?
C5 N1 B1 C10' -42.4(5) . . . . ?
C5 N1 B1 C13' 73.6(3) . . . . ?
C6 N2 C2 C1 -64.0(2) . . . . ?
C6 N2 C4 C3 51.8(2) . . . . ?
C7 B1 C10 C11 175.6(2) . . . . ?
C7 B1 C13 C14 -59.5(3) . . . . ?
C7 B1 C10' C11' 70.3(8) . . . . ?
C7 B1 C13' C14' -177.0(7) . . . . ?
C8 C7 B1 N1 171.68(17) . . . . ?
C8 C7 B1 C10 56.1(2) . . . . ?
C8 C7 B1 C13 -63.0(3) . . . . ?
C8 C7 B1 C10' 27.6(5) . . . . ?
C8 C7 B1 C13' -82.8(3) . . . . ?
B1 N1 C1 C2 173.18(17) . . . . ?
B1 N1 C3 C4 174.54(17) . . . . ?
B1 N1 C5 C6 174.42(18) . . . . ?
B1 C7 C8 C9 108.1(3) . . . . ?
B1 C10 C11 C12 -128.2(3) . . . . ?
B1 C13 C14 C15 -123.9(3) . . . . ?
B1 C10' C11' C12' 119.2(12) . . . . ?
B1 C13' C14' C15 133.0(7) . . . . ?
C10 B1 C13 C14 -177.4(2) . . . . ?
C13 B1 C10 C11 -60.0(3) . . . . ?
C10' B1 C13' C14' 53.2(8) . . . . ?
C13' B1 C10' C11' 173.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Org
_database_code_depnum_ccdc_archive 'CCDC 2288952'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-08-16 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-08-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 N2 O S'
_chemical_formula_sum            'C14 H22 N2 O S'
_chemical_formula_weight         266.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.7916(4)
_cell_length_b                   6.2242(2)
_cell_length_c                   11.7768(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.897(2)
_cell_angle_gamma                90
_cell_volume                     748.40(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5319
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      3.11
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.8676.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9895
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3721
_reflns_number_total             3943
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.039
_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)+(0.0358P)²+0.0575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0767
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9)
2.e X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.f Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.85635(4) 0.52078(8) 0.51751(4) 0.01549(11) Uani 1 1 d . . . . .
O1 O 0.99822(12) 0.5468(2) 0.58986(11) 0.0187(3) Uani 1 1 d . . . . .
N1 N 0.82339(15) 0.6588(3) 0.38996(13) 0.0165(3) Uani 1 1 d . . . . .
H1 H 0.8681 0.7809 0.3961 0.020 Uiso 1 1 d R U . . .
N2 N 0.59079(13) 0.5220(3) 0.18724(12) 0.0168(3) Uani 1 1 d . . . . .
C1 C 0.82690(16) 0.5233(4) 0.28692(14) 0.0153(3) Uani 1 1 d . . . . .
H1A H 0.8999 0.4169 0.3156 0.018 Uiso 1 1 calc R U . . .
C2 C 0.69823(18) 0.4027(3) 0.23742(16) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.69522(19) 0.1813(3) 0.24497(17) 0.0182(4) Uani 1 1 d . . . . .
H3 H 0.7731 0.1025 0.2827 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5759(2) 0.0755(3) 0.19628(18) 0.0227(5) Uani 1 1 d . . . . .
H4 H 0.5707 -0.0766 0.1995 0.027 Uiso 1 1 calc R U . . .
C5 C 0.46543(19) 0.1973(3) 0.14322(18) 0.0207(4) Uani 1 1 d . . . . .
H5 H 0.3829 0.1296 0.1081 0.025 Uiso 1 1 calc R U . . .
C6 C 0.47569(18) 0.4202(3) 0.14149(17) 0.0175(4) Uani 1 1 d . . . . .
C7 C 0.35840(19) 0.5628(4) 0.08950(19) 0.0260(5) Uani 1 1 d . . . . .
H7A H 0.3405 0.6424 0.1543 0.039 Uiso 1 1 calc R U . . .
H7B H 0.2822 0.4746 0.0473 0.039 Uiso 1 1 calc R U . . .
H7C H 0.3761 0.6643 0.0330 0.039 Uiso 1 1 calc R U . . .
C8 C 0.85360(19) 0.6690(3) 0.19261(17) 0.0179(4) Uani 1 1 d . . . . .
H8A H 0.7755 0.7591 0.1547 0.021 Uiso 1 1 calc R U . . .
H8B H 0.9277 0.7658 0.2324 0.021 Uiso 1 1 calc R U . . .
C9 C 0.88535(19) 0.5420(4) 0.09770(16) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.8209 0.4456 0.0505 0.025 Uiso 1 1 calc R U . . .
C10 C 0.9970(2) 0.5557(4) 0.07559(19) 0.0279(5) Uani 1 1 d . . . . .
H10A H 1.0635 0.6507 0.1212 0.033 Uiso 1 1 calc R U . . .
H10B H 1.0113 0.4707 0.0140 0.033 Uiso 1 1 calc R U . . .
C11 C 0.76360(19) 0.6852(4) 0.59250(18) 0.0200(4) Uani 1 1 d . . . . .
C12 C 0.7897(2) 0.9236(3) 0.5862(2) 0.0234(4) Uani 1 1 d . . . . .
H12A H 0.8841 0.9503 0.6184 0.035 Uiso 1 1 calc R U . . .
H12B H 0.7453 1.0031 0.6337 0.035 Uiso 1 1 calc R U . . .
H12C H 0.7564 0.9715 0.5025 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8097(3) 0.6061(4) 0.72255(19) 0.0323(5) Uani 1 1 d . . . . .
H13A H 0.7939 0.4513 0.7242 0.048 Uiso 1 1 calc R U . . .
H13B H 0.7612 0.6815 0.7679 0.048 Uiso 1 1 calc R U . . .
H13C H 0.9035 0.6350 0.7589 0.048 Uiso 1 1 calc R U . . .
C14 C 0.6201(2) 0.6302(4) 0.5299(2) 0.0346(6) Uani 1 1 d . . . . .
H14A H 0.5939 0.6796 0.4464 0.052 Uiso 1 1 calc R U . . .
H14B H 0.5661 0.7013 0.5714 0.052 Uiso 1 1 calc R U . . .
H14C H 0.6081 0.4743 0.5315 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1 O1 1.5004(13) . ?
S1 N1 1.6657(16) . ?
S1 C11 1.844(2) . ?
N1 H1 0.8907 . ?
N1 C1 1.488(2) . ?
N2 C2 1.342(2) . ?
N2 C6 1.342(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.519(3) . ?
C1 C8 1.532(3) . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 C7 1.504(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.496(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.316(3) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C12 1.517(3) . ?
C11 C13 1.530(3) . ?
C11 C14 1.522(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
O1 S1 N1 109.70(8) . . ?
O1 S1 C11 106.29(9) . . ?
N1 S1 C11 98.93(9) . . ?
S1 N1 H1 114.5 . . ?
C1 N1 S1 112.87(13) . . ?
C1 N1 H1 113.2 . . ?
C6 N2 C2 118.10(19) . . ?
N1 C1 H1A 108.9 . . ?
N1 C1 C2 109.36(14) . . ?
N1 C1 C8 108.43(18) . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 C8 112.18(14) . . ?
C8 C1 H1A 108.9 . . ?
N2 C2 C1 116.60(18) . . ?
N2 C2 C3 123.03(18) . . ?
C3 C2 C1 120.37(18) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.84(19) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.32(19) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.54(19) . . ?
C6 C5 H5 120.2 . . ?
N2 C6 C5 122.14(19) . . ?
N2 C6 C7 115.62(19) . . ?
C5 C6 C7 122.23(18) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C8 H8A 109.3 . . ?
C1 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C1 111.78(17) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9 118.0 . . ?
C10 C9 C8 124.0(2) . . ?
C10 C9 H9 118.0 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C12 C11 S1 112.43(14) . . ?
C12 C11 C13 111.0(2) . . ?
C12 C11 C14 111.83(19) . . ?
C13 C11 S1 104.48(15) . . ?
C14 C11 S1 105.54(15) . . ?
C14 C11 C13 111.25(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
S1 N1 C1 C2 81.01(17) . . . . ?
S1 N1 C1 C8 -156.39(12) . . . . ?
O1 S1 N1 C1 96.78(13) . . . . ?
O1 S1 C11 C12 66.33(17) . . . . ?
O1 S1 C11 C13 -54.10(17) . . . . ?
O1 S1 C11 C14 -171.50(15) . . . . ?
N1 S1 C11 C12 -47.33(16) . . . . ?
N1 S1 C11 C13 -167.77(15) . . . . ?
N1 S1 C11 C14 74.83(16) . . . . ?
N1 C1 C2 N2 65.5(2) . . . . ?
N1 C1 C2 C3 -114.5(2) . . . . ?
N1 C1 C8 C9 168.54(15) . . . . ?
N2 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C3 C4 -178.61(16) . . . . ?
C1 C8 C9 C10 -119.1(2) . . . . ?
C2 N2 C6 C5 -0.9(3) . . . . ?
C2 N2 C6 C7 178.42(16) . . . . ?
C2 C1 C8 C9 -70.6(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 N2 1.8(3) . . . . ?
C4 C5 C6 C7 -177.54(18) . . . . ?
C6 N2 C2 C1 179.31(15) . . . . ?
C6 N2 C2 C3 -0.7(3) . . . . ?
C8 C1 C2 N2 -54.8(2) . . . . ?
C8 C1 C2 C3 125.2(2) . . . . ?
C11 S1 N1 C1 -152.25(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NK1
_database_code_depnum_ccdc_archive 'CCDC 2298366'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2023-09-29 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H40 B Cu F2 O2 P2'
_chemical_formula_sum            'C40 H40 B Cu F2 O2 P2'
_chemical_formula_weight         727.02

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'
B B 0.0090 0.0039 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   22.02359(16)
_cell_length_b                   9.06591(6)
_cell_length_c                   18.14329(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3622.56(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26871
_cell_measurement_theta_min      4.688
_cell_measurement_theta_max      79.426

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    2.043
_shelx_estimated_absorpt_T_min   0.579
_shelx_estimated_absorpt_T_max   0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30742
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.014
_diffrn_reflns_theta_max         79.884
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_point_group_measured_fraction_full 0.713
_reflns_number_total             5494
_reflns_number_gt                5437
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.358
_reflns_Friedel_fraction_max     0.379
_reflns_Friedel_fraction_full    0.404

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+1.2008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.001(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5494
_refine_ls_number_parameters     435
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.58962(2) 0.26012(3) 0.49866(2) 0.01565(9) Uani 1 1 d . . . . .
P1 P 0.65922(3) 0.24058(5) 0.41009(4) 0.01396(12) Uani 1 1 d . . . . .
P2 P 0.61586(2) 0.33570(5) 0.61142(3) 0.01422(11) Uani 1 1 d . . . . .
F1 F 0.43813(8) 0.16157(18) 0.41293(10) 0.0316(4) Uani 1 1 d . . . . .
F2 F 0.42513(8) 0.22285(17) 0.53308(11) 0.0289(3) Uani 1 1 d . . . . .
O1 O 0.51696(8) 0.10835(16) 0.49664(13) 0.0249(4) Uani 1 1 d . . . . .
O2 O 0.50190(8) 0.34654(18) 0.46477(12) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.64033(11) 0.1315(2) 0.32807(14) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.68120(12) 0.1098(3) 0.27050(15) 0.0208(5) Uani 1 1 d . . . . .
H2 H 0.7212 0.1481 0.2740 0.025 Uiso 1 1 calc R U . . .
C3 C 0.66372(13) 0.0323(3) 0.20793(15) 0.0236(5) Uani 1 1 d . . . . .
H3 H 0.6917 0.0186 0.1687 0.028 Uiso 1 1 calc R U . . .
C4 C 0.60517(13) -0.0255(3) 0.20270(15) 0.0234(5) Uani 1 1 d . . . . .
H4 H 0.5933 -0.0792 0.1601 0.028 Uiso 1 1 calc R U . . .
C5 C 0.56427(12) -0.0042(3) 0.25984(15) 0.0231(5) Uani 1 1 d . . . . .
H5 H 0.5243 -0.0430 0.2562 0.028 Uiso 1 1 calc R U . . .
C6 C 0.58159(11) 0.0738(2) 0.32247(15) 0.0197(5) Uani 1 1 d . . . . .
H6 H 0.5534 0.0879 0.3615 0.024 Uiso 1 1 calc R U . . .
C7 C 0.68318(11) 0.4186(2) 0.37206(14) 0.0190(5) Uani 1 1 d . . . . .
C8 C 0.74260(13) 0.4472(3) 0.34778(15) 0.0249(5) Uani 1 1 d . . . . .
H8 H 0.7726 0.3721 0.3508 0.030 Uiso 1 1 calc R U . . .
C9 C 0.75780(16) 0.5850(3) 0.31925(18) 0.0339(7) Uani 1 1 d . . . . .
H9 H 0.7981 0.6041 0.3031 0.041 Uiso 1 1 calc R U . . .
C10 C 0.71410(17) 0.6937(3) 0.31446(17) 0.0365(7) Uani 1 1 d . . . . .
H10 H 0.7244 0.7875 0.2947 0.044 Uiso 1 1 calc R U . . .
C11 C 0.65551(17) 0.6672(3) 0.33813(18) 0.0352(7) Uani 1 1 d . . . . .
H11 H 0.6258 0.7428 0.3346 0.042 Uiso 1 1 calc R U . . .
C12 C 0.63984(14) 0.5305(3) 0.36704(16) 0.0275(6) Uani 1 1 d . . . . .
H12 H 0.5995 0.5131 0.3834 0.033 Uiso 1 1 calc R U . . .
C13 C 0.73029(11) 0.1620(2) 0.44331(13) 0.0158(4) Uani 1 1 d . . . . .
C14 C 0.76790(12) 0.2485(2) 0.48819(16) 0.0212(5) Uani 1 1 d . . . . .
H14 H 0.7575 0.3484 0.4978 0.025 Uiso 1 1 calc R U . . .
C15 C 0.82025(12) 0.1889(3) 0.51867(16) 0.0265(5) Uani 1 1 d . . . . .
H15 H 0.8455 0.2480 0.5491 0.032 Uiso 1 1 calc R U . . .
C16 C 0.83579(11) 0.0430(3) 0.50472(16) 0.0256(5) Uani 1 1 d . . . . .
H16 H 0.8717 0.0025 0.5255 0.031 Uiso 1 1 calc R U . . .
C17 C 0.79900(12) -0.0428(3) 0.46068(15) 0.0236(5) Uani 1 1 d . . . . .
H17 H 0.8100 -0.1421 0.4507 0.028 Uiso 1 1 calc R U . . .
C18 C 0.74593(11) 0.0149(2) 0.43065(14) 0.0192(5) Uani 1 1 d . . . . .
H18 H 0.7203 -0.0459 0.4015 0.023 Uiso 1 1 calc R U . . .
C19 C 0.68321(10) 0.4513(2) 0.61103(15) 0.0185(4) Uani 1 1 d . . . . .
C20 C 0.73518(12) 0.4187(3) 0.65129(16) 0.0253(5) Uani 1 1 d . . . . .
H20 H 0.7350 0.3385 0.6850 0.030 Uiso 1 1 calc R U . . .
C21 C 0.78746(14) 0.5028(4) 0.64251(19) 0.0376(7) Uani 1 1 d . . . . .
H21 H 0.8231 0.4788 0.6695 0.045 Uiso 1 1 calc R U . . .
C22 C 0.78766(15) 0.6226(3) 0.5941(2) 0.0402(8) Uani 1 1 d . . . . .
H22 H 0.8233 0.6802 0.5880 0.048 Uiso 1 1 calc R U . . .
C23 C 0.73536(15) 0.6567(3) 0.5549(2) 0.0369(7) Uani 1 1 d . . . . .
H23 H 0.7350 0.7394 0.5227 0.044 Uiso 1 1 calc R U . . .
C24 C 0.68369(13) 0.5709(3) 0.56240(17) 0.0260(6) Uani 1 1 d . . . . .
H24 H 0.6484 0.5934 0.5344 0.031 Uiso 1 1 calc R U . . .
C25 C 0.63251(11) 0.1879(2) 0.67698(14) 0.0182(5) Uani 1 1 d . . . . .
C26 C 0.61327(12) 0.1918(3) 0.75002(15) 0.0236(5) Uani 1 1 d . . . . .
H26 H 0.5936 0.2774 0.7684 0.028 Uiso 1 1 calc R U . . .
C27 C 0.62255(14) 0.0719(3) 0.79637(17) 0.0294(6) Uani 1 1 d . . . . .
H27 H 0.6090 0.0756 0.8460 0.035 Uiso 1 1 calc R U . . .
C28 C 0.65173(13) -0.0535(3) 0.76994(18) 0.0283(6) Uani 1 1 d . . . . .
H28 H 0.6573 -0.1365 0.8011 0.034 Uiso 1 1 calc R U . . .
C29 C 0.67262(13) -0.0566(3) 0.69791(17) 0.0272(6) Uani 1 1 d . . . . .
H29 H 0.6937 -0.1410 0.6804 0.033 Uiso 1 1 calc R U . . .
C30 C 0.66298(11) 0.0625(3) 0.65111(15) 0.0219(5) Uani 1 1 d . . . . .
H30 H 0.6770 0.0589 0.6016 0.026 Uiso 1 1 calc R U . . .
C31 C 0.55861(11) 0.4453(2) 0.65863(14) 0.0183(4) Uani 1 1 d . . . . .
C32 C 0.50070(11) 0.3828(3) 0.66292(16) 0.0236(5) Uani 1 1 d . . . . .
H32 H 0.4932 0.2886 0.6418 0.028 Uiso 1 1 calc R U . . .
C33 C 0.45423(13) 0.4580(3) 0.69793(18) 0.0299(6) Uani 1 1 d . . . . .
H33 H 0.4152 0.4143 0.7018 0.036 Uiso 1 1 calc R U . . .
C34 C 0.46440(14) 0.5967(3) 0.7274(2) 0.0370(7) Uani 1 1 d . . . . .
H34 H 0.4320 0.6493 0.7497 0.044 Uiso 1 1 calc R U . . .
C35 C 0.52198(15) 0.6589(3) 0.7243(2) 0.0363(7) Uani 1 1 d . . . . .
H35 H 0.5290 0.7533 0.7454 0.044 Uiso 1 1 calc R U . . .
C36 C 0.56945(13) 0.5832(3) 0.69037(17) 0.0266(5) Uani 1 1 d . . . . .
H36 H 0.6090 0.6252 0.6888 0.032 Uiso 1 1 calc R U . . .
C37 C 0.47270(14) 0.4858(3) 0.47296(18) 0.0313(6) Uani 1 1 d . . . . .
H37A H 0.5040 0.5637 0.4773 0.038 Uiso 1 1 calc R U . . .
H37B H 0.4488 0.4855 0.5192 0.038 Uiso 1 1 calc R U . . .
C38 C 0.4318(3) 0.5221(6) 0.4104(3) 0.0812(18) Uani 1 1 d . . . . .
H38A H 0.4121 0.6173 0.4196 0.122 Uiso 1 1 calc R U . . .
H38B H 0.4008 0.4452 0.4056 0.122 Uiso 1 1 calc R U . . .
H38C H 0.4555 0.5277 0.3648 0.122 Uiso 1 1 calc R U . . .
C39 C 0.50637(14) -0.0421(3) 0.5063(3) 0.0436(9) Uani 1 1 d . . . . .
H39A H 0.4837 -0.0805 0.4632 0.052 Uiso 1 1 calc R U . . .
H39B H 0.4808 -0.0569 0.5506 0.052 Uiso 1 1 calc R U . . .
C40 C 0.56396(15) -0.1270(3) 0.5148(2) 0.0419(9) Uani 1 1 d . . . . .
H40A H 0.5859 -0.0916 0.5584 0.063 Uiso 1 1 calc R U . . .
H40B H 0.5893 -0.1132 0.4709 0.063 Uiso 1 1 calc R U . . .
H40C H 0.5546 -0.2320 0.5208 0.063 Uiso 1 1 calc R U . . .
B1 B 0.46818(12) 0.2099(3) 0.47636(17) 0.0219(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.1108(16) . ?
Cu1 O2 2.1735(17) . ?
Cu1 P1 2.2279(7) . ?
Cu1 P2 2.2336(7) . ?
P1 C13 1.822(2) . ?
P1 C7 1.833(2) . ?
P1 C1 1.834(3) . ?
P2 C19 1.816(2) . ?
P2 C31 1.819(2) . ?
P2 C25 1.829(2) . ?
F1 B1 1.398(3) . ?
F2 B1 1.404(3) . ?
O1 C39 1.395(3) . ?
O1 B1 1.462(3) . ?
O2 C37 1.425(3) . ?
O2 B1 1.460(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.399(3) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.396(3) . ?
C7 C8 1.405(4) . ?
C8 C9 1.394(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.396(3) . ?
C13 C14 1.402(3) . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.390(4) . ?
C19 C24 1.397(4) . ?
C20 C21 1.390(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.396(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.392(4) . ?
C25 C30 1.401(3) . ?
C26 C27 1.389(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.397(3) . ?
C31 C32 1.398(3) . ?
C32 C33 1.384(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.389(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.486(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.492(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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
O1 Cu1 O2 63.65(6) . . ?
O1 Cu1 P1 117.21(6) . . ?
O2 Cu1 P1 115.86(6) . . ?
O1 Cu1 P2 114.33(7) . . ?
O2 Cu1 P2 112.24(6) . . ?
P1 Cu1 P2 120.47(2) . . ?
C13 P1 C7 102.81(11) . . ?
C13 P1 C1 104.62(11) . . ?
C7 P1 C1 103.57(11) . . ?
C13 P1 Cu1 112.54(8) . . ?
C7 P1 Cu1 113.55(8) . . ?
C1 P1 Cu1 118.16(8) . . ?
C19 P2 C31 104.63(11) . . ?
C19 P2 C25 105.18(11) . . ?
C31 P2 C25 103.46(11) . . ?
C19 P2 Cu1 112.63(9) . . ?
C31 P2 Cu1 114.80(8) . . ?
C25 P2 Cu1 115.01(8) . . ?
C39 O1 B1 121.6(2) . . ?
C39 O1 Cu1 139.65(17) . . ?
B1 O1 Cu1 98.70(13) . . ?
C37 O2 B1 120.5(2) . . ?
C37 O2 Cu1 133.72(16) . . ?
B1 O2 Cu1 96.06(14) . . ?
C2 C1 C6 119.3(2) . . ?
C2 C1 P1 122.55(18) . . ?
C6 C1 P1 118.05(19) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 118.9(2) . . ?
C12 C7 P1 117.9(2) . . ?
C8 C7 P1 123.26(18) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C18 C13 C14 119.0(2) . . ?
C18 C13 P1 122.07(19) . . ?
C14 C13 P1 118.73(17) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C20 C19 C24 119.4(2) . . ?
C20 C19 P2 123.21(19) . . ?
C24 C19 P2 117.1(2) . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C26 C25 C30 119.1(2) . . ?
C26 C25 P2 122.66(18) . . ?
C30 C25 P2 118.2(2) . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 119.9(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 119.7(2) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.6(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C25 119.9(3) . . ?
C29 C30 H30 120.0 . . ?
C25 C30 H30 120.0 . . ?
C36 C31 C32 119.7(2) . . ?
C36 C31 P2 124.35(19) . . ?
C32 C31 P2 115.93(18) . . ?
C33 C32 C31 120.0(2) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.3(3) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.1(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 120.2(3) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 119.6(3) . . ?
C35 C36 H36 120.2 . . ?
C31 C36 H36 120.2 . . ?
O2 C37 C38 112.9(3) . . ?
O2 C37 H37A 109.0 . . ?
C38 C37 H37A 109.0 . . ?
O2 C37 H37B 109.0 . . ?
C38 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O1 C39 C40 112.0(2) . . ?
O1 C39 H39A 109.2 . . ?
C40 C39 H39A 109.2 . . ?
O1 C39 H39B 109.2 . . ?
C40 C39 H39B 109.2 . . ?
H39A C39 H39B 107.9 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
F1 B1 F2 108.1(2) . . ?
F1 B1 O2 112.8(2) . . ?
F2 B1 O2 112.2(2) . . ?
F1 B1 O1 111.0(2) . . ?
F2 B1 O1 111.4(2) . . ?
O2 B1 O1 101.34(19) . . ?

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
C13 P1 C1 C2 -52.4(2) . . . . ?
C7 P1 C1 C2 55.0(2) . . . . ?
Cu1 P1 C1 C2 -178.44(17) . . . . ?
C13 P1 C1 C6 130.38(18) . . . . ?
C7 P1 C1 C6 -122.25(19) . . . . ?
Cu1 P1 C1 C6 4.3(2) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
P1 C1 C2 C3 -176.85(19) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
P1 C1 C6 C5 177.21(18) . . . . ?
C13 P1 C7 C12 -156.3(2) . . . . ?
C1 P1 C7 C12 94.9(2) . . . . ?
Cu1 P1 C7 C12 -34.5(2) . . . . ?
C13 P1 C7 C8 23.8(2) . . . . ?
C1 P1 C7 C8 -84.9(2) . . . . ?
Cu1 P1 C7 C8 145.7(2) . . . . ?
C12 C7 C8 C9 0.0(4) . . . . ?
P1 C7 C8 C9 179.9(2) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C7 -0.3(5) . . . . ?
C8 C7 C12 C11 0.3(4) . . . . ?
P1 C7 C12 C11 -179.5(2) . . . . ?
C7 P1 C13 C18 -135.6(2) . . . . ?
C1 P1 C13 C18 -27.7(2) . . . . ?
Cu1 P1 C13 C18 101.9(2) . . . . ?
C7 P1 C13 C14 49.9(2) . . . . ?
C1 P1 C13 C14 157.8(2) . . . . ?
Cu1 P1 C13 C14 -72.7(2) . . . . ?
C18 C13 C14 C15 0.8(4) . . . . ?
P1 C13 C14 C15 175.5(2) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C13 1.7(4) . . . . ?
C14 C13 C18 C17 -1.8(4) . . . . ?
P1 C13 C18 C17 -176.26(19) . . . . ?
C31 P2 C19 C20 111.8(2) . . . . ?
C25 P2 C19 C20 3.2(3) . . . . ?
Cu1 P2 C19 C20 -122.8(2) . . . . ?
C31 P2 C19 C24 -74.1(2) . . . . ?
C25 P2 C19 C24 177.25(19) . . . . ?
Cu1 P2 C19 C24 51.3(2) . . . . ?
C24 C19 C20 C21 -0.9(4) . . . . ?
P2 C19 C20 C21 173.0(2) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C22 C23 C24 C19 1.7(5) . . . . ?
C20 C19 C24 C23 -0.5(4) . . . . ?
P2 C19 C24 C23 -174.8(2) . . . . ?
C19 P2 C25 C26 96.8(2) . . . . ?
C31 P2 C25 C26 -12.7(2) . . . . ?
Cu1 P2 C25 C26 -138.69(19) . . . . ?
C19 P2 C25 C30 -86.8(2) . . . . ?
C31 P2 C25 C30 163.71(19) . . . . ?
Cu1 P2 C25 C30 37.7(2) . . . . ?
C30 C25 C26 C27 -1.7(4) . . . . ?
P2 C25 C26 C27 174.7(2) . . . . ?
C25 C26 C27 C28 0.4(4) . . . . ?
C26 C27 C28 C29 1.5(4) . . . . ?
C27 C28 C29 C30 -2.1(4) . . . . ?
C28 C29 C30 C25 0.7(4) . . . . ?
C26 C25 C30 C29 1.1(4) . . . . ?
P2 C25 C30 C29 -175.4(2) . . . . ?
C19 P2 C31 C36 -3.9(3) . . . . ?
C25 P2 C31 C36 106.1(2) . . . . ?
Cu1 P2 C31 C36 -127.8(2) . . . . ?
C19 P2 C31 C32 176.8(2) . . . . ?
C25 P2 C31 C32 -73.2(2) . . . . ?
Cu1 P2 C31 C32 52.9(2) . . . . ?
C36 C31 C32 C33 0.6(4) . . . . ?
P2 C31 C32 C33 179.9(2) . . . . ?
C31 C32 C33 C34 1.5(5) . . . . ?
C32 C33 C34 C35 -2.3(5) . . . . ?
C33 C34 C35 C36 1.2(6) . . . . ?
C34 C35 C36 C31 0.8(5) . . . . ?
C32 C31 C36 C35 -1.7(4) . . . . ?
P2 C31 C36 C35 179.0(3) . . . . ?
B1 O2 C37 C38 -74.8(4) . . . . ?
Cu1 O2 C37 C38 148.1(4) . . . . ?
B1 O1 C39 C40 170.8(3) . . . . ?
Cu1 O1 C39 C40 -6.6(6) . . . . ?
C37 O2 B1 F1 86.6(3) . . . . ?
Cu1 O2 B1 F1 -123.05(19) . . . . ?
C37 O2 B1 F2 -35.8(3) . . . . ?
Cu1 O2 B1 F2 114.6(2) . . . . ?
C37 O2 B1 O1 -154.7(2) . . . . ?
Cu1 O2 B1 O1 -4.3(2) . . . . ?
C39 O1 B1 F1 -53.8(4) . . . . ?
Cu1 O1 B1 F1 124.54(19) . . . . ?
C39 O1 B1 F2 66.7(4) . . . . ?
Cu1 O1 B1 F2 -115.02(18) . . . . ?
C39 O1 B1 O2 -173.8(3) . . . . ?
Cu1 O1 B1 O2 4.5(2) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Alex120d
_database_code_depnum_ccdc_archive 'CCDC 2298367'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2023-09-29 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H48 Cu P4, B F4'
_chemical_formula_sum            'C52 H48 B Cu F4 P4'
_chemical_formula_weight         947.14

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'
B B 0.0090 0.0039 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

_cell_length_a                   14.0344(3)
_cell_length_b                   18.8088(3)
_cell_length_c                   18.9839(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.5447(19)
_cell_angle_gamma                90
_cell_volume                     5010.96(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14487
_cell_measurement_theta_min      3.9
_cell_measurement_theta_max      79.7

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             1960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.214
_shelx_estimated_absorpt_T_min   0.538
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47124
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.308
_diffrn_reflns_theta_max         79.673
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             10502
_reflns_number_gt                7727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.03P)²+40P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10502
_refine_ls_number_parameters     475
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1466
_refine_ls_R_factor_gt           0.1164
_refine_ls_wR_factor_ref         0.2470
_refine_ls_wR_factor_gt          0.2282
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.76665(7) 0.29592(5) 0.28363(5) 0.0433(3) Uani 1 1 d . . . . .
P1 P 0.77310(12) 0.18571(8) 0.33488(9) 0.0432(4) Uani 1 1 d . . . . .
P2 P 0.83692(14) 0.24735(9) 0.18682(9) 0.0494(4) Uani 1 1 d . . . . .
P3 P 0.84588(13) 0.38494(8) 0.34165(9) 0.0457(4) Uani 1 1 d . . . . .
P4 P 0.63855(13) 0.37022(9) 0.27233(9) 0.0462(4) Uani 1 1 d . . . . .
C1 C 0.8418(5) 0.1309(4) 0.2716(4) 0.0543(18) Uani 1 1 d . . . . .
H1A H 0.8808 0.0962 0.2984 0.065 Uiso 1 1 calc R U . . .
H1B H 0.7964 0.1038 0.2417 0.065 Uiso 1 1 calc R U . . .
C2 C 0.9066(5) 0.1736(4) 0.2245(4) 0.0544(17) Uani 1 1 d . . . . .
H2A H 0.9316 0.1431 0.1863 0.065 Uiso 1 1 calc R U . . .
H2B H 0.9613 0.1924 0.2521 0.065 Uiso 1 1 calc R U . . .
C3 C 0.8417(5) 0.1772(3) 0.4173(3) 0.0446(15) Uani 1 1 d . . . . .
C4 C 0.9405(5) 0.1805(3) 0.4141(4) 0.0517(17) Uani 1 1 d . . . . .
H4 H 0.9711 0.1846 0.3699 0.062 Uiso 1 1 calc R U . . .
C5 C 0.9950(6) 0.1777(4) 0.4763(4) 0.060(2) Uani 1 1 d . . . . .
H5 H 1.0626 0.1791 0.4745 0.073 Uiso 1 1 calc R U . . .
C6 C 0.9500(6) 0.1729(4) 0.5397(4) 0.062(2) Uani 1 1 d . . . . .
H6 H 0.9868 0.1718 0.5819 0.075 Uiso 1 1 calc R U . . .
C7 C 0.8518(7) 0.1697(4) 0.5435(4) 0.065(2) Uani 1 1 d . . . . .
H7 H 0.8212 0.1660 0.5878 0.079 Uiso 1 1 calc R U . . .
C8 C 0.7980(6) 0.1719(4) 0.4809(4) 0.0547(17) Uani 1 1 d . . . . .
H8 H 0.7304 0.1697 0.4828 0.066 Uiso 1 1 calc R U . . .
C9 C 0.6689(5) 0.1301(3) 0.3491(4) 0.0493(16) Uani 1 1 d . . . . .
C10 C 0.6793(6) 0.0610(4) 0.3733(4) 0.0587(19) Uani 1 1 d . . . . .
H10 H 0.7411 0.0434 0.3845 0.070 Uiso 1 1 calc R U . . .
C11 C 0.6009(6) 0.0176(4) 0.3814(4) 0.063(2) Uani 1 1 d . . . . .
H11 H 0.6088 -0.0295 0.3986 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5114(6) 0.0424(4) 0.3647(4) 0.0565(18) Uani 1 1 d . . . . .
H12 H 0.4573 0.0127 0.3709 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5004(5) 0.1104(4) 0.3389(4) 0.0551(17) Uani 1 1 d . . . . .
H13 H 0.4388 0.1272 0.3263 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5791(5) 0.1543(3) 0.3313(4) 0.0515(17) Uani 1 1 d . . . . .
H14 H 0.5710 0.2013 0.3138 0.062 Uiso 1 1 calc R U . . .
C15 C 0.7551(6) 0.1996(4) 0.1278(4) 0.0571(18) Uani 1 1 d . . . . .
C16 C 0.6592(6) 0.2064(4) 0.1352(4) 0.064(2) Uani 1 1 d . . . . .
H16 H 0.6349 0.2367 0.1709 0.077 Uiso 1 1 calc R U . . .
C17 C 0.5959(7) 0.1697(5) 0.0912(5) 0.082(3) Uani 1 1 d . . . . .
H17 H 0.5289 0.1744 0.0967 0.099 Uiso 1 1 calc R U . . .
C18 C 0.6329(9) 0.1265(5) 0.0396(5) 0.094(4) Uani 1 1 d . . . . .
H18 H 0.5905 0.1018 0.0089 0.112 Uiso 1 1 calc R U . . .
C19 C 0.7278(9) 0.1182(5) 0.0313(5) 0.086(3) Uani 1 1 d . . . . .
H19 H 0.7512 0.0875 -0.0043 0.103 Uiso 1 1 calc R U . . .
C20 C 0.7915(8) 0.1551(4) 0.0753(4) 0.073(2) Uani 1 1 d . . . . .
H20 H 0.8583 0.1500 0.0696 0.087 Uiso 1 1 calc R U . . .
C21 C 0.9189(8) 0.2918(5) 0.1290(5) 0.0842(12) Uani 1 1 d . . . . .
C22 C 0.8905(8) 0.3140(5) 0.0600(5) 0.0842(12) Uani 1 1 d . . . . .
H22 H 0.8288 0.3018 0.0428 0.101 Uiso 1 1 calc R U . . .
C23 C 0.9513(8) 0.3529(5) 0.0175(6) 0.0842(12) Uani 1 1 d . . . . .
H23 H 0.9312 0.3670 -0.0283 0.101 Uiso 1 1 calc R U . . .
C24 C 1.0366(8) 0.3705(5) 0.0406(5) 0.0842(12) Uani 1 1 d . . . . .
H24 H 1.0777 0.3964 0.0105 0.101 Uiso 1 1 calc R U . . .
C25 C 1.0687(8) 0.3521(5) 0.1078(5) 0.0842(12) Uani 1 1 d . . . . .
H25 H 1.1307 0.3658 0.1231 0.101 Uiso 1 1 calc R U . . .
C26 C 1.0093(8) 0.3133(5) 0.1530(6) 0.0842(12) Uani 1 1 d . . . . .
H26 H 1.0302 0.3018 0.1994 0.101 Uiso 1 1 calc R U . . .
C27 C 0.7787(5) 0.4647(3) 0.3153(4) 0.0503(17) Uani 1 1 d . . . . .
H27A H 0.7979 0.5056 0.3450 0.060 Uiso 1 1 calc R U . . .
H27B H 0.7918 0.4765 0.2655 0.060 Uiso 1 1 calc R U . . .
C28 C 0.6718(5) 0.4488(3) 0.3247(4) 0.0524(17) Uani 1 1 d . . . . .
H28A H 0.6336 0.4903 0.3092 0.063 Uiso 1 1 calc R U . . .
H28B H 0.6585 0.4400 0.3751 0.063 Uiso 1 1 calc R U . . .
C29 C 0.8342(5) 0.3881(4) 0.4379(4) 0.0520(17) Uani 1 1 d . . . . .
C30 C 0.8878(6) 0.4356(4) 0.4777(4) 0.065(2) Uani 1 1 d . . . . .
H30 H 0.9333 0.4656 0.4558 0.079 Uiso 1 1 calc R U . . .
C31 C 0.8740(7) 0.4386(6) 0.5503(5) 0.080(3) Uani 1 1 d . . . . .
H31 H 0.9106 0.4709 0.5779 0.096 Uiso 1 1 calc R U . . .
C32 C 0.8098(8) 0.3965(5) 0.5818(4) 0.078(3) Uani 1 1 d . . . . .
H32 H 0.8016 0.3997 0.6313 0.094 Uiso 1 1 calc R U . . .
C33 C 0.7556(8) 0.3489(5) 0.5435(4) 0.082(3) Uani 1 1 d . . . . .
H33 H 0.7102 0.3193 0.5659 0.098 Uiso 1 1 calc R U . . .
C34 C 0.7696(7) 0.3452(4) 0.4698(4) 0.065(2) Uani 1 1 d . . . . .
H34 H 0.7335 0.3124 0.4424 0.078 Uiso 1 1 calc R U . . .
C35 C 0.9714(5) 0.4061(4) 0.3277(4) 0.0528(17) Uani 1 1 d . . . . .
C36 C 1.0024(6) 0.4670(4) 0.2961(4) 0.0568(18) Uani 1 1 d . . . . .
H36 H 0.9579 0.5024 0.2822 0.068 Uiso 1 1 calc R U . . .
C37 C 1.1000(6) 0.4773(5) 0.2842(4) 0.070(2) Uani 1 1 d . . . . .
H37 H 1.1215 0.5197 0.2622 0.084 Uiso 1 1 calc R U . . .
C38 C 1.1631(7) 0.4268(6) 0.3041(5) 0.083(3) Uani 1 1 d . . . . .
H38 H 1.2291 0.4335 0.2957 0.100 Uiso 1 1 calc R U . . .
C39 C 1.1327(7) 0.3665(6) 0.3359(6) 0.093(3) Uani 1 1 d . . . . .
H39 H 1.1778 0.3315 0.3500 0.112 Uiso 1 1 calc R U . . .
C40 C 1.0369(7) 0.3554(5) 0.3480(5) 0.078(3) Uani 1 1 d . . . . .
H40 H 1.0163 0.3130 0.3704 0.094 Uiso 1 1 calc R U . . .
C41 C 0.5248(7) 0.3430(5) 0.3056(6) 0.0878(13) Uani 1 1 d . . . . .
C42 C 0.5068(7) 0.3380(5) 0.3767(6) 0.0878(13) Uani 1 1 d . . . . .
H42 H 0.5513 0.3584 0.4089 0.105 Uiso 1 1 calc R U . . .
C43 C 0.4276(7) 0.3047(5) 0.4034(6) 0.0878(13) Uani 1 1 d . . . . .
H43 H 0.4193 0.3008 0.4528 0.105 Uiso 1 1 calc R U . . .
C44 C 0.3618(7) 0.2778(5) 0.3584(6) 0.0878(13) Uani 1 1 d . . . . .
H44 H 0.3060 0.2564 0.3769 0.105 Uiso 1 1 calc R U . . .
C45 C 0.3734(7) 0.2804(5) 0.2857(6) 0.0878(13) Uani 1 1 d . . . . .
H45 H 0.3273 0.2599 0.2549 0.105 Uiso 1 1 calc R U . . .
C46 C 0.4542(7) 0.3138(5) 0.2590(6) 0.0878(13) Uani 1 1 d . . . . .
H46 H 0.4625 0.3171 0.2095 0.105 Uiso 1 1 calc R U . . .
C47 C 0.6153(5) 0.4104(3) 0.1859(4) 0.0500(17) Uani 1 1 d . . . . .
C48 C 0.5416(5) 0.4605(3) 0.1777(4) 0.0552(19) Uani 1 1 d . . . . .
H48 H 0.4992 0.4702 0.2152 0.066 Uiso 1 1 calc R U . . .
C49 C 0.5322(6) 0.4955(4) 0.1135(5) 0.062(2) Uani 1 1 d . . . . .
H49 H 0.4829 0.5296 0.1073 0.075 Uiso 1 1 calc R U . . .
C50 C 0.5928(6) 0.4815(4) 0.0593(4) 0.062(2) Uani 1 1 d . . . . .
H50 H 0.5857 0.5068 0.0163 0.074 Uiso 1 1 calc R U . . .
C51 C 0.6648(6) 0.4310(4) 0.0658(4) 0.061(2) Uani 1 1 d . . . . .
H51 H 0.7055 0.4201 0.0275 0.073 Uiso 1 1 calc R U . . .
C52 C 0.6750(5) 0.3966(3) 0.1313(4) 0.0494(17) Uani 1 1 d . . . . .
H52 H 0.7248 0.3629 0.1377 0.059 Uiso 1 1 calc R U . . .
F1 F 0.2335(5) 0.6253(6) 0.2306(5) 0.238(3) Uani 1 1 d D . . . .
F2 F 0.3623(7) 0.6851(4) 0.1866(6) 0.238(3) Uani 1 1 d D . . . .
F3 F 0.3793(6) 0.5710(5) 0.2268(5) 0.238(3) Uani 1 1 d D . . . .
F4 F 0.2959(7) 0.5928(6) 0.1245(4) 0.238(3) Uani 1 1 d D . . . .
B1 B 0.3178(5) 0.6186(4) 0.1921(4) 0.238(3) Uani 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 P2 2.285(2) . ?
Cu1 P4 2.2855(19) . ?
Cu1 P3 2.2869(18) . ?
Cu1 P1 2.2914(17) . ?
P1 C9 1.820(7) . ?
P1 C3 1.837(6) . ?
P1 C1 1.859(7) . ?
P2 C21 1.804(10) . ?
P2 C15 1.831(7) . ?
P2 C2 1.838(7) . ?
P3 C35 1.828(8) . ?
P3 C29 1.837(7) . ?
P3 C27 1.838(6) . ?
P4 C41 1.797(10) . ?
P4 C47 1.833(6) . ?
P4 C28 1.840(7) . ?
C1 C2 1.514(11) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.363(10) . ?
C3 C4 1.390(10) . ?
C4 C5 1.401(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(10) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.379(9) . ?
C9 C10 1.386(9) . ?
C10 C11 1.382(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(10) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.361(12) . ?
C15 C20 1.401(11) . ?
C16 C17 1.397(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.351(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.402(12) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.403(14) . ?
C21 C22 1.428(14) . ?
C22 C23 1.389(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.312(14) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.406(13) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.542(10) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C34 1.361(11) . ?
C29 C30 1.386(10) . ?
C30 C31 1.395(11) . ?
C30 H30 0.9500 . ?
C31 C32 1.343(13) . ?
C31 H31 0.9500 . ?
C32 C33 1.378(13) . ?
C32 H32 0.9500 . ?
C33 C34 1.416(11) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.366(10) . ?
C35 C40 1.377(11) . ?
C36 C37 1.403(11) . ?
C36 H36 0.9500 . ?
C37 C38 1.351(13) . ?
C37 H37 0.9500 . ?
C38 C39 1.355(14) . ?
C38 H38 0.9500 . ?
C39 C40 1.382(13) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.379(15) . ?
C41 C46 1.432(15) . ?
C42 C43 1.376(13) . ?
C42 H42 0.9500 . ?
C43 C44 1.350(15) . ?
C43 H43 0.9500 . ?
C44 C45 1.393(15) . ?
C44 H44 0.9500 . ?
C45 C46 1.396(13) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C52 1.364(10) . ?
C47 C48 1.406(10) . ?
C48 C49 1.390(10) . ?
C48 H48 0.9500 . ?
C49 C50 1.368(12) . ?
C49 H49 0.9500 . ?
C50 C51 1.392(11) . ?
C50 H50 0.9500 . ?
C51 C52 1.409(9) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
F1 B1 1.402(3) . ?
F2 B1 1.402(3) . ?
F3 B1 1.403(3) . ?
F4 B1 1.403(3) . ?

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
P2 Cu1 P4 120.95(7) . . ?
P2 Cu1 P3 117.95(8) . . ?
P4 Cu1 P3 88.62(7) . . ?
P2 Cu1 P1 87.95(7) . . ?
P4 Cu1 P1 128.38(8) . . ?
P3 Cu1 P1 116.15(6) . . ?
C9 P1 C3 103.9(3) . . ?
C9 P1 C1 101.5(3) . . ?
C3 P1 C1 103.4(3) . . ?
C9 P1 Cu1 123.6(2) . . ?
C3 P1 Cu1 117.3(2) . . ?
C1 P1 Cu1 104.2(2) . . ?
C21 P2 C15 104.8(4) . . ?
C21 P2 C2 104.3(4) . . ?
C15 P2 C2 101.3(3) . . ?
C21 P2 Cu1 125.9(3) . . ?
C15 P2 Cu1 114.5(3) . . ?
C2 P2 Cu1 102.8(2) . . ?
C35 P3 C29 103.4(3) . . ?
C35 P3 C27 106.0(3) . . ?
C29 P3 C27 101.2(3) . . ?
C35 P3 Cu1 123.6(2) . . ?
C29 P3 Cu1 117.1(2) . . ?
C27 P3 Cu1 102.7(2) . . ?
C41 P4 C47 106.3(4) . . ?
C41 P4 C28 105.1(5) . . ?
C47 P4 C28 101.2(3) . . ?
C41 P4 Cu1 119.6(3) . . ?
C47 P4 Cu1 118.0(3) . . ?
C28 P4 Cu1 104.2(2) . . ?
C2 C1 P1 114.0(5) . . ?
C2 C1 H1A 108.8 . . ?
P1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 P2 108.0(5) . . ?
C1 C2 H2A 110.1 . . ?
P2 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
P2 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C8 C3 C4 120.0(6) . . ?
C8 C3 P1 121.6(5) . . ?
C4 C3 P1 118.4(5) . . ?
C3 C4 C5 119.9(7) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.3(8) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 121.2(7) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 118.9(8) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C3 C8 C7 120.6(7) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C14 C9 C10 119.0(7) . . ?
C14 C9 P1 120.6(5) . . ?
C10 C9 P1 120.3(5) . . ?
C11 C10 C9 120.7(7) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.1(7) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.8(7) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.2(7) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.3(6) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C20 119.8(8) . . ?
C16 C15 P2 120.4(6) . . ?
C20 C15 P2 119.8(7) . . ?
C15 C16 C17 121.0(9) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 118.3(10) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C19 C18 C17 121.9(8) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 119.8(10) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 119.0(10) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C26 C21 C22 117.3(9) . . ?
C26 C21 P2 121.0(8) . . ?
C22 C21 P2 121.3(8) . . ?
C23 C22 C21 121.2(11) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 120.2(11) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 121.9(10) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C24 C25 C26 120.0(11) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 119.4(10) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C28 C27 P3 107.9(4) . . ?
C28 C27 H27A 110.1 . . ?
P3 C27 H27A 110.1 . . ?
C28 C27 H27B 110.1 . . ?
P3 C27 H27B 110.1 . . ?
H27A C27 H27B 108.4 . . ?
C27 C28 P4 109.6(5) . . ?
C27 C28 H28A 109.8 . . ?
P4 C28 H28A 109.8 . . ?
C27 C28 H28B 109.8 . . ?
P4 C28 H28B 109.8 . . ?
H28A C28 H28B 108.2 . . ?
C34 C29 C30 120.0(7) . . ?
C34 C29 P3 119.3(5) . . ?
C30 C29 P3 120.6(6) . . ?
C29 C30 C31 119.0(8) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C32 C31 C30 121.0(8) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 121.2(8) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C32 C33 C34 118.1(9) . . ?
C32 C33 H33 120.9 . . ?
C34 C33 H33 120.9 . . ?
C29 C34 C33 120.7(8) . . ?
C29 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C40 119.3(8) . . ?
C36 C35 P3 123.9(6) . . ?
C40 C35 P3 116.8(6) . . ?
C35 C36 C37 120.2(8) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C38 C37 C36 119.7(9) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C37 C38 C39 120.3(9) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C38 C39 C40 120.8(9) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C35 C40 C39 119.7(9) . . ?
C35 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C42 C41 C46 116.6(10) . . ?
C42 C41 P4 122.3(9) . . ?
C46 C41 P4 120.2(9) . . ?
C43 C42 C41 123.1(12) . . ?
C43 C42 H42 118.4 . . ?
C41 C42 H42 118.4 . . ?
C44 C43 C42 119.2(11) . . ?
C44 C43 H43 120.4 . . ?
C42 C43 H43 120.4 . . ?
C43 C44 C45 121.8(10) . . ?
C43 C44 H44 119.1 . . ?
C45 C44 H44 119.1 . . ?
C44 C45 C46 118.7(11) . . ?
C44 C45 H45 120.7 . . ?
C46 C45 H45 120.7 . . ?
C45 C46 C41 120.5(11) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
C52 C47 C48 120.0(6) . . ?
C52 C47 P4 119.7(5) . . ?
C48 C47 P4 120.0(6) . . ?
C49 C48 C47 118.5(8) . . ?
C49 C48 H48 120.7 . . ?
C47 C48 H48 120.7 . . ?
C50 C49 C48 120.9(7) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 H49 119.5 . . ?
C49 C50 C51 121.4(7) . . ?
C49 C50 H50 119.3 . . ?
C51 C50 H50 119.3 . . ?
C50 C51 C52 117.3(8) . . ?
C50 C51 H51 121.3 . . ?
C52 C51 H51 121.3 . . ?
C47 C52 C51 121.7(7) . . ?
C47 C52 H52 119.1 . . ?
C51 C52 H52 119.1 . . ?
F1 B1 F2 109.7(3) . . ?
F1 B1 F3 109.4(3) . . ?
F2 B1 F3 109.3(3) . . ?
F1 B1 F4 109.3(3) . . ?
F2 B1 F4 109.5(3) . . ?
F3 B1 F4 109.7(3) . . ?

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
C9 P1 C1 C2 153.3(5) . . . . ?
C3 P1 C1 C2 -99.2(5) . . . . ?
Cu1 P1 C1 C2 23.9(5) . . . . ?
P1 C1 C2 P2 -49.0(6) . . . . ?
C21 P2 C2 C1 -177.5(5) . . . . ?
C15 P2 C2 C1 -68.8(5) . . . . ?
Cu1 P2 C2 C1 49.8(5) . . . . ?
C9 P1 C3 C8 -36.1(6) . . . . ?
C1 P1 C3 C8 -141.8(6) . . . . ?
Cu1 P1 C3 C8 104.2(5) . . . . ?
C9 P1 C3 C4 147.6(5) . . . . ?
C1 P1 C3 C4 41.9(6) . . . . ?
Cu1 P1 C3 C4 -72.1(5) . . . . ?
C8 C3 C4 C5 0.5(10) . . . . ?
P1 C3 C4 C5 176.9(5) . . . . ?
C3 C4 C5 C6 -1.0(10) . . . . ?
C4 C5 C6 C7 1.0(11) . . . . ?
C5 C6 C7 C8 -0.5(12) . . . . ?
C4 C3 C8 C7 0.0(10) . . . . ?
P1 C3 C8 C7 -176.3(6) . . . . ?
C6 C7 C8 C3 0.0(11) . . . . ?
C3 P1 C9 C14 134.5(6) . . . . ?
C1 P1 C9 C14 -118.4(6) . . . . ?
Cu1 P1 C9 C14 -2.5(7) . . . . ?
C3 P1 C9 C10 -50.0(7) . . . . ?
C1 P1 C9 C10 57.1(6) . . . . ?
Cu1 P1 C9 C10 173.0(5) . . . . ?
C14 C9 C10 C11 -1.7(12) . . . . ?
P1 C9 C10 C11 -177.3(6) . . . . ?
C9 C10 C11 C12 0.7(13) . . . . ?
C10 C11 C12 C13 0.9(12) . . . . ?
C11 C12 C13 C14 -1.4(12) . . . . ?
C10 C9 C14 C13 1.2(11) . . . . ?
P1 C9 C14 C13 176.7(6) . . . . ?
C12 C13 C14 C9 0.4(11) . . . . ?
C21 P2 C15 C16 -129.2(7) . . . . ?
C2 P2 C15 C16 122.6(6) . . . . ?
Cu1 P2 C15 C16 12.8(7) . . . . ?
C21 P2 C15 C20 51.5(7) . . . . ?
C2 P2 C15 C20 -56.7(7) . . . . ?
Cu1 P2 C15 C20 -166.5(5) . . . . ?
C20 C15 C16 C17 0.0(12) . . . . ?
P2 C15 C16 C17 -179.2(6) . . . . ?
C15 C16 C17 C18 -0.4(12) . . . . ?
C16 C17 C18 C19 0.9(15) . . . . ?
C17 C18 C19 C20 -1.0(16) . . . . ?
C16 C15 C20 C19 -0.2(12) . . . . ?
P2 C15 C20 C19 179.1(7) . . . . ?
C18 C19 C20 C15 0.6(14) . . . . ?
C15 P2 C21 C26 -157.9(8) . . . . ?
C2 P2 C21 C26 -51.9(9) . . . . ?
Cu1 P2 C21 C26 65.9(9) . . . . ?
C15 P2 C21 C22 29.6(9) . . . . ?
C2 P2 C21 C22 135.6(8) . . . . ?
Cu1 P2 C21 C22 -106.6(8) . . . . ?
C26 C21 C22 C23 2.3(14) . . . . ?
P2 C21 C22 C23 175.1(7) . . . . ?
C21 C22 C23 C24 -0.3(15) . . . . ?
C22 C23 C24 C25 -1.1(15) . . . . ?
C23 C24 C25 C26 0.4(15) . . . . ?
C22 C21 C26 C25 -2.9(14) . . . . ?
P2 C21 C26 C25 -175.7(7) . . . . ?
C24 C25 C26 C21 1.7(14) . . . . ?
C35 P3 C27 C28 178.8(4) . . . . ?
C29 P3 C27 C28 -73.5(5) . . . . ?
Cu1 P3 C27 C28 47.9(5) . . . . ?
P3 C27 C28 P4 -57.3(5) . . . . ?
C41 P4 C28 C27 164.7(5) . . . . ?
C47 P4 C28 C27 -84.8(5) . . . . ?
Cu1 P4 C28 C27 38.2(5) . . . . ?
C35 P3 C29 C34 -149.0(6) . . . . ?
C27 P3 C29 C34 101.4(6) . . . . ?
Cu1 P3 C29 C34 -9.3(7) . . . . ?
C35 P3 C29 C30 33.4(7) . . . . ?
C27 P3 C29 C30 -76.2(7) . . . . ?
Cu1 P3 C29 C30 173.1(5) . . . . ?
C34 C29 C30 C31 -0.3(12) . . . . ?
P3 C29 C30 C31 177.3(7) . . . . ?
C29 C30 C31 C32 -0.1(14) . . . . ?
C30 C31 C32 C33 0.2(16) . . . . ?
C31 C32 C33 C34 0.2(15) . . . . ?
C30 C29 C34 C33 0.7(12) . . . . ?
P3 C29 C34 C33 -176.9(7) . . . . ?
C32 C33 C34 C29 -0.6(14) . . . . ?
C29 P3 C35 C36 -112.7(6) . . . . ?
C27 P3 C35 C36 -6.7(7) . . . . ?
Cu1 P3 C35 C36 111.2(6) . . . . ?
C29 P3 C35 C40 70.1(7) . . . . ?
C27 P3 C35 C40 176.1(6) . . . . ?
Cu1 P3 C35 C40 -66.1(7) . . . . ?
C40 C35 C36 C37 0.5(11) . . . . ?
P3 C35 C36 C37 -176.7(6) . . . . ?
C35 C36 C37 C38 0.0(12) . . . . ?
C36 C37 C38 C39 -0.5(15) . . . . ?
C37 C38 C39 C40 0.5(17) . . . . ?
C36 C35 C40 C39 -0.5(13) . . . . ?
P3 C35 C40 C39 176.9(8) . . . . ?
C38 C39 C40 C35 0.0(16) . . . . ?
C47 P4 C41 C42 -152.9(8) . . . . ?
C28 P4 C41 C42 -46.1(9) . . . . ?
Cu1 P4 C41 C42 70.3(9) . . . . ?
C47 P4 C41 C46 38.2(8) . . . . ?
C28 P4 C41 C46 144.9(7) . . . . ?
Cu1 P4 C41 C46 -98.6(7) . . . . ?
C46 C41 C42 C43 2.2(14) . . . . ?
P4 C41 C42 C43 -167.2(7) . . . . ?
C41 C42 C43 C44 -2.5(14) . . . . ?
C42 C43 C44 C45 2.3(14) . . . . ?
C43 C44 C45 C46 -1.8(14) . . . . ?
C44 C45 C46 C41 1.5(14) . . . . ?
C42 C41 C46 C45 -1.6(13) . . . . ?
P4 C41 C46 C45 167.9(7) . . . . ?
C41 P4 C47 C52 -138.9(6) . . . . ?
C28 P4 C47 C52 111.6(5) . . . . ?
Cu1 P4 C47 C52 -1.3(6) . . . . ?
C41 P4 C47 C48 47.1(6) . . . . ?
C28 P4 C47 C48 -62.5(6) . . . . ?
Cu1 P4 C47 C48 -175.3(4) . . . . ?
C52 C47 C48 C49 -0.7(9) . . . . ?
P4 C47 C48 C49 173.4(5) . . . . ?
C47 C48 C49 C50 0.3(10) . . . . ?
C48 C49 C50 C51 1.2(10) . . . . ?
C49 C50 C51 C52 -2.2(10) . . . . ?
C48 C47 C52 C51 -0.4(9) . . . . ?
P4 C47 C52 C51 -174.5(5) . . . . ?
C50 C51 C52 C47 1.8(9) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 173 47 ' '
2 0.069 0.656 0.302 7 0 ' '
3 0.251 0.466 0.105 39 6 ' '
4 0.249 0.966 0.395 39 6 ' '
5 0.194 0.240 0.177 7 1 ' '
6 0.305 0.740 0.323 7 1 ' '
7 0.500 0.500 0.500 173 47 ' '
8 0.430 0.156 0.198 7 0 ' '
9 0.569 0.844 0.802 7 0 ' '
10 0.751 1.034 0.605 39 6 ' '
11 0.749 0.534 0.895 39 6 ' '
12 0.694 0.260 0.677 7 1 ' '
13 0.805 0.760 0.823 7 1 ' '
14 0.930 0.344 0.698 7 0 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_refine_diff_density_max         1.746
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.112

_shelxl_version_number           2013-4



