# Supplementary Information (SI) for Chemical Science.
# 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_p(co)p
_database_code_depnum_ccdc_archive 'CCDC 2367862'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2024-07-03
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H30 N2 O P2'
_chemical_formula_sum            'C15 H30 N2 O P2'
_chemical_formula_weight         316.35
_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 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7343(6)
_cell_length_b                   11.6579(5)
_cell_length_c                   14.1462(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.366(2)
_cell_angle_gamma                90
_cell_volume                     1927.85(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.05
_cell_measurement_theta_min      5.10
_shelx_estimated_absorpt_T_max   0.823
_shelx_estimated_absorpt_T_min   0.687
_exptl_absorpt_coefficient_mu    2.029
_exptl_absorpt_correction_T_max  0.6617
_exptl_absorpt_correction_T_min  0.5063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1536 before and 0.0799 after correction.
The Ratio of minimum to maximum transmission is 0.7652.
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    1.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38129
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         3.781
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker Platinum135 CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Rigaku MicroMax-007HF'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3121
_reflns_number_total             3469
_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 v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 v2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT v8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.049
_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)+(0.0366P)²+0.6323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0778
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_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
P1 P 0.61501(3) 0.54374(3) 0.64542(3) 0.02203(10) Uani 1 1 d . . . . .
P2 P 0.76127(3) 0.35660(3) 0.62162(3) 0.02401(11) Uani 1 1 d . . . . .
O1 O 0.80697(8) 0.46400(8) 0.80773(7) 0.0268(2) Uani 1 1 d . . . . .
N1 N 0.56167(10) 0.72113(10) 0.74737(9) 0.0259(3) Uani 1 1 d . . . . .
N2 N 0.91764(10) 0.18028(9) 0.69436(9) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.74387(11) 0.45714(10) 0.71553(10) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.62988(12) 0.63606(11) 0.74657(11) 0.0230(3) Uani 1 1 d . . . . .
H2 H 0.6960(14) 0.6253(13) 0.8112(13) 0.028 Uiso 1 1 d . U . . .
C3 C 0.86680(11) 0.27231(11) 0.71105(11) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.8906(13) 0.2949(13) 0.7814(12) 0.027 Uiso 1 1 d . U . . .
C4 C 0.44960(14) 0.86928(13) 0.62161(12) 0.0360(4) Uani 1 1 d . . . . .
H4A H 0.438475 0.919094 0.672679 0.054 Uiso 1 1 calc R U . . .
H4B H 0.385494 0.879031 0.554814 0.054 Uiso 1 1 calc R U . . .
H4C H 0.521181 0.889846 0.615340 0.054 Uiso 1 1 calc R U . . .
C5 C 0.45528(12) 0.74477(12) 0.65580(11) 0.0278(3) Uani 1 1 d . . . . .
H5 H 0.457038 0.695982 0.598304 0.033 Uiso 1 1 calc R U . . .
C6 C 0.35152(13) 0.70799(14) 0.67656(12) 0.0352(3) Uani 1 1 d . . . . .
H6A H 0.358636 0.626707 0.695744 0.053 Uiso 1 1 calc R U . . .
H6B H 0.281857 0.719580 0.614346 0.053 Uiso 1 1 calc R U . . .
H6C H 0.347358 0.754051 0.732922 0.053 Uiso 1 1 calc R U . . .
C7 C 0.69399(16) 0.86026(14) 0.86919(14) 0.0434(4) Uani 1 1 d . . . . .
H7A H 0.760191 0.808764 0.890438 0.065 Uiso 1 1 calc R U . . .
H7B H 0.702290 0.913087 0.925599 0.065 Uiso 1 1 calc R U . . .
H7C H 0.689487 0.904196 0.808635 0.065 Uiso 1 1 calc R U . . .
C8 C 0.58529(13) 0.78996(13) 0.84261(11) 0.0323(3) Uani 1 1 d . . . . .
H8 H 0.520493 0.845093 0.827546 0.039 Uiso 1 1 calc R U . . .
C9 C 0.58874(16) 0.71435(14) 0.93151(12) 0.0420(4) Uani 1 1 d . . . . .
H9A H 0.516605 0.672041 0.911247 0.063 Uiso 1 1 calc R U . . .
H9B H 0.599477 0.762359 0.991511 0.063 Uiso 1 1 calc R U . . .
H9C H 0.652355 0.659971 0.948998 0.063 Uiso 1 1 calc R U . . .
C10 C 0.98575(14) 0.16802(15) 0.55385(12) 0.0373(4) Uani 1 1 d . . . . .
H10A H 1.002185 0.250400 0.562161 0.056 Uiso 1 1 calc R U . . .
H10B H 0.962790 0.146844 0.481349 0.056 Uiso 1 1 calc R U . . .
H10C H 1.054397 0.124875 0.596150 0.056 Uiso 1 1 calc R U . . .
C11 C 0.88967(13) 0.14011(12) 0.58768(11) 0.0275(3) Uani 1 1 d . . . . .
H11 H 0.820844 0.183977 0.541773 0.033 Uiso 1 1 calc R U . . .
C12 C 0.85769(15) 0.01378(13) 0.57509(13) 0.0387(4) Uani 1 1 d . . . . .
H12A H 0.924926 -0.032465 0.615202 0.058 Uiso 1 1 calc R U . . .
H12B H 0.830547 -0.007356 0.502216 0.058 Uiso 1 1 calc R U . . .
H12C H 0.796963 -0.000303 0.599743 0.058 Uiso 1 1 calc R U . . .
C13 C 1.10514(14) 0.19890(15) 0.84220(13) 0.0405(4) Uani 1 1 d . . . . .
H13A H 1.131275 0.240461 0.795317 0.061 Uiso 1 1 calc R U . . .
H13B H 1.168661 0.154159 0.891037 0.061 Uiso 1 1 calc R U . . .
H13C H 1.078103 0.253814 0.879997 0.061 Uiso 1 1 calc R U . . .
C14 C 1.00817(13) 0.11877(12) 0.78062(11) 0.0294(3) Uani 1 1 d . . . . .
H14 H 1.040681 0.058560 0.749648 0.035 Uiso 1 1 calc R U . . .
C15 C 0.95721(16) 0.05785(15) 0.84797(13) 0.0429(4) Uani 1 1 d . . . . .
H15A H 0.924479 0.114694 0.879553 0.064 Uiso 1 1 calc R U . . .
H15B H 1.017310 0.014632 0.902053 0.064 Uiso 1 1 calc R U . . .
H15C H 0.897096 0.005038 0.805591 0.064 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
P1 C1 1.8451(13) . ?
P1 C2 1.7398(14) . ?
P2 C1 1.8497(13) . ?
P2 C3 1.7388(14) . ?
O1 C1 1.2336(16) . ?
N1 C2 1.3214(17) . ?
N1 C5 1.4824(18) . ?
N1 C8 1.4926(17) . ?
N2 C3 1.3219(17) . ?
N2 C11 1.4823(17) . ?
N2 C14 1.4887(17) . ?
C2 H2 0.974(17) . ?
C3 H3 0.955(16) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C5 1.523(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.524(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C8 1.522(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.522(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C11 1.515(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.519(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C14 1.518(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.524(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C2 P1 C1 96.48(6) . . ?
C3 P2 C1 96.52(6) . . ?
C2 N1 C5 120.54(11) . . ?
C2 N1 C8 120.89(12) . . ?
C5 N1 C8 118.42(11) . . ?
C3 N2 C11 120.09(11) . . ?
C3 N2 C14 121.29(11) . . ?
C11 N2 C14 118.53(10) . . ?
P1 C1 P2 107.15(7) . . ?
O1 C1 P1 126.89(10) . . ?
O1 C1 P2 125.95(10) . . ?
P1 C2 H2 117.6(9) . . ?
N1 C2 P1 127.87(11) . . ?
N1 C2 H2 114.5(9) . . ?
P2 C3 H3 115.9(9) . . ?
N2 C3 P2 128.36(11) . . ?
N2 C3 H3 115.7(9) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
N1 C5 C4 111.50(12) . . ?
N1 C5 H5 107.3 . . ?
N1 C5 C6 109.94(12) . . ?
C4 C5 H5 107.3 . . ?
C4 C5 C6 113.19(12) . . ?
C6 C5 H5 107.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
N1 C8 C7 110.51(12) . . ?
N1 C8 H8 107.4 . . ?
N1 C8 C9 111.34(12) . . ?
C7 C8 H8 107.4 . . ?
C7 C8 C9 112.48(14) . . ?
C9 C8 H8 107.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
N2 C11 C10 110.83(12) . . ?
N2 C11 H11 107.1 . . ?
N2 C11 C12 111.75(12) . . ?
C10 C11 H11 107.1 . . ?
C10 C11 C12 112.55(13) . . ?
C12 C11 H11 107.1 . . ?
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 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
N2 C14 C13 111.30(12) . . ?
N2 C14 H14 107.4 . . ?
N2 C14 C15 110.71(12) . . ?
C13 C14 H14 107.4 . . ?
C13 C14 C15 112.29(13) . . ?
C15 C14 H14 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C1 P1 C2 N1 -179.03(13) . . . . ?
C1 P2 C3 N2 178.57(13) . . . . ?
C2 P1 C1 P2 -174.16(7) . . . . ?
C2 P1 C1 O1 6.05(13) . . . . ?
C2 N1 C5 C4 -126.37(14) . . . . ?
C2 N1 C5 C6 107.25(14) . . . . ?
C2 N1 C8 C7 67.31(17) . . . . ?
C2 N1 C8 C9 -58.46(18) . . . . ?
C3 P2 C1 P1 -169.26(7) . . . . ?
C3 P2 C1 O1 10.53(13) . . . . ?
C3 N2 C11 C10 105.63(15) . . . . ?
C3 N2 C11 C12 -127.95(14) . . . . ?
C3 N2 C14 C13 -55.92(18) . . . . ?
C3 N2 C14 C15 69.71(17) . . . . ?
C5 N1 C2 P1 2.5(2) . . . . ?
C5 N1 C8 C7 -117.12(14) . . . . ?
C5 N1 C8 C9 117.11(14) . . . . ?
C8 N1 C2 P1 177.96(11) . . . . ?
C8 N1 C5 C4 58.05(17) . . . . ?
C8 N1 C5 C6 -68.33(16) . . . . ?
C11 N2 C3 P2 2.66(19) . . . . ?
C11 N2 C14 C13 120.68(14) . . . . ?
C11 N2 C14 C15 -113.69(14) . . . . ?
C14 N2 C3 P2 179.21(11) . . . . ?
C14 N2 C11 C10 -71.01(16) . . . . ?
C14 N2 C11 C12 55.40(17) . . . . ?

_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_bis(phospholine)
_database_code_depnum_ccdc_archive 'CCDC 2367864'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2024-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H20 P2'
_chemical_formula_sum            'C12 H20 P2'
_chemical_formula_weight         226.22
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1758(3)
_cell_length_b                   5.3182(3)
_cell_length_c                   11.4365(6)
_cell_angle_alpha                88.010(2)
_cell_angle_beta                 83.733(2)
_cell_angle_gamma                80.367(2)
_cell_volume                     308.46(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      3.59
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1538 before and 0.1019 after correction.
 
For component 2:
 wR2(int) was 0.1526 before and 0.1069 after correction.
 The Ratio of minimum to maximum transmission is 0.35.

Final HKLF 4 output contains 14712 reflections, Rint = 0.0795
 (12262 with I > 3sig(I), Rint = 0.0779)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             122
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2333
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.636
_diffrn_reflns_theta_min         3.585
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker Photon III Area Detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1110
_reflns_number_total             1167
_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 v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 v2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT v8.40B (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         1167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.142
_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)+(0.0588P)²+0.2721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1272
_refine_special_details          Twin
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_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
P1 P 0.60956(11) 0.61660(11) 0.54864(5) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.3206(5) 0.7823(5) 0.6453(2) 0.0266(5) Uani 1 1 d . . . . .
H1A H 0.345780 0.957957 0.661193 0.032 Uiso 1 1 calc R U . . .
H1B H 0.157120 0.791929 0.606579 0.032 Uiso 1 1 calc R U . . .
C2 C 0.3016(4) 0.6303(4) 0.7578(2) 0.0236(5) Uani 1 1 d . . . . .
C3 C 0.4909(4) 0.4276(4) 0.7688(2) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.7012(4) 0.3764(5) 0.6661(2) 0.0252(5) Uani 1 1 d . . . . .
H4A H 0.710285 0.201675 0.636997 0.030 Uiso 1 1 calc R U . . .
H4B H 0.875479 0.392880 0.690246 0.030 Uiso 1 1 calc R U . . .
C5 C 0.0756(5) 0.7247(5) 0.8478(2) 0.0302(6) Uani 1 1 d . . . . .
H5A H -0.091098 0.721324 0.815097 0.045 Uiso 1 1 calc R U . . .
H5B H 0.085086 0.899863 0.868695 0.045 Uiso 1 1 calc R U . . .
H5C H 0.085330 0.614649 0.918191 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5163(5) 0.2532(5) 0.8744(2) 0.0304(6) Uani 1 1 d . . . . .
H6A H 0.682730 0.261408 0.906363 0.046 Uiso 1 1 calc R U . . .
H6B H 0.513808 0.077921 0.851331 0.046 Uiso 1 1 calc R U . . .
H6C H 0.368837 0.306363 0.934404 0.046 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
P1 P1 2.2146(11) 2_666 ?
P1 C1 1.871(2) . ?
P1 C4 1.865(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.498(4) . ?
C2 C3 1.343(3) . ?
C2 C5 1.502(3) . ?
C3 C4 1.511(3) . ?
C3 C6 1.500(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C1 P1 P1 97.21(8) . 2_666 ?
C4 P1 P1 97.47(8) . 2_666 ?
C4 P1 C1 92.15(10) . . ?
P1 C1 H1A 110.3 . . ?
P1 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
C2 C1 P1 107.23(15) . . ?
C2 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
C1 C2 C5 116.4(2) . . ?
C3 C2 C1 116.8(2) . . ?
C3 C2 C5 126.8(2) . . ?
C2 C3 C4 116.4(2) . . ?
C2 C3 C6 126.1(2) . . ?
C6 C3 C4 117.47(19) . . ?
P1 C4 H4A 110.3 . . ?
P1 C4 H4B 110.3 . . ?
C3 C4 P1 107.15(15) . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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 P1 C1 C2 93.51(16) 2_666 . . . ?
P1 P1 C4 C3 -93.30(15) 2_666 . . . ?
P1 C1 C2 C3 3.4(3) . . . . ?
P1 C1 C2 C5 -178.01(17) . . . . ?
C1 P1 C4 C3 4.27(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C6 178.2(2) . . . . ?
C2 C3 C4 P1 -3.3(3) . . . . ?
C4 P1 C1 C2 -4.30(17) . . . . ?
C5 C2 C3 C4 -178.5(2) . . . . ?
C5 C2 C3 C6 -0.3(4) . . . . ?
C6 C3 C4 P1 178.35(17) . . . . ?

_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_dimer_aminocarbene_caac
_database_code_depnum_ccdc_archive 'CCDC 2367865'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2024-07-03
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H50 N2'
_chemical_formula_sum            'C30 H50 N2'
_chemical_formula_weight         438.72
_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 0.0181 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'
N N 0.0311 0.0180 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.5119(4)
_cell_length_b                   15.7592(6)
_cell_length_c                   16.7454(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.3031(10)
_cell_angle_gamma                90
_cell_volume                     2729.30(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.55
_cell_measurement_theta_min      3.88
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.6617
_exptl_absorpt_correction_T_min  0.5979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0858 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.9036.
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    1.068
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34037
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         3.881
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker Platinum135 CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Rigaku MicroMax-007HF'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4729
_reflns_number_total             4985
_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 v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 v2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT v8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4985
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.024
_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)+(0.0505P)²+0.9547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0988
_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 Ternary CH refined with riding coordinates:
 C18(H18), C21(H21), C25(H25), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C24(H24)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_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 0.57107(8) 0.74580(5) 0.28127(5) 0.01450(18) Uani 1 1 d . . . . .
N2 N 0.32065(8) 0.77389(5) 0.34921(5) 0.01753(19) Uani 1 1 d . . . . .
C1 C 0.51400(9) 0.69111(6) 0.33057(6) 0.0143(2) Uani 1 1 d . . . . .
C2 C 0.58606(9) 0.60561(6) 0.33865(6) 0.0150(2) Uani 1 1 d . . . . .
C3 C 0.69916(9) 0.62203(6) 0.29309(6) 0.0162(2) Uani 1 1 d . . . . .
H3A H 0.779345 0.634835 0.332046 0.019 Uiso 1 1 calc R U . . .
H3B H 0.714556 0.571507 0.260990 0.019 Uiso 1 1 calc R U . . .
C4 C 0.65972(9) 0.69839(6) 0.23679(6) 0.0160(2) Uani 1 1 d . . . . .
C5 C 0.77576(10) 0.75180(7) 0.22478(7) 0.0212(2) Uani 1 1 d . . . . .
H5A H 0.745558 0.803613 0.194944 0.032 Uiso 1 1 calc R U . . .
H5B H 0.829828 0.719182 0.193875 0.032 Uiso 1 1 calc R U . . .
H5C H 0.826480 0.766939 0.277815 0.032 Uiso 1 1 calc R U . . .
C6 C 0.58768(11) 0.66876(7) 0.15319(6) 0.0209(2) Uani 1 1 d . . . . .
H6A H 0.504866 0.643239 0.159132 0.031 Uiso 1 1 calc R U . . .
H6B H 0.640292 0.626657 0.130820 0.031 Uiso 1 1 calc R U . . .
H6C H 0.572042 0.717512 0.116414 0.031 Uiso 1 1 calc R U . . .
C7 C 0.49660(10) 0.53277(6) 0.30016(6) 0.0186(2) Uani 1 1 d . . . . .
H7A H 0.418749 0.531155 0.325782 0.022 Uiso 1 1 calc R U . . .
H7B H 0.468007 0.544649 0.241642 0.022 Uiso 1 1 calc R U . . .
C8 C 0.56291(11) 0.44574(7) 0.30989(7) 0.0220(2) Uani 1 1 d . . . . .
H8A H 0.500230 0.401335 0.287026 0.026 Uiso 1 1 calc R U . . .
H8B H 0.635160 0.444925 0.279236 0.026 Uiso 1 1 calc R U . . .
C9 C 0.61470(12) 0.42627(7) 0.39915(7) 0.0262(3) Uani 1 1 d . . . . .
H9A H 0.541482 0.420463 0.428623 0.031 Uiso 1 1 calc R U . . .
H9B H 0.662238 0.371756 0.403526 0.031 Uiso 1 1 calc R U . . .
C10 C 0.70465(11) 0.49669(7) 0.43786(7) 0.0250(2) Uani 1 1 d . . . . .
H10A H 0.782036 0.498833 0.411804 0.030 Uiso 1 1 calc R U . . .
H10B H 0.733625 0.484254 0.496229 0.030 Uiso 1 1 calc R U . . .
C11 C 0.63603(10) 0.58279(6) 0.42842(6) 0.0196(2) Uani 1 1 d . . . . .
H11A H 0.696788 0.627319 0.453421 0.023 Uiso 1 1 calc R U . . .
H11B H 0.562265 0.581579 0.457800 0.023 Uiso 1 1 calc R U . . .
C12 C 0.57546(9) 0.83636(6) 0.29253(6) 0.0149(2) Uani 1 1 d . . . . .
C13 C 0.65596(9) 0.87170(6) 0.36126(6) 0.0170(2) Uani 1 1 d . . . . .
C14 C 0.65407(10) 0.95960(7) 0.37291(6) 0.0203(2) Uani 1 1 d . . . . .
H14 H 0.705704 0.983651 0.419806 0.024 Uiso 1 1 calc R U . . .
C15 C 0.57856(10) 1.01214(7) 0.31754(7) 0.0220(2) Uani 1 1 d . . . . .
H15 H 0.577848 1.071618 0.326660 0.026 Uiso 1 1 calc R U . . .
C16 C 0.50409(10) 0.97756(7) 0.24882(6) 0.0211(2) Uani 1 1 d . . . . .
H16 H 0.454507 1.014036 0.210053 0.025 Uiso 1 1 calc R U . . .
C17 C 0.50032(9) 0.89000(6) 0.23525(6) 0.0167(2) Uani 1 1 d . . . . .
C18 C 0.74600(10) 0.81928(7) 0.42384(6) 0.0211(2) Uani 1 1 d . . . . .
H18 H 0.746857 0.760023 0.402588 0.025 Uiso 1 1 calc R U . . .
C19 C 0.69950(12) 0.81549(7) 0.50561(7) 0.0273(3) Uani 1 1 d . . . . .
H19A H 0.691256 0.873243 0.525790 0.041 Uiso 1 1 calc R U . . .
H19B H 0.762239 0.783773 0.544783 0.041 Uiso 1 1 calc R U . . .
H19C H 0.615320 0.787050 0.498457 0.041 Uiso 1 1 calc R U . . .
C20 C 0.88532(11) 0.85340(8) 0.43631(7) 0.0300(3) Uani 1 1 d . . . . .
H20A H 0.912375 0.859300 0.383538 0.045 Uiso 1 1 calc R U . . .
H20B H 0.943235 0.813753 0.470265 0.045 Uiso 1 1 calc R U . . .
H20C H 0.889087 0.908875 0.463080 0.045 Uiso 1 1 calc R U . . .
C21 C 0.41427(10) 0.85654(7) 0.15912(6) 0.0183(2) Uani 1 1 d . . . . .
H21 H 0.411700 0.793262 0.162994 0.022 Uiso 1 1 calc R U . . .
C22 C 0.46958(11) 0.87986(7) 0.08286(6) 0.0231(2) Uani 1 1 d . . . . .
H22A H 0.467153 0.941595 0.075682 0.035 Uiso 1 1 calc R U . . .
H22B H 0.417619 0.852826 0.035216 0.035 Uiso 1 1 calc R U . . .
H22C H 0.559165 0.860018 0.089119 0.035 Uiso 1 1 calc R U . . .
C23 C 0.27528(10) 0.88988(7) 0.15118(7) 0.0233(2) Uani 1 1 d . . . . .
H23A H 0.242102 0.877015 0.200924 0.035 Uiso 1 1 calc R U . . .
H23B H 0.220462 0.862478 0.104860 0.035 Uiso 1 1 calc R U . . .
H23C H 0.274593 0.951420 0.142706 0.035 Uiso 1 1 calc R U . . .
C24 C 0.40913(10) 0.70412(6) 0.36444(6) 0.0172(2) Uani 1 1 d . . . . .
H24 H 0.391799 0.662834 0.402420 0.021 Uiso 1 1 calc R U . . .
C25 C 0.18613(10) 0.74395(7) 0.32155(7) 0.0225(2) Uani 1 1 d . . . . .
H25 H 0.130589 0.795550 0.309751 0.027 Uiso 1 1 calc R U . . .
C26 C 0.17804(12) 0.69560(8) 0.24165(7) 0.0310(3) Uani 1 1 d . . . . .
H26A H 0.220557 0.728585 0.204335 0.047 Uiso 1 1 calc R U . . .
H26B H 0.087105 0.686641 0.217306 0.047 Uiso 1 1 calc R U . . .
H26C H 0.221256 0.640578 0.252094 0.047 Uiso 1 1 calc R U . . .
C27 C 0.12644(12) 0.68921(8) 0.38128(8) 0.0315(3) Uani 1 1 d . . . . .
H27A H 0.177814 0.637455 0.393844 0.047 Uiso 1 1 calc R U . . .
H27B H 0.037652 0.673997 0.356737 0.047 Uiso 1 1 calc R U . . .
H27C H 0.125815 0.721276 0.431355 0.047 Uiso 1 1 calc R U . . .
C28 C 0.34203(10) 0.84121(6) 0.41220(6) 0.0207(2) Uani 1 1 d . . . . .
H28 H 0.432603 0.861483 0.413840 0.025 Uiso 1 1 calc R U . . .
C29 C 0.33520(14) 0.81360(8) 0.49932(7) 0.0324(3) Uani 1 1 d . . . . .
H29A H 0.244582 0.806250 0.504782 0.049 Uiso 1 1 calc R U . . .
H29B H 0.375250 0.857155 0.537484 0.049 Uiso 1 1 calc R U . . .
H29C H 0.381427 0.759797 0.511274 0.049 Uiso 1 1 calc R U . . .
C30 C 0.25578(12) 0.91850(7) 0.38845(8) 0.0301(3) Uani 1 1 d . . . . .
H30A H 0.260346 0.935126 0.332644 0.045 Uiso 1 1 calc R U . . .
H30B H 0.285419 0.965627 0.425290 0.045 Uiso 1 1 calc R U . . .
H30C H 0.166271 0.904314 0.392200 0.045 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 C1 1.4006(12) . ?
N1 C4 1.4932(12) . ?
N1 C12 1.4392(12) . ?
N2 C24 1.4332(13) . ?
N2 C25 1.4840(13) . ?
N2 C28 1.4845(13) . ?
C1 C2 1.5397(13) . ?
C1 C24 1.3426(14) . ?
C2 C3 1.5450(13) . ?
C2 C7 1.5494(13) . ?
C2 C11 1.5435(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5392(13) . ?
C4 C5 1.5247(14) . ?
C4 C6 1.5402(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5340(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5275(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5254(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5314(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4151(14) . ?
C12 C17 1.4097(14) . ?
C13 C14 1.3994(14) . ?
C13 C18 1.5236(14) . ?
C14 H14 0.9500 . ?
C14 C15 1.3828(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.3826(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.3980(15) . ?
C17 C21 1.5196(14) . ?
C18 H18 1.0000 . ?
C18 C19 1.5352(15) . ?
C18 C20 1.5389(16) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 1.0000 . ?
C21 C22 1.5394(14) . ?
C21 C23 1.5358(14) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24 0.9500 . ?
C25 H25 1.0000 . ?
C25 C26 1.5288(16) . ?
C25 C27 1.5371(16) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28 1.0000 . ?
C28 C29 1.5364(15) . ?
C28 C30 1.5279(15) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
C1 N1 C4 110.94(8) . . ?
C1 N1 C12 122.69(8) . . ?
C12 N1 C4 123.60(8) . . ?
C24 N2 C25 111.31(8) . . ?
C24 N2 C28 114.26(8) . . ?
C25 N2 C28 117.62(8) . . ?
N1 C1 C2 109.54(8) . . ?
C24 C1 N1 128.73(9) . . ?
C24 C1 C2 121.65(9) . . ?
C1 C2 C3 102.71(7) . . ?
C1 C2 C7 111.05(8) . . ?
C1 C2 C11 111.47(8) . . ?
C3 C2 C7 112.46(8) . . ?
C11 C2 C3 111.23(8) . . ?
C11 C2 C7 107.94(8) . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 C2 106.66(8) . . ?
C4 C3 H3A 110.4 . . ?
C4 C3 H3B 110.4 . . ?
N1 C4 C3 102.09(7) . . ?
N1 C4 C5 112.02(8) . . ?
N1 C4 C6 110.85(8) . . ?
C3 C4 C6 110.76(8) . . ?
C5 C4 C3 112.22(8) . . ?
C5 C4 C6 108.81(8) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.0 . . ?
C2 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C2 112.82(8) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.05(9) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 C8 110.79(9) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 C11 110.85(9) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C2 C11 H11A 109.2 . . ?
C2 C11 H11B 109.2 . . ?
C10 C11 C2 112.27(8) . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 N1 119.83(9) . . ?
C17 C12 N1 120.30(9) . . ?
C17 C12 C13 119.88(9) . . ?
C12 C13 C18 123.61(9) . . ?
C14 C13 C12 118.79(9) . . ?
C14 C13 C18 117.61(9) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.33(10) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.59(10) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.31(10) . . ?
C17 C16 H16 119.3 . . ?
C12 C17 C21 122.67(9) . . ?
C16 C17 C12 119.02(9) . . ?
C16 C17 C21 118.30(9) . . ?
C13 C18 H18 107.8 . . ?
C13 C18 C19 112.13(9) . . ?
C13 C18 C20 111.28(9) . . ?
C19 C18 H18 107.8 . . ?
C19 C18 C20 109.85(9) . . ?
C20 C18 H18 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21 108.1 . . ?
C17 C21 C22 110.90(8) . . ?
C17 C21 C23 111.61(8) . . ?
C22 C21 H21 108.1 . . ?
C23 C21 H21 108.1 . . ?
C23 C21 C22 109.95(8) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24 116.6 . . ?
C1 C24 N2 126.71(9) . . ?
C1 C24 H24 116.6 . . ?
N2 C25 H25 107.0 . . ?
N2 C25 C26 109.41(9) . . ?
N2 C25 C27 116.90(9) . . ?
C26 C25 H25 107.0 . . ?
C26 C25 C27 108.94(9) . . ?
C27 C25 H25 107.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 H28 105.7 . . ?
N2 C28 C29 116.45(9) . . ?
N2 C28 C30 112.18(9) . . ?
C29 C28 H28 105.7 . . ?
C30 C28 H28 105.7 . . ?
C30 C28 C29 110.28(9) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
N1 C1 C2 C3 4.63(10) . . . . ?
N1 C1 C2 C7 -115.79(9) . . . . ?
N1 C1 C2 C11 123.81(9) . . . . ?
N1 C1 C24 N2 8.72(17) . . . . ?
N1 C12 C13 C14 -177.04(9) . . . . ?
N1 C12 C13 C18 3.24(14) . . . . ?
N1 C12 C17 C16 178.42(9) . . . . ?
N1 C12 C17 C21 -1.24(14) . . . . ?
C1 N1 C4 C3 -26.09(10) . . . . ?
C1 N1 C4 C5 -146.34(8) . . . . ?
C1 N1 C4 C6 91.91(9) . . . . ?
C1 N1 C12 C13 70.07(12) . . . . ?
C1 N1 C12 C17 -110.17(11) . . . . ?
C1 C2 C3 C4 -20.49(9) . . . . ?
C1 C2 C7 C8 -177.68(8) . . . . ?
C1 C2 C11 C10 178.36(8) . . . . ?
C2 C1 C24 N2 -167.66(9) . . . . ?
C2 C3 C4 N1 28.07(9) . . . . ?
C2 C3 C4 C5 148.19(8) . . . . ?
C2 C3 C4 C6 -89.99(9) . . . . ?
C2 C7 C8 C9 55.99(11) . . . . ?
C3 C2 C7 C8 67.86(11) . . . . ?
C3 C2 C11 C10 -67.67(11) . . . . ?
C4 N1 C1 C2 13.83(10) . . . . ?
C4 N1 C1 C24 -162.90(10) . . . . ?
C4 N1 C12 C13 -89.34(11) . . . . ?
C4 N1 C12 C17 90.42(11) . . . . ?
C7 C2 C3 C4 98.96(9) . . . . ?
C7 C2 C11 C10 56.14(11) . . . . ?
C7 C8 C9 C10 -55.23(12) . . . . ?
C8 C9 C10 C11 56.35(12) . . . . ?
C9 C10 C11 C2 -58.16(12) . . . . ?
C11 C2 C3 C4 -139.83(8) . . . . ?
C11 C2 C7 C8 -55.21(11) . . . . ?
C12 N1 C1 C2 -147.89(9) . . . . ?
C12 N1 C1 C24 35.39(15) . . . . ?
C12 N1 C4 C3 135.44(9) . . . . ?
C12 N1 C4 C5 15.18(13) . . . . ?
C12 N1 C4 C6 -106.56(10) . . . . ?
C12 C13 C14 C15 -2.02(15) . . . . ?
C12 C13 C18 C19 -109.86(11) . . . . ?
C12 C13 C18 C20 126.64(10) . . . . ?
C12 C17 C21 C22 -109.79(11) . . . . ?
C12 C17 C21 C23 127.26(10) . . . . ?
C13 C12 C17 C16 -1.81(14) . . . . ?
C13 C12 C17 C21 178.52(9) . . . . ?
C13 C14 C15 C16 -0.57(16) . . . . ?
C14 C13 C18 C19 70.42(12) . . . . ?
C14 C13 C18 C20 -53.08(13) . . . . ?
C14 C15 C16 C17 2.02(16) . . . . ?
C15 C16 C17 C12 -0.82(15) . . . . ?
C15 C16 C17 C21 178.86(9) . . . . ?
C16 C17 C21 C22 70.54(12) . . . . ?
C16 C17 C21 C23 -52.41(12) . . . . ?
C17 C12 C13 C14 3.19(14) . . . . ?
C17 C12 C13 C18 -176.52(9) . . . . ?
C18 C13 C14 C15 177.71(10) . . . . ?
C24 N2 C25 C26 -61.84(11) . . . . ?
C24 N2 C25 C27 62.53(12) . . . . ?
C24 N2 C28 C29 -58.20(12) . . . . ?
C24 N2 C28 C30 173.43(9) . . . . ?
C24 C1 C2 C3 -178.37(9) . . . . ?
C24 C1 C2 C7 61.21(12) . . . . ?
C24 C1 C2 C11 -59.19(12) . . . . ?
C25 N2 C24 C1 123.37(11) . . . . ?
C25 N2 C28 C29 75.11(12) . . . . ?
C25 N2 C28 C30 -53.27(12) . . . . ?
C28 N2 C24 C1 -100.43(12) . . . . ?
C28 N2 C25 C26 163.57(9) . . . . ?
C28 N2 C25 C27 -72.06(12) . . . . ?

_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_bis(carbene)p2
_database_code_depnum_ccdc_archive 'CCDC 2367863'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2024-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H30 N2 P2'
_chemical_formula_sum            'C14 H30 N2 P2'
_chemical_formula_weight         288.34
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.7119(16)
_cell_length_b                   11.7054(15)
_cell_length_c                   14.533(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.731(4)
_cell_angle_gamma                90
_cell_volume                     1824.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.5547
_exptl_absorpt_correction_T_min  0.5293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1348 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.9542.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            79435
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.560
_diffrn_reflns_theta_min         2.576
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon III Area Detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2679
_reflns_number_total             3363
_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 v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 v2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT v8.40B (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.078
_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)+(0.0463P)²+1.1604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1220
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Same fragment restrains
{P1, P2, N1, N2, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14}
sigma for 1-2: 0.02, 1-3: 0.04
as in
{P1', P2', N1', N2', C1', C2', C3', C4', C5', C6', C7', C8', C9', C10', C11',
C12', C13', C14'}
4. Others
 Sof(P1')=Sof(P2')=Sof(N1')=Sof(N2')=Sof(C1')=Sof(H1')=Sof(C2')=Sof(H2')=
 Sof(C3')=Sof(H3'A)=Sof(H3'B)=Sof(H3'C)=Sof(C4')=Sof(H4')=Sof(C5')=Sof(H5'A)=
 Sof(H5'B)=Sof(H5'C)=Sof(C6')=Sof(H6'A)=Sof(H6'B)=Sof(H6'C)=Sof(C7')=Sof(H7')=
 Sof(C8')=Sof(H8'A)=Sof(H8'B)=Sof(H8'C)=Sof(C9')=Sof(H9'A)=Sof(H9'B)=Sof(H9'C)=
 Sof(C10')=Sof(H10')=Sof(C11')=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12')=
 Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C13')=Sof(H13')=Sof(C14')=Sof(H14D)=
 Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(P1)=Sof(P2)=Sof(N1)=Sof(N2)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=
 Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C10)=Sof(H10)=Sof(C11)=
 Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C13)=
 Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C13(H13), C4'(H4'), C7'(H7'), C10'(H10'), C13'(H13')
5.b Aromatic/amide H refined with riding coordinates:
 C1'(H1'), C2'(H2')
5.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,
 H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C),
 C3'(H3'A,H3'B,H3'C), C5'(H5'A,H5'B,H5'C), C6'(H6'A,H6'B,H6'C), C8'(H8'A,H8'B,
 H8'C), C9'(H9'A,H9'B,H9'C), C11'(H11D,H11E,H11F), C12'(H12D,H12E,H12F),
 C14'(H14D,H14E,H14F)
;
_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
P1 P 0.47740(6) 0.66921(6) 0.79163(5) 0.0307(2) Uani 0.6836(12) 1 d D . P A 1
P2 P 0.51163(6) 0.57415(6) 0.67535(5) 0.0298(2) Uani 0.6836(12) 1 d D . P A 1
N1 N 0.3024(4) 0.8407(5) 0.7366(4) 0.0416(12) Uani 0.6836(12) 1 d D . P A 1
N2 N 0.6957(6) 0.4103(6) 0.7304(4) 0.0356(11) Uani 0.6836(12) 1 d D . P A 1
C1 C 0.3611(4) 0.7544(4) 0.7129(3) 0.0325(9) Uani 0.6836(12) 1 d D . P A 1
H1 H 0.333(3) 0.740(3) 0.640(2) 0.039 Uiso 0.6836(12) 1 d . U P A 1
C2 C 0.6308(5) 0.4908(5) 0.7544(3) 0.0281(10) Uani 0.6836(12) 1 d D . P A 1
H2 H 0.658(3) 0.500(2) 0.827(2) 0.034 Uiso 0.6836(12) 1 d . U P A 1
C3 C 0.2367(9) 0.9671(8) 0.5925(8) 0.065(2) Uani 0.6836(12) 1 d D . P A 1
H3A H 0.305790 1.017157 0.632819 0.097 Uiso 0.6836(12) 1 calc R U P A 1
H3B H 0.167165 1.013436 0.547147 0.097 Uiso 0.6836(12) 1 calc R U P A 1
H3C H 0.264630 0.914995 0.552893 0.097 Uiso 0.6836(12) 1 calc R U P A 1
C4 C 0.1940(3) 0.8979(3) 0.6618(3) 0.0467(8) Uani 0.6836(12) 1 d D . P A 1
H4 H 0.161298 0.952761 0.698093 0.056 Uiso 0.6836(12) 1 calc R U P A 1
C5 C 0.0896(5) 0.8143(8) 0.6048(7) 0.0691(18) Uani 0.6836(12) 1 d D . P A 1
H5A H 0.120119 0.757886 0.570233 0.104 Uiso 0.6836(12) 1 calc R U P A 1
H5B H 0.019123 0.856089 0.555313 0.104 Uiso 0.6836(12) 1 calc R U P A 1
H5C H 0.062561 0.775218 0.652200 0.104 Uiso 0.6836(12) 1 calc R U P A 1
C6 C 0.3676(7) 0.9984(5) 0.8569(5) 0.0599(14) Uani 0.6836(12) 1 d D . P A 1
H6A H 0.423113 1.018536 0.823820 0.090 Uiso 0.6836(12) 1 calc R U P A 1
H6B H 0.408311 1.016950 0.928583 0.090 Uiso 0.6836(12) 1 calc R U P A 1
H6C H 0.289727 1.041754 0.826305 0.090 Uiso 0.6836(12) 1 calc R U P A 1
C7 C 0.3393(4) 0.8718(4) 0.8444(3) 0.0647(10) Uani 0.6836(12) 1 d D . P A 1
H7 H 0.419387 0.831115 0.883379 0.078 Uiso 0.6836(12) 1 calc R U P A 1
C8 C 0.2491(5) 0.8337(5) 0.8857(4) 0.0709(15) Uani 0.6836(12) 1 d D . P A 1
H8A H 0.170854 0.876014 0.853097 0.106 Uiso 0.6836(12) 1 calc R U P A 1
H8B H 0.283562 0.848206 0.958280 0.106 Uiso 0.6836(12) 1 calc R U P A 1
H8C H 0.233227 0.751806 0.873268 0.106 Uiso 0.6836(12) 1 calc R U P A 1
C9 C 0.7754(10) 0.4191(9) 0.5937(7) 0.0468(19) Uani 0.6836(12) 1 d D . P A 1
H9A H 0.800245 0.498252 0.613998 0.070 Uiso 0.6836(12) 1 calc R U P A 1
H9B H 0.748050 0.412011 0.520795 0.070 Uiso 0.6836(12) 1 calc R U P A 1
H9C H 0.846499 0.368276 0.627620 0.070 Uiso 0.6836(12) 1 calc R U P A 1
C10 C 0.6687(3) 0.3862(2) 0.6230(2) 0.0335(6) Uani 0.6836(12) 1 d D . P A 1
H10 H 0.594321 0.432758 0.580998 0.040 Uiso 0.6836(12) 1 calc R U P A 1
C11 C 0.6357(7) 0.2616(6) 0.5981(6) 0.0475(15) Uani 0.6836(12) 1 d D . P A 1
H11A H 0.709383 0.214161 0.633514 0.071 Uiso 0.6836(12) 1 calc R U P A 1
H11B H 0.607334 0.250036 0.525434 0.071 Uiso 0.6836(12) 1 calc R U P A 1
H11C H 0.568981 0.239864 0.619097 0.071 Uiso 0.6836(12) 1 calc R U P A 1
C12 C 0.9021(6) 0.4353(9) 0.8724(7) 0.061(2) Uani 0.6836(12) 1 d D . P A 1
H12A H 0.933761 0.477631 0.829422 0.091 Uiso 0.6836(12) 1 calc R U P A 1
H12B H 0.970554 0.392836 0.923355 0.091 Uiso 0.6836(12) 1 calc R U P A 1
H12C H 0.866625 0.488956 0.905571 0.091 Uiso 0.6836(12) 1 calc R U P A 1
C13 C 0.8010(3) 0.3517(3) 0.8082(2) 0.0388(7) Uani 0.6836(12) 1 d D . P A 1
H13 H 0.838800 0.298794 0.774144 0.047 Uiso 0.6836(12) 1 calc R U P A 1
C14 C 0.7522(8) 0.2793(7) 0.8731(6) 0.0602(18) Uani 0.6836(12) 1 d D . P A 1
H14A H 0.716002 0.329602 0.908140 0.090 Uiso 0.6836(12) 1 calc R U P A 1
H14B H 0.821250 0.235848 0.922405 0.090 Uiso 0.6836(12) 1 calc R U P A 1
H14C H 0.688220 0.226364 0.829911 0.090 Uiso 0.6836(12) 1 calc R U P A 1
P1' P 0.41735(14) 0.66833(13) 0.67690(12) 0.0316(5) Uani 0.3164(12) 1 d D . P A
2
P2' P 0.56784(14) 0.58140(13) 0.79666(12) 0.0325(5) Uani 0.3164(12) 1 d D . P A
2
N1' N 0.2707(10) 0.8235(11) 0.7262(9) 0.040(2) Uani 0.3164(12) 1 d D . P A 2
N2' N 0.7111(14) 0.4264(14) 0.7452(11) 0.042(2) Uani 0.3164(12) 1 d D . P A 2
C1' C 0.3678(9) 0.7522(9) 0.7505(6) 0.030(2) Uani 0.3164(12) 1 d D . P A 2
H1' H 0.417956 0.747273 0.820487 0.036 Uiso 0.3164(12) 1 calc R U P A 2
C2' C 0.6159(12) 0.5003(11) 0.7213(7) 0.031(2) Uani 0.3164(12) 1 d D . P A 2
H2' H 0.567572 0.508784 0.651275 0.037 Uiso 0.3164(12) 1 calc R U P A 2
C3' C 0.1920(10) 0.8139(12) 0.8568(8) 0.064(3) Uani 0.3164(12) 1 d D . P A 2
H3'A H 0.117857 0.775535 0.808243 0.095 Uiso 0.3164(12) 1 calc R U P A 2
H3'B H 0.168833 0.858571 0.903758 0.095 Uiso 0.3164(12) 1 calc R U P A 2
H3'C H 0.254457 0.756609 0.894228 0.095 Uiso 0.3164(12) 1 calc R U P A 2
C4' C 0.2485(6) 0.8969(6) 0.7987(4) 0.0435(15) Uani 0.3164(12) 1 d D . P A 2
H4' H 0.184027 0.954983 0.761116 0.052 Uiso 0.3164(12) 1 calc R U P A 2
C5' C 0.3619(14) 0.9583(13) 0.8736(11) 0.077(4) Uani 0.3164(12) 1 d D . P A 2
H5'A H 0.432935 0.905663 0.898301 0.115 Uiso 0.3164(12) 1 calc R U P A 2
H5'B H 0.343942 0.985485 0.930117 0.115 Uiso 0.3164(12) 1 calc R U P A 2
H5'C H 0.382164 1.023590 0.840591 0.115 Uiso 0.3164(12) 1 calc R U P A 2
C6' C 0.0590(11) 0.8256(16) 0.5929(14) 0.056(3) Uani 0.3164(12) 1 d D . P A 2
H6'A H 0.049842 0.749744 0.617585 0.084 Uiso 0.3164(12) 1 calc R U P A 2
H6'B H 0.009818 0.829514 0.520193 0.084 Uiso 0.3164(12) 1 calc R U P A 2
H6'C H 0.029331 0.883767 0.626564 0.084 Uiso 0.3164(12) 1 calc R U P A 2
C7' C 0.1966(6) 0.8473(7) 0.6153(5) 0.0445(15) Uani 0.3164(12) 1 d D . P A 2
H7' H 0.222952 0.790828 0.575995 0.053 Uiso 0.3164(12) 1 calc R U P A 2
C8' C 0.2077(18) 0.9632(15) 0.5788(15) 0.048(3) Uani 0.3164(12) 1 d D . P A 2
H8'A H 0.188010 1.020320 0.619548 0.072 Uiso 0.3164(12) 1 calc R U P A 2
H8'B H 0.149344 0.970888 0.508386 0.072 Uiso 0.3164(12) 1 calc R U P A 2
H8'C H 0.293097 0.975027 0.584461 0.072 Uiso 0.3164(12) 1 calc R U P A 2
C9' C 0.7805(19) 0.2988(17) 0.8955(15) 0.064(4) Uani 0.3164(12) 1 d D . P A 2
H9'A H 0.691738 0.284269 0.877579 0.096 Uiso 0.3164(12) 1 calc R U P A 2
H9'B H 0.825072 0.299420 0.968789 0.096 Uiso 0.3164(12) 1 calc R U P A 2
H9'C H 0.814750 0.238536 0.867143 0.096 Uiso 0.3164(12) 1 calc R U P A 2
C10' C 0.7958(8) 0.4115(8) 0.8543(6) 0.0611(19) Uani 0.3164(12) 1 d D . P A 2
H10' H 0.773408 0.471747 0.892892 0.073 Uiso 0.3164(12) 1 calc R U P A 2
C11' C 0.9280(13) 0.4360(19) 0.8644(16) 0.050(3) Uani 0.3164(12) 1 d D . P A 2
H11D H 0.960679 0.369029 0.842477 0.075 Uiso 0.3164(12) 1 calc R U P A 2
H11E H 0.981141 0.452867 0.934774 0.075 Uiso 0.3164(12) 1 calc R U P A 2
H11F H 0.927181 0.501774 0.822464 0.075 Uiso 0.3164(12) 1 calc R U P A 2
C12' C 0.6238(15) 0.2816(14) 0.6143(13) 0.051(3) Uani 0.3164(12) 1 d D . P A 2
H12D H 0.606371 0.230886 0.660756 0.076 Uiso 0.3164(12) 1 calc R U P A 2
H12E H 0.641153 0.235802 0.565026 0.076 Uiso 0.3164(12) 1 calc R U P A 2
H12F H 0.551182 0.330539 0.579410 0.076 Uiso 0.3164(12) 1 calc R U P A 2
C13' C 0.7367(7) 0.3559(6) 0.6731(6) 0.0437(15) Uani 0.3164(12) 1 d D . P A 2
H13' H 0.807584 0.303919 0.711809 0.052 Uiso 0.3164(12) 1 calc R U P A 2
C14' C 0.779(2) 0.434(2) 0.6084(17) 0.050(4) Uani 0.3164(12) 1 d D . P A 2
H14D H 0.718068 0.495039 0.579585 0.075 Uiso 0.3164(12) 1 calc R U P A 2
H14E H 0.786912 0.389248 0.554103 0.075 Uiso 0.3164(12) 1 calc R U P A 2
H14F H 0.860484 0.467474 0.650142 0.075 Uiso 0.3164(12) 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
P1 P2 2.1909(10) . ?
P1 C1 1.704(4) . ?
P2 C2 1.712(4) . ?
N1 C1 1.343(5) . ?
N1 C4 1.459(5) . ?
N1 C7 1.493(7) . ?
N2 C2 1.342(5) . ?
N2 C10 1.490(6) . ?
N2 C13 1.465(6) . ?
C1 H1 0.98(3) . ?
C2 H2 0.98(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C4 1.525(9) . ?
C4 H4 1.0000 . ?
C4 C5 1.524(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 C7 1.514(7) . ?
C7 H7 1.0000 . ?
C7 C8 1.478(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C10 1.523(9) . ?
C10 H10 1.0000 . ?
C10 C11 1.516(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C13 1.530(9) . ?
C13 H13 1.0000 . ?
C13 C14 1.538(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
P1' P2' 2.168(2) . ?
P1' C1' 1.716(7) . ?
P2' C2' 1.707(9) . ?
N1' C1' 1.338(11) . ?
N1' C4' 1.461(11) . ?
N1' C7' 1.518(13) . ?
N2' C2' 1.341(12) . ?
N2' C10' 1.504(14) . ?
N2' C13' 1.457(12) . ?
C1' H1' 0.9500 . ?
C2' H2' 0.9500 . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' H3'C 0.9800 . ?
C3' C4' 1.596(12) . ?
C4' H4' 1.0000 . ?
C4' C5' 1.517(13) . ?
C5' H5'A 0.9800 . ?
C5' H5'B 0.9800 . ?
C5' H5'C 0.9800 . ?
C6' H6'A 0.9800 . ?
C6' H6'B 0.9800 . ?
C6' H6'C 0.9800 . ?
C6' C7' 1.531(13) . ?
C7' H7' 1.0000 . ?
C7' C8' 1.481(15) . ?
C8' H8'A 0.9800 . ?
C8' H8'B 0.9800 . ?
C8' H8'C 0.9800 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C9' C10' 1.488(16) . ?
C10' H10' 1.0000 . ?
C10' C11' 1.522(13) . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C12' C13' 1.525(14) . ?
C13' H13' 1.0000 . ?
C13' C14' 1.533(16) . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 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
C1 P1 P2 97.15(15) . . ?
C2 P2 P1 97.18(16) . . ?
C1 N1 C4 122.4(5) . . ?
C1 N1 C7 119.4(4) . . ?
C4 N1 C7 117.9(4) . . ?
C2 N2 C10 120.1(4) . . ?
C2 N2 C13 121.2(5) . . ?
C13 N2 C10 118.6(4) . . ?
P1 C1 H1 116.7(18) . . ?
N1 C1 P1 128.4(4) . . ?
N1 C1 H1 114.8(18) . . ?
P2 C2 H2 119.3(17) . . ?
N2 C2 P2 128.4(4) . . ?
N2 C2 H2 112.4(17) . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
N1 C4 C3 108.5(5) . . ?
N1 C4 H4 107.7 . . ?
N1 C4 C5 112.2(4) . . ?
C3 C4 H4 107.7 . . ?
C5 C4 C3 112.7(6) . . ?
C5 C4 H4 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
N1 C7 C6 108.7(4) . . ?
N1 C7 H7 106.7 . . ?
C6 C7 H7 106.7 . . ?
C8 C7 N1 113.7(4) . . ?
C8 C7 C6 113.9(5) . . ?
C8 C7 H7 106.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
N2 C10 C9 113.1(5) . . ?
N2 C10 H10 107.6 . . ?
N2 C10 C11 111.0(5) . . ?
C9 C10 H10 107.6 . . ?
C11 C10 C9 109.6(5) . . ?
C11 C10 H10 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
N2 C13 C12 112.0(5) . . ?
N2 C13 H13 108.1 . . ?
N2 C13 C14 109.0(5) . . ?
C12 C13 H13 108.1 . . ?
C12 C13 C14 111.5(5) . . ?
C14 C13 H13 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1' P1' P2' 97.9(3) . . ?
C2' P2' P1' 96.7(3) . . ?
C1' N1' C4' 123.7(9) . . ?
C1' N1' C7' 117.1(9) . . ?
C4' N1' C7' 117.8(8) . . ?
C2' N2' C10' 118.4(10) . . ?
C2' N2' C13' 124.7(11) . . ?
C13' N2' C10' 116.9(9) . . ?
P1' C1' H1' 114.4 . . ?
N1' C1' P1' 131.1(8) . . ?
N1' C1' H1' 114.4 . . ?
P2' C2' H2' 114.9 . . ?
N2' C2' P2' 130.3(9) . . ?
N2' C2' H2' 114.9 . . ?
H3'A C3' H3'B 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
C4' C3' H3'A 109.5 . . ?
C4' C3' H3'B 109.5 . . ?
C4' C3' H3'C 109.5 . . ?
N1' C4' C3' 104.8(9) . . ?
N1' C4' H4' 108.7 . . ?
N1' C4' C5' 116.0(9) . . ?
C3' C4' H4' 108.7 . . ?
C5' C4' C3' 109.8(8) . . ?
C5' C4' H4' 108.7 . . ?
C4' C5' H5'A 109.5 . . ?
C4' C5' H5'B 109.5 . . ?
C4' C5' H5'C 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
H6'A C6' H6'B 109.5 . . ?
H6'A C6' H6'C 109.5 . . ?
H6'B C6' H6'C 109.5 . . ?
C7' C6' H6'A 109.5 . . ?
C7' C6' H6'B 109.5 . . ?
C7' C6' H6'C 109.5 . . ?
N1' C7' C6' 107.3(10) . . ?
N1' C7' H7' 108.0 . . ?
C6' C7' H7' 108.0 . . ?
C8' C7' N1' 117.0(10) . . ?
C8' C7' C6' 108.2(11) . . ?
C8' C7' H7' 108.0 . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C10' C9' H9'A 109.5 . . ?
C10' C9' H9'B 109.5 . . ?
C10' C9' H9'C 109.5 . . ?
N2' C10' H10' 107.4 . . ?
N2' C10' C11' 107.1(12) . . ?
C9' C10' N2' 113.1(12) . . ?
C9' C10' H10' 107.4 . . ?
C9' C10' C11' 114.2(12) . . ?
C11' C10' H10' 107.4 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
H12D C12' H12E 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C13' C12' H12D 109.5 . . ?
C13' C12' H12E 109.5 . . ?
C13' C12' H12F 109.5 . . ?
N2' C13' C12' 110.1(10) . . ?
N2' C13' H13' 107.8 . . ?
N2' C13' C14' 108.4(13) . . ?
C12' C13' H13' 107.8 . . ?
C12' C13' C14' 114.8(12) . . ?
C14' C13' H13' 107.8 . . ?
C13' C14' H14D 109.5 . . ?
C13' C14' H14E 109.5 . . ?
C13' C14' H14F 109.5 . . ?
H14D C14' H14E 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 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 P2 C2 N2 179.6(7) . . . . ?
P2 P1 C1 N1 -175.0(6) . . . . ?
C1 N1 C4 C3 -69.7(8) . . . . ?
C1 N1 C4 C5 55.5(8) . . . . ?
C1 N1 C7 C6 127.3(6) . . . . ?
C1 N1 C7 C8 -104.8(6) . . . . ?
C2 N2 C10 C9 113.1(8) . . . . ?
C2 N2 C10 C11 -123.2(8) . . . . ?
C2 N2 C13 C12 -57.9(10) . . . . ?
C2 N2 C13 C14 65.9(9) . . . . ?
C4 N1 C1 P1 -172.6(4) . . . . ?
C4 N1 C7 C6 -59.4(7) . . . . ?
C4 N1 C7 C8 68.5(6) . . . . ?
C7 N1 C1 P1 0.5(9) . . . . ?
C7 N1 C4 C3 117.2(7) . . . . ?
C7 N1 C4 C5 -117.7(6) . . . . ?
C10 N2 C2 P2 1.4(12) . . . . ?
C10 N2 C13 C12 116.8(6) . . . . ?
C10 N2 C13 C14 -119.4(7) . . . . ?
C13 N2 C2 P2 176.0(5) . . . . ?
C13 N2 C10 C9 -61.6(9) . . . . ?
C13 N2 C10 C11 62.1(8) . . . . ?
P1' P2' C2' N2' 177.4(17) . . . . ?
P2' P1' C1' N1' -174.8(13) . . . . ?
C1' N1' C4' C3' -77.8(15) . . . . ?
C1' N1' C4' C5' 43.5(18) . . . . ?
C1' N1' C7' C6' 128.4(13) . . . . ?
C1' N1' C7' C8' -109.9(16) . . . . ?
C2' N2' C10' C9' 109(2) . . . . ?
C2' N2' C10' C11' -124.0(18) . . . . ?
C2' N2' C13' C12' -57(2) . . . . ?
C2' N2' C13' C14' 69(2) . . . . ?
C4' N1' C1' P1' -174.2(9) . . . . ?
C4' N1' C7' C6' -64.4(15) . . . . ?
C4' N1' C7' C8' 57.3(16) . . . . ?
C7' N1' C1' P1' -8(2) . . . . ?
C7' N1' C4' C3' 115.9(11) . . . . ?
C7' N1' C4' C5' -122.8(11) . . . . ?
C10' N2' C2' P2' -3(3) . . . . ?
C10' N2' C13' C12' 120.5(15) . . . . ?
C10' N2' C13' C14' -113.2(18) . . . . ?
C13' N2' C2' P2' 175.3(12) . . . . ?
C13' N2' C10' C9' -69(2) . . . . ?
C13' N2' C10' C11' 58(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
