# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_ooo
_database_code_depnum_ccdc_archive 'CCDC 2195572'
loop_
_audit_author_name
_audit_author_address
'Yue Guo'
;Yangzhou Universuty
China
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_audit_creation_date             2022-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl2 Cu, C20 H20 P'
_chemical_formula_sum            'C20 H20 Cl2 Cu P'
_chemical_formula_weight         425.77
_chemical_absolute_configuration ?
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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                   9.4777(4)
_cell_length_b                   12.2690(6)
_cell_length_c                   9.6477(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.7870(10)
_cell_angle_gamma                90
_cell_volume                     992.49(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6547
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.449
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0791 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.9218.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14950
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.362
_diffrn_reflns_theta_min         2.386
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3658
_reflns_number_total             4928
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4928
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.031
_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)+(0.0290P)²+0.0056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0739
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C14(H14), C6(H6), C12(H12), C10(H10), C17(H17), C7(H7), C16(H16),
 C8(H8), C11(H11), C13(H13), C4(H4), C18(H18), C5(H5), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cu1 Cu 0.11332(5) 0.54603(4) 0.09758(5) 0.06569(18) Uani 1 1 d . . . . .
P1 P 0.57938(9) 0.43086(7) 0.66544(9) 0.03707(19) Uani 1 1 d . . . . .
Cl1 Cl 0.09082(12) 0.60330(11) 0.29050(13) 0.0749(3) Uani 1 1 d . . . . .
Cl2 Cl 0.13085(14) 0.49770(13) -0.10105(14) 0.0968(5) Uani 1 1 d . . . . .
C15 C 0.5662(4) 0.5561(3) 0.7546(3) 0.0393(7) Uani 1 1 d . . . . .
C20 C 0.4233(4) 0.6118(3) 0.7030(4) 0.0514(9) Uani 1 1 d . . . . .
H20 H 0.3295 0.5818 0.6255 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3930(4) 0.3602(3) 0.5924(4) 0.0415(8) Uani 1 1 d . . . . .
C14 C 0.7709(4) 0.4367(3) 0.5181(4) 0.0473(8) Uani 1 1 d . . . . .
H14 H 0.8460 0.3983 0.6040 0.057 Uiso 1 1 calc R U . . .
C6 C 0.1136(4) 0.2427(4) 0.4894(5) 0.0613(11) Uani 1 1 d . . . . .
H6 H 0.0197 0.2029 0.4549 0.074 Uiso 1 1 calc R U . . .
C12 C 0.6946(4) 0.5233(3) 0.2729(4) 0.0548(10) Uani 1 1 d . . . . .
H12 H 0.7183 0.5443 0.1934 0.066 Uiso 1 1 calc R U . . .
C10 C 0.5129(4) 0.5194(3) 0.3800(4) 0.0483(9) Uani 1 1 d . . . . .
H10 H 0.4152 0.5382 0.3740 0.058 Uiso 1 1 calc R U . . .
C17 C 0.6992(6) 0.7028(3) 0.9319(4) 0.0616(11) Uani 1 1 d . . . . .
H17 H 0.7926 0.7334 1.0092 0.074 Uiso 1 1 calc R U . . .
C7 C 0.1928(5) 0.2448(3) 0.4014(5) 0.0594(10) Uani 1 1 d . . . . .
H7 H 0.1519 0.2070 0.3071 0.071 Uiso 1 1 calc R U . . .
C2 C 0.7375(4) 0.3483(3) 0.8076(4) 0.0497(9) Uani 1 1 d . . . . .
H2A H 0.7436 0.2814 0.7571 0.060 Uiso 1 1 calc R U . . .
H2B H 0.8376 0.3867 0.8410 0.060 Uiso 1 1 calc R U . . .
C16 C 0.7036(4) 0.6027(3) 0.8695(4) 0.0492(9) Uani 1 1 d . . . . .
H16 H 0.8002 0.5661 0.9051 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3332(4) 0.3029(3) 0.4526(4) 0.0503(9) Uani 1 1 d . . . . .
H8 H 0.3874 0.3036 0.3933 0.060 Uiso 1 1 calc R U . . .
C11 C 0.5478(4) 0.5480(4) 0.2615(4) 0.0566(9) Uani 1 1 d . . . . .
H11 H 0.4721 0.5842 0.1735 0.068 Uiso 1 1 calc R U . . .
C13 C 0.8055(4) 0.4684(3) 0.3999(4) 0.0551(9) Uani 1 1 d . . . . .
H13 H 0.9045 0.4522 0.4069 0.066 Uiso 1 1 calc R U . . .
C9 C 0.6245(4) 0.4621(3) 0.5086(3) 0.0369(7) Uani 1 1 d . . . . .
C4 C 0.3110(4) 0.3585(3) 0.6799(4) 0.0483(9) Uani 1 1 d . . . . .
H4 H 0.3497 0.3975 0.7731 0.058 Uiso 1 1 calc R U . . .
C18 C 0.5582(5) 0.7571(3) 0.8804(4) 0.0592(10) Uani 1 1 d . . . . .
H18 H 0.5555 0.8248 0.9223 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1727(4) 0.2992(3) 0.6290(5) 0.0569(10) Uani 1 1 d . . . . .
H5 H 0.1189 0.2972 0.6886 0.068 Uiso 1 1 calc R U . . .
C1 C 0.7202(5) 0.3188(4) 0.9525(4) 0.0691(12) Uani 1 1 d . . . . .
H1A H 0.6187 0.2845 0.9209 0.104 Uiso 1 1 calc R U . . .
H1B H 0.7269 0.3838 1.0107 0.104 Uiso 1 1 calc R U . . .
H1C H 0.8040 0.2697 1.0170 0.104 Uiso 1 1 calc R U . . .
C19 C 0.4205(5) 0.7119(3) 0.7669(5) 0.0629(11) Uani 1 1 d . . . . .
H19 H 0.3244 0.7489 0.7326 0.075 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
Cu1 Cl1 2.0914(12) . ?
Cu1 Cl2 2.0852(12) . ?
P1 C15 1.794(4) . ?
P1 C3 1.791(3) . ?
P1 C2 1.800(3) . ?
P1 C9 1.795(3) . ?
C15 C20 1.386(4) . ?
C15 C16 1.380(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.379(5) . ?
C3 C8 1.386(5) . ?
C3 C4 1.389(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(5) . ?
C14 C9 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(5) . ?
C6 C5 1.380(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(5) . ?
C12 C13 1.364(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(4) . ?
C10 C9 1.388(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.377(5) . ?
C17 C18 1.362(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.525(5) . ?
C16 H16 0.9300 . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(6) . ?
C5 H5 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C19 H19 0.9300 . ?

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
Cl2 Cu1 Cl1 176.66(6) . . ?
C15 P1 C2 109.66(15) . . ?
C15 P1 C9 108.58(15) . . ?
C3 P1 C15 109.08(15) . . ?
C3 P1 C2 110.21(17) . . ?
C3 P1 C9 110.52(14) . . ?
C9 P1 C2 108.76(15) . . ?
C20 C15 P1 121.7(3) . . ?
C16 C15 P1 119.3(3) . . ?
C16 C15 C20 118.9(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.8(4) . . ?
C19 C20 H20 120.1 . . ?
C8 C3 P1 120.6(2) . . ?
C8 C3 C4 119.5(3) . . ?
C4 C3 P1 119.8(3) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C9 119.9(3) . . ?
C9 C14 H14 120.0 . . ?
C7 C6 H6 119.9 . . ?
C7 C6 C5 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.5(3) . . ?
C11 C10 H10 120.2 . . ?
C11 C10 C9 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
P1 C2 H2A 108.5 . . ?
P1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C1 C2 P1 115.1(2) . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(4) . . ?
C17 C16 H16 119.6 . . ?
C3 C8 H8 120.1 . . ?
C7 C8 C3 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C9 P1 121.4(3) . . ?
C14 C9 C10 119.8(3) . . ?
C10 C9 P1 118.7(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.7 . . ?

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
P1 C15 C20 C19 -175.2(3) . . . . ?
P1 C15 C16 C17 175.1(3) . . . . ?
P1 C3 C8 C7 177.1(3) . . . . ?
P1 C3 C4 C5 -176.3(3) . . . . ?
C15 P1 C3 C8 142.6(3) . . . . ?
C15 P1 C3 C4 -40.3(3) . . . . ?
C15 P1 C2 C1 58.9(3) . . . . ?
C15 P1 C9 C14 110.8(3) . . . . ?
C15 P1 C9 C10 -64.9(3) . . . . ?
C15 C20 C19 C18 0.4(6) . . . . ?
C20 C15 C16 C17 0.0(5) . . . . ?
C3 P1 C15 C20 -30.4(3) . . . . ?
C3 P1 C15 C16 154.6(3) . . . . ?
C3 P1 C2 C1 -61.2(3) . . . . ?
C3 P1 C9 C14 -129.6(3) . . . . ?
C3 P1 C9 C10 54.7(3) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C6 C7 C8 C3 -0.7(6) . . . . ?
C17 C18 C19 C20 -0.5(6) . . . . ?
C7 C6 C5 C4 0.3(6) . . . . ?
C2 P1 C15 C20 -151.2(3) . . . . ?
C2 P1 C15 C16 33.8(3) . . . . ?
C2 P1 C3 C8 -97.0(3) . . . . ?
C2 P1 C3 C4 80.1(3) . . . . ?
C2 P1 C9 C14 -8.5(3) . . . . ?
C2 P1 C9 C10 175.8(3) . . . . ?
C16 C15 C20 C19 -0.2(5) . . . . ?
C16 C17 C18 C19 0.2(6) . . . . ?
C8 C3 C4 C5 0.9(5) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C11 C10 C9 P1 177.3(3) . . . . ?
C11 C10 C9 C14 1.5(5) . . . . ?
C13 C14 C9 P1 -175.7(3) . . . . ?
C13 C14 C9 C10 0.0(5) . . . . ?
C13 C12 C11 C10 1.4(6) . . . . ?
C9 P1 C15 C20 90.1(3) . . . . ?
C9 P1 C15 C16 -84.9(3) . . . . ?
C9 P1 C3 C8 23.3(3) . . . . ?
C9 P1 C3 C4 -159.7(3) . . . . ?
C9 P1 C2 C1 177.5(3) . . . . ?
C9 C14 C13 C12 -0.9(6) . . . . ?
C9 C10 C11 C12 -2.2(6) . . . . ?
C4 C3 C8 C7 0.0(6) . . . . ?
C18 C17 C16 C15 0.0(6) . . . . ?
C5 C6 C7 C8 0.6(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 
# 
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# Please retain this information to preserve the provenance of 
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data_cubr112
_database_code_depnum_ccdc_archive 'CCDC 2195573'
loop_
_audit_author_name
_audit_author_address
'Yue Guo'
;Yangzhou Universuty
China
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_audit_creation_date             2022-08-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br2 Cu, C20 H20 P'
_chemical_formula_sum            'C20 H20 Br2 Cu P'
_chemical_formula_weight         514.69
_chemical_absolute_configuration ?
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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                   9.7557(4)
_cell_length_b                   12.2416(5)
_cell_length_c                   9.7625(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.6090(10)
_cell_angle_gamma                90
_cell_volume                     1023.54(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.048
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16823
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.686
_diffrn_reflns_theta_min         2.376
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3667
_reflns_number_total             5718
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5718
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.0138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0865
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C2(H2), C13(H13), C15(H15), C10(H10), C3(H3), C16(H16),
 C17(H17), C1(H1), C5(H5), C4(H4), C9(H9), C8(H8), C14(H14)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
Br1 Br 0.70294(7) 0.39930(6) 0.91634(7) 0.0714(2) Uani 1 1 d . . . . .
Cu1 Cu 0.90442(9) 0.45259(6) 0.88697(8) 0.0633(2) Uani 1 1 d . . . . .
Br2 Br 1.11406(8) 0.49456(6) 0.86609(8) 0.0823(2) Uani 1 1 d . . . . .
P1 P 0.33115(14) 0.57015(9) 0.41986(13) 0.0362(3) Uani 1 1 d . . . . .
C12 C 0.2438(5) 0.4447(4) 0.4335(5) 0.0386(10) Uani 1 1 d . . . . .
C18 C 0.4083(6) 0.6410(4) 0.6023(5) 0.0400(11) Uani 1 1 d . . . . .
C11 C 0.1281(6) 0.3966(5) 0.2978(6) 0.0500(12) Uani 1 1 d . . . . .
H11 H 0.0920 0.4327 0.2030 0.060 Uiso 1 1 calc R U . . .
C7 C 0.2943(6) 0.3913(4) 0.5740(6) 0.0487(12) Uani 1 1 d . . . . .
H7 H 0.3699 0.4226 0.6661 0.058 Uiso 1 1 calc R U . . .
C2 C 0.7311(6) 0.4500(5) 0.4524(7) 0.0568(14) Uani 1 1 d . . . . .
H2 H 0.8163 0.4104 0.5251 0.068 Uiso 1 1 calc R U . . .
C13 C 0.3233(6) 0.6444(4) 0.6839(6) 0.0484(12) Uani 1 1 d . . . . .
H13 H 0.2288 0.6073 0.6453 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5179(7) 0.7571(5) 0.8781(6) 0.0600(15) Uani 1 1 d . . . . .
H15 H 0.5551 0.7961 0.9709 0.072 Uiso 1 1 calc R U . . .
C10 C 0.0668(7) 0.2966(5) 0.3023(8) 0.0589(14) Uani 1 1 d . . . . .
H10 H -0.0090 0.2644 0.2111 0.071 Uiso 1 1 calc R U . . .
C3 C 0.7218(7) 0.4789(5) 0.3110(7) 0.0560(14) Uani 1 1 d . . . . .
H3 H 0.8007 0.4585 0.2885 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4869(6) 0.5394(4) 0.3771(5) 0.0379(10) Uani 1 1 d . . . . .
C16 C 0.6023(7) 0.7544(5) 0.7988(7) 0.0590(15) Uani 1 1 d . . . . .
H16 H 0.6969 0.7913 0.8384 0.071 Uiso 1 1 calc R U . . .
C17 C 0.5473(6) 0.6969(4) 0.6602(6) 0.0492(13) Uani 1 1 d . . . . .
H17 H 0.6042 0.6961 0.6063 0.059 Uiso 1 1 calc R U . . .
C1 C 0.6145(6) 0.4801(4) 0.4851(5) 0.0489(12) Uani 1 1 d . . . . .
H1 H 0.6207 0.4607 0.5800 0.059 Uiso 1 1 calc R U . . .
C5 C 0.4779(6) 0.5683(4) 0.2362(6) 0.0487(12) Uani 1 1 d . . . . .
H5 H 0.3930 0.6081 0.1632 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5971(7) 0.5373(5) 0.2048(6) 0.0555(14) Uani 1 1 d . . . . .
H4 H 0.5916 0.5566 0.1102 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1185(7) 0.2452(5) 0.4424(8) 0.0610(15) Uani 1 1 d . . . . .
H9 H 0.0760 0.1780 0.4464 0.073 Uiso 1 1 calc R U . . .
C8 C 0.2308(7) 0.2904(5) 0.5757(7) 0.0603(15) Uani 1 1 d . . . . .
H8 H 0.2656 0.2533 0.6697 0.072 Uiso 1 1 calc R U . . .
C19 C 0.1880(6) 0.6527(4) 0.2651(6) 0.0514(13) Uani 1 1 d . . . . .
H19A H 0.2363 0.7210 0.2612 0.062 Uiso 1 1 calc R U . . .
H19B H 0.1555 0.6153 0.1667 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3778(7) 0.7018(5) 0.8197(7) 0.0569(14) Uani 1 1 d . . . . .
H14 H 0.3204 0.7038 0.8730 0.068 Uiso 1 1 calc R U . . .
C20 C 0.0447(7) 0.6776(5) 0.2820(9) 0.0696(18) Uani 1 1 d . . . . .
H20A H -0.0240 0.7246 0.1984 0.104 Uiso 1 1 calc R U . . .
H20B H 0.0757 0.7133 0.3800 0.104 Uiso 1 1 calc R U . . .
H20C H -0.0085 0.6108 0.2781 0.104 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
Br1 Cu1 2.2161(10) . ?
Cu1 Br2 2.2108(9) . ?
P1 C12 1.792(5) . ?
P1 C18 1.790(5) . ?
P1 C6 1.798(5) . ?
P1 C19 1.798(5) . ?
C12 C11 1.394(7) . ?
C12 C7 1.380(6) . ?
C18 C13 1.399(7) . ?
C18 C17 1.376(7) . ?
C11 H11 0.9300 . ?
C11 C10 1.372(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(8) . ?
C2 C1 1.371(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(8) . ?
C15 C14 1.380(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.364(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.363(8) . ?
C6 C1 1.390(7) . ?
C6 C5 1.381(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(7) . ?
C17 H17 0.9300 . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.390(7) . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.355(8) . ?
C8 H8 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.515(8) . ?
C14 H14 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
Br2 Cu1 Br1 175.82(5) . . ?
C12 P1 C6 108.8(2) . . ?
C12 P1 C19 109.8(2) . . ?
C18 P1 C12 109.2(2) . . ?
C18 P1 C6 109.5(2) . . ?
C18 P1 C19 110.6(2) . . ?
C6 P1 C19 109.0(2) . . ?
C11 C12 P1 119.3(4) . . ?
C7 C12 P1 121.6(4) . . ?
C7 C12 C11 119.1(4) . . ?
C13 C18 P1 120.0(4) . . ?
C17 C18 P1 120.8(4) . . ?
C17 C18 C13 119.2(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.9(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C7 H7 120.5 . . ?
C12 C7 C8 119.0(5) . . ?
C8 C7 H7 120.5 . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(5) . . ?
C18 C13 H13 119.8 . . ?
C14 C13 C18 120.5(5) . . ?
C14 C13 H13 119.8 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C11 C10 H10 120.4 . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 H10 120.4 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C1 C6 P1 118.9(3) . . ?
C5 C6 P1 121.3(4) . . ?
C5 C6 C1 119.7(4) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(6) . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.9(5) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C2 C1 C6 120.4(4) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C5 H5 120.4 . . ?
C6 C5 C4 119.2(5) . . ?
C4 C5 H5 120.4 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 121.0(5) . . ?
C8 C9 H9 119.5 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.9(5) . . ?
C9 C8 H8 119.6 . . ?
P1 C19 H19A 108.7 . . ?
P1 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 P1 114.1(4) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
P1 C12 C11 C10 175.2(4) . . . . ?
P1 C12 C7 C8 -175.1(4) . . . . ?
P1 C18 C13 C14 -177.3(4) . . . . ?
P1 C18 C17 C16 177.7(4) . . . . ?
P1 C6 C1 C2 176.4(4) . . . . ?
P1 C6 C5 C4 -176.3(4) . . . . ?
C12 P1 C18 C13 -41.4(5) . . . . ?
C12 P1 C18 C17 141.8(4) . . . . ?
C12 P1 C6 C1 -63.1(4) . . . . ?
C12 P1 C6 C5 113.3(4) . . . . ?
C12 P1 C19 C20 56.9(5) . . . . ?
C12 C11 C10 C9 1.2(8) . . . . ?
C12 C7 C8 C9 -1.2(8) . . . . ?
C18 P1 C12 C11 155.9(4) . . . . ?
C18 P1 C12 C7 -27.7(5) . . . . ?
C18 P1 C6 C1 56.2(4) . . . . ?
C18 P1 C6 C5 -127.4(4) . . . . ?
C18 P1 C19 C20 -63.7(5) . . . . ?
C18 C13 C14 C15 -0.1(9) . . . . ?
C11 C12 C7 C8 1.3(7) . . . . ?
C11 C10 C9 C8 -1.1(9) . . . . ?
C7 C12 C11 C10 -1.3(8) . . . . ?
C2 C3 C4 C5 -0.2(9) . . . . ?
C13 C18 C17 C16 0.9(8) . . . . ?
C15 C16 C17 C18 -0.8(9) . . . . ?
C10 C9 C8 C7 1.2(9) . . . . ?
C3 C2 C1 C6 0.0(8) . . . . ?
C6 P1 C12 C11 -84.7(4) . . . . ?
C6 P1 C12 C7 91.7(4) . . . . ?
C6 P1 C18 C13 -160.4(4) . . . . ?
C6 P1 C18 C17 22.8(5) . . . . ?
C6 P1 C19 C20 175.9(4) . . . . ?
C6 C5 C4 C3 0.0(8) . . . . ?
C16 C15 C14 C13 0.2(9) . . . . ?
C17 C18 C13 C14 -0.4(8) . . . . ?
C1 C2 C3 C4 0.1(9) . . . . ?
C1 C6 C5 C4 0.1(8) . . . . ?
C5 C6 C1 C2 -0.1(8) . . . . ?
C19 P1 C12 C11 34.5(5) . . . . ?
C19 P1 C12 C7 -149.1(4) . . . . ?
C19 P1 C18 C13 79.5(4) . . . . ?
C19 P1 C18 C17 -97.3(5) . . . . ?
C19 P1 C6 C1 177.2(4) . . . . ?
C19 P1 C6 C5 -6.3(5) . . . . ?
C14 C15 C16 C17 0.3(9) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
