# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1878867'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H47 Al N3 P'
_chemical_formula_weight         543.68

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'
Al Al 0.0645 0.0514 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.081(2)
_cell_length_b                   19.984(3)
_cell_length_c                   16.631(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.198(4)
_cell_angle_gamma                90
_cell_volume                     3307.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11370
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.65

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57435
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.1450
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         28.771
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8571
_reflns_number_gt                5690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+0.2360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8571
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Al1 Al 0.07060(5) 0.15722(2) 0.89430(3) 0.02173(13) Uani 1 1 d . . . . .
C1 C 0.00502(14) 0.06294(7) 0.76891(11) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.0673(2) 0.14071(12) 1.01032(14) 0.0449(6) Uani 1 1 d . . . . .
H2A H 0.0469 0.0945 1.0182 0.067 Uiso 1 1 d R U . . .
H2B H -0.0002 0.1683 1.0283 0.067 Uiso 1 1 d R U . . .
H2C H 0.1536 0.1512 1.0412 0.067 Uiso 1 1 d R U . . .
C3 C 0.0455(2) 0.25136(9) 0.86122(17) 0.0469(6) Uani 1 1 d . . . . .
H3A H 0.1272 0.2756 0.8788 0.070 Uiso 1 1 d R U . . .
H3B H -0.0257 0.2705 0.8858 0.070 Uiso 1 1 d R U . . .
H3C H 0.0228 0.2540 0.8030 0.070 Uiso 1 1 d R U . . .
C4 C 0.36845(16) 0.12833(9) 0.89722(13) 0.0296(4) Uani 1 1 d . . . . .
H4 H 0.4251 0.1187 0.8559 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4075(2) 0.08093(11) 0.96741(16) 0.0492(6) Uani 1 1 d . . . . .
H5A H 0.3523 0.0889 1.0084 0.074 Uiso 1 1 d R U . . .
H5B H 0.5001 0.0878 0.9902 0.074 Uiso 1 1 d R U . . .
H5C H 0.3951 0.0357 0.9482 0.074 Uiso 1 1 d R U . . .
C6 C 0.3933(2) 0.20042(10) 0.92480(15) 0.0434(6) Uani 1 1 d . . . . .
H6A H 0.3699 0.2299 0.8792 0.065 Uiso 1 1 d R U . . .
H6B H 0.4864 0.2063 0.9472 0.065 Uiso 1 1 d R U . . .
H6C H 0.3389 0.2106 0.9656 0.065 Uiso 1 1 d R U . . .
C7 C -0.19399(15) 0.09140(9) 0.82818(12) 0.0266(4) Uani 1 1 d . . . . .
H7 H -0.2426 0.0846 0.7729 0.032 Uiso 1 1 calc R U . . .
C8 C -0.2158(2) 0.03066(11) 0.87888(15) 0.0440(6) Uani 1 1 d . . . . .
H8A H -0.1829 -0.0086 0.8551 0.066 Uiso 1 1 d R U . . .
H8B H -0.3099 0.0255 0.8807 0.066 Uiso 1 1 d R U . . .
H8C H -0.1680 0.0366 0.9332 0.066 Uiso 1 1 d R U . . .
C9 C -0.24675(18) 0.15470(10) 0.86264(16) 0.0443(6) Uani 1 1 d . . . . .
H9A H -0.1998 0.1616 0.9169 0.066 Uiso 1 1 d R U . . .
H9B H -0.3412 0.1502 0.8640 0.066 Uiso 1 1 d R U . . .
H9C H -0.2319 0.1922 0.8292 0.066 Uiso 1 1 d R U . . .
C10 C 0.23627(15) 0.09895(8) 0.69012(11) 0.0221(4) Uani 1 1 d . . . . .
C11 C 0.28471(19) 0.16399(9) 0.68692(14) 0.0339(5) Uani 1 1 d . . . . .
H11 H 0.2961 0.1907 0.7333 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3160(2) 0.18881(11) 0.61431(16) 0.0468(6) Uani 1 1 d . . . . .
H12 H 0.3500 0.2319 0.6124 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2968(2) 0.14972(11) 0.54484(14) 0.0424(5) Uani 1 1 d . . . . .
H13 H 0.3171 0.1668 0.4962 0.051 Uiso 1 1 calc R U . . .
C14 C 0.24766(19) 0.08564(10) 0.54739(13) 0.0371(5) Uani 1 1 d . . . . .
H14 H 0.2345 0.0595 0.5005 0.045 Uiso 1 1 calc R U . . .
C15 C 0.21800(17) 0.06020(9) 0.61959(12) 0.0285(4) Uani 1 1 d . . . . .
H15 H 0.1855 0.0167 0.6212 0.034 Uiso 1 1 calc R U . . .
C16 C 0.25453(15) -0.01359(8) 0.80258(11) 0.0204(3) Uani 1 1 d . . . . .
C17 C 0.36490(17) -0.03697(9) 0.77011(13) 0.0308(4) Uani 1 1 d . . . . .
H17 H 0.4044 -0.0104 0.7346 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4154(2) -0.10026(10) 0.79110(15) 0.0419(5) Uani 1 1 d . . . . .
H18 H 0.4893 -0.1159 0.7697 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3573(2) -0.13994(10) 0.84315(14) 0.0398(5) Uani 1 1 d . . . . .
H19 H 0.3905 -0.1827 0.8558 0.048 Uiso 1 1 calc R U . . .
C20 C 0.24986(18) -0.11632(9) 0.87677(13) 0.0329(4) Uani 1 1 d . . . . .
H20 H 0.2121 -0.1428 0.9132 0.039 Uiso 1 1 calc R U . . .
C21 C 0.19839(16) -0.05371(8) 0.85650(12) 0.0250(4) Uani 1 1 d . . . . .
H21 H 0.1255 -0.0381 0.8790 0.030 Uiso 1 1 calc R U . . .
C22 C -0.16859(15) 0.00716(8) 0.67555(11) 0.0207(3) Uani 1 1 d . . . . .
C23 C -0.25274(17) 0.05381(9) 0.62853(12) 0.0269(4) Uani 1 1 d . . . . .
C24 C -0.38297(18) 0.03468(11) 0.59717(13) 0.0353(5) Uani 1 1 d . . . . .
H24 H -0.4404 0.0654 0.5674 0.042 Uiso 1 1 calc R U . . .
C25 C -0.42913(17) -0.02902(11) 0.60918(13) 0.0363(5) Uani 1 1 d . . . . .
H25 H -0.5175 -0.0406 0.5889 0.044 Uiso 1 1 calc R U . . .
C26 C -0.34396(18) -0.07514(10) 0.65124(12) 0.0314(4) Uani 1 1 d . . . . .
H26 H -0.3750 -0.1184 0.6575 0.038 Uiso 1 1 calc R U . . .
C27 C -0.21231(16) -0.05895(8) 0.68479(11) 0.0239(4) Uani 1 1 d . . . . .
C28 C -0.1987(2) 0.12173(10) 0.60993(15) 0.0408(5) Uani 1 1 d . . . . .
H28 H -0.1260 0.1331 0.6543 0.049 Uiso 1 1 calc R U . . .
C29 C -0.3033(3) 0.17799(12) 0.6035(2) 0.0691(8) Uani 1 1 d . . . . .
H29A H -0.3698 0.1705 0.5562 0.104 Uiso 1 1 d R U . . .
H29B H -0.2602 0.2203 0.5985 0.104 Uiso 1 1 d R U . . .
H29C H -0.3458 0.1783 0.6512 0.104 Uiso 1 1 d R U . . .
C30 C -0.1391(3) 0.11780(12) 0.53169(19) 0.0656(8) Uani 1 1 d . . . . .
H30A H -0.0765 0.0813 0.5352 0.098 Uiso 1 1 d R U . . .
H30B H -0.0935 0.1589 0.5238 0.098 Uiso 1 1 d R U . . .
H30C H -0.2099 0.1106 0.4866 0.098 Uiso 1 1 d R U . . .
C31 C -0.11539(19) -0.10943(9) 0.72884(13) 0.0322(4) Uani 1 1 d . . . . .
H31 H -0.0616 -0.0862 0.7747 0.039 Uiso 1 1 calc R U . . .
C32 C -0.1830(3) -0.16840(11) 0.76376(18) 0.0639(8) Uani 1 1 d . . . . .
H32A H -0.2406 -0.1525 0.8004 0.096 Uiso 1 1 d R U . . .
H32B H -0.1156 -0.1973 0.7926 0.096 Uiso 1 1 d R U . . .
H32C H -0.2354 -0.1927 0.7200 0.096 Uiso 1 1 d R U . . .
C33 C -0.0185(3) -0.13370(12) 0.67298(17) 0.0605(7) Uani 1 1 d . . . . .
H33A H 0.0507 -0.1606 0.7037 0.091 Uiso 1 1 d R U . . .
H33B H 0.0214 -0.0956 0.6511 0.091 Uiso 1 1 d R U . . .
H33C H -0.0662 -0.1597 0.6292 0.091 Uiso 1 1 d R U . . .
N1 N -0.04888(12) 0.09943(7) 0.82373(9) 0.0208(3) Uani 1 1 d . . . . .
N2 N 0.22550(12) 0.11945(6) 0.85902(9) 0.0201(3) Uani 1 1 d . . . . .
N3 N -0.03496(13) 0.02347(7) 0.70861(9) 0.0211(3) Uani 1 1 d . . . . .
P1 P 0.18811(4) 0.06947(2) 0.78340(3) 0.01788(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Al1 N2 1.9092(14) . ?
Al1 N1 1.9261(15) . ?
Al1 C2 1.963(2) . ?
Al1 C3 1.965(2) . ?
C1 N3 1.289(2) . ?
C1 N1 1.348(2) . ?
C1 P1 1.8275(15) . ?
C4 N2 1.490(2) . ?
C4 C5 1.506(3) . ?
C4 C6 1.520(2) . ?
C7 N1 1.4852(19) . ?
C7 C8 1.514(3) . ?
C7 C9 1.520(2) . ?
C10 C11 1.392(2) . ?
C10 C15 1.393(3) . ?
C10 P1 1.7973(18) . ?
C11 C12 1.387(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.380(3) . ?
C16 C21 1.389(2) . ?
C16 C17 1.393(2) . ?
C16 P1 1.7991(16) . ?
C17 C18 1.387(3) . ?
C18 C19 1.372(3) . ?
C19 C20 1.380(3) . ?
C20 C21 1.376(2) . ?
C22 C27 1.409(2) . ?
C22 N3 1.409(2) . ?
C22 C23 1.410(2) . ?
C23 C24 1.387(2) . ?
C23 C28 1.513(3) . ?
C24 C25 1.381(3) . ?
C25 C26 1.373(3) . ?
C26 C27 1.393(2) . ?
C27 C31 1.510(3) . ?
C28 C30 1.520(3) . ?
C28 C29 1.533(3) . ?
C31 C32 1.522(3) . ?
C31 C33 1.531(3) . ?
N2 P1 1.6031(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Al1 N1 92.19(6) . . ?
N2 Al1 C2 112.26(8) . . ?
N1 Al1 C2 113.01(8) . . ?
N2 Al1 C3 111.57(8) . . ?
N1 Al1 C3 111.31(9) . . ?
C2 Al1 C3 114.48(11) . . ?
N3 C1 N1 138.39(14) . . ?
N3 C1 P1 109.27(11) . . ?
N1 C1 P1 112.33(12) . . ?
N2 C4 C5 111.75(15) . . ?
N2 C4 C6 110.06(14) . . ?
C5 C4 C6 110.62(18) . . ?
N1 C7 C8 110.24(14) . . ?
N1 C7 C9 109.62(14) . . ?
C8 C7 C9 111.52(17) . . ?
C11 C10 C15 119.13(17) . . ?
C11 C10 P1 118.93(15) . . ?
C15 C10 P1 121.80(13) . . ?
C12 C11 C10 119.8(2) . . ?
C13 C12 C11 120.29(19) . . ?
C14 C13 C12 120.2(2) . . ?
C13 C14 C15 119.9(2) . . ?
C14 C15 C10 120.67(18) . . ?
C21 C16 C17 119.33(15) . . ?
C21 C16 P1 117.93(12) . . ?
C17 C16 P1 122.59(13) . . ?
C18 C17 C16 119.49(17) . . ?
C19 C18 C17 120.61(17) . . ?
C18 C19 C20 119.99(17) . . ?
C21 C20 C19 120.11(17) . . ?
C20 C21 C16 120.43(15) . . ?
C27 C22 N3 118.06(15) . . ?
C27 C22 C23 120.63(15) . . ?
N3 C22 C23 121.08(15) . . ?
C24 C23 C22 118.41(17) . . ?
C24 C23 C28 121.37(18) . . ?
C22 C23 C28 120.15(16) . . ?
C25 C24 C23 121.37(18) . . ?
C26 C25 C24 119.66(17) . . ?
C25 C26 C27 121.76(17) . . ?
C26 C27 C22 117.95(17) . . ?
C26 C27 C31 122.70(16) . . ?
C22 C27 C31 119.34(15) . . ?
C23 C28 C30 109.47(18) . . ?
C23 C28 C29 113.96(19) . . ?
C30 C28 C29 109.9(2) . . ?
C27 C31 C32 114.08(17) . . ?
C27 C31 C33 110.09(17) . . ?
C32 C31 C33 110.75(19) . . ?
C1 N1 C7 118.82(14) . . ?
C1 N1 Al1 117.14(10) . . ?
C7 N1 Al1 124.01(11) . . ?
C4 N2 P1 119.92(11) . . ?
C4 N2 Al1 127.22(12) . . ?
P1 N2 Al1 112.71(7) . . ?
C1 N3 C22 127.28(14) . . ?
N2 P1 C10 114.26(8) . . ?
N2 P1 C16 113.67(8) . . ?
C10 P1 C16 108.13(8) . . ?
N2 P1 C1 104.70(7) . . ?
C10 P1 C1 108.43(8) . . ?
C16 P1 C1 107.27(7) . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Compound2b
_database_code_depnum_ccdc_archive 'CCDC 1891458'
_audit_update_record             
;
2019-01-17 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H41 Al N3 P'
_chemical_formula_weight         501.61

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'
Al Al 0.0645 0.0514 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.073(2)
_cell_length_b                   15.298(3)
_cell_length_c                   15.849(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.731(4)
_cell_angle_gamma                90
_cell_volume                     2885.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9354
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.33

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48996
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.1076
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5923
_reflns_number_gt                4388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+2.7319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5923
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Al1 Al 0.58781(6) 0.33226(5) 0.07444(5) 0.01582(18) Uani 1 1 d . . . . .
P1 P 0.81557(5) 0.07979(4) 0.16982(4) 0.01286(15) Uani 1 1 d . . . . .
C1 C 0.5799(2) 0.40692(19) 0.17289(19) 0.0299(7) Uani 1 1 d . . . . .
H1A H 0.6325 0.3866 0.2212 0.045 Uiso 1 1 d R U . . .
H1B H 0.5052 0.4050 0.1862 0.045 Uiso 1 1 d R U . . .
H1C H 0.5980 0.4659 0.1597 0.045 Uiso 1 1 d R U . . .
C2 C 0.4927(2) 0.36198(19) -0.03423(18) 0.0271(6) Uani 1 1 d . . . . .
H2A H 0.5166 0.4168 -0.0545 0.041 Uiso 1 1 d R U . . .
H2B H 0.4159 0.3665 -0.0260 0.041 Uiso 1 1 d R U . . .
H2C H 0.4989 0.3172 -0.0756 0.041 Uiso 1 1 d R U . . .
C3 C 0.5343(2) 0.13325(16) 0.11793(16) 0.0170(5) Uani 1 1 d . . . . .
H3 H 0.5709 0.0797 0.1026 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5278(2) 0.13110(18) 0.21330(17) 0.0235(6) Uani 1 1 d . . . . .
H4A H 0.6024 0.1297 0.2460 0.035 Uiso 1 1 d R U . . .
H4B H 0.4875 0.0799 0.2257 0.035 Uiso 1 1 d R U . . .
H4C H 0.4895 0.1823 0.2282 0.035 Uiso 1 1 d R U . . .
C5 C 0.4173(2) 0.13926(19) 0.06452(19) 0.0272(6) Uani 1 1 d . . . . .
H5A H 0.3833 0.1937 0.0761 0.041 Uiso 1 1 d R U . . .
H5B H 0.3721 0.0917 0.0790 0.041 Uiso 1 1 d R U . . .
H5C H 0.4227 0.1362 0.0049 0.041 Uiso 1 1 d R U . . .
C6 C 0.8459(2) 0.31524(15) 0.05801(15) 0.0147(5) Uani 1 1 d . . . . .
C7 C 0.8747(2) 0.34266(16) -0.01994(16) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.9845(2) 0.37033(17) -0.02102(18) 0.0250(6) Uani 1 1 d . . . . .
H8 H 1.0043 0.3877 -0.0727 0.030 Uiso 1 1 calc R U . . .
C9 C 1.0654(2) 0.37283(17) 0.05274(19) 0.0244(6) Uani 1 1 d . . . . .
C10 C 1.0332(2) 0.34924(16) 0.12928(17) 0.0207(6) Uani 1 1 d . . . . .
H10 H 1.0860 0.3518 0.1793 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9244(2) 0.32176(15) 0.13423(15) 0.0154(5) Uani 1 1 d . . . . .
C12 C 0.7888(2) 0.3441(2) -0.10035(17) 0.0290(7) Uani 1 1 d . . . . .
H12A H 0.7676 0.2852 -0.1169 0.044 Uiso 1 1 d R U . . .
H12B H 0.8200 0.3719 -0.1453 0.044 Uiso 1 1 d R U . . .
H12C H 0.7237 0.3759 -0.0903 0.044 Uiso 1 1 d R U . . .
C13 C 0.8933(2) 0.30137(17) 0.22021(16) 0.0204(6) Uani 1 1 d . . . . .
H13A H 0.8211 0.3262 0.2234 0.031 Uiso 1 1 d R U . . .
H13B H 0.9487 0.3258 0.2646 0.031 Uiso 1 1 d R U . . .
H13C H 0.8903 0.2392 0.2275 0.031 Uiso 1 1 d R U . . .
C14 C 1.1840(3) 0.4015(2) 0.0487(2) 0.0391(8) Uani 1 1 d . . . . .
H14A H 1.2224 0.4150 0.1053 0.059 Uiso 1 1 d R U . . .
H14B H 1.1821 0.4525 0.0131 0.059 Uiso 1 1 d R U . . .
H14C H 1.2229 0.3553 0.0249 0.059 Uiso 1 1 d R U . . .
C15 C 0.70227(19) 0.20650(15) 0.07959(14) 0.0129(5) Uani 1 1 d . . . . .
C16 C 0.7603(3) 0.0874(2) -0.01199(17) 0.0312(7) Uani 1 1 d . . . . .
H16 H 0.7547 0.0245 -0.0014 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8598(3) 0.0980(3) -0.0532(2) 0.0479(9) Uani 1 1 d . . . . .
H17A H 0.8735 0.1591 -0.0601 0.072 Uiso 1 1 d R U . . .
H17B H 0.8470 0.0702 -0.1083 0.072 Uiso 1 1 d R U . . .
H17C H 0.9239 0.0719 -0.0181 0.072 Uiso 1 1 d R U . . .
C18 C 0.6524(3) 0.1114(2) -0.07197(18) 0.0339(7) Uani 1 1 d . . . . .
H18A H 0.6518 0.1732 -0.0829 0.051 Uiso 1 1 d R U . . .
H18B H 0.5888 0.0962 -0.0459 0.051 Uiso 1 1 d R U . . .
H18C H 0.6487 0.0803 -0.1250 0.051 Uiso 1 1 d R U . . .
C19 C 0.9695(2) 0.07975(15) 0.18272(15) 0.0153(5) Uani 1 1 d . . . . .
C20 C 1.0326(2) 0.13022(17) 0.13507(18) 0.0212(6) Uani 1 1 d . . . . .
H20 H 0.9965 0.1617 0.0882 0.025 Uiso 1 1 calc R U . . .
C21 C 1.1489(2) 0.13381(18) 0.1571(2) 0.0285(7) Uani 1 1 d . . . . .
H21 H 1.1900 0.1680 0.1249 0.034 Uiso 1 1 calc R U . . .
C22 C 1.2042(2) 0.08708(18) 0.2263(2) 0.0291(7) Uani 1 1 d . . . . .
H22 H 1.2821 0.0889 0.2402 0.035 Uiso 1 1 calc R U . . .
C23 C 1.1422(2) 0.03749(17) 0.27504(18) 0.0247(6) Uani 1 1 d . . . . .
H23 H 1.1785 0.0064 0.3221 0.030 Uiso 1 1 calc R U . . .
C24 C 1.0263(2) 0.03436(16) 0.25357(16) 0.0184(5) Uani 1 1 d . . . . .
H24 H 0.9855 0.0014 0.2869 0.022 Uiso 1 1 calc R U . . .
C25 C 0.7876(2) -0.03766(16) 0.15298(16) 0.0164(5) Uani 1 1 d . . . . .
C26 C 0.8554(2) -0.09353(17) 0.11423(17) 0.0219(6) Uani 1 1 d . . . . .
H26 H 0.9158 -0.0709 0.0918 0.026 Uiso 1 1 calc R U . . .
C27 C 0.8335(2) -0.18230(18) 0.10886(19) 0.0298(7) Uani 1 1 d . . . . .
H27 H 0.8787 -0.2189 0.0823 0.036 Uiso 1 1 calc R U . . .
C28 C 0.7454(3) -0.21667(18) 0.1426(2) 0.0330(7) Uani 1 1 d . . . . .
H28 H 0.7312 -0.2764 0.1390 0.040 Uiso 1 1 calc R U . . .
C29 C 0.6778(3) -0.16260(19) 0.18188(19) 0.0326(7) Uani 1 1 d . . . . .
H29 H 0.6181 -0.1860 0.2047 0.039 Uiso 1 1 calc R U . . .
C30 C 0.6987(2) -0.07340(17) 0.18735(17) 0.0234(6) Uani 1 1 d . . . . .
H30 H 0.6533 -0.0373 0.2141 0.028 Uiso 1 1 calc R U . . .
N1 N 0.60032(17) 0.20858(13) 0.09982(13) 0.0160(4) Uani 1 1 d . . . . .
N2 N 0.73344(16) 0.28756(13) 0.06002(12) 0.0136(4) Uani 1 1 d . . . . .
N3 N 0.76756(17) 0.13024(13) 0.07410(12) 0.0136(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Al1 N1 1.935(2) . ?
Al1 N2 1.936(2) . ?
Al1 C1 1.949(3) . ?
Al1 C2 1.955(3) . ?
Al1 C15 2.362(2) . ?
P1 N3 1.713(2) . ?
P1 C19 1.835(2) . ?
P1 C25 1.839(2) . ?
C3 N1 1.457(3) . ?
C3 C5 1.522(3) . ?
C3 C4 1.527(4) . ?
C6 C7 1.403(3) . ?
C6 C11 1.408(3) . ?
C6 N2 1.427(3) . ?
C7 C8 1.394(4) . ?
C7 C12 1.501(4) . ?
C8 C9 1.391(4) . ?
C9 C10 1.383(4) . ?
C9 C14 1.510(4) . ?
C10 C11 1.394(3) . ?
C11 C13 1.506(3) . ?
C15 N1 1.324(3) . ?
C15 N2 1.347(3) . ?
C15 N3 1.419(3) . ?
C16 C17 1.471(4) . ?
C16 N3 1.503(3) . ?
C16 C18 1.522(4) . ?
C19 C20 1.393(4) . ?
C19 C24 1.398(3) . ?
C20 C21 1.390(4) . ?
C21 C22 1.384(4) . ?
C22 C23 1.388(4) . ?
C23 C24 1.383(4) . ?
C25 C30 1.395(4) . ?
C25 C26 1.395(4) . ?
C26 C27 1.383(4) . ?
C27 C28 1.374(4) . ?
C28 C29 1.382(5) . ?
C29 C30 1.388(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Al1 N2 68.81(9) . . ?
N1 Al1 C1 114.79(12) . . ?
N2 Al1 C1 118.04(11) . . ?
N1 Al1 C2 115.09(11) . . ?
N2 Al1 C2 112.84(11) . . ?
C1 Al1 C2 117.89(13) . . ?
N1 Al1 C15 34.08(8) . . ?
N2 Al1 C15 34.77(8) . . ?
C1 Al1 C15 123.87(11) . . ?
C2 Al1 C15 118.22(11) . . ?
N3 P1 C19 106.46(11) . . ?
N3 P1 C25 106.57(10) . . ?
C19 P1 C25 99.97(11) . . ?
N1 C3 C5 109.3(2) . . ?
N1 C3 C4 109.5(2) . . ?
C5 C3 C4 110.7(2) . . ?
C7 C6 C11 120.2(2) . . ?
C7 C6 N2 119.1(2) . . ?
C11 C6 N2 120.5(2) . . ?
C8 C7 C6 118.7(2) . . ?
C8 C7 C12 120.5(2) . . ?
C6 C7 C12 120.8(2) . . ?
C9 C8 C7 122.1(2) . . ?
C10 C9 C8 117.9(2) . . ?
C10 C9 C14 121.5(3) . . ?
C8 C9 C14 120.5(3) . . ?
C9 C10 C11 122.4(2) . . ?
C10 C11 C6 118.5(2) . . ?
C10 C11 C13 119.6(2) . . ?
C6 C11 C13 121.8(2) . . ?
N1 C15 N2 109.9(2) . . ?
N1 C15 N3 125.7(2) . . ?
N2 C15 N3 124.3(2) . . ?
N1 C15 Al1 54.99(12) . . ?
N2 C15 Al1 55.04(12) . . ?
N3 C15 Al1 174.51(16) . . ?
C17 C16 N3 115.3(3) . . ?
C17 C16 C18 111.9(3) . . ?
N3 C16 C18 112.0(2) . . ?
C20 C19 C24 118.1(2) . . ?
C20 C19 P1 125.14(19) . . ?
C24 C19 P1 116.11(19) . . ?
C21 C20 C19 120.5(3) . . ?
C22 C21 C20 120.7(3) . . ?
C21 C22 C23 119.4(2) . . ?
C24 C23 C22 120.0(3) . . ?
C23 C24 C19 121.3(2) . . ?
C30 C25 C26 118.6(2) . . ?
C30 C25 P1 117.42(19) . . ?
C26 C25 P1 123.75(19) . . ?
C27 C26 C25 120.5(3) . . ?
C28 C27 C26 120.3(3) . . ?
C27 C28 C29 120.1(3) . . ?
C28 C29 C30 120.1(3) . . ?
C29 C30 C25 120.3(3) . . ?
C15 N1 C3 126.2(2) . . ?
C15 N1 Al1 90.92(15) . . ?
C3 N1 Al1 142.04(16) . . ?
C15 N2 C6 125.59(19) . . ?
C15 N2 Al1 90.19(14) . . ?
C6 N2 Al1 141.62(16) . . ?
C15 N3 C16 117.81(19) . . ?
C15 N3 P1 115.11(15) . . ?
C16 N3 P1 124.51(17) . . ?

_refine_diff_density_max         1.032
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.094

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1878868'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H42 N3 P'
_chemical_formula_weight         487.64

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.093(3)
_cell_length_b                   15.955(2)
_cell_length_c                   10.358(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2824.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17470
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.80

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64643
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         28.732
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7297
_reflns_number_gt                6421
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.5061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7297
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.03401(10) 0.01396(12) 0.77867(18) 0.0108(4) Uani 1 1 d . . . . .
C2 C -0.04681(12) -0.05064(13) 0.95625(18) 0.0140(4) Uani 1 1 d . . . . .
H2 H -0.0106 -0.0234 1.0164 0.017 Uiso 1 1 calc R U . . .
C3 C -0.05774(14) -0.14127(13) 0.9989(2) 0.0220(5) Uani 1 1 d . . . . .
H3A H -0.0888 -0.1705 0.9361 0.033 Uiso 1 1 d R U . . .
H3B H -0.0838 -0.1425 1.0810 0.033 Uiso 1 1 d R U . . .
H3C H -0.0076 -0.1679 1.0063 0.033 Uiso 1 1 d R U . . .
C4 C -0.12425(12) -0.00305(15) 0.9591(2) 0.0200(5) Uani 1 1 d . . . . .
H4A H -0.1156 0.0543 0.9351 0.030 Uiso 1 1 d R U . . .
H4B H -0.1458 -0.0052 1.0446 0.030 Uiso 1 1 d R U . . .
H4C H -0.1601 -0.0284 0.8994 0.030 Uiso 1 1 d R U . . .
C5 C 0.15499(12) 0.01975(12) 0.91803(19) 0.0147(4) Uani 1 1 d . . . . .
H5 H 0.1904 0.0663 0.9382 0.018 Uiso 1 1 calc R U . . .
C6 C 0.19555(13) -0.03324(15) 0.8160(2) 0.0227(5) Uani 1 1 d . . . . .
H6A H 0.1641 -0.0815 0.7971 0.034 Uiso 1 1 d R U . . .
H6B H 0.2456 -0.0510 0.8478 0.034 Uiso 1 1 d R U . . .
H6C H 0.2025 -0.0007 0.7389 0.034 Uiso 1 1 d R U . . .
C7 C 0.14472(13) -0.03010(14) 1.0418(2) 0.0218(5) Uani 1 1 d . . . . .
H7A H 0.1176 0.0034 1.1044 0.033 Uiso 1 1 d R U . . .
H7B H 0.1951 -0.0455 1.0751 0.033 Uiso 1 1 d R U . . .
H7C H 0.1149 -0.0798 1.0240 0.033 Uiso 1 1 d R U . . .
C8 C 0.07400(11) 0.17073(12) 1.06526(19) 0.0138(4) Uani 1 1 d . . . . .
C9 C 0.01046(12) 0.14804(13) 1.1431(2) 0.0180(4) Uani 1 1 d . . . . .
H9 H -0.0376 0.1364 1.1048 0.022 Uiso 1 1 calc R U . . .
C10 C 0.01782(14) 0.14252(14) 1.2764(2) 0.0239(5) Uani 1 1 d . . . . .
H10 H -0.0243 0.1252 1.3265 0.029 Uiso 1 1 calc R U . . .
C11 C 0.08820(14) 0.16300(15) 1.3343(2) 0.0252(5) Uani 1 1 d . . . . .
H11 H 0.0934 0.1596 1.4235 0.030 Uiso 1 1 calc R U . . .
C12 C 0.15100(14) 0.18859(14) 1.2593(2) 0.0213(5) Uani 1 1 d . . . . .
H12 H 0.1978 0.2037 1.2985 0.026 Uiso 1 1 calc R U . . .
C13 C 0.14419(12) 0.19170(12) 1.1255(2) 0.0168(4) Uani 1 1 d . . . . .
H13 H 0.1869 0.2079 1.0758 0.020 Uiso 1 1 calc R U . . .
C14 C 0.13861(11) 0.21910(12) 0.82076(19) 0.0133(4) Uani 1 1 d . . . . .
C15 C 0.17785(12) 0.18810(13) 0.71192(19) 0.0158(4) Uani 1 1 d . . . . .
H15 H 0.1637 0.1364 0.6777 0.019 Uiso 1 1 calc R U . . .
C16 C 0.23769(13) 0.23381(14) 0.6547(2) 0.0197(4) Uani 1 1 d . . . . .
H16 H 0.2632 0.2126 0.5824 0.024 Uiso 1 1 calc R U . . .
C17 C 0.25963(13) 0.31104(14) 0.7047(2) 0.0221(5) Uani 1 1 d . . . . .
H17 H 0.3012 0.3404 0.6686 0.027 Uiso 1 1 calc R U . . .
C18 C 0.21926(13) 0.34412(15) 0.8086(2) 0.0227(5) Uani 1 1 d . . . . .
H18 H 0.2327 0.3967 0.8405 0.027 Uiso 1 1 calc R U . . .
C19 C 0.15866(12) 0.29934(13) 0.8658(2) 0.0182(4) Uani 1 1 d . . . . .
H19 H 0.1312 0.3227 0.9345 0.022 Uiso 1 1 calc R U . . .
C20 C -0.01387(11) 0.00122(13) 0.56701(18) 0.0123(4) Uani 1 1 d . . . . .
C21 C -0.09039(12) 0.03466(13) 0.55584(19) 0.0141(4) Uani 1 1 d . . . . .
C22 C -0.13858(12) 0.00354(13) 0.45862(19) 0.0160(4) Uani 1 1 d . . . . .
H22 H -0.1894 0.0238 0.4510 0.019 Uiso 1 1 calc R U . . .
C23 C -0.11238(12) -0.05714(14) 0.3728(2) 0.0192(4) Uani 1 1 d . . . . .
H23 H -0.1455 -0.0771 0.3085 0.023 Uiso 1 1 calc R U . . .
C24 C -0.03686(12) -0.08800(13) 0.3831(2) 0.0171(4) Uani 1 1 d . . . . .
H24 H -0.0195 -0.1281 0.3246 0.021 Uiso 1 1 calc R U . . .
C25 C 0.01360(12) -0.05973(13) 0.48001(19) 0.0137(4) Uani 1 1 d . . . . .
C26 C -0.11618(11) 0.10587(13) 0.64372(19) 0.0148(4) Uani 1 1 d . . . . .
H26 H -0.0924 0.0959 0.7284 0.018 Uiso 1 1 calc R U . . .
C27 C -0.20471(12) 0.11119(15) 0.6642(2) 0.0221(5) Uani 1 1 d . . . . .
H27A H -0.2294 0.1274 0.5848 0.033 Uiso 1 1 d R U . . .
H27B H -0.2161 0.1520 0.7297 0.033 Uiso 1 1 d R U . . .
H27C H -0.2242 0.0574 0.6907 0.033 Uiso 1 1 d R U . . .
C28 C -0.08398(13) 0.18970(13) 0.5938(2) 0.0199(4) Uani 1 1 d . . . . .
H28A H -0.0282 0.1860 0.5853 0.030 Uiso 1 1 d R U . . .
H28B H -0.0970 0.2335 0.6536 0.030 Uiso 1 1 d R U . . .
H28C H -0.1067 0.2019 0.5112 0.030 Uiso 1 1 d R U . . .
C29 C 0.09606(12) -0.09441(13) 0.49362(19) 0.0149(4) Uani 1 1 d . . . . .
H29 H 0.1284 -0.0512 0.5343 0.018 Uiso 1 1 calc R U . . .
C30 C 0.13402(14) -0.1177(2) 0.3646(2) 0.0346(6) Uani 1 1 d . . . . .
H30A H 0.1055 -0.1632 0.3263 0.052 Uiso 1 1 d R U . . .
H30B H 0.1872 -0.1346 0.3790 0.052 Uiso 1 1 d R U . . .
H30C H 0.1330 -0.0703 0.3077 0.052 Uiso 1 1 d R U . . .
C31 C 0.09646(13) -0.17159(15) 0.5817(2) 0.0252(5) Uani 1 1 d . . . . .
H31A H 0.0704 -0.1586 0.6613 0.038 Uiso 1 1 d R U . . .
H31B H 0.1495 -0.1879 0.5992 0.038 Uiso 1 1 d R U . . .
H31C H 0.0696 -0.2168 0.5394 0.038 Uiso 1 1 d R U . . .
N1 N -0.01113(10) -0.04989(11) 0.82664(16) 0.0135(3) Uani 1 1 d . . . . .
H1N H -0.0437 -0.0742 0.7646 0.016 Uiso 1 1 d R U . . .
N2 N 0.08081(9) 0.05775(10) 0.86992(15) 0.0106(3) Uani 1 1 d . . . . .
N3 N 0.03852(9) 0.03581(10) 0.65946(16) 0.0123(3) Uani 1 1 d . . . . .
P1 P 0.05663(3) 0.16059(3) 0.89038(5) 0.01103(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.285(2) . ?
C1 N1 1.371(2) . ?
C1 N2 1.422(2) . ?
C2 N1 1.474(2) . ?
C2 C3 1.523(3) . ?
C2 C4 1.526(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N2 1.491(2) . ?
C5 C7 1.519(3) . ?
C5 C6 1.520(3) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.393(3) . ?
C8 C9 1.400(3) . ?
C8 P1 1.843(2) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.402(3) . ?
C14 C19 1.405(3) . ?
C14 P1 1.832(2) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.406(3) . ?
C20 C21 1.417(3) . ?
C20 N3 1.422(2) . ?
C21 C22 1.392(3) . ?
C21 C26 1.521(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.398(3) . ?
C24 H24 0.9300 . ?
C25 C29 1.521(3) . ?
C26 C27 1.530(3) . ?
C26 C28 1.536(3) . ?
C26 H26 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.531(3) . ?
C29 C31 1.532(3) . ?
C29 H29 0.9800 . ?
C30 H30A 0.9601 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
N1 H1N 0.9337 . ?
N2 P1 1.7053(17) . ?

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
N3 C1 N1 125.69(18) . . ?
N3 C1 N2 118.14(17) . . ?
N1 C1 N2 116.15(16) . . ?
N1 C2 C3 108.81(17) . . ?
N1 C2 C4 111.86(16) . . ?
C3 C2 C4 111.10(18) . . ?
N1 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C4 C2 H2 108.3 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.6 . . ?
C2 C4 H4B 109.4 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.4 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C7 113.37(17) . . ?
N2 C5 C6 112.43(16) . . ?
C7 C5 C6 110.37(17) . . ?
N2 C5 H5 106.7 . . ?
C7 C5 H5 106.7 . . ?
C6 C5 H5 106.7 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.6 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.4 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.20(18) . . ?
C13 C8 P1 126.87(15) . . ?
C9 C8 P1 114.71(15) . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C15 C14 C19 118.15(19) . . ?
C15 C14 P1 120.19(15) . . ?
C19 C14 P1 121.35(15) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C25 C20 C21 121.07(18) . . ?
C25 C20 N3 119.30(17) . . ?
C21 C20 N3 119.33(18) . . ?
C22 C21 C20 118.08(19) . . ?
C22 C21 C26 121.85(18) . . ?
C20 C21 C26 119.98(17) . . ?
C23 C22 C21 121.39(19) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 119.93(19) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C20 118.50(18) . . ?
C24 C25 C29 121.39(18) . . ?
C20 C25 C29 120.11(17) . . ?
C21 C26 C27 114.27(17) . . ?
C21 C26 C28 110.19(16) . . ?
C27 C26 C28 110.66(18) . . ?
C21 C26 H26 107.1 . . ?
C27 C26 H26 107.1 . . ?
C28 C26 H26 107.1 . . ?
C26 C27 H27A 109.3 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.4 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.4 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 C30 113.60(18) . . ?
C25 C29 C31 110.60(16) . . ?
C30 C29 C31 108.79(19) . . ?
C25 C29 H29 107.9 . . ?
C30 C29 H29 107.9 . . ?
C31 C29 H29 107.9 . . ?
C29 C30 H30A 109.2 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.7 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.6 . . ?
C29 C31 H31B 109.6 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.3 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C1 N1 C2 124.66(16) . . ?
C1 N1 H1N 113.2 . . ?
C2 N1 H1N 112.1 . . ?
C1 N2 C5 120.05(15) . . ?
C1 N2 P1 114.77(13) . . ?
C5 N2 P1 123.76(13) . . ?
C1 N3 C20 120.25(16) . . ?
N2 P1 C14 104.84(9) . . ?
N2 P1 C8 99.65(9) . . ?
C14 P1 C8 102.65(9) . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Compound4
_database_code_depnum_ccdc_archive 'CCDC 1881080'
_audit_update_record             
;
2018-11-25 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H46 N3 P Zn'
_chemical_formula_weight         581.07

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.379(3)
_cell_length_b                   12.334(2)
_cell_length_c                   17.878(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.758(5)
_cell_angle_gamma                90
_cell_volume                     3211.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1416
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      17.10

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.839
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            116226
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         28.859
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8356
_reflns_number_gt                7122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+1.0004P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8356
_refine_ls_number_parameters     342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1364
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.533
_refine_ls_restrained_S_all      1.533
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.72162(2) 0.11274(2) 0.36882(2) 0.02140(9) Uani 1 1 d . . . . .
C1 C 0.77325(12) -0.09215(15) 0.32370(11) 0.0127(3) Uani 1 1 d . . . . .
C2 C 0.6918(3) 0.2385(3) 0.4227(2) 0.0626(10) Uani 1 1 d . . . . .
H2A H 0.7407 0.2907 0.4289 0.075 Uiso 1 1 calc R U . . .
H2B H 0.6367 0.2705 0.3864 0.075 Uiso 1 1 calc R U . . .
C3 C 0.6770(3) 0.2313(4) 0.49806(18) 0.0772(15) Uani 1 1 d . . . . .
H3A H 0.6306 0.1929 0.5129 0.116 Uiso 1 1 d R U . . .
H3B H 0.6734 0.3069 0.5096 0.116 Uiso 1 1 d R U . . .
H3C H 0.7369 0.2043 0.5272 0.116 Uiso 1 1 d R U . . .
C4 C 0.73003(19) -0.10969(18) 0.44325(14) 0.0286(5) Uani 1 1 d . . . . .
H4 H 0.7488 -0.1848 0.4392 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6275(2) -0.1073(3) 0.43315(19) 0.0469(7) Uani 1 1 d . . . . .
H5A H 0.6083 -0.0343 0.4381 0.070 Uiso 1 1 d R U . . .
H5B H 0.6157 -0.1519 0.4729 0.070 Uiso 1 1 d R U . . .
H5C H 0.5939 -0.1350 0.3818 0.070 Uiso 1 1 d R U . . .
C6 C 0.7867(2) -0.0640(3) 0.52302(15) 0.0474(8) Uani 1 1 d . . . . .
H6A H 0.8504 -0.0601 0.5269 0.071 Uiso 1 1 d R U . . .
H6B H 0.7801 -0.1093 0.5645 0.071 Uiso 1 1 d R U . . .
H6C H 0.7644 0.0075 0.5280 0.071 Uiso 1 1 d R U . . .
C7 C 0.71261(15) 0.20361(16) 0.20535(13) 0.0210(4) Uani 1 1 d . . . . .
H7 H 0.7205 0.1766 0.1564 0.025 Uiso 1 1 calc R U . . .
C8 C 0.61174(16) 0.2300(2) 0.18861(15) 0.0306(5) Uani 1 1 d . . . . .
H8A H 0.5768 0.1649 0.1715 0.046 Uiso 1 1 d R U . . .
H8B H 0.5933 0.2834 0.1475 0.046 Uiso 1 1 d R U . . .
H8C H 0.6010 0.2572 0.2352 0.046 Uiso 1 1 d R U . . .
C9 C 0.77128(17) 0.30411(19) 0.23031(18) 0.0353(6) Uani 1 1 d . . . . .
H9A H 0.7665 0.3223 0.2811 0.053 Uiso 1 1 d R U . . .
H9B H 0.7475 0.3626 0.1941 0.053 Uiso 1 1 d R U . . .
H9C H 0.8346 0.2920 0.2352 0.053 Uiso 1 1 d R U . . .
C10 C 0.88395(12) -0.00187(15) 0.23176(10) 0.0130(3) Uani 1 1 d . . . . .
C11 C 0.91372(14) -0.08553(17) 0.19296(12) 0.0180(4) Uani 1 1 d . . . . .
H11 H 0.8752 -0.1437 0.1717 0.022 Uiso 1 1 calc R U . . .
C12 C 1.00114(14) -0.08091(18) 0.18656(12) 0.0213(4) Uani 1 1 d . . . . .
H12 H 1.0208 -0.1359 0.1602 0.026 Uiso 1 1 calc R U . . .
C13 C 1.05973(14) 0.00505(19) 0.21905(13) 0.0236(4) Uani 1 1 d . . . . .
H13 H 1.1178 0.0079 0.2136 0.028 Uiso 1 1 calc R U . . .
C14 C 1.03147(14) 0.08631(18) 0.25948(14) 0.0242(4) Uani 1 1 d . . . . .
H14 H 1.0712 0.1427 0.2826 0.029 Uiso 1 1 calc R U . . .
C15 C 0.94352(13) 0.08333(16) 0.26534(12) 0.0183(4) Uani 1 1 d . . . . .
H15 H 0.9242 0.1385 0.2918 0.022 Uiso 1 1 calc R U . . .
C16 C 0.68993(13) -0.05348(15) 0.15450(11) 0.0144(3) Uani 1 1 d . . . . .
C17 C 0.60423(14) -0.08326(18) 0.15981(12) 0.0203(4) Uani 1 1 d . . . . .
H17 H 0.5936 -0.0787 0.2081 0.024 Uiso 1 1 calc R U . . .
C18 C 0.53497(15) -0.1196(2) 0.09343(14) 0.0282(5) Uani 1 1 d . . . . .
H18 H 0.4781 -0.1389 0.0973 0.034 Uiso 1 1 calc R U . . .
C19 C 0.55057(17) -0.1269(2) 0.02178(14) 0.0317(5) Uani 1 1 d . . . . .
H19 H 0.5045 -0.1522 -0.0225 0.038 Uiso 1 1 calc R U . . .
C20 C 0.63445(17) -0.0968(2) 0.01591(13) 0.0304(5) Uani 1 1 d . . . . .
H20 H 0.6447 -0.1018 -0.0325 0.037 Uiso 1 1 calc R U . . .
C21 C 0.70420(14) -0.05874(19) 0.08186(12) 0.0216(4) Uani 1 1 d . . . . .
H21 H 0.7601 -0.0370 0.0771 0.026 Uiso 1 1 calc R U . . .
C22 C 0.81498(12) -0.28028(15) 0.35802(11) 0.0136(3) Uiso 1 1 d . . . . .
C23 C 0.89741(13) -0.29093(16) 0.42242(11) 0.0167(4) Uani 1 1 d . . . . .
C24 C 0.91215(15) -0.38755(17) 0.46550(12) 0.0212(4) Uani 1 1 d . . . . .
H24 H 0.9660 -0.3961 0.5077 0.025 Uiso 1 1 calc R U . . .
C25 C 0.84818(16) -0.47135(17) 0.44673(13) 0.0235(4) Uani 1 1 d . . . . .
H25 H 0.8592 -0.5347 0.4765 0.028 Uiso 1 1 calc R U . . .
C26 C 0.76755(15) -0.46007(16) 0.38324(12) 0.0201(4) Uani 1 1 d . . . . .
H26 H 0.7248 -0.5161 0.3711 0.024 Uiso 1 1 calc R U . . .
C27 C 0.74982(13) -0.36554(16) 0.33732(11) 0.0154(4) Uani 1 1 d . . . . .
C28 C 0.96811(15) -0.19941(18) 0.44187(12) 0.0216(4) Uiso 1 1 d . . . . .
H28 H 0.9345 -0.1309 0.4277 0.026 Uiso 1 1 calc R U . . .
C29 C 1.03166(16) -0.2093(2) 0.39192(14) 0.0301(5) Uani 1 1 d . . . . .
H29A H 1.0645 -0.2764 0.4057 0.045 Uiso 1 1 d R U . . .
H29B H 1.0745 -0.1500 0.4031 0.045 Uiso 1 1 d R U . . .
H29C H 0.9970 -0.2095 0.3366 0.045 Uiso 1 1 d R U . . .
C30 C 1.02479(18) -0.1932(2) 0.52946(14) 0.0328(5) Uani 1 1 d . . . . .
H30A H 0.9844 -0.1907 0.5607 0.049 Uiso 1 1 d R U . . .
H30B H 1.0618 -0.1289 0.5386 0.049 Uiso 1 1 d R U . . .
H30C H 1.0638 -0.2558 0.5440 0.049 Uiso 1 1 d R U . . .
C31 C 0.66360(14) -0.35228(17) 0.26620(12) 0.0190(4) Uani 1 1 d . . . . .
H31 H 0.6409 -0.2783 0.2676 0.023 Uiso 1 1 calc R U . . .
C32 C 0.58568(16) -0.4303(2) 0.26542(15) 0.0306(5) Uani 1 1 d . . . . .
H32A H 0.6039 -0.5033 0.2591 0.046 Uiso 1 1 d R U . . .
H32B H 0.5313 -0.4125 0.2226 0.046 Uiso 1 1 d R U . . .
H32C H 0.5733 -0.4241 0.3146 0.046 Uiso 1 1 d R U . . .
C33 C 0.68653(16) -0.36439(18) 0.18953(13) 0.0237(4) Uani 1 1 d . . . . .
H33A H 0.7076 -0.4374 0.1882 0.036 Uiso 1 1 d R U . . .
H33B H 0.7340 -0.3148 0.1879 0.036 Uiso 1 1 d R U . . .
H33C H 0.6327 -0.3521 0.1448 0.036 Uiso 1 1 d R U . . .
N1 N 0.74550(13) -0.04565(14) 0.37938(10) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.74225(12) 0.11697(13) 0.26586(10) 0.0158(3) Uani 1 1 d . . . . .
N3 N 0.80044(11) -0.18741(13) 0.30900(9) 0.0144(3) Uani 1 1 d . . . . .
P1 P 0.77184(3) 0.00021(4) 0.24304(3) 0.01148(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 C2 1.957(3) . ?
Zn1 N1 1.9855(18) . ?
Zn1 N2 1.9666(17) . ?
C1 N3 1.302(2) . ?
C1 N1 1.332(2) . ?
C1 P1 1.8324(19) . ?
C2 C3 1.439(5) . ?
C4 N1 1.469(3) . ?
C4 C5 1.529(4) . ?
C4 C6 1.521(4) . ?
C7 C9 1.513(3) . ?
C7 N2 1.484(3) . ?
C7 C8 1.518(3) . ?
C10 C15 1.397(3) . ?
C10 C11 1.400(3) . ?
C10 P1 1.7995(19) . ?
C11 C12 1.387(3) . ?
C12 C13 1.392(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.390(3) . ?
C16 C17 1.401(3) . ?
C16 C21 1.386(3) . ?
C16 P1 1.8023(19) . ?
C17 C18 1.389(3) . ?
C18 C19 1.380(3) . ?
C19 C20 1.379(4) . ?
C20 C21 1.396(3) . ?
C22 C27 1.417(3) . ?
C22 C23 1.418(3) . ?
C22 N3 1.416(2) . ?
C23 C24 1.397(3) . ?
C23 C28 1.528(3) . ?
C24 C25 1.392(3) . ?
C25 C26 1.393(3) . ?
C26 C27 1.401(3) . ?
C27 C31 1.522(3) . ?
C28 C29 1.526(3) . ?
C28 C30 1.530(3) . ?
C31 C32 1.533(3) . ?
C31 C33 1.529(3) . ?
N2 P1 1.6021(16) . ?

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 Zn1 N1 143.00(12) . . ?
C2 Zn1 N2 125.02(12) . . ?
N1 Zn1 N2 91.98(7) . . ?
N3 C1 N1 137.75(18) . . ?
N3 C1 P1 108.99(13) . . ?
N1 C1 P1 113.25(14) . . ?
C3 C2 Zn1 123.0(3) . . ?
N1 C4 C5 108.5(2) . . ?
N1 C4 C6 110.0(2) . . ?
C5 C4 C6 111.2(2) . . ?
C9 C7 N2 111.14(18) . . ?
C9 C7 C8 110.93(19) . . ?
N2 C7 C8 110.66(18) . . ?
C15 C10 C11 119.60(17) . . ?
C15 C10 P1 117.44(14) . . ?
C11 C10 P1 122.94(15) . . ?
C12 C11 C10 119.39(19) . . ?
C13 C12 C11 120.8(2) . . ?
C14 C13 C12 119.96(19) . . ?
C13 C14 C15 119.8(2) . . ?
C10 C15 C14 120.47(19) . . ?
C17 C16 C21 119.14(18) . . ?
C17 C16 P1 116.36(15) . . ?
C21 C16 P1 124.30(15) . . ?
C16 C17 C18 120.4(2) . . ?
C19 C18 C17 120.0(2) . . ?
C20 C19 C18 119.9(2) . . ?
C19 C20 C21 120.7(2) . . ?
C20 C21 C16 119.80(19) . . ?
C27 C22 C23 121.05(17) . . ?
C27 C22 N3 118.75(17) . . ?
C23 C22 N3 119.97(17) . . ?
C22 C23 C24 118.07(19) . . ?
C22 C23 C28 120.09(17) . . ?
C24 C23 C28 121.82(18) . . ?
C25 C24 C23 121.6(2) . . ?
C24 C25 C26 119.83(19) . . ?
C25 C26 C27 121.00(19) . . ?
C26 C27 C22 118.45(18) . . ?
C26 C27 C31 122.13(18) . . ?
C22 C27 C31 119.42(17) . . ?
C23 C28 C29 110.54(18) . . ?
C23 C28 C30 113.53(18) . . ?
C29 C28 C30 109.98(19) . . ?
C27 C31 C32 114.11(18) . . ?
C27 C31 C33 110.39(16) . . ?
C32 C31 C33 109.59(18) . . ?
C1 N1 C4 121.33(17) . . ?
C1 N1 Zn1 116.52(13) . . ?
C4 N1 Zn1 122.11(13) . . ?
C7 N2 P1 120.49(14) . . ?
C7 N2 Zn1 126.67(13) . . ?
P1 N2 Zn1 111.04(9) . . ?
C1 N3 C22 127.03(16) . . ?
N2 P1 C16 112.23(9) . . ?
N2 P1 C10 113.72(9) . . ?
C16 P1 C10 108.70(9) . . ?
N2 P1 C1 106.91(9) . . ?
C16 P1 C1 106.91(9) . . ?
C10 P1 C1 108.06(8) . . ?

_refine_diff_density_max         1.545
_refine_diff_density_min         -1.432
_refine_diff_density_rms         0.090

_shelxl_version_number           2014-3



