# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ct2_100k_0m
_database_code_depnum_ccdc_archive 'CCDC 1949306'
loop_
_audit_author_name
_audit_author_address
'Giancarlo Terraneo'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H28 N O3 P'
_chemical_formula_sum            'C35 H28 N O3 P'
_chemical_formula_weight         541.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.7093(5)
_cell_length_b                   14.9332(9)
_cell_length_c                   23.5619(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2712.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6351
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      23.93

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_T_max  0.7461

_exptl_special_details           
;
 Bruker KRYOFLEX low temperature device
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33737
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.230
_diffrn_reflns_theta_max         30.616
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8296
_reflns_number_gt                6406
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.998

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
'Some reflections under the beamstop have been omitted'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.0944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         8296
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
N1 N 0.4734(3) 0.57886(13) 0.67975(8) 0.0142(4) Uani 1 1 d . . . . .
P1 P 0.66847(8) 0.61796(4) 0.68924(3) 0.01575(14) Uani 1 1 d . . . . .
O3 O 0.6674(2) 0.69875(11) 0.73361(7) 0.0189(4) Uani 1 1 d . . . . .
O2 O 0.7983(2) 0.54967(11) 0.70263(7) 0.0211(4) Uani 1 1 d . . . . .
O1 O 0.7041(2) 0.67730(11) 0.63444(7) 0.0184(4) Uani 1 1 d . . . . .
C1 C 0.6181(3) 0.66010(15) 0.58288(10) 0.0163(5) Uani 1 1 d . . . . .
C3 C 0.6395(4) 0.65355(17) 0.48258(11) 0.0241(6) Uani 1 1 d . . . . .
H3 H 0.703532 0.659846 0.449372 0.029 Uiso 1 1 calc R U . . .
C2 C 0.7168(3) 0.66980(16) 0.53335(11) 0.0214(6) Uani 1 1 d . . . . .
H2 H 0.832630 0.686970 0.535190 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4634(3) 0.62721(17) 0.47922(10) 0.0201(5) Uani 1 1 d . . . . .
C5 C 0.3840(4) 0.60685(18) 0.42653(11) 0.0263(6) Uani 1 1 d . . . . .
H5 H 0.447971 0.611902 0.393225 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2154(4) 0.57999(19) 0.42398(11) 0.0286(7) Uani 1 1 d . . . . .
H6 H 0.165812 0.566019 0.389105 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1158(4) 0.57327(18) 0.47384(11) 0.0245(6) Uani 1 1 d . . . . .
H7 H 0.000434 0.555481 0.471643 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1873(3) 0.59265(16) 0.52541(10) 0.0196(5) Uani 1 1 d . . . . .
H8 H 0.119578 0.588302 0.557961 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3640(3) 0.61942(15) 0.53007(9) 0.0161(5) Uani 1 1 d . . . . .
C10 C 0.4462(3) 0.63739(15) 0.58330(10) 0.0149(5) Uani 1 1 d . . . . .
C11 C 0.3544(3) 0.62718(16) 0.64019(9) 0.0136(5) Uani 1 1 d . . . . .
H11 H 0.254306 0.588013 0.633813 0.016 Uiso 1 1 calc R U . . .
C12 C 0.4220(3) 0.48850(15) 0.70183(9) 0.0141(5) Uani 1 1 d . . . . .
H12 H 0.529378 0.455236 0.709056 0.017 Uiso 1 1 calc R U . . .
C13 C 0.3277(4) 0.49701(17) 0.75833(9) 0.0194(5) Uani 1 1 d . . . . .
H13A H 0.223375 0.531127 0.753152 0.029 Uiso 1 1 calc R U . . .
H13B H 0.401351 0.526808 0.785219 0.029 Uiso 1 1 calc R U . . .
H13C H 0.298943 0.438447 0.772262 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5813(3) 0.42671(16) 0.59285(10) 0.0179(5) Uani 1 1 d . . . . .
H14 H 0.650491 0.453849 0.620214 0.021 Uiso 1 1 calc R U . . .
C15 C 0.3213(3) 0.43669(14) 0.65655(9) 0.0143(5) Uani 1 1 d . . . . .
C16 C 0.1483(3) 0.41807(16) 0.66435(10) 0.0173(5) Uani 1 1 d . . . . .
H16 H 0.094829 0.435701 0.697910 0.021 Uiso 1 1 calc R U . . .
C17 C 0.0498(3) 0.37292(17) 0.62279(11) 0.0214(5) Uani 1 1 d . . . . .
H17 H -0.066417 0.360045 0.629517 0.026 Uiso 1 1 calc R U . . .
C18 C 0.1244(3) 0.34825(16) 0.57300(11) 0.0206(6) Uani 1 1 d . . . . .
H18 H 0.058487 0.319248 0.545529 0.025 Uiso 1 1 calc R U . . .
C19 C 0.3031(3) 0.36646(16) 0.56252(10) 0.0187(5) Uani 1 1 d . . . . .
C20 C 0.3819(4) 0.34204(17) 0.51032(11) 0.0240(6) Uani 1 1 d . . . . .
H20 H 0.316549 0.312734 0.482827 0.029 Uiso 1 1 calc R U . . .
C21 C 0.5515(4) 0.36086(17) 0.49994(11) 0.0258(6) Uani 1 1 d . . . . .
H21 H 0.600537 0.345669 0.465193 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6527(4) 0.40323(16) 0.54163(11) 0.0221(6) Uani 1 1 d . . . . .
H22 H 0.768905 0.415447 0.534450 0.027 Uiso 1 1 calc R U . . .
C23 C 0.4030(3) 0.41024(15) 0.60485(10) 0.0148(5) Uani 1 1 d . . . . .
C24 C 0.6185(4) 0.67978(16) 0.79025(10) 0.0205(6) Uani 1 1 d . . . . .
C25 C 0.7188(4) 0.62432(19) 0.82363(11) 0.0273(6) Uani 1 1 d . . . . .
H25 H 0.822450 0.600768 0.810052 0.033 Uiso 1 1 calc R U . . .
C26 C 0.6609(5) 0.60443(18) 0.87819(11) 0.0345(7) Uani 1 1 d . . . . .
H26 H 0.725874 0.566554 0.901193 0.041 Uiso 1 1 calc R U . . .
C27 C 0.5081(5) 0.64033(19) 0.89847(12) 0.0361(8) Uani 1 1 d . . . . .
H27 H 0.469421 0.625802 0.934703 0.043 Uiso 1 1 calc R U . . .
C28 C 0.4126(4) 0.69792(19) 0.86484(12) 0.0322(7) Uani 1 1 d . . . . .
H28 H 0.311530 0.723548 0.878997 0.039 Uiso 1 1 calc R U . . .
C29 C 0.4667(4) 0.71778(17) 0.81000(11) 0.0249(6) Uani 1 1 d . . . . .
H29 H 0.401919 0.755874 0.787059 0.030 Uiso 1 1 calc R U . . .
C30 C 0.2846(3) 0.71469(16) 0.66453(9) 0.0142(5) Uani 1 1 d . . . . .
C31 C 0.1327(3) 0.71288(16) 0.69638(10) 0.0179(5) Uani 1 1 d . . . . .
H31 H 0.073447 0.659144 0.701131 0.022 Uiso 1 1 calc R U . . .
C32 C 0.0683(3) 0.79074(17) 0.72122(11) 0.0219(6) Uani 1 1 d . . . . .
H32 H -0.033502 0.788827 0.742334 0.026 Uiso 1 1 calc R U . . .
C33 C 0.1561(3) 0.87110(16) 0.71448(10) 0.0203(5) Uani 1 1 d . . . . .
H33 H 0.114702 0.922965 0.731628 0.024 Uiso 1 1 calc R U . . .
C34 C 0.3059(3) 0.87357(16) 0.68198(10) 0.0178(5) Uani 1 1 d . . . . .
H34 H 0.364505 0.927451 0.677042 0.021 Uiso 1 1 calc R U . . .
C35 C 0.3689(3) 0.79644(15) 0.65685(10) 0.0152(5) Uani 1 1 d . . . . .
H35 H 0.468465 0.799110 0.634627 0.018 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 C11 1.494(3) . ?
N1 C12 1.499(3) . ?
N1 P1 1.629(2) . ?
P1 O2 1.4634(18) . ?
P1 O1 1.5898(17) . ?
P1 O3 1.5965(17) . ?
O3 C24 1.415(3) . ?
O1 C1 1.408(3) . ?
C1 C10 1.367(3) . ?
C1 C2 1.401(3) . ?
C3 C2 1.358(4) . ?
C3 C4 1.416(4) . ?
C4 C5 1.417(4) . ?
C4 C9 1.427(3) . ?
C5 C6 1.362(4) . ?
C6 C7 1.407(4) . ?
C7 C8 1.365(3) . ?
C8 C9 1.424(4) . ?
C9 C10 1.431(3) . ?
C10 C11 1.523(3) . ?
C11 C30 1.525(3) . ?
C12 C13 1.522(3) . ?
C12 C15 1.530(3) . ?
C14 C22 1.372(3) . ?
C14 C23 1.425(4) . ?
C15 C16 1.375(4) . ?
C15 C23 1.427(3) . ?
C16 C17 1.411(3) . ?
C17 C18 1.358(4) . ?
C18 C19 1.426(4) . ?
C19 C20 1.419(3) . ?
C19 C23 1.419(3) . ?
C20 C21 1.359(4) . ?
C21 C22 1.405(4) . ?
C24 C25 1.379(4) . ?
C24 C29 1.382(4) . ?
C25 C26 1.393(4) . ?
C26 C27 1.379(5) . ?
C27 C28 1.382(4) . ?
C28 C29 1.390(4) . ?
C30 C31 1.391(3) . ?
C30 C35 1.395(3) . ?
C31 C32 1.393(3) . ?
C32 C33 1.387(3) . ?
C33 C34 1.387(3) . ?
C34 C35 1.383(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C12 119.30(18) . . ?
C11 N1 P1 118.64(15) . . ?
C12 N1 P1 121.25(15) . . ?
O2 P1 O1 116.45(10) . . ?
O2 P1 O3 112.88(10) . . ?
O1 P1 O3 96.41(9) . . ?
O2 P1 N1 114.29(10) . . ?
O1 P1 N1 104.36(10) . . ?
O3 P1 N1 110.86(10) . . ?
C24 O3 P1 117.89(14) . . ?
C1 O1 P1 121.17(15) . . ?
C10 C1 C2 123.9(2) . . ?
C10 C1 O1 119.7(2) . . ?
C2 C1 O1 116.3(2) . . ?
C2 C3 C4 121.3(2) . . ?
C3 C2 C1 118.5(2) . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 C9 119.4(2) . . ?
C5 C4 C9 119.1(2) . . ?
C6 C5 C4 120.9(2) . . ?
C5 C6 C7 120.3(3) . . ?
C8 C7 C6 120.5(3) . . ?
C7 C8 C9 120.9(2) . . ?
C8 C9 C4 118.2(2) . . ?
C8 C9 C10 123.0(2) . . ?
C4 C9 C10 118.9(2) . . ?
C1 C10 C9 118.0(2) . . ?
C1 C10 C11 118.8(2) . . ?
C9 C10 C11 123.1(2) . . ?
N1 C11 C10 108.20(18) . . ?
N1 C11 C30 113.33(18) . . ?
C10 C11 C30 114.15(19) . . ?
N1 C12 C13 110.75(19) . . ?
N1 C12 C15 110.32(18) . . ?
C13 C12 C15 114.2(2) . . ?
C22 C14 C23 121.2(2) . . ?
C16 C15 C23 119.1(2) . . ?
C16 C15 C12 120.1(2) . . ?
C23 C15 C12 120.8(2) . . ?
C15 C16 C17 121.8(2) . . ?
C18 C17 C16 120.1(2) . . ?
C17 C18 C19 120.5(2) . . ?
C20 C19 C23 119.7(2) . . ?
C20 C19 C18 121.0(2) . . ?
C23 C19 C18 119.3(2) . . ?
C21 C20 C19 120.9(2) . . ?
C20 C21 C22 120.1(2) . . ?
C14 C22 C21 120.5(3) . . ?
C19 C23 C14 117.6(2) . . ?
C19 C23 C15 119.2(2) . . ?
C14 C23 C15 123.2(2) . . ?
C25 C24 C29 122.0(2) . . ?
C25 C24 O3 120.6(2) . . ?
C29 C24 O3 117.4(2) . . ?
C24 C25 C26 118.3(3) . . ?
C27 C26 C25 120.7(3) . . ?
C26 C27 C28 119.9(3) . . ?
C27 C28 C29 120.4(3) . . ?
C24 C29 C28 118.7(3) . . ?
C31 C30 C35 118.6(2) . . ?
C31 C30 C11 118.9(2) . . ?
C35 C30 C11 122.4(2) . . ?
C30 C31 C32 120.7(2) . . ?
C33 C32 C31 120.0(2) . . ?
C34 C33 C32 119.5(2) . . ?
C35 C34 C33 120.5(2) . . ?
C34 C35 C30 120.6(2) . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_am21
_database_code_depnum_ccdc_archive 'CCDC 1949309'
loop_
_audit_author_name
_audit_author_address
'Giancarlo Terraneo'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 Cl N O3 P'
_chemical_formula_sum            'C27 H25 Cl N O3 P'
_chemical_formula_weight         477.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.1528(7)
_cell_length_b                   15.2774(16)
_cell_length_c                   43.271(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4728.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6468
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.60

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.6261
_exptl_absorpt_correction_T_max  0.7459

_exptl_special_details           
;
 
 Bruker KRYOFLEX low temperature device. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18644
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_theta_min         1.942
_diffrn_reflns_theta_max         29.790
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 0.900
_reflns_number_total             11601
_reflns_number_gt                9465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_max     0.716
_reflns_Friedel_fraction_full    0.808

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0632P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2966 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         11601
_refine_ls_number_parameters     599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Cl1 Cl -0.39173(15) 0.63453(10) 0.59538(3) 0.0566(4) Uani 1 1 d . . . . .
Cl2 Cl -0.27107(16) 1.12245(7) 0.79728(2) 0.0381(2) Uani 1 1 d . . . . .
P1 P -0.34003(12) 0.53027(6) 0.53952(2) 0.02135(19) Uani 1 1 d . . . . .
P2 P -0.26513(11) 1.00280(6) 0.74393(2) 0.01970(18) Uani 1 1 d . . . . .
O1 O 0.1657(3) 0.40120(16) 0.65587(4) 0.0219(5) Uani 1 1 d . . . . .
O2 O -0.3222(3) 0.42631(16) 0.53417(5) 0.0225(5) Uani 1 1 d . . . . .
O3 O -0.4920(3) 0.57578(18) 0.52344(6) 0.0299(6) Uani 1 1 d . . . . .
O4 O 0.4016(4) 0.7945(2) 0.83733(5) 0.0345(7) Uani 1 1 d . . . . .
O5 O -0.2764(3) 0.89817(17) 0.74223(5) 0.0221(5) Uani 1 1 d . . . . .
O6 O -0.4027(3) 1.05275(19) 0.72595(5) 0.0291(6) Uani 1 1 d . . . . .
N1 N -0.1296(4) 0.56612(19) 0.53167(6) 0.0191(6) Uani 1 1 d . . . . .
N2 N -0.0454(3) 1.02096(19) 0.73467(5) 0.0175(5) Uani 1 1 d . . . . .
C1 C 0.1470(5) 0.3126(2) 0.66574(7) 0.0254(7) Uani 1 1 d . . . . .
H25 H 0.023179 0.290579 0.659903 0.038 Uiso 1 1 calc R U . . .
H3 H 0.161186 0.309478 0.688238 0.038 Uiso 1 1 calc R U . . .
H1 H 0.243595 0.276729 0.655856 0.038 Uiso 1 1 calc R U . . .
C2 C 0.1350(4) 0.4190(2) 0.62522(6) 0.0171(6) Uani 1 1 d . . . . .
C3 C 0.0985(4) 0.3563(2) 0.60296(7) 0.0189(6) Uani 1 1 d . . . . .
H4 H 0.096415 0.296013 0.608279 0.023 Uiso 1 1 calc R U . . .
C4 C 0.0647(4) 0.3828(2) 0.57251(7) 0.0177(6) Uani 1 1 d . . . . .
H5 H 0.037140 0.339844 0.557304 0.021 Uiso 1 1 calc R U . . .
C5 C 0.0703(4) 0.4697(2) 0.56407(6) 0.0160(6) Uani 1 1 d . . . . .
C6 C 0.0260(4) 0.5015(2) 0.53136(6) 0.0156(6) Uani 1 1 d . . . . .
H22 H 0.139662 0.531769 0.523195 0.019 Uiso 1 1 calc R U . . .
C7 C -0.1001(5) 0.6491(2) 0.51440(7) 0.0228(7) Uani 1 1 d . . . . .
H18 H -0.223586 0.679630 0.513495 0.027 Uiso 1 1 calc R U . . .
C8 C -0.0416(6) 0.6299(2) 0.48096(7) 0.0279(8) Uani 1 1 d . . . . .
C9 C -0.1777(7) 0.5991(3) 0.46083(9) 0.0400(10) Uani 1 1 d . . . . .
H17 H -0.303095 0.591813 0.467599 0.048 Uiso 1 1 calc R U . . .
C10 C -0.1267(9) 0.5789(3) 0.43015(9) 0.0527(13) Uani 1 1 d . . . . .
H16 H -0.218580 0.558410 0.416045 0.063 Uiso 1 1 calc R U . . .
C11 C 0.0571(9) 0.5887(4) 0.42048(9) 0.0573(15) Uani 1 1 d . . . . .
H2 H 0.091007 0.573451 0.399951 0.069 Uiso 1 1 calc R U . . .
C12 C 0.1445(4) 0.5064(2) 0.61709(6) 0.0188(6) Uani 1 1 d . . . . .
H24 H 0.173183 0.549123 0.632307 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1124(4) 0.5318(2) 0.58681(6) 0.0180(6) Uani 1 1 d . . . . .
H23 H 0.119016 0.591964 0.581432 0.022 Uiso 1 1 calc R U . . .
C14 C -0.2006(4) 0.3945(2) 0.51134(7) 0.0183(6) Uani 1 1 d . . . . .
C15 C -0.0244(4) 0.4288(2) 0.50891(6) 0.0156(6) Uani 1 1 d . . . . .
C16 C 0.0949(5) 0.3977(2) 0.48494(6) 0.0189(6) Uani 1 1 d . . . . .
C17 C 0.2773(5) 0.4316(2) 0.47944(6) 0.0207(7) Uani 1 1 d . . . . .
H11 H 0.325910 0.475769 0.492659 0.025 Uiso 1 1 calc R U . . .
C18 C 0.3838(5) 0.4014(3) 0.45532(7) 0.0262(8) Uani 1 1 d . . . . .
H10 H 0.502980 0.426581 0.451431 0.031 Uiso 1 1 calc R U . . .
C19 C 0.3181(6) 0.3340(3) 0.43647(7) 0.0329(9) Uani 1 1 d . . . . .
H9 H 0.394113 0.312550 0.420136 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1455(6) 0.2988(3) 0.44135(7) 0.0327(9) Uani 1 1 d . . . . .
H8 H 0.103557 0.252169 0.428595 0.039 Uiso 1 1 calc R U . . .
C21 C 0.0279(5) 0.3306(2) 0.46508(7) 0.0235(7) Uani 1 1 d . . . . .
C22 C -0.1528(5) 0.2948(2) 0.47000(8) 0.0286(8) Uani 1 1 d . . . . .
H6 H -0.194982 0.248030 0.457339 0.034 Uiso 1 1 calc R U . . .
C23 C -0.2666(5) 0.3265(2) 0.49259(7) 0.0239(7) Uani 1 1 d . . . . .
H7 H -0.388297 0.303074 0.495558 0.029 Uiso 1 1 calc R U . . .
C24 C -0.3785(5) 0.5261(3) 0.58064(8) 0.0327(9) Uani 1 1 d . . . . .
H12 H -0.496344 0.494494 0.585090 0.039 Uiso 1 1 calc R U . . .
H13 H -0.274650 0.494237 0.590757 0.039 Uiso 1 1 calc R U . . .
C25 C 0.1900(7) 0.6203(3) 0.44037(8) 0.0445(12) Uani 1 1 d . . . . .
H14 H 0.315202 0.628084 0.433575 0.053 Uiso 1 1 calc R U . . .
C26 C 0.1399(6) 0.6410(3) 0.47078(8) 0.0339(9) Uani 1 1 d . . . . .
H15 H 0.231852 0.662954 0.484591 0.041 Uiso 1 1 calc R U . . .
C27 C 0.0335(5) 0.7091(2) 0.53168(8) 0.0265(8) Uani 1 1 d . . . . .
H21 H -0.020567 0.724569 0.551756 0.040 Uiso 1 1 calc R U . . .
H20 H 0.054176 0.762418 0.519560 0.040 Uiso 1 1 calc R U . . .
H19 H 0.152943 0.678983 0.534841 0.040 Uiso 1 1 calc R U . . .
C28 C 0.1330(7) 1.0822(3) 0.62470(8) 0.0409(11) Uani 1 1 d . . . . .
H26 H 0.157785 1.077559 0.603190 0.049 Uiso 1 1 calc R U . . .
C29 C -0.0487(7) 1.0778(3) 0.63533(8) 0.0422(11) Uani 1 1 d . . . . .
H41 H -0.148442 1.069091 0.621165 0.051 Uiso 1 1 calc R U . . .
C30 C -0.0858(6) 1.0862(3) 0.66654(8) 0.0315(9) Uani 1 1 d . . . . .
H44 H -0.211088 1.083437 0.673763 0.038 Uiso 1 1 calc R U . . .
C31 C 0.0602(5) 1.0986(2) 0.68748(7) 0.0221(7) Uani 1 1 d . . . . .
C32 C 0.0115(5) 1.1077(2) 0.72176(7) 0.0202(7) Uani 1 1 d . . . . .
H48 H -0.099982 1.147027 0.723136 0.024 Uiso 1 1 calc R U . . .
C33 C 0.0837(4) 0.9465(2) 0.72948(6) 0.0174(6) Uani 1 1 d . . . . .
H49 H 0.192122 0.969786 0.717419 0.021 Uiso 1 1 calc R U . . .
C34 C 0.1630(4) 0.9075(2) 0.75913(6) 0.0168(6) Uani 1 1 d . . . . .
C35 C 0.1678(4) 0.9550(2) 0.78659(6) 0.0194(6) Uani 1 1 d . . . . .
H30 H 0.116316 1.012321 0.787169 0.023 Uiso 1 1 calc R U . . .
C36 C 0.2472(5) 0.9197(3) 0.81320(7) 0.0232(7) Uani 1 1 d . . . . .
H29 H 0.247905 0.952365 0.831881 0.028 Uiso 1 1 calc R U . . .
C37 C 0.3247(4) 0.8371(3) 0.81229(7) 0.0233(7) Uani 1 1 d . . . . .
C38 C 0.4080(6) 0.8427(4) 0.86555(8) 0.0439(13) Uani 1 1 d . . . . .
H50 H 0.476787 0.897369 0.862312 0.066 Uiso 1 1 calc R U . . .
H27 H 0.471154 0.807708 0.881413 0.066 Uiso 1 1 calc R U . . .
H28 H 0.280370 0.855988 0.872321 0.066 Uiso 1 1 calc R U . . .
C39 C 0.2435(4) 0.8251(2) 0.75876(7) 0.0188(6) Uani 1 1 d . . . . .
H32 H 0.242582 0.792231 0.740120 0.023 Uiso 1 1 calc R U . . .
C40 C 0.3255(5) 0.7893(2) 0.78495(7) 0.0241(7) Uani 1 1 d . . . . .
H31 H 0.381366 0.732982 0.784207 0.029 Uiso 1 1 calc R U . . .
C41 C -0.1933(4) 0.8574(2) 0.71655(7) 0.0210(7) Uani 1 1 d . . . . .
C42 C -0.3008(5) 0.7961(2) 0.70038(8) 0.0260(7) Uani 1 1 d . . . . .
H38 H -0.423444 0.781651 0.707074 0.031 Uiso 1 1 calc R U . . .
C43 C -0.2260(5) 0.7575(3) 0.67486(8) 0.0300(8) Uani 1 1 d . . . . .
H37 H -0.297022 0.715813 0.663570 0.036 Uiso 1 1 calc R U . . .
C44 C -0.0417(5) 0.7794(3) 0.66498(7) 0.0262(8) Uani 1 1 d . . . . .
C45 C 0.0679(5) 0.8396(2) 0.68248(7) 0.0200(7) Uani 1 1 d . . . . .
C46 C -0.0127(4) 0.8794(2) 0.70914(6) 0.0180(6) Uani 1 1 d . . . . .
C47 C 0.2526(5) 0.8584(2) 0.67229(7) 0.0231(7) Uani 1 1 d . . . . .
H36 H 0.328904 0.897570 0.683754 0.028 Uiso 1 1 calc R U . . .
C48 C 0.3207(5) 0.8200(3) 0.64597(7) 0.0300(8) Uani 1 1 d . . . . .
H35 H 0.444645 0.832781 0.639472 0.036 Uiso 1 1 calc R U . . .
C49 C 0.2111(6) 0.7624(3) 0.62847(8) 0.0345(9) Uani 1 1 d . . . . .
H34 H 0.260309 0.737345 0.610091 0.041 Uiso 1 1 calc R U . . .
C50 C 0.0345(6) 0.7422(3) 0.63769(8) 0.0330(9) Uani 1 1 d . . . . .
H33 H -0.038547 0.702853 0.625743 0.040 Uiso 1 1 calc R U . . .
C51 C -0.3076(5) 1.0126(3) 0.78480(7) 0.0243(7) Uani 1 1 d . . . . .
H39 H -0.437694 0.994803 0.789424 0.029 Uiso 1 1 calc R U . . .
H40 H -0.222369 0.972967 0.796184 0.029 Uiso 1 1 calc R U . . .
C52 C 0.2789(6) 1.0934(3) 0.64520(8) 0.0355(10) Uani 1 1 d . . . . .
H42 H 0.403763 1.095294 0.637774 0.043 Uiso 1 1 calc R U . . .
C53 C 0.2438(5) 1.1018(2) 0.67692(7) 0.0257(7) Uani 1 1 d . . . . .
H43 H 0.344089 1.109618 0.691034 0.031 Uiso 1 1 calc R U . . .
C54 C 0.1649(5) 1.1489(2) 0.74126(7) 0.0243(7) Uani 1 1 d . . . . .
H46 H 0.118911 1.157982 0.762356 0.037 Uiso 1 1 calc R U . . .
H47 H 0.200907 1.205292 0.732271 0.037 Uiso 1 1 calc R U . . .
H45 H 0.273695 1.109932 0.741732 0.037 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
Cl1 C24 1.778(5) . ?
Cl2 C51 1.783(4) . ?
P1 O3 1.466(2) . ?
P1 O2 1.610(3) . ?
P1 N1 1.637(3) . ?
P1 C24 1.802(3) . ?
P2 O6 1.468(2) . ?
P2 O5 1.602(3) . ?
P2 N2 1.646(3) . ?
P2 C51 1.801(3) . ?
O1 C2 1.371(3) . ?
O1 C1 1.426(4) . ?
O2 C14 1.403(4) . ?
O4 C37 1.379(4) . ?
O4 C38 1.426(5) . ?
O5 C41 1.405(4) . ?
N1 C7 1.486(4) . ?
N1 C6 1.487(4) . ?
N2 C33 1.482(4) . ?
N2 C32 1.494(4) . ?
C1 H25 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C12 1.381(5) . ?
C2 C3 1.383(4) . ?
C3 C4 1.399(4) . ?
C3 H4 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H5 0.9500 . ?
C5 C13 1.399(4) . ?
C5 C6 1.530(4) . ?
C6 C15 1.518(4) . ?
C6 H22 1.0000 . ?
C7 C27 1.521(5) . ?
C7 C8 1.534(4) . ?
C7 H18 1.0000 . ?
C8 C26 1.381(6) . ?
C8 C9 1.388(5) . ?
C9 C10 1.411(6) . ?
C9 H17 0.9500 . ?
C10 C11 1.388(8) . ?
C10 H16 0.9500 . ?
C11 C25 1.370(7) . ?
C11 H2 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H24 0.9500 . ?
C13 H23 0.9500 . ?
C14 C15 1.369(4) . ?
C14 C23 1.400(4) . ?
C15 C16 1.425(4) . ?
C16 C21 1.422(5) . ?
C16 C17 1.424(5) . ?
C17 C18 1.372(4) . ?
C17 H11 0.9500 . ?
C18 C19 1.395(5) . ?
C18 H10 0.9500 . ?
C19 C20 1.363(6) . ?
C19 H9 0.9500 . ?
C20 C21 1.413(5) . ?
C20 H8 0.9500 . ?
C21 C22 1.419(5) . ?
C22 C23 1.361(5) . ?
C22 H6 0.9500 . ?
C23 H7 0.9500 . ?
C24 H12 0.9900 . ?
C24 H13 0.9900 . ?
C25 C26 1.400(5) . ?
C25 H14 0.9500 . ?
C26 H15 0.9500 . ?
C27 H21 0.9800 . ?
C27 H20 0.9800 . ?
C27 H19 0.9800 . ?
C28 C52 1.380(6) . ?
C28 C29 1.380(6) . ?
C28 H26 0.9500 . ?
C29 C30 1.382(5) . ?
C29 H41 0.9500 . ?
C30 C31 1.396(5) . ?
C30 H44 0.9500 . ?
C31 C53 1.391(5) . ?
C31 C32 1.530(4) . ?
C32 C54 1.521(5) . ?
C32 H48 1.0000 . ?
C33 C46 1.517(4) . ?
C33 C34 1.525(4) . ?
C33 H49 1.0000 . ?
C34 C39 1.384(5) . ?
C34 C35 1.393(4) . ?
C35 C36 1.392(4) . ?
C35 H30 0.9500 . ?
C36 C37 1.379(5) . ?
C36 H29 0.9500 . ?
C37 C40 1.390(5) . ?
C38 H50 0.9800 . ?
C38 H27 0.9800 . ?
C38 H28 0.9800 . ?
C39 C40 1.388(4) . ?
C39 H32 0.9500 . ?
C40 H31 0.9500 . ?
C41 C46 1.372(4) . ?
C41 C42 1.400(5) . ?
C42 C43 1.361(5) . ?
C42 H38 0.9500 . ?
C43 C44 1.425(5) . ?
C43 H37 0.9500 . ?
C44 C50 1.419(5) . ?
C44 C45 1.427(5) . ?
C45 C47 1.422(5) . ?
C45 C46 1.426(4) . ?
C47 C48 1.370(4) . ?
C47 H36 0.9500 . ?
C48 C49 1.402(6) . ?
C48 H35 0.9500 . ?
C49 C50 1.360(6) . ?
C49 H34 0.9500 . ?
C50 H33 0.9500 . ?
C51 H39 0.9900 . ?
C51 H40 0.9900 . ?
C52 C53 1.401(4) . ?
C52 H42 0.9500 . ?
C53 H43 0.9500 . ?
C54 H46 0.9800 . ?
C54 H47 0.9800 . ?
C54 H45 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
O3 P1 O2 117.27(14) . . ?
O3 P1 N1 115.13(15) . . ?
O2 P1 N1 103.13(13) . . ?
O3 P1 C24 111.86(17) . . ?
O2 P1 C24 96.85(18) . . ?
N1 P1 C24 110.93(15) . . ?
O6 P2 O5 117.42(15) . . ?
O6 P2 N2 115.05(15) . . ?
O5 P2 N2 101.84(14) . . ?
O6 P2 C51 111.37(15) . . ?
O5 P2 C51 96.85(15) . . ?
N2 P2 C51 112.72(14) . . ?
C2 O1 C1 117.6(3) . . ?
C14 O2 P1 119.5(2) . . ?
C37 O4 C38 116.2(3) . . ?
C41 O5 P2 117.2(2) . . ?
C7 N1 C6 117.1(3) . . ?
C7 N1 P1 121.3(2) . . ?
C6 N1 P1 117.9(2) . . ?
C33 N2 C32 117.0(2) . . ?
C33 N2 P2 120.2(2) . . ?
C32 N2 P2 120.0(2) . . ?
O1 C1 H25 109.5 . . ?
O1 C1 H3 109.5 . . ?
H25 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H25 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C2 C12 115.5(3) . . ?
O1 C2 C3 124.5(3) . . ?
C12 C2 C3 120.0(3) . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H4 120.4 . . ?
C4 C3 H4 120.4 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H5 119.2 . . ?
C3 C4 H5 119.2 . . ?
C4 C5 C13 118.2(3) . . ?
C4 C5 C6 123.0(3) . . ?
C13 C5 C6 118.7(3) . . ?
N1 C6 C15 108.3(2) . . ?
N1 C6 C5 110.9(2) . . ?
C15 C6 C5 114.1(3) . . ?
N1 C6 H22 107.8 . . ?
C15 C6 H22 107.8 . . ?
C5 C6 H22 107.8 . . ?
N1 C7 C27 110.9(3) . . ?
N1 C7 C8 110.5(3) . . ?
C27 C7 C8 114.0(3) . . ?
N1 C7 H18 107.0 . . ?
C27 C7 H18 107.0 . . ?
C8 C7 H18 107.0 . . ?
C26 C8 C9 120.0(4) . . ?
C26 C8 C7 122.2(3) . . ?
C9 C8 C7 117.7(4) . . ?
C8 C9 C10 118.9(5) . . ?
C8 C9 H17 120.6 . . ?
C10 C9 H17 120.6 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H16 119.8 . . ?
C9 C10 H16 119.8 . . ?
C25 C11 C10 120.4(4) . . ?
C25 C11 H2 119.8 . . ?
C10 C11 H2 119.8 . . ?
C2 C12 C13 120.2(3) . . ?
C2 C12 H24 119.9 . . ?
C13 C12 H24 119.9 . . ?
C12 C13 C5 120.7(3) . . ?
C12 C13 H23 119.6 . . ?
C5 C13 H23 119.6 . . ?
C15 C14 C23 123.4(3) . . ?
C15 C14 O2 119.4(3) . . ?
C23 C14 O2 117.1(3) . . ?
C14 C15 C16 118.6(3) . . ?
C14 C15 C6 116.7(3) . . ?
C16 C15 C6 124.6(3) . . ?
C21 C16 C17 118.1(3) . . ?
C21 C16 C15 118.6(3) . . ?
C17 C16 C15 123.3(3) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H11 119.6 . . ?
C16 C17 H11 119.6 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H10 119.8 . . ?
C19 C18 H10 119.8 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H9 119.8 . . ?
C18 C19 H9 119.8 . . ?
C19 C20 C21 121.1(4) . . ?
C19 C20 H8 119.5 . . ?
C21 C20 H8 119.5 . . ?
C20 C21 C22 121.3(3) . . ?
C20 C21 C16 119.1(3) . . ?
C22 C21 C16 119.6(3) . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H6 119.5 . . ?
C21 C22 H6 119.5 . . ?
C22 C23 C14 118.6(3) . . ?
C22 C23 H7 120.7 . . ?
C14 C23 H7 120.7 . . ?
Cl1 C24 P1 109.2(2) . . ?
Cl1 C24 H12 109.8 . . ?
P1 C24 H12 109.8 . . ?
Cl1 C24 H13 109.8 . . ?
P1 C24 H13 109.8 . . ?
H12 C24 H13 108.3 . . ?
C11 C25 C26 119.5(5) . . ?
C11 C25 H14 120.3 . . ?
C26 C25 H14 120.3 . . ?
C8 C26 C25 120.8(4) . . ?
C8 C26 H15 119.6 . . ?
C25 C26 H15 119.6 . . ?
C7 C27 H21 109.5 . . ?
C7 C27 H20 109.5 . . ?
H21 C27 H20 109.5 . . ?
C7 C27 H19 109.5 . . ?
H21 C27 H19 109.5 . . ?
H20 C27 H19 109.5 . . ?
C52 C28 C29 120.2(3) . . ?
C52 C28 H26 119.9 . . ?
C29 C28 H26 119.9 . . ?
C28 C29 C30 120.1(4) . . ?
C28 C29 H41 119.9 . . ?
C30 C29 H41 119.9 . . ?
C29 C30 C31 120.2(4) . . ?
C29 C30 H44 119.9 . . ?
C31 C30 H44 119.9 . . ?
C53 C31 C30 119.8(3) . . ?
C53 C31 C32 122.1(3) . . ?
C30 C31 C32 118.1(3) . . ?
N2 C32 C54 110.9(2) . . ?
N2 C32 C31 110.1(3) . . ?
C54 C32 C31 114.3(3) . . ?
N2 C32 H48 107.1 . . ?
C54 C32 H48 107.1 . . ?
C31 C32 H48 107.1 . . ?
N2 C33 C46 108.9(2) . . ?
N2 C33 C34 113.9(2) . . ?
C46 C33 C34 113.1(3) . . ?
N2 C33 H49 106.8 . . ?
C46 C33 H49 106.8 . . ?
C34 C33 H49 106.8 . . ?
C39 C34 C35 118.3(3) . . ?
C39 C34 C33 120.1(3) . . ?
C35 C34 C33 121.5(3) . . ?
C36 C35 C34 120.9(3) . . ?
C36 C35 H30 119.6 . . ?
C34 C35 H30 119.6 . . ?
C37 C36 C35 119.7(3) . . ?
C37 C36 H29 120.2 . . ?
C35 C36 H29 120.2 . . ?
C36 C37 O4 124.8(3) . . ?
C36 C37 C40 120.4(3) . . ?
O4 C37 C40 114.8(3) . . ?
O4 C38 H50 109.5 . . ?
O4 C38 H27 109.5 . . ?
H50 C38 H27 109.5 . . ?
O4 C38 H28 109.5 . . ?
H50 C38 H28 109.5 . . ?
H27 C38 H28 109.5 . . ?
C34 C39 C40 121.6(3) . . ?
C34 C39 H32 119.2 . . ?
C40 C39 H32 119.2 . . ?
C39 C40 C37 119.1(3) . . ?
C39 C40 H31 120.4 . . ?
C37 C40 H31 120.4 . . ?
C46 C41 C42 124.3(3) . . ?
C46 C41 O5 118.3(3) . . ?
C42 C41 O5 117.4(3) . . ?
C43 C42 C41 118.7(3) . . ?
C43 C42 H38 120.7 . . ?
C41 C42 H38 120.7 . . ?
C42 C43 C44 120.4(3) . . ?
C42 C43 H37 119.8 . . ?
C44 C43 H37 119.8 . . ?
C50 C44 C43 120.8(3) . . ?
C50 C44 C45 119.2(3) . . ?
C43 C44 C45 120.0(3) . . ?
C47 C45 C46 122.7(3) . . ?
C47 C45 C44 118.4(3) . . ?
C46 C45 C44 118.8(3) . . ?
C41 C46 C45 117.8(3) . . ?
C41 C46 C33 117.2(3) . . ?
C45 C46 C33 125.0(3) . . ?
C48 C47 C45 120.1(3) . . ?
C48 C47 H36 119.9 . . ?
C45 C47 H36 119.9 . . ?
C47 C48 C49 121.3(4) . . ?
C47 C48 H35 119.4 . . ?
C49 C48 H35 119.4 . . ?
C50 C49 C48 120.2(3) . . ?
C50 C49 H34 119.9 . . ?
C48 C49 H34 119.9 . . ?
C49 C50 C44 120.7(4) . . ?
C49 C50 H33 119.6 . . ?
C44 C50 H33 119.6 . . ?
Cl2 C51 P2 110.55(19) . . ?
Cl2 C51 H39 109.5 . . ?
P2 C51 H39 109.5 . . ?
Cl2 C51 H40 109.5 . . ?
P2 C51 H40 109.5 . . ?
H39 C51 H40 108.1 . . ?
C28 C52 C53 120.4(4) . . ?
C28 C52 H42 119.8 . . ?
C53 C52 H42 119.8 . . ?
C31 C53 C52 119.2(3) . . ?
C31 C53 H43 120.4 . . ?
C52 C53 H43 120.4 . . ?
C32 C54 H46 109.5 . . ?
C32 C54 H47 109.5 . . ?
H46 C54 H47 109.5 . . ?
C32 C54 H45 109.5 . . ?
H46 C54 H45 109.5 . . ?
H47 C54 H45 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
O3 P1 O2 C14 94.8(2) . . . . ?
N1 P1 O2 C14 -32.9(2) . . . . ?
C24 P1 O2 C14 -146.3(2) . . . . ?
O6 P2 O5 C41 81.6(2) . . . . ?
N2 P2 O5 C41 -45.0(2) . . . . ?
C51 P2 O5 C41 -160.0(2) . . . . ?
O3 P1 N1 C7 11.2(3) . . . . ?
O2 P1 N1 C7 140.2(2) . . . . ?
C24 P1 N1 C7 -117.1(3) . . . . ?
O3 P1 N1 C6 -146.4(2) . . . . ?
O2 P1 N1 C6 -17.4(2) . . . . ?
C24 P1 N1 C6 85.3(3) . . . . ?
O6 P2 N2 C33 -131.9(2) . . . . ?
O5 P2 N2 C33 -3.8(2) . . . . ?
C51 P2 N2 C33 98.9(2) . . . . ?
O6 P2 N2 C32 28.6(3) . . . . ?
O5 P2 N2 C32 156.8(2) . . . . ?
C51 P2 N2 C32 -100.5(2) . . . . ?
C1 O1 C2 C12 176.5(3) . . . . ?
C1 O1 C2 C3 -4.2(5) . . . . ?
O1 C2 C3 C4 178.4(3) . . . . ?
C12 C2 C3 C4 -2.4(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C13 0.4(4) . . . . ?
C3 C4 C5 C6 -177.3(3) . . . . ?
C7 N1 C6 C15 -103.2(3) . . . . ?
P1 N1 C6 C15 55.4(3) . . . . ?
C7 N1 C6 C5 130.8(3) . . . . ?
P1 N1 C6 C5 -70.6(3) . . . . ?
C4 C5 C6 N1 122.5(3) . . . . ?
C13 C5 C6 N1 -55.3(4) . . . . ?
C4 C5 C6 C15 -0.2(4) . . . . ?
C13 C5 C6 C15 -177.9(3) . . . . ?
C6 N1 C7 C27 -74.1(3) . . . . ?
P1 N1 C7 C27 128.1(3) . . . . ?
C6 N1 C7 C8 53.3(4) . . . . ?
P1 N1 C7 C8 -104.5(3) . . . . ?
N1 C7 C8 C26 -105.5(4) . . . . ?
C27 C7 C8 C26 20.2(5) . . . . ?
N1 C7 C8 C9 73.5(4) . . . . ?
C27 C7 C8 C9 -160.9(3) . . . . ?
C26 C8 C9 C10 0.6(6) . . . . ?
C7 C8 C9 C10 -178.4(3) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C9 C10 C11 C25 -1.7(7) . . . . ?
O1 C2 C12 C13 -178.9(3) . . . . ?
C3 C2 C12 C13 1.8(5) . . . . ?
C2 C12 C13 C5 -0.1(5) . . . . ?
C4 C5 C13 C12 -1.0(4) . . . . ?
C6 C5 C13 C12 176.8(3) . . . . ?
P1 O2 C14 C15 45.0(4) . . . . ?
P1 O2 C14 C23 -136.7(3) . . . . ?
C23 C14 C15 C16 3.8(5) . . . . ?
O2 C14 C15 C16 -178.0(3) . . . . ?
C23 C14 C15 C6 -179.1(3) . . . . ?
O2 C14 C15 C6 -0.9(4) . . . . ?
N1 C6 C15 C14 -47.2(4) . . . . ?
C5 C6 C15 C14 76.8(3) . . . . ?
N1 C6 C15 C16 129.6(3) . . . . ?
C5 C6 C15 C16 -106.3(3) . . . . ?
C14 C15 C16 C21 -1.7(4) . . . . ?
C6 C15 C16 C21 -178.5(3) . . . . ?
C14 C15 C16 C17 177.1(3) . . . . ?
C6 C15 C16 C17 0.3(5) . . . . ?
C21 C16 C17 C18 1.2(5) . . . . ?
C15 C16 C17 C18 -177.6(3) . . . . ?
C16 C17 C18 C19 -2.8(5) . . . . ?
C17 C18 C19 C20 1.6(5) . . . . ?
C18 C19 C20 C21 1.2(6) . . . . ?
C19 C20 C21 C22 179.2(3) . . . . ?
C19 C20 C21 C16 -2.8(5) . . . . ?
C17 C16 C21 C20 1.5(5) . . . . ?
C15 C16 C21 C20 -179.6(3) . . . . ?
C17 C16 C21 C22 179.6(3) . . . . ?
C15 C16 C21 C22 -1.5(5) . . . . ?
C20 C21 C22 C23 -179.0(3) . . . . ?
C16 C21 C22 C23 3.0(5) . . . . ?
C21 C22 C23 C14 -1.1(5) . . . . ?
C15 C14 C23 C22 -2.4(5) . . . . ?
O2 C14 C23 C22 179.3(3) . . . . ?
O3 P1 C24 Cl1 -60.3(2) . . . . ?
O2 P1 C24 Cl1 176.61(17) . . . . ?
N1 P1 C24 Cl1 69.7(2) . . . . ?
C10 C11 C25 C26 1.3(7) . . . . ?
C9 C8 C26 C25 -1.0(6) . . . . ?
C7 C8 C26 C25 177.9(3) . . . . ?
C11 C25 C26 C8 0.0(6) . . . . ?
C52 C28 C29 C30 1.2(7) . . . . ?
C28 C29 C30 C31 -0.3(7) . . . . ?
C29 C30 C31 C53 -0.6(6) . . . . ?
C29 C30 C31 C32 179.8(4) . . . . ?
C33 N2 C32 C54 -75.4(3) . . . . ?
P2 N2 C32 C54 123.4(3) . . . . ?
C33 N2 C32 C31 52.0(3) . . . . ?
P2 N2 C32 C31 -109.1(3) . . . . ?
C53 C31 C32 N2 -106.7(4) . . . . ?
C30 C31 C32 N2 72.9(4) . . . . ?
C53 C31 C32 C54 18.8(5) . . . . ?
C30 C31 C32 C54 -161.6(3) . . . . ?
C32 N2 C33 C46 -115.3(3) . . . . ?
P2 N2 C33 C46 45.9(3) . . . . ?
C32 N2 C33 C34 117.5(3) . . . . ?
P2 N2 C33 C34 -81.3(3) . . . . ?
N2 C33 C34 C39 162.8(3) . . . . ?
C46 C33 C34 C39 37.8(4) . . . . ?
N2 C33 C34 C35 -21.5(4) . . . . ?
C46 C33 C34 C35 -146.5(3) . . . . ?
C39 C34 C35 C36 -1.7(5) . . . . ?
C33 C34 C35 C36 -177.5(3) . . . . ?
C34 C35 C36 C37 1.0(5) . . . . ?
C35 C36 C37 O4 -177.9(3) . . . . ?
C35 C36 C37 C40 0.6(5) . . . . ?
C38 O4 C37 C36 -3.3(5) . . . . ?
C38 O4 C37 C40 178.2(3) . . . . ?
C35 C34 C39 C40 0.8(5) . . . . ?
C33 C34 C39 C40 176.7(3) . . . . ?
C34 C39 C40 C37 0.7(5) . . . . ?
C36 C37 C40 C39 -1.4(5) . . . . ?
O4 C37 C40 C39 177.1(3) . . . . ?
P2 O5 C41 C46 50.6(4) . . . . ?
P2 O5 C41 C42 -130.1(3) . . . . ?
C46 C41 C42 C43 -2.7(5) . . . . ?
O5 C41 C42 C43 178.0(3) . . . . ?
C41 C42 C43 C44 0.1(5) . . . . ?
C42 C43 C44 C50 -177.4(4) . . . . ?
C42 C43 C44 C45 2.2(5) . . . . ?
C50 C44 C45 C47 -1.8(5) . . . . ?
C43 C44 C45 C47 178.7(3) . . . . ?
C50 C44 C45 C46 177.4(3) . . . . ?
C43 C44 C45 C46 -2.2(5) . . . . ?
C42 C41 C46 C45 2.6(5) . . . . ?
O5 C41 C46 C45 -178.1(3) . . . . ?
C42 C41 C46 C33 -179.3(3) . . . . ?
O5 C41 C46 C33 0.0(4) . . . . ?
C47 C45 C46 C41 179.0(3) . . . . ?
C44 C45 C46 C41 -0.1(5) . . . . ?
C47 C45 C46 C33 1.0(5) . . . . ?
C44 C45 C46 C33 -178.1(3) . . . . ?
N2 C33 C46 C41 -46.2(4) . . . . ?
C34 C33 C46 C41 81.4(4) . . . . ?
N2 C33 C46 C45 131.7(3) . . . . ?
C34 C33 C46 C45 -100.6(4) . . . . ?
C46 C45 C47 C48 -178.1(3) . . . . ?
C44 C45 C47 C48 1.0(5) . . . . ?
C45 C47 C48 C49 0.4(6) . . . . ?
C47 C48 C49 C50 -1.1(6) . . . . ?
C48 C49 C50 C44 0.3(6) . . . . ?
C43 C44 C50 C49 -179.3(4) . . . . ?
C45 C44 C50 C49 1.1(6) . . . . ?
O6 P2 C51 Cl2 -65.7(2) . . . . ?
O5 P2 C51 Cl2 171.25(17) . . . . ?
N2 P2 C51 Cl2 65.3(2) . . . . ?
C29 C28 C52 C53 -1.1(6) . . . . ?
C30 C31 C53 C52 0.7(5) . . . . ?
C32 C31 C53 C52 -179.8(3) . . . . ?
C28 C52 C53 C31 0.2(6) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_am20
_database_code_depnum_ccdc_archive 'CCDC 1949307'
loop_
_audit_author_name
_audit_author_address
'Giancarlo Terraneo'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 Cl N O3 P'
_chemical_formula_sum            'C27 H25 Cl N O3 P1'
_chemical_formula_weight         477.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.8897(3)
_cell_length_b                   14.6971(6)
_cell_length_c                   12.2755(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.491(3)
_cell_angle_gamma                90
_cell_volume                     1208.70(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4155
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      27.22

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.6623
_exptl_absorpt_correction_T_max  0.7463

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15596
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.685
_diffrn_reflns_theta_max         32.014
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             7538
_reflns_number_gt                5301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.801
_reflns_Friedel_fraction_full    0.889

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Carbon C21 has large ADP. I try to split it but
the quality of the refinement does not improve.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.0323P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1895 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7538
_refine_ls_number_parameters     300
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
P1 P 0.63552(10) 1.01125(5) 0.65633(5) 0.04152(17) Uani 1 1 d . . . . .
Cl1 Cl 0.6778(2) 1.18623(8) 0.55713(9) 0.0970(4) Uani 1 1 d . . . . .
O1 O 0.8243(3) 1.02484(16) 0.73920(16) 0.0521(5) Uani 1 1 d . . . . .
N1 N 0.4345(3) 1.03369(14) 0.70092(16) 0.0365(5) Uani 1 1 d . . . . .
O2 O 0.5908(3) 0.91088(15) 0.60590(17) 0.0525(5) Uani 1 1 d . . . . .
C1 C 0.2648(4) 0.96854(17) 0.6730(2) 0.0351(5) Uani 1 1 d . . . . .
H1 H 0.1729 0.9834 0.7205 0.042 Uiso 1 1 calc R U . . .
C2 C 0.3445(4) 0.87369(17) 0.7040(2) 0.0394(6) Uani 1 1 d . . . . .
C15 C 0.4396(4) 1.03250(18) 0.90277(19) 0.0420(6) Uani 1 1 d . . . . .
C13 C 0.4452(4) 1.09090(18) 0.8018(2) 0.0421(6) Uani 1 1 d . . . . .
H13 H 0.5751 1.1215 0.8178 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2662(5) 0.8124(2) 0.7730(2) 0.0458(7) Uani 1 1 d . . . . .
C22 C 0.1485(4) 0.97631(19) 0.55081(19) 0.0387(5) Uani 1 1 d . . . . .
C11 C 0.5092(5) 0.8490(2) 0.6690(2) 0.0468(6) Uani 1 1 d . . . . .
C20 C 0.2836(5) 1.0341(2) 0.9563(2) 0.0530(7) Uani 1 1 d . . . . .
H20 H 0.1743 1.0715 0.9287 0.064 Uiso 1 1 calc R U . . .
C27 C 0.1329(4) 1.0585(2) 0.4944(2) 0.0469(6) Uani 1 1 d . . . . .
H27 H 0.1979 1.1096 0.5303 0.056 Uiso 1 1 calc R U . . .
C23 C 0.0491(5) 0.9020(2) 0.4964(2) 0.0513(7) Uani 1 1 d . . . . .
H23 H 0.0582 0.8461 0.5326 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1007(5) 0.8327(2) 0.8174(3) 0.0556(8) Uani 1 1 d . . . . .
H4 H 0.0324 0.8871 0.7987 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3657(5) 0.7278(2) 0.8009(3) 0.0564(8) Uani 1 1 d . . . . .
C7 C 0.2958(7) 0.6682(2) 0.8737(3) 0.0714(12) Uani 1 1 d . . . . .
H7 H 0.3587 0.6124 0.8920 0.086 Uiso 1 1 calc R U . . .
C16 C 0.5977(5) 0.9739(2) 0.9451(2) 0.0501(7) Uani 1 1 d . . . . .
H16 H 0.7039 0.9709 0.9104 0.060 Uiso 1 1 calc R U . . .
C6 C 0.1408(7) 0.6905(3) 0.9167(3) 0.0783(13) Uani 1 1 d . . . . .
H6 H 0.0998 0.6510 0.9661 0.094 Uiso 1 1 calc R U . . .
C26 C 0.0211(5) 1.0656(3) 0.3846(2) 0.0576(8) Uani 1 1 d . . . . .
H26 H 0.0134 1.1210 0.3472 0.069 Uiso 1 1 calc R U . . .
C10 C 0.6052(5) 0.7648(2) 0.6937(3) 0.0604(9) Uani 1 1 d . . . . .
H10 H 0.7167 0.7503 0.6667 0.073 Uiso 1 1 calc R U . . .
C25 C -0.0776(6) 0.9915(3) 0.3319(2) 0.0630(9) Uani 1 1 d . . . . .
H25 H -0.1528 0.9962 0.2586 0.076 Uiso 1 1 calc R U . . .
C17 C 0.6001(6) 0.9204(2) 1.0369(2) 0.0604(9) Uani 1 1 d . . . . .
H17 H 0.7063 0.8810 1.0630 0.072 Uiso 1 1 calc R U . . .
O3 O 0.4684(6) 0.8704(2) 1.1830(3) 0.0984(11) Uani 1 1 d . . . . .
C19 C 0.2867(6) 0.9813(3) 1.0499(3) 0.0618(9) Uani 1 1 d . . . . .
H19 H 0.1814 0.9838 1.0854 0.074 Uiso 1 1 calc R U . . .
C9 C 0.5324(6) 0.7058(2) 0.7571(3) 0.0655(10) Uani 1 1 d . . . . .
H9 H 0.5928 0.6492 0.7728 0.079 Uiso 1 1 calc R U . . .
C18 C 0.4469(7) 0.9249(2) 1.0902(3) 0.0636(9) Uani 1 1 d . . . . .
C24 C -0.0653(6) 0.9104(3) 0.3871(3) 0.0669(10) Uani 1 1 d . . . . .
H24 H -0.1339 0.8601 0.3514 0.080 Uiso 1 1 calc R U . . .
C5 C 0.0396(6) 0.7730(3) 0.8879(3) 0.0702(10) Uani 1 1 d . . . . .
H5 H -0.0698 0.7872 0.9170 0.084 Uiso 1 1 calc R U . . .
C12 C 0.6340(5) 1.0703(2) 0.5277(2) 0.0548(8) Uani 1 1 d . . . . .
H12A H 0.7370 1.0459 0.4939 0.066 Uiso 1 1 calc R U . . .
H12B H 0.5060 1.0623 0.4753 0.066 Uiso 1 1 calc R U . . .
C14 C 0.2868(6) 1.1648(2) 0.7765(3) 0.0602(9) Uani 1 1 d . . . . .
H14A H 0.3056 1.2008 0.7145 0.090 Uiso 1 1 calc R U . . .
H14B H 0.2979 1.2029 0.8411 0.090 Uiso 1 1 calc R U . . .
H14C H 0.1569 1.1373 0.7578 0.090 Uiso 1 1 calc R U . . .
C21 C 0.3180(14) 0.8777(6) 1.2446(7) 0.164(4) Uani 1 1 d . . . . .
H21A H 0.3582 0.8443 1.3134 0.246 Uiso 1 1 calc R U . . .
H21B H 0.1951 0.8531 1.2011 0.246 Uiso 1 1 calc R U . . .
H21C H 0.2993 0.9405 1.2609 0.246 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 O1 1.466(2) . ?
P1 O2 1.602(2) . ?
P1 N1 1.637(2) . ?
P1 C12 1.801(3) . ?
Cl1 C12 1.753(4) . ?
N1 C13 1.485(3) . ?
N1 C1 1.488(3) . ?
O2 C11 1.395(4) . ?
C1 C2 1.514(4) . ?
C1 C22 1.531(3) . ?
C1 H1 0.9800 . ?
C2 C11 1.353(4) . ?
C2 C3 1.426(4) . ?
C15 C20 1.385(4) . ?
C15 C16 1.391(4) . ?
C15 C13 1.515(4) . ?
C13 C14 1.519(4) . ?
C13 H13 0.9800 . ?
C3 C4 1.405(5) . ?
C3 C8 1.422(4) . ?
C22 C23 1.376(4) . ?
C22 C27 1.384(4) . ?
C11 C10 1.403(5) . ?
C20 C19 1.382(5) . ?
C20 H20 0.9300 . ?
C27 C26 1.392(4) . ?
C27 H27 0.9300 . ?
C23 C24 1.394(4) . ?
C23 H23 0.9300 . ?
C4 C5 1.365(5) . ?
C4 H4 0.9300 . ?
C8 C9 1.414(6) . ?
C8 C7 1.414(5) . ?
C7 C6 1.338(6) . ?
C7 H7 0.9300 . ?
C16 C17 1.370(4) . ?
C16 H16 0.9300 . ?
C6 C5 1.403(6) . ?
C6 H6 0.9300 . ?
C26 C25 1.365(5) . ?
C26 H26 0.9300 . ?
C10 C9 1.339(6) . ?
C10 H10 0.9300 . ?
C25 C24 1.363(6) . ?
C25 H25 0.9300 . ?
C17 C18 1.367(5) . ?
C17 H17 0.9300 . ?
O3 C18 1.373(4) . ?
O3 C21 1.422(7) . ?
C19 C18 1.377(5) . ?
C19 H19 0.9300 . ?
C9 H9 0.9300 . ?
C24 H24 0.9300 . ?
C5 H5 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 116.95(13) . . ?
O1 P1 N1 115.04(11) . . ?
O2 P1 N1 102.32(11) . . ?
O1 P1 C12 111.44(14) . . ?
O2 P1 C12 98.27(14) . . ?
N1 P1 C12 111.35(14) . . ?
C13 N1 C1 116.1(2) . . ?
C13 N1 P1 120.80(17) . . ?
C1 N1 P1 118.29(17) . . ?
C11 O2 P1 116.85(17) . . ?
N1 C1 C2 108.4(2) . . ?
N1 C1 C22 112.4(2) . . ?
C2 C1 C22 113.0(2) . . ?
N1 C1 H1 107.6 . . ?
C2 C1 H1 107.6 . . ?
C22 C1 H1 107.6 . . ?
C11 C2 C3 118.7(3) . . ?
C11 C2 C1 116.7(2) . . ?
C3 C2 C1 124.5(3) . . ?
C20 C15 C16 117.4(3) . . ?
C20 C15 C13 123.3(2) . . ?
C16 C15 C13 119.3(3) . . ?
N1 C13 C15 110.8(2) . . ?
N1 C13 C14 109.9(2) . . ?
C15 C13 C14 114.7(3) . . ?
N1 C13 H13 107.0 . . ?
C15 C13 H13 107.0 . . ?
C14 C13 H13 107.0 . . ?
C4 C3 C8 118.8(3) . . ?
C4 C3 C2 123.4(3) . . ?
C8 C3 C2 117.8(3) . . ?
C23 C22 C27 118.6(2) . . ?
C23 C22 C1 120.3(2) . . ?
C27 C22 C1 121.1(2) . . ?
C2 C11 O2 118.6(3) . . ?
C2 C11 C10 123.8(3) . . ?
O2 C11 C10 117.7(3) . . ?
C19 C20 C15 121.5(3) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C22 C27 C26 120.7(3) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C22 C23 C24 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 C3 119.8(3) . . ?
C7 C8 C3 118.5(4) . . ?
C6 C7 C8 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C25 C26 C27 120.1(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C9 C10 C11 118.4(4) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C18 O3 C21 116.6(4) . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C17 C18 O3 115.1(3) . . ?
C17 C18 C19 120.1(3) . . ?
O3 C18 C19 124.8(4) . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
Cl1 C12 P1 108.79(17) . . ?
Cl1 C12 H12A 109.9 . . ?
P1 C12 H12A 109.9 . . ?
Cl1 C12 H12B 109.9 . . ?
P1 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 P1 N1 C13 18.9(2) . . . . ?
O2 P1 N1 C13 146.83(19) . . . . ?
C12 P1 N1 C13 -109.1(2) . . . . ?
O1 P1 N1 C1 -135.51(17) . . . . ?
O2 P1 N1 C1 -7.62(19) . . . . ?
C12 P1 N1 C1 96.5(2) . . . . ?
O1 P1 O2 C11 83.2(2) . . . . ?
N1 P1 O2 C11 -43.5(2) . . . . ?
C12 P1 O2 C11 -157.6(2) . . . . ?
C13 N1 C1 C2 -105.6(2) . . . . ?
P1 N1 C1 C2 50.1(2) . . . . ?
C13 N1 C1 C22 128.8(2) . . . . ?
P1 N1 C1 C22 -75.6(2) . . . . ?
N1 C1 C2 C11 -47.9(3) . . . . ?
C22 C1 C2 C11 77.4(3) . . . . ?
N1 C1 C2 C3 127.6(2) . . . . ?
C22 C1 C2 C3 -107.1(3) . . . . ?
C1 N1 C13 C15 53.3(3) . . . . ?
P1 N1 C13 C15 -101.7(2) . . . . ?
C1 N1 C13 C14 -74.5(3) . . . . ?
P1 N1 C13 C14 130.5(2) . . . . ?
C20 C15 C13 N1 -114.0(3) . . . . ?
C16 C15 C13 N1 66.0(3) . . . . ?
C20 C15 C13 C14 11.2(4) . . . . ?
C16 C15 C13 C14 -168.8(3) . . . . ?
C11 C2 C3 C4 177.5(3) . . . . ?
C1 C2 C3 C4 2.0(4) . . . . ?
C11 C2 C3 C8 -0.4(4) . . . . ?
C1 C2 C3 C8 -175.8(2) . . . . ?
N1 C1 C22 C23 152.1(3) . . . . ?
C2 C1 C22 C23 29.0(4) . . . . ?
N1 C1 C22 C27 -31.0(4) . . . . ?
C2 C1 C22 C27 -154.1(3) . . . . ?
C3 C2 C11 O2 -177.0(2) . . . . ?
C1 C2 C11 O2 -1.3(3) . . . . ?
C3 C2 C11 C10 2.1(4) . . . . ?
C1 C2 C11 C10 177.9(3) . . . . ?
P1 O2 C11 C2 51.7(3) . . . . ?
P1 O2 C11 C10 -127.5(2) . . . . ?
C16 C15 C20 C19 1.6(5) . . . . ?
C13 C15 C20 C19 -178.4(3) . . . . ?
C23 C22 C27 C26 -0.7(4) . . . . ?
C1 C22 C27 C26 -177.7(3) . . . . ?
C27 C22 C23 C24 -0.4(5) . . . . ?
C1 C22 C23 C24 176.7(3) . . . . ?
C8 C3 C4 C5 1.4(4) . . . . ?
C2 C3 C4 C5 -176.4(3) . . . . ?
C4 C3 C8 C9 179.9(3) . . . . ?
C2 C3 C8 C9 -2.1(4) . . . . ?
C4 C3 C8 C7 -1.0(4) . . . . ?
C2 C3 C8 C7 176.9(3) . . . . ?
C9 C8 C7 C6 178.4(3) . . . . ?
C3 C8 C7 C6 -0.6(5) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
C13 C15 C16 C17 179.3(3) . . . . ?
C8 C7 C6 C5 1.8(6) . . . . ?
C22 C27 C26 C25 1.1(5) . . . . ?
C2 C11 C10 C9 -1.2(5) . . . . ?
O2 C11 C10 C9 177.9(3) . . . . ?
C27 C26 C25 C24 -0.3(6) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
C15 C20 C19 C18 -0.9(5) . . . . ?
C11 C10 C9 C8 -1.4(5) . . . . ?
C7 C8 C9 C10 -175.9(3) . . . . ?
C3 C8 C9 C10 3.1(5) . . . . ?
C16 C17 C18 O3 -178.1(3) . . . . ?
C16 C17 C18 C19 1.9(6) . . . . ?
C21 O3 C18 C17 176.1(6) . . . . ?
C21 O3 C18 C19 -3.8(8) . . . . ?
C20 C19 C18 C17 -0.9(6) . . . . ?
C20 C19 C18 O3 179.0(4) . . . . ?
C26 C25 C24 C23 -0.8(6) . . . . ?
C22 C23 C24 C25 1.2(6) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C7 C6 C5 C4 -1.4(6) . . . . ?
O1 P1 C12 Cl1 -57.3(2) . . . . ?
O2 P1 C12 Cl1 179.34(18) . . . . ?
N1 P1 C12 Cl1 72.6(2) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_gabri6
_database_code_depnum_ccdc_archive 'CCDC 1949308'
loop_
_audit_author_name
_audit_author_address
'Giancarlo Terraneo'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 Cl N O3 P'
_chemical_formula_sum            'C27 H25 Cl N O3 P'
_chemical_formula_weight         477.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.1428(10)
_cell_length_b                   11.1701(12)
_cell_length_c                   25.718(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2339.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      30.65

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.6741
_exptl_absorpt_correction_T_max  0.7461

_exptl_special_details           
;
 Bruker KRYOFLEX low temperature device
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26392
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.988
_diffrn_reflns_theta_max         30.657
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7133
_reflns_number_gt                6596
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.998

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0545P)²+0.4094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7133
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.82956(11) 0.31464(5) 0.97048(2) 0.03792(18) Uani 1 1 d . . . . .
P1 P 0.78772(7) 0.38576(4) 0.85827(2) 0.01514(11) Uani 1 1 d . . . . .
O1 O 0.94519(18) 0.46750(12) 0.87034(6) 0.0171(3) Uani 1 1 d . . . . .
O2 O 0.7784(2) 0.33059(14) 0.80648(6) 0.0222(3) Uani 1 1 d . . . . .
O3 O 0.41222(19) 0.54695(14) 0.95754(6) 0.0198(3) Uani 1 1 d . . . . .
N1 N 0.6348(2) 0.47627(14) 0.87311(6) 0.0131(3) Uani 1 1 d . . . . .
C1 C 0.8245(3) 1.01603(17) 0.81064(8) 0.0211(4) Uani 1 1 d . . . . .
H1 H 0.8290 1.0952 0.7995 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6914(3) 0.97640(17) 0.84101(8) 0.0198(4) Uani 1 1 d . . . . .
H25 H 0.6076 1.0294 0.8496 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6842(3) 0.85959(16) 0.85814(8) 0.0166(4) Uani 1 1 d . . . . .
H24 H 0.5946 0.8344 0.8777 0.020 Uiso 1 1 calc R U . . .
C4 C 0.8112(2) 0.77729(16) 0.84630(7) 0.0134(3) Uani 1 1 d . . . . .
C5 C 0.8097(2) 0.65559(16) 0.86374(7) 0.0128(3) Uani 1 1 d . . . . .
C6 C 0.6690(2) 0.59968(15) 0.89324(7) 0.0123(3) Uani 1 1 d . . . . .
H23 H 0.5717 0.6477 0.8849 0.015 Uiso 1 1 calc R U . . .
C7 C 0.4794(2) 0.46913(17) 0.84240(7) 0.0144(3) Uani 1 1 d . . . . .
H15 H 0.4005 0.5207 0.8605 0.017 Uiso 1 1 calc R U . . .
C8 C 0.4061(3) 0.34434(17) 0.84348(8) 0.0157(4) Uani 1 1 d . . . . .
C9 C 0.3957(3) 0.2830(2) 0.89095(8) 0.0218(4) Uani 1 1 d . . . . .
H11 H 0.4412 0.3165 0.9207 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3177(3) 0.1724(2) 0.89380(8) 0.0251(5) Uani 1 1 d . . . . .
H10 H 0.3149 0.1310 0.9252 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2442(3) 0.12376(19) 0.85001(9) 0.0237(4) Uani 1 1 d . . . . .
H2 H 0.1896 0.0508 0.8522 0.028 Uiso 1 1 calc R U . . .
C12 C 0.9418(3) 0.58508(17) 0.85152(7) 0.0153(4) Uani 1 1 d . . . . .
C13 C 1.0751(3) 0.62313(19) 0.82133(8) 0.0178(4) Uani 1 1 d . . . . .
H5 H 1.1609 0.5710 0.8137 0.021 Uiso 1 1 calc R U . . .
C14 C 1.0768(3) 0.73852(19) 0.80325(8) 0.0182(4) Uani 1 1 d . . . . .
H4 H 1.1638 0.7651 0.7829 0.022 Uiso 1 1 calc R U . . .
C15 C 0.9462(3) 0.81757(18) 0.81557(7) 0.0156(4) Uani 1 1 d . . . . .
C16 C 0.9476(3) 0.93776(18) 0.79750(8) 0.0185(4) Uani 1 1 d . . . . .
H3 H 1.0333 0.9638 0.7765 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8220(3) 0.26775(17) 0.90495(8) 0.0213(4) Uani 1 1 d . . . . .
H7 H 0.7350 0.2090 0.9013 0.026 Uiso 1 1 calc R U . . .
H6 H 0.9247 0.2283 0.8965 0.026 Uiso 1 1 calc R U . . .
C18 C 0.2522(3) 0.18401(19) 0.80306(8) 0.0219(4) Uani 1 1 d . . . . .
H9 H 0.2030 0.1514 0.7737 0.026 Uiso 1 1 calc R U . . .
C19 C 0.3338(3) 0.29328(18) 0.79971(8) 0.0190(4) Uani 1 1 d . . . . .
H8 H 0.3401 0.3326 0.7679 0.023 Uiso 1 1 calc R U . . .
C20 C 0.5006(3) 0.52342(19) 0.78838(8) 0.0181(4) Uani 1 1 d . . . . .
H12 H 0.5460 0.6024 0.7915 0.027 Uiso 1 1 calc R U . . .
H13 H 0.3958 0.5278 0.7714 0.027 Uiso 1 1 calc R U . . .
H14 H 0.5735 0.4742 0.7683 0.027 Uiso 1 1 calc R U . . .
C21 C 0.6880(2) 0.60516(15) 0.95193(7) 0.0130(3) Uani 1 1 d . . . . .
C22 C 0.5511(3) 0.57959(16) 0.98351(8) 0.0159(4) Uani 1 1 d . . . . .
C23 C 0.2668(3) 0.5238(2) 0.98672(10) 0.0269(5) Uani 1 1 d . . . . .
H18 H 0.2870 0.4598 1.0108 0.040 Uiso 1 1 calc R U . . .
H16 H 0.1798 0.5013 0.9635 0.040 Uiso 1 1 calc R U . . .
H17 H 0.2358 0.5946 1.0055 0.040 Uiso 1 1 calc R U . . .
C24 C 0.5616(3) 0.59060(18) 1.03764(8) 0.0204(4) Uani 1 1 d . . . . .
H22 H 0.4712 0.5731 1.0584 0.024 Uiso 1 1 calc R U . . .
C25 C 0.7081(3) 0.62788(18) 1.06002(8) 0.0222(4) Uani 1 1 d . . . . .
H21 H 0.7151 0.6362 1.0959 0.027 Uiso 1 1 calc R U . . .
C26 C 0.8433(3) 0.65260(18) 1.02966(8) 0.0209(4) Uani 1 1 d . . . . .
H20 H 0.9412 0.6767 1.0451 0.025 Uiso 1 1 calc R U . . .
C27 C 0.8328(3) 0.64129(16) 0.97556(7) 0.0164(4) Uani 1 1 d . . . . .
H19 H 0.9243 0.6582 0.9552 0.020 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
Cl1 C17 1.766(2) . ?
P1 O2 1.4696(15) . ?
P1 O1 1.6044(16) . ?
P1 N1 1.6485(17) . ?
P1 C17 1.804(2) . ?
O1 C12 1.400(2) . ?
O3 C22 1.363(3) . ?
O3 C23 1.426(3) . ?
N1 C7 1.494(2) . ?
N1 C6 1.499(2) . ?
C1 C16 1.373(3) . ?
C1 C2 1.407(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H25 0.9300 . ?
C3 C4 1.417(3) . ?
C3 H24 0.9300 . ?
C4 C15 1.427(3) . ?
C4 C5 1.432(2) . ?
C5 C12 1.369(3) . ?
C5 C6 1.510(3) . ?
C6 C21 1.519(2) . ?
C6 H23 0.9800 . ?
C7 C8 1.517(3) . ?
C7 C20 1.526(3) . ?
C7 H15 0.9800 . ?
C8 C19 1.392(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.391(3) . ?
C9 H11 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C18 1.384(3) . ?
C11 H2 0.9300 . ?
C12 C13 1.401(3) . ?
C13 C14 1.370(3) . ?
C13 H5 0.9300 . ?
C14 C15 1.419(3) . ?
C14 H4 0.9300 . ?
C15 C16 1.421(3) . ?
C16 H3 0.9300 . ?
C17 H7 0.9700 . ?
C17 H6 0.9700 . ?
C18 C19 1.392(3) . ?
C18 H9 0.9300 . ?
C19 H8 0.9300 . ?
C20 H12 0.9600 . ?
C20 H13 0.9600 . ?
C20 H14 0.9600 . ?
C21 C27 1.387(3) . ?
C21 C22 1.408(3) . ?
C22 C24 1.400(3) . ?
C23 H18 0.9600 . ?
C23 H16 0.9600 . ?
C23 H17 0.9600 . ?
C24 C25 1.389(3) . ?
C24 H22 0.9300 . ?
C25 C26 1.378(3) . ?
C25 H21 0.9300 . ?
C26 C27 1.400(3) . ?
C26 H20 0.9300 . ?
C27 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O1 117.07(9) . . ?
O2 P1 N1 115.35(9) . . ?
O1 P1 N1 102.11(8) . . ?
O2 P1 C17 107.73(9) . . ?
O1 P1 C17 99.41(10) . . ?
N1 P1 C17 114.26(10) . . ?
C12 O1 P1 116.82(13) . . ?
C22 O3 C23 118.67(17) . . ?
C7 N1 C6 112.89(14) . . ?
C7 N1 P1 119.00(13) . . ?
C6 N1 P1 120.27(13) . . ?
C16 C1 C2 119.92(18) . . ?
C16 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H25 119.7 . . ?
C1 C2 H25 119.7 . . ?
C2 C3 C4 120.96(19) . . ?
C2 C3 H24 119.5 . . ?
C4 C3 H24 119.5 . . ?
C3 C4 C15 118.48(16) . . ?
C3 C4 C5 122.87(18) . . ?
C15 C4 C5 118.65(17) . . ?
C12 C5 C4 117.89(17) . . ?
C12 C5 C6 118.27(16) . . ?
C4 C5 C6 123.81(17) . . ?
N1 C6 C5 110.34(15) . . ?
N1 C6 C21 113.55(14) . . ?
C5 C6 C21 113.92(16) . . ?
N1 C6 H23 106.1 . . ?
C5 C6 H23 106.1 . . ?
C21 C6 H23 106.1 . . ?
N1 C7 C8 111.88(16) . . ?
N1 C7 C20 111.33(16) . . ?
C8 C7 C20 115.26(16) . . ?
N1 C7 H15 105.9 . . ?
C8 C7 H15 105.9 . . ?
C20 C7 H15 105.9 . . ?
C19 C8 C9 118.56(18) . . ?
C19 C8 C7 121.87(18) . . ?
C9 C8 C7 119.26(17) . . ?
C10 C9 C8 120.49(19) . . ?
C10 C9 H11 119.8 . . ?
C8 C9 H11 119.8 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C18 C11 C10 119.85(19) . . ?
C18 C11 H2 120.1 . . ?
C10 C11 H2 120.1 . . ?
C5 C12 O1 118.41(17) . . ?
C5 C12 C13 124.15(18) . . ?
O1 C12 C13 117.45(18) . . ?
C14 C13 C12 118.77(19) . . ?
C14 C13 H5 120.6 . . ?
C12 C13 H5 120.6 . . ?
C13 C14 C15 120.14(19) . . ?
C13 C14 H4 119.9 . . ?
C15 C14 H4 119.9 . . ?
C14 C15 C16 120.60(19) . . ?
C14 C15 C4 120.35(17) . . ?
C16 C15 C4 119.05(19) . . ?
C1 C16 C15 121.03(19) . . ?
C1 C16 H3 119.5 . . ?
C15 C16 H3 119.5 . . ?
Cl1 C17 P1 115.06(11) . . ?
Cl1 C17 H7 108.5 . . ?
P1 C17 H7 108.5 . . ?
Cl1 C17 H6 108.5 . . ?
P1 C17 H6 108.5 . . ?
H7 C17 H6 107.5 . . ?
C11 C18 C19 120.19(19) . . ?
C11 C18 H9 119.9 . . ?
C19 C18 H9 119.9 . . ?
C8 C19 C18 120.72(19) . . ?
C8 C19 H8 119.6 . . ?
C18 C19 H8 119.6 . . ?
C7 C20 H12 109.5 . . ?
C7 C20 H13 109.5 . . ?
H12 C20 H13 109.5 . . ?
C7 C20 H14 109.5 . . ?
H12 C20 H14 109.5 . . ?
H13 C20 H14 109.5 . . ?
C27 C21 C22 118.65(17) . . ?
C27 C21 C6 122.27(17) . . ?
C22 C21 C6 118.97(17) . . ?
O3 C22 C24 124.12(19) . . ?
O3 C22 C21 115.37(17) . . ?
C24 C22 C21 120.5(2) . . ?
O3 C23 H18 109.5 . . ?
O3 C23 H16 109.5 . . ?
H18 C23 H16 109.5 . . ?
O3 C23 H17 109.5 . . ?
H18 C23 H17 109.5 . . ?
H16 C23 H17 109.5 . . ?
C25 C24 C22 119.4(2) . . ?
C25 C24 H22 120.3 . . ?
C22 C24 H22 120.3 . . ?
C26 C25 C24 120.78(19) . . ?
C26 C25 H21 119.6 . . ?
C24 C25 H21 119.6 . . ?
C25 C26 C27 119.8(2) . . ?
C25 C26 H20 120.1 . . ?
C27 C26 H20 120.1 . . ?
C21 C27 C26 120.9(2) . . ?
C21 C27 H19 119.5 . . ?
C26 C27 H19 119.5 . . ?

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
O2 P1 O1 C12 80.85(15) . . . . ?
N1 P1 O1 C12 -46.11(15) . . . . ?
C17 P1 O1 C12 -163.59(14) . . . . ?
O2 P1 N1 C7 17.82(17) . . . . ?
O1 P1 N1 C7 145.89(14) . . . . ?
C17 P1 N1 C7 -107.85(15) . . . . ?
O2 P1 N1 C6 -129.14(14) . . . . ?
O1 P1 N1 C6 -1.07(15) . . . . ?
C17 P1 N1 C6 105.19(15) . . . . ?
C16 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C15 -0.8(3) . . . . ?
C2 C3 C4 C5 179.30(18) . . . . ?
C3 C4 C5 C12 -177.76(18) . . . . ?
C15 C4 C5 C12 2.4(3) . . . . ?
C3 C4 C5 C6 4.3(3) . . . . ?
C15 C4 C5 C6 -175.60(17) . . . . ?
C7 N1 C6 C5 -107.82(18) . . . . ?
P1 N1 C6 C5 41.00(19) . . . . ?
C7 N1 C6 C21 122.88(17) . . . . ?
P1 N1 C6 C21 -88.29(18) . . . . ?
C12 C5 C6 N1 -40.6(2) . . . . ?
C4 C5 C6 N1 137.40(17) . . . . ?
C12 C5 C6 C21 88.5(2) . . . . ?
C4 C5 C6 C21 -93.5(2) . . . . ?
C6 N1 C7 C8 -153.82(16) . . . . ?
P1 N1 C7 C8 56.9(2) . . . . ?
C6 N1 C7 C20 75.6(2) . . . . ?
P1 N1 C7 C20 -73.67(18) . . . . ?
N1 C7 C8 C19 -140.8(2) . . . . ?
C20 C7 C8 C19 -12.2(3) . . . . ?
N1 C7 C8 C9 45.7(3) . . . . ?
C20 C7 C8 C9 174.3(2) . . . . ?
C19 C8 C9 C10 1.3(3) . . . . ?
C7 C8 C9 C10 175.0(2) . . . . ?
C8 C9 C10 C11 -2.4(4) . . . . ?
C9 C10 C11 C18 1.7(4) . . . . ?
C4 C5 C12 O1 177.17(16) . . . . ?
C6 C5 C12 O1 -4.7(3) . . . . ?
C4 C5 C12 C13 -2.6(3) . . . . ?
C6 C5 C12 C13 175.47(18) . . . . ?
P1 O1 C12 C5 53.2(2) . . . . ?
P1 O1 C12 C13 -127.02(17) . . . . ?
C5 C12 C13 C14 1.1(3) . . . . ?
O1 C12 C13 C14 -178.69(17) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 179.31(19) . . . . ?
C13 C14 C15 C4 -0.8(3) . . . . ?
C3 C4 C15 C14 179.35(18) . . . . ?
C5 C4 C15 C14 -0.8(3) . . . . ?
C3 C4 C15 C16 -0.7(3) . . . . ?
C5 C4 C15 C16 179.16(17) . . . . ?
C2 C1 C16 C15 -2.2(3) . . . . ?
C14 C15 C16 C1 -177.84(19) . . . . ?
C4 C15 C16 C1 2.2(3) . . . . ?
O2 P1 C17 Cl1 -177.78(13) . . . . ?
O1 P1 C17 Cl1 59.72(15) . . . . ?
N1 P1 C17 Cl1 -48.21(17) . . . . ?
C10 C11 C18 C19 0.0(4) . . . . ?
C9 C8 C19 C18 0.3(3) . . . . ?
C7 C8 C19 C18 -173.2(2) . . . . ?
C11 C18 C19 C8 -1.0(3) . . . . ?
N1 C6 C21 C27 117.97(19) . . . . ?
C5 C6 C21 C27 -9.5(2) . . . . ?
N1 C6 C21 C22 -65.9(2) . . . . ?
C5 C6 C21 C22 166.66(16) . . . . ?
C23 O3 C22 C24 0.8(3) . . . . ?
C23 O3 C22 C21 -177.80(18) . . . . ?
C27 C21 C22 O3 178.74(16) . . . . ?
C6 C21 C22 O3 2.5(2) . . . . ?
C27 C21 C22 C24 0.0(3) . . . . ?
C6 C21 C22 C24 -176.23(17) . . . . ?
O3 C22 C24 C25 -178.14(18) . . . . ?
C21 C22 C24 C25 0.4(3) . . . . ?
C22 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C27 0.7(3) . . . . ?
C22 C21 C27 C26 -0.2(3) . . . . ?
C6 C21 C27 C26 175.96(17) . . . . ?
C25 C26 C27 C21 -0.2(3) . . . . ?

_refine_diff_density_max         0.733
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-3

