# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_2bae
_database_code_depnum_ccdc_archive 'CCDC 1984986'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H28 N3, 3(Cl)'
_chemical_formula_sum            'C18 H28 Cl3 N3'
_chemical_formula_weight         392.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   39.208(3)
_cell_length_b                   4.9186(3)
_cell_length_c                   5.1714(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.465(3)
_cell_angle_gamma                90
_cell_volume                     997.26(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5869
_cell_measurement_theta_min      3.1175
_cell_measurement_theta_max      26.7418

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.465
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            6324
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_max         26.742
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2107
_reflns_number_gt                2036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.985
_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 Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+1.5010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2107
_refine_ls_number_parameters     123
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.092
_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 0.5000 0.5593(10) 0.5000 0.0090(11) Uani 1 2 d S T P . .
H11 H 0.5008(18) 0.680(11) 0.631(9) 0.033(16) Uiso 1 1 d . . . . .
C2 C 0.53222(9) 0.3990(10) 0.4989(10) 0.0105(7) Uani 1 1 d . . . . .
H21 H 0.5332 0.2838 0.3422 0.013 Uiso 1 1 calc R U . . .
H22 H 0.5334 0.2795 0.6528 0.013 Uiso 1 1 calc R U . . .
C3 C 0.56182(8) 0.5981(10) 0.5023(10) 0.0111(7) Uani 1 1 d . . . . .
H31 H 0.5602 0.7198 0.3503 0.013 Uiso 1 1 calc R U . . .
H32 H 0.5608 0.7115 0.6602 0.013 Uiso 1 1 calc R U . . .
N4 N 0.59482(8) 0.4486(7) 0.4971(8) 0.0097(7) Uani 1 1 d D . . . .
H41 H 0.5953(14) 0.372(11) 0.348(6) 0.022(15) Uiso 1 1 d D . . . .
H42 H 0.5981(14) 0.340(10) 0.622(8) 0.028(17) Uiso 1 1 d D . . . .
C5 C 0.62508(10) 0.6378(9) 0.5077(11) 0.0149(9) Uani 1 1 d . . . . .
H51 H 0.6262 0.7247 0.6802 0.018 Uiso 1 1 calc R U . . .
H52 H 0.6220 0.7831 0.3771 0.018 Uiso 1 1 calc R U . . .
C6 C 0.65819(11) 0.4906(10) 0.4576(9) 0.0169(10) Uani 1 1 d . . . . .
C7 C 0.66961(12) 0.2829(11) 0.6184(10) 0.0247(11) Uani 1 1 d . . . . .
H71 H 0.6564 0.2292 0.7626 0.030 Uiso 1 1 calc R U . . .
C8 C 0.70053(12) 0.1528(11) 0.5684(11) 0.0318(14) Uani 1 1 d . . . . .
H81 H 0.7082 0.0092 0.6773 0.038 Uiso 1 1 calc R U . . .
C9 C 0.71971(13) 0.2317(13) 0.3638(11) 0.0313(13) Uani 1 1 d . . . . .
H91 H 0.7409 0.1443 0.3316 0.038 Uiso 1 1 calc R U . . .
C10 C 0.70862(13) 0.4391(14) 0.2016(11) 0.0362(14) Uani 1 1 d . . . . .
H101 H 0.7223 0.4936 0.0597 0.043 Uiso 1 1 calc R U . . .
C11 C 0.67748(12) 0.5678(13) 0.2463(10) 0.0295(12) Uani 1 1 d . . . . .
H111 H 0.6696 0.7068 0.1332 0.035 Uiso 1 1 calc R U . . .
Cl1 Cl 0.59490(2) 0.10536(15) -0.0004(2) 0.0141(2) Uani 1 1 d . . . . .
Cl2 Cl 0.5000 0.8953(2) 0.0000 0.0129(3) Uani 1 2 d S T P . .


_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 C2 1.489(5) . ?
N1 C2 1.489(5) 2_656 ?
N1 H11 0.90(5) . ?
C2 C3 1.518(4) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 N4 1.488(5) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C5 1.509(5) . ?
N4 H41 0.856(14) . ?
N4 H42 0.849(14) . ?
C5 C6 1.511(6) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C11 1.387(7) . ?
C6 C7 1.389(7) . ?
C7 C8 1.397(7) . ?
C7 H71 0.9500 . ?
C8 C9 1.360(7) . ?
C8 H81 0.9500 . ?
C9 C10 1.388(9) . ?
C9 H91 0.9500 . ?
C10 C11 1.396(7) . ?
C10 H101 0.9500 . ?
C11 H111 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C2 116.1(5) . 2_656 ?
C2 N1 H11 109(4) . . ?
C2 N1 H11 112(4) 2_656 . ?
N1 C2 C3 107.9(3) . . ?
N1 C2 H21 110.1 . . ?
C3 C2 H21 110.1 . . ?
N1 C2 H22 110.1 . . ?
C3 C2 H22 110.1 . . ?
H21 C2 H22 108.4 . . ?
N4 C3 C2 110.2(3) . . ?
N4 C3 H31 109.6 . . ?
C2 C3 H31 109.6 . . ?
N4 C3 H32 109.6 . . ?
C2 C3 H32 109.6 . . ?
H31 C3 H32 108.1 . . ?
C3 N4 C5 112.2(4) . . ?
C3 N4 H41 105(4) . . ?
C5 N4 H41 106(4) . . ?
C3 N4 H42 115(4) . . ?
C5 N4 H42 104(4) . . ?
H41 N4 H42 114(5) . . ?
N4 C5 C6 112.0(4) . . ?
N4 C5 H51 109.2 . . ?
C6 C5 H51 109.2 . . ?
N4 C5 H52 109.2 . . ?
C6 C5 H52 109.2 . . ?
H51 C5 H52 107.9 . . ?
C11 C6 C7 119.9(5) . . ?
C11 C6 C5 118.6(4) . . ?
C7 C6 C5 121.5(4) . . ?
C6 C7 C8 120.2(5) . . ?
C6 C7 H71 119.9 . . ?
C8 C7 H71 119.9 . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H81 120.0 . . ?
C7 C8 H81 120.0 . . ?
C8 C9 C10 120.5(5) . . ?
C8 C9 H91 119.7 . . ?
C10 C9 H91 119.7 . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H101 119.9 . . ?
C11 C10 H101 119.9 . . ?
C6 C11 C10 119.3(5) . . ?
C6 C11 H111 120.3 . . ?
C10 C11 H111 120.3 . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_dmampin
_database_code_depnum_ccdc_archive 'CCDC 1984993'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H10 N O2 P'
_chemical_formula_sum            'C3 H10 N O2 P'
_chemical_formula_weight         123.09

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   9.7130(3)
_cell_length_b                   10.9592(3)
_cell_length_c                   5.5558(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     591.40(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6528
_cell_measurement_theta_min      3.6673
_cell_measurement_theta_max      30.0245

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.335
_exptl_absorpt_coefficient_mu    0.362
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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 8.3333
_diffrn_reflns_number            6686
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1343
_reflns_number_gt                1329
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.994

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

_computing_data_collection       'Bruker Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0288P)²+0.1265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 591 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1343
_refine_ls_number_parameters     74
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0522
_refine_ls_wR_factor_gt          0.0520
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.149
_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 0.03473(4) 0.17442(3) 0.85054(10) 0.01175(12) Uani 1 1 d . . . . .
H1 H 0.098(2) 0.1350(19) 1.049(4) 0.012(5) Uiso 1 1 d . . . . .
O11 O -0.06865(13) 0.08082(11) 0.7701(2) 0.0175(3) Uani 1 1 d . . . . .
O12 O -0.00800(13) 0.30402(11) 0.8844(3) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.17599(18) 0.17696(14) 0.6326(3) 0.0144(3) Uani 1 1 d . . . . .
H21 H 0.1452 0.2240 0.4903 0.017 Uiso 1 1 calc R U . . .
H22 H 0.2538 0.2222 0.7055 0.017 Uiso 1 1 calc R U . . .
N3 N 0.22891(14) 0.05665(13) 0.5469(3) 0.0126(3) Uani 1 1 d . . . . .
H31 H 0.165(3) 0.019(2) 0.462(4) 0.023(6) Uiso 1 1 d . . . . .
C4 C 0.34841(17) 0.07509(15) 0.3817(3) 0.0179(4) Uani 1 1 d . . . . .
H41 H 0.3210 0.1286 0.2487 0.021 Uiso 1 1 calc R U . . .
H42 H 0.3781 -0.0039 0.3173 0.021 Uiso 1 1 calc R U . . .
H43 H 0.4245 0.1127 0.4706 0.021 Uiso 1 1 calc R U . . .
C5 C 0.27009(18) -0.02629(16) 0.7482(4) 0.0176(3) Uani 1 1 d . . . . .
H51 H 0.3104 -0.1010 0.6818 0.021 Uiso 1 1 calc R U . . .
H52 H 0.1888 -0.0471 0.8443 0.021 Uiso 1 1 calc R U . . .
H53 H 0.3380 0.0149 0.8503 0.021 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 O12 1.4916(12) . ?
P1 O11 1.5033(12) . ?
P1 C2 1.8301(18) . ?
P1 H1 1.33(2) . ?
C2 N3 1.493(2) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.494(2) . ?
N3 C5 1.495(2) . ?
N3 H31 0.89(2) . ?
C4 H41 0.9800 . ?
C4 H42 0.9800 . ?
C4 H43 0.9800 . ?
C5 H51 0.9800 . ?
C5 H52 0.9800 . ?
C5 H53 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
O12 P1 O11 120.09(7) . . ?
O12 P1 C2 106.11(8) . . ?
O11 P1 C2 108.34(8) . . ?
O12 P1 H1 109.5(9) . . ?
O11 P1 H1 109.5(9) . . ?
C2 P1 H1 101.8(9) . . ?
N3 C2 P1 117.10(11) . . ?
N3 C2 H21 108.0 . . ?
P1 C2 H21 108.0 . . ?
N3 C2 H22 108.0 . . ?
P1 C2 H22 108.0 . . ?
H21 C2 H22 107.3 . . ?
C2 N3 C4 110.12(13) . . ?
C2 N3 C5 112.98(15) . . ?
C4 N3 C5 109.51(13) . . ?
C2 N3 H31 109.9(15) . . ?
C4 N3 H31 106.4(16) . . ?
C5 N3 H31 107.7(16) . . ?
N3 C4 H41 109.5 . . ?
N3 C4 H42 109.5 . . ?
H41 C4 H42 109.5 . . ?
N3 C4 H43 109.5 . . ?
H41 C4 H43 109.5 . . ?
H42 C4 H43 109.5 . . ?
N3 C5 H51 109.5 . . ?
N3 C5 H52 109.5 . . ?
H51 C5 H52 109.5 . . ?
N3 C5 H53 109.5 . . ?
H51 C5 H53 109.5 . . ?
H52 C5 H53 109.5 . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_dbammpin
_database_code_depnum_ccdc_archive 'CCDC 1984988'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N O2 P, C10 H18 N, H2 O'
_chemical_formula_sum            'C26 H39 N2 O3 P'
_chemical_formula_weight         458.56

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4395(2)
_cell_length_b                   17.5869(5)
_cell_length_c                   22.0784(6)
_cell_angle_alpha                89.2506(16)
_cell_angle_beta                 89.6121(12)
_cell_angle_gamma                83.8238(12)
_cell_volume                     2485.64(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6768
_cell_measurement_theta_min      2.7680
_cell_measurement_theta_max      26.4811

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.589
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.137
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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 8.3333
_diffrn_reflns_number            30757
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         0.922
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10831
_reflns_number_gt                7572
_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 Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0466P)²+0.8606P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10831
_refine_ls_number_parameters     627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
P1A P 0.04768(7) 0.36238(3) 0.06573(2) 0.01633(12) Uani 1 1 d . . . . .
H1A H -0.095(3) 0.3127(11) 0.0762(8) 0.021(5) Uiso 1 1 d . . . . .
O11A O -0.0120(2) 0.43426(7) 0.10074(6) 0.0208(3) Uani 1 1 d . . . . .
O12A O 0.0743(2) 0.37089(8) -0.00158(6) 0.0245(3) Uani 1 1 d . . . . .
C2A C 0.2777(3) 0.31200(11) 0.10091(9) 0.0188(4) Uani 1 1 d . . . . .
H2A H 0.2331 0.2978 0.1427 0.023 Uiso 1 1 calc R U . . .
C21A C 0.4513(3) 0.36350(12) 0.10941(10) 0.0271(5) Uani 1 1 d . . . . .
H21A H 0.5748 0.3333 0.1263 0.032 Uiso 1 1 calc R U . . .
H21B H 0.4035 0.4048 0.1372 0.032 Uiso 1 1 calc R U . . .
H21C H 0.4872 0.3855 0.0702 0.032 Uiso 1 1 calc R U . . .
N3A N 0.3383(2) 0.23891(9) 0.07000(7) 0.0199(4) Uani 1 1 d . . . . .
C4A C 0.4347(3) 0.18018(11) 0.11187(9) 0.0250(5) Uani 1 1 d . . . . .
H4A H 0.5346 0.2033 0.1380 0.030 Uiso 1 1 calc R U . . .
H4B H 0.5144 0.1393 0.0882 0.030 Uiso 1 1 calc R U . . .
C5A C 0.2784(3) 0.14539(11) 0.15112(9) 0.0213(5) Uani 1 1 d . . . . .
C6A C 0.3187(4) 0.12832(12) 0.21179(9) 0.0290(5) Uani 1 1 d . . . . .
H6A H 0.4447 0.1410 0.2292 0.035 Uiso 1 1 calc R U . . .
C7A C 0.1783(4) 0.09327(13) 0.24707(11) 0.0375(6) Uani 1 1 d . . . . .
H7A H 0.2086 0.0821 0.2885 0.045 Uiso 1 1 calc R U . . .
C8A C -0.0049(4) 0.07438(13) 0.22281(11) 0.0387(6) Uani 1 1 d . . . . .
H8A H -0.1014 0.0503 0.2472 0.046 Uiso 1 1 calc R U . . .
C9A C -0.0474(4) 0.09080(13) 0.16259(11) 0.0381(6) Uani 1 1 d . . . . .
H9A H -0.1734 0.0777 0.1454 0.046 Uiso 1 1 calc R U . . .
C10A C 0.0926(3) 0.12629(12) 0.12703(10) 0.0305(5) Uani 1 1 d . . . . .
H10A H 0.0611 0.1377 0.0857 0.037 Uiso 1 1 calc R U . . .
C11A C 0.4669(3) 0.24644(11) 0.01557(9) 0.0226(5) Uani 1 1 d . . . . .
H11A H 0.6116 0.2533 0.0275 0.027 Uiso 1 1 calc R U . . .
H11B H 0.4107 0.2922 -0.0081 0.027 Uiso 1 1 calc R U . . .
C12A C 0.4682(3) 0.17627(11) -0.02312(9) 0.0220(4) Uani 1 1 d . . . . .
C13A C 0.6503(4) 0.12851(13) -0.03352(10) 0.0330(5) Uani 1 1 d . . . . .
H13A H 0.7783 0.1407 -0.0170 0.040 Uiso 1 1 calc R U . . .
C14A C 0.6470(4) 0.06301(14) -0.06790(11) 0.0423(6) Uani 1 1 d . . . . .
H14A H 0.7723 0.0303 -0.0744 0.051 Uiso 1 1 calc R U . . .
C15A C 0.4636(4) 0.04551(14) -0.09249(11) 0.0415(6) Uani 1 1 d . . . . .
H15A H 0.4617 0.0007 -0.1160 0.050 Uiso 1 1 calc R U . . .
C16A C 0.2809(4) 0.09312(13) -0.08305(10) 0.0376(6) Uani 1 1 d . . . . .
H16A H 0.1536 0.0813 -0.1002 0.045 Uiso 1 1 calc R U . . .
C17A C 0.2846(3) 0.15788(12) -0.04860(9) 0.0289(5) Uani 1 1 d . . . . .
H17A H 0.1589 0.1904 -0.0423 0.035 Uiso 1 1 calc R U . . .
P1X P 0.47473(8) 0.64392(3) 0.43397(2) 0.02074(13) Uani 1 1 d . . . . .
H1X H 0.314(3) 0.6845(11) 0.4083(9) 0.025(5) Uiso 1 1 d . . . . .
O11X O 0.5317(2) 0.57475(8) 0.39601(6) 0.0282(3) Uani 1 1 d . . . . .
O12X O 0.4306(2) 0.62878(8) 0.49974(6) 0.0302(4) Uani 1 1 d . . . . .
C2X C 0.6700(3) 0.71037(11) 0.42659(9) 0.0226(5) Uani 1 1 d . . . . .
H2X H 0.6814 0.7219 0.3823 0.027 Uiso 1 1 calc R U . . .
C21X C 0.8862(3) 0.67525(13) 0.44626(11) 0.0355(6) Uani 1 1 d . . . . .
H21X H 0.9834 0.7145 0.4447 0.043 Uiso 1 1 calc R U . . .
H21Y H 0.9355 0.6336 0.4189 0.043 Uiso 1 1 calc R U . . .
H21Z H 0.8787 0.6551 0.4877 0.043 Uiso 1 1 calc R U . . .
N3X N 0.5906(3) 0.78321(9) 0.45530(7) 0.0203(4) Uani 1 1 d . . . . .
C4X C 0.6808(3) 0.84874(12) 0.42831(9) 0.0265(5) Uani 1 1 d . . . . .
H4X H 0.8348 0.8376 0.4270 0.032 Uiso 1 1 calc R U . . .
H4Y H 0.6463 0.8940 0.4542 0.032 Uiso 1 1 calc R U . . .
C5X C 0.6015(3) 0.86711(11) 0.36510(9) 0.0224(4) Uani 1 1 d . . . . .
C6X C 0.3893(3) 0.88819(12) 0.35586(10) 0.0273(5) Uani 1 1 d . . . . .
H6X H 0.2947 0.8880 0.3890 0.033 Uiso 1 1 calc R U . . .
C7X C 0.3154(4) 0.90933(12) 0.29892(10) 0.0304(5) Uani 1 1 d . . . . .
H7X H 0.1706 0.9244 0.2933 0.037 Uiso 1 1 calc R U . . .
C8X C 0.4503(4) 0.90863(12) 0.25023(10) 0.0308(5) Uani 1 1 d . . . . .
H8X H 0.3989 0.9234 0.2111 0.037 Uiso 1 1 calc R U . . .
C9X C 0.6598(4) 0.88643(12) 0.25839(10) 0.0328(5) Uani 1 1 d . . . . .
H9X H 0.7531 0.8854 0.2248 0.039 Uiso 1 1 calc R U . . .
C10X C 0.7350(3) 0.86545(12) 0.31575(10) 0.0286(5) Uani 1 1 d . . . . .
H10X H 0.8796 0.8498 0.3211 0.034 Uiso 1 1 calc R U . . .
C11X C 0.6080(3) 0.78300(12) 0.52137(9) 0.0231(5) Uani 1 1 d . . . . .
H11X H 0.7513 0.7927 0.5326 0.028 Uiso 1 1 calc R U . . .
H11Y H 0.5833 0.7320 0.5376 0.028 Uiso 1 1 calc R U . . .
C12X C 0.4519(3) 0.84344(11) 0.54959(9) 0.0224(4) Uani 1 1 d . . . . .
C13X C 0.2496(3) 0.85711(12) 0.52789(9) 0.0276(5) Uani 1 1 d . . . . .
H13X H 0.2089 0.8293 0.4941 0.033 Uiso 1 1 calc R U . . .
C14X C 0.1056(4) 0.91093(13) 0.55484(10) 0.0338(5) Uani 1 1 d . . . . .
H14X H -0.0322 0.9201 0.5394 0.041 Uiso 1 1 calc R U . . .
C15X C 0.1634(4) 0.95108(13) 0.60420(10) 0.0349(6) Uani 1 1 d . . . . .
H15X H 0.0652 0.9880 0.6227 0.042 Uiso 1 1 calc R U . . .
C16X C 0.3628(4) 0.93774(13) 0.62656(10) 0.0327(5) Uani 1 1 d . . . . .
H16X H 0.4021 0.9649 0.6608 0.039 Uiso 1 1 calc R U . . .
C17X C 0.5067(3) 0.88449(12) 0.59892(9) 0.0278(5) Uani 1 1 d . . . . .
H17X H 0.6450 0.8761 0.6141 0.033 Uiso 1 1 calc R U . . .
N30A N 0.2110(3) 0.56158(10) 0.08577(8) 0.0189(4) Uani 1 1 d . . . . .
H30A H 0.340(4) 0.5487(12) 0.0743(9) 0.023(6) Uiso 1 1 d . . . . .
H30B H 0.137(3) 0.5876(12) 0.0543(9) 0.023(6) Uiso 1 1 d . . . . .
H30C H 0.142(4) 0.5135(14) 0.0944(10) 0.040(7) Uiso 1 1 d . . . . .
C31A C 0.2067(3) 0.61276(11) 0.13977(8) 0.0174(4) Uani 1 1 d . . . . .
C32A C -0.0186(3) 0.64921(12) 0.15039(9) 0.0258(5) Uani 1 1 d . . . . .
H32A H -0.0701 0.6783 0.1138 0.031 Uiso 1 1 calc R U . . .
H32B H -0.1112 0.6088 0.1586 0.031 Uiso 1 1 calc R U . . .
C33A C 0.3454(3) 0.67570(12) 0.12731(10) 0.0263(5) Uani 1 1 d . . . . .
H33A H 0.2944 0.7058 0.0912 0.032 Uiso 1 1 calc R U . . .
H33B H 0.4899 0.6529 0.1190 0.032 Uiso 1 1 calc R U . . .
C34A C 0.2804(4) 0.56636(12) 0.19562(9) 0.0298(5) Uani 1 1 d . . . . .
H34A H 0.4251 0.5425 0.1892 0.036 Uiso 1 1 calc R U . . .
H34B H 0.1898 0.5251 0.2029 0.036 Uiso 1 1 calc R U . . .
C35A C -0.0216(3) 0.70310(13) 0.20472(10) 0.0287(5) Uani 1 1 d . . . . .
H35A H -0.1673 0.7276 0.2114 0.034 Uiso 1 1 calc R U . . .
C36A C 0.1211(3) 0.76459(12) 0.19285(10) 0.0306(5) Uani 1 1 d . . . . .
H36A H 0.1178 0.7991 0.2280 0.037 Uiso 1 1 calc R U . . .
H36B H 0.0722 0.7954 0.1569 0.037 Uiso 1 1 calc R U . . .
C37A C 0.3436(3) 0.72820(13) 0.18217(10) 0.0303(5) Uani 1 1 d . . . . .
H37A H 0.4374 0.7690 0.1742 0.036 Uiso 1 1 calc R U . . .
C38A C 0.4186(3) 0.68135(14) 0.23797(11) 0.0382(6) Uani 1 1 d . . . . .
H38A H 0.4205 0.7153 0.2733 0.046 Uiso 1 1 calc R U . . .
H38B H 0.5625 0.6570 0.2310 0.046 Uiso 1 1 calc R U . . .
C39A C 0.2720(4) 0.61928(13) 0.25111(10) 0.0352(6) Uani 1 1 d . . . . .
H39A H 0.3200 0.5891 0.2880 0.042 Uiso 1 1 calc R U . . .
C40A C 0.0501(4) 0.65632(14) 0.26055(10) 0.0369(6) Uani 1 1 d . . . . .
H40A H -0.0442 0.6163 0.2682 0.044 Uiso 1 1 calc R U . . .
H40B H 0.0446 0.6899 0.2963 0.044 Uiso 1 1 calc R U . . .
N30X N 0.8152(3) 0.44823(10) 0.42090(8) 0.0198(4) Uani 1 1 d . . . . .
H30X H 0.939(4) 0.4575(12) 0.4337(9) 0.025(6) Uiso 1 1 d . . . . .
H30Y H 0.741(4) 0.4238(14) 0.4516(11) 0.044(7) Uiso 1 1 d . . . . .
H30Z H 0.737(4) 0.4960(14) 0.4117(10) 0.035(6) Uiso 1 1 d . . . . .
C31X C 0.8393(3) 0.39961(11) 0.36563(8) 0.0165(4) Uani 1 1 d . . . . .
C32X C 0.6265(3) 0.39894(12) 0.33512(9) 0.0230(5) Uani 1 1 d . . . . .
H32X H 0.5265 0.3783 0.3636 0.028 Uiso 1 1 calc R U . . .
H32Y H 0.5704 0.4517 0.3234 0.028 Uiso 1 1 calc R U . . .
C33X C 0.9914(3) 0.43204(11) 0.32165(9) 0.0219(4) Uani 1 1 d . . . . .
H33X H 1.1277 0.4343 0.3416 0.026 Uiso 1 1 calc R U . . .
H33Y H 0.9365 0.4846 0.3091 0.026 Uiso 1 1 calc R U . . .
C34X C 0.9228(3) 0.31834(11) 0.38476(9) 0.0222(4) Uani 1 1 d . . . . .
H34X H 0.8252 0.2979 0.4141 0.027 Uiso 1 1 calc R U . . .
H34Y H 1.0599 0.3187 0.4047 0.027 Uiso 1 1 calc R U . . .
C35X C 0.6538(3) 0.34880(13) 0.27878(9) 0.0271(5) Uani 1 1 d . . . . .
H35X H 0.5158 0.3486 0.2583 0.033 Uiso 1 1 calc R U . . .
C36X C 0.8085(3) 0.38000(14) 0.23490(9) 0.0290(5) Uani 1 1 d . . . . .
H36X H 0.7554 0.4326 0.2219 0.035 Uiso 1 1 calc R U . . .
H36Y H 0.8247 0.3476 0.1985 0.035 Uiso 1 1 calc R U . . .
C37X C 1.0197(3) 0.38070(12) 0.26596(9) 0.0237(5) Uani 1 1 d . . . . .
H37X H 1.1213 0.4012 0.2372 0.028 Uiso 1 1 calc R U . . .
C38X C 1.1009(3) 0.29946(12) 0.28534(9) 0.0275(5) Uani 1 1 d . . . . .
H38X H 1.2379 0.2996 0.3053 0.033 Uiso 1 1 calc R U . . .
H38Y H 1.1203 0.2666 0.2492 0.033 Uiso 1 1 calc R U . . .
C39X C 0.9465(3) 0.26749(12) 0.32894(9) 0.0263(5) Uani 1 1 d . . . . .
H39X H 1.0007 0.2142 0.3414 0.032 Uiso 1 1 calc R U . . .
C40X C 0.7344(3) 0.26687(13) 0.29807(10) 0.0312(5) Uani 1 1 d . . . . .
H40X H 0.6338 0.2464 0.3264 0.037 Uiso 1 1 calc R U . . .
H40Y H 0.7491 0.2336 0.2621 0.037 Uiso 1 1 calc R U . . .
O1W O -0.3475(2) 0.53237(11) 0.05714(8) 0.0341(4) Uani 1 1 d . . . . .
H11W H -0.260(4) 0.4985(15) 0.0730(11) 0.043(7) Uiso 1 1 d . . . . .
H12W H -0.275(5) 0.5632(17) 0.0388(13) 0.060(10) Uiso 1 1 d . . . . .
O2W O 0.2443(2) 0.47195(10) 0.45041(8) 0.0301(4) Uani 1 1 d . . . . .
H21W H 0.307(5) 0.5074(19) 0.4300(14) 0.077(11) Uiso 1 1 d . . . . .
H22W H 0.334(5) 0.4390(17) 0.4660(12) 0.059(9) Uiso 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
P1A O12A 1.5022(14) . ?
P1A O11A 1.5034(13) . ?
P1A C2A 1.8161(18) . ?
P1A H1A 1.35(2) . ?
C2A N3A 1.477(2) . ?
C2A C21A 1.527(3) . ?
C2A H2A 1.0000 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
N3A C4A 1.467(2) . ?
N3A C11A 1.468(2) . ?
C4A C5A 1.499(3) . ?
C4A H4A 0.9900 . ?
C4A H4B 0.9900 . ?
C5A C10A 1.388(3) . ?
C5A C6A 1.389(3) . ?
C6A C7A 1.379(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.374(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.380(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.384(3) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?
C11A C12A 1.509(3) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C17A 1.384(3) . ?
C12A C13A 1.386(3) . ?
C13A C14A 1.390(3) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.370(4) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.385(3) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.380(3) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9500 . ?
P1X O11X 1.4978(14) . ?
P1X O12X 1.5037(15) . ?
P1X C2X 1.812(2) . ?
P1X H1X 1.318(19) . ?
C2X N3X 1.477(2) . ?
C2X C21X 1.524(3) . ?
C2X H2X 1.0000 . ?
C21X H21X 0.9800 . ?
C21X H21Y 0.9800 . ?
C21X H21Z 0.9800 . ?
N3X C4X 1.464(3) . ?
N3X C11X 1.464(2) . ?
C4X C5X 1.508(3) . ?
C4X H4X 0.9900 . ?
C4X H4Y 0.9900 . ?
C5X C10X 1.382(3) . ?
C5X C6X 1.393(3) . ?
C6X C7X 1.380(3) . ?
C6X H6X 0.9500 . ?
C7X C8X 1.377(3) . ?
C7X H7X 0.9500 . ?
C8X C9X 1.376(3) . ?
C8X H8X 0.9500 . ?
C9X C10X 1.390(3) . ?
C9X H9X 0.9500 . ?
C10X H10X 0.9500 . ?
C11X C12X 1.519(3) . ?
C11X H11X 0.9900 . ?
C11X H11Y 0.9900 . ?
C12X C17X 1.383(3) . ?
C12X C13X 1.387(3) . ?
C13X C14X 1.388(3) . ?
C13X H13X 0.9500 . ?
C14X C15X 1.381(3) . ?
C14X H14X 0.9500 . ?
C15X C16X 1.374(3) . ?
C15X H15X 0.9500 . ?
C16X C17X 1.389(3) . ?
C16X H16X 0.9500 . ?
C17X H17X 0.9500 . ?
N30A C31A 1.502(2) . ?
N30A H30A 0.87(2) . ?
N30A H30B 0.93(2) . ?
N30A H30C 1.01(3) . ?
C31A C33A 1.517(3) . ?
C31A C34A 1.520(3) . ?
C31A C32A 1.540(3) . ?
C32A C35A 1.537(3) . ?
C32A H32A 0.9900 . ?
C32A H32B 0.9900 . ?
C33A C37A 1.532(3) . ?
C33A H33A 0.9900 . ?
C33A H33B 0.9900 . ?
C34A C39A 1.545(3) . ?
C34A H34A 0.9900 . ?
C34A H34B 0.9900 . ?
C35A C36A 1.512(3) . ?
C35A C40A 1.519(3) . ?
C35A H35A 1.0000 . ?
C36A C37A 1.523(3) . ?
C36A H36A 0.9900 . ?
C36A H36B 0.9900 . ?
C37A C38A 1.525(3) . ?
C37A H37A 1.0000 . ?
C38A C39A 1.542(3) . ?
C38A H38A 0.9900 . ?
C38A H38B 0.9900 . ?
C39A C40A 1.520(3) . ?
C39A H39A 1.0000 . ?
C40A H40A 0.9900 . ?
C40A H40B 0.9900 . ?
N30X C31X 1.497(2) . ?
N30X H30X 0.88(2) . ?
N30X H30Y 0.95(3) . ?
N30X H30Z 0.95(2) . ?
C31X C33X 1.523(3) . ?
C31X C34X 1.527(3) . ?
C31X C32X 1.533(3) . ?
C32X C35X 1.532(3) . ?
C32X H32X 0.9900 . ?
C32X H32Y 0.9900 . ?
C33X C37X 1.533(3) . ?
C33X H33X 0.9900 . ?
C33X H33Y 0.9900 . ?
C34X C39X 1.529(3) . ?
C34X H34X 0.9900 . ?
C34X H34Y 0.9900 . ?
C35X C36X 1.524(3) . ?
C35X C40X 1.534(3) . ?
C35X H35X 1.0000 . ?
C36X C37X 1.529(3) . ?
C36X H36X 0.9900 . ?
C36X H36Y 0.9900 . ?
C37X C38X 1.524(3) . ?
C37X H37X 1.0000 . ?
C38X C39X 1.524(3) . ?
C38X H38X 0.9900 . ?
C38X H38Y 0.9900 . ?
C39X C40X 1.532(3) . ?
C39X H39X 1.0000 . ?
C40X H40X 0.9900 . ?
C40X H40Y 0.9900 . ?
O1W H11W 0.85(3) . ?
O1W H12W 0.85(3) . ?
O2W H21W 0.89(4) . ?
O2W H22W 0.84(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
O12A P1A O11A 117.04(8) . . ?
O12A P1A C2A 111.97(8) . . ?
O11A P1A C2A 107.95(8) . . ?
O12A P1A H1A 108.2(8) . . ?
O11A P1A H1A 109.3(8) . . ?
C2A P1A H1A 101.1(8) . . ?
N3A C2A C21A 116.01(16) . . ?
N3A C2A P1A 110.39(12) . . ?
C21A C2A P1A 112.30(14) . . ?
N3A C2A H2A 105.8 . . ?
C21A C2A H2A 105.8 . . ?
P1A C2A H2A 105.8 . . ?
C2A C21A H21A 109.5 . . ?
C2A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C2A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C4A N3A C11A 111.77(14) . . ?
C4A N3A C2A 111.75(15) . . ?
C11A N3A C2A 113.84(16) . . ?
N3A C4A C5A 112.96(15) . . ?
N3A C4A H4A 109.0 . . ?
C5A C4A H4A 109.0 . . ?
N3A C4A H4B 109.0 . . ?
C5A C4A H4B 109.0 . . ?
H4A C4A H4B 107.8 . . ?
C10A C5A C6A 118.1(2) . . ?
C10A C5A C4A 120.67(18) . . ?
C6A C5A C4A 121.16(19) . . ?
C7A C6A C5A 121.0(2) . . ?
C7A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
C8A C7A C6A 120.5(2) . . ?
C8A C7A H7A 119.7 . . ?
C6A C7A H7A 119.7 . . ?
C7A C8A C9A 119.3(2) . . ?
C7A C8A H8A 120.4 . . ?
C9A C8A H8A 120.4 . . ?
C8A C9A C10A 120.4(2) . . ?
C8A C9A H9A 119.8 . . ?
C10A C9A H9A 119.8 . . ?
C9A C10A C5A 120.7(2) . . ?
C9A C10A H10A 119.7 . . ?
C5A C10A H10A 119.7 . . ?
N3A C11A C12A 110.43(17) . . ?
N3A C11A H11A 109.6 . . ?
C12A C11A H11A 109.6 . . ?
N3A C11A H11B 109.6 . . ?
C12A C11A H11B 109.6 . . ?
H11A C11A H11B 108.1 . . ?
C17A C12A C13A 118.47(19) . . ?
C17A C12A C11A 120.05(17) . . ?
C13A C12A C11A 121.48(19) . . ?
C12A C13A C14A 120.6(2) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A H13A 119.7 . . ?
C15A C14A C13A 120.1(2) . . ?
C15A C14A H14A 119.9 . . ?
C13A C14A H14A 119.9 . . ?
C14A C15A C16A 120.0(2) . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C17A C16A C15A 119.7(2) . . ?
C17A C16A H16A 120.1 . . ?
C15A C16A H16A 120.1 . . ?
C16A C17A C12A 121.1(2) . . ?
C16A C17A H17A 119.4 . . ?
C12A C17A H17A 119.4 . . ?
O11X P1X O12X 115.95(9) . . ?
O11X P1X C2X 110.72(9) . . ?
O12X P1X C2X 110.22(9) . . ?
O11X P1X H1X 107.8(8) . . ?
O12X P1X H1X 110.9(9) . . ?
C2X P1X H1X 100.1(9) . . ?
N3X C2X C21X 116.26(17) . . ?
N3X C2X P1X 109.03(13) . . ?
C21X C2X P1X 112.56(15) . . ?
N3X C2X H2X 106.1 . . ?
C21X C2X H2X 106.1 . . ?
P1X C2X H2X 106.1 . . ?
C2X C21X H21X 109.5 . . ?
C2X C21X H21Y 109.5 . . ?
H21X C21X H21Y 109.5 . . ?
C2X C21X H21Z 109.5 . . ?
H21X C21X H21Z 109.5 . . ?
H21Y C21X H21Z 109.5 . . ?
C4X N3X C11X 110.99(16) . . ?
C4X N3X C2X 112.36(16) . . ?
C11X N3X C2X 114.56(15) . . ?
N3X C4X C5X 112.29(16) . . ?
N3X C4X H4X 109.1 . . ?
C5X C4X H4X 109.1 . . ?
N3X C4X H4Y 109.1 . . ?
C5X C4X H4Y 109.1 . . ?
H4X C4X H4Y 107.9 . . ?
C10X C5X C6X 118.59(19) . . ?
C10X C5X C4X 121.72(19) . . ?
C6X C5X C4X 119.68(19) . . ?
C7X C6X C5X 120.5(2) . . ?
C7X C6X H6X 119.7 . . ?
C5X C6X H6X 119.7 . . ?
C8X C7X C6X 120.3(2) . . ?
C8X C7X H7X 119.8 . . ?
C6X C7X H7X 119.8 . . ?
C9X C8X C7X 119.8(2) . . ?
C9X C8X H8X 120.1 . . ?
C7X C8X H8X 120.1 . . ?
C8X C9X C10X 120.0(2) . . ?
C8X C9X H9X 120.0 . . ?
C10X C9X H9X 120.0 . . ?
C5X C10X C9X 120.7(2) . . ?
C5X C10X H10X 119.7 . . ?
C9X C10X H10X 119.7 . . ?
N3X C11X C12X 111.56(16) . . ?
N3X C11X H11X 109.3 . . ?
C12X C11X H11X 109.3 . . ?
N3X C11X H11Y 109.3 . . ?
C12X C11X H11Y 109.3 . . ?
H11X C11X H11Y 108.0 . . ?
C17X C12X C13X 118.39(19) . . ?
C17X C12X C11X 120.59(18) . . ?
C13X C12X C11X 120.99(18) . . ?
C12X C13X C14X 120.8(2) . . ?
C12X C13X H13X 119.6 . . ?
C14X C13X H13X 119.6 . . ?
C15X C14X C13X 119.8(2) . . ?
C15X C14X H14X 120.1 . . ?
C13X C14X H14X 120.1 . . ?
C16X C15X C14X 120.0(2) . . ?
C16X C15X H15X 120.0 . . ?
C14X C15X H15X 120.0 . . ?
C15X C16X C17X 119.8(2) . . ?
C15X C16X H16X 120.1 . . ?
C17X C16X H16X 120.1 . . ?
C12X C17X C16X 121.1(2) . . ?
C12X C17X H17X 119.5 . . ?
C16X C17X H17X 119.5 . . ?
C31A N30A H30A 109.9(13) . . ?
C31A N30A H30B 109.0(12) . . ?
H30A N30A H30B 109.6(19) . . ?
C31A N30A H30C 112.3(13) . . ?
H30A N30A H30C 109.0(19) . . ?
H30B N30A H30C 106.9(18) . . ?
N30A C31A C33A 109.18(16) . . ?
N30A C31A C34A 109.89(16) . . ?
C33A C31A C34A 110.67(16) . . ?
N30A C31A C32A 109.08(15) . . ?
C33A C31A C32A 108.90(16) . . ?
C34A C31A C32A 109.09(17) . . ?
C35A C32A C31A 108.96(16) . . ?
C35A C32A H32A 109.9 . . ?
C31A C32A H32A 109.9 . . ?
C35A C32A H32B 109.9 . . ?
C31A C32A H32B 109.9 . . ?
H32A C32A H32B 108.3 . . ?
C31A C33A C37A 109.81(17) . . ?
C31A C33A H33A 109.7 . . ?
C37A C33A H33A 109.7 . . ?
C31A C33A H33B 109.7 . . ?
C37A C33A H33B 109.7 . . ?
H33A C33A H33B 108.2 . . ?
C31A C34A C39A 109.48(17) . . ?
C31A C34A H34A 109.8 . . ?
C39A C34A H34A 109.8 . . ?
C31A C34A H34B 109.8 . . ?
C39A C34A H34B 109.8 . . ?
H34A C34A H34B 108.2 . . ?
C36A C35A C40A 110.08(18) . . ?
C36A C35A C32A 110.28(18) . . ?
C40A C35A C32A 108.59(18) . . ?
C36A C35A H35A 109.3 . . ?
C40A C35A H35A 109.3 . . ?
C32A C35A H35A 109.3 . . ?
C35A C36A C37A 109.92(18) . . ?
C35A C36A H36A 109.7 . . ?
C37A C36A H36A 109.7 . . ?
C35A C36A H36B 109.7 . . ?
C37A C36A H36B 109.7 . . ?
H36A C36A H36B 108.2 . . ?
C36A C37A C38A 109.41(19) . . ?
C36A C37A C33A 108.79(17) . . ?
C38A C37A C33A 109.52(18) . . ?
C36A C37A H37A 109.7 . . ?
C38A C37A H37A 109.7 . . ?
C33A C37A H37A 109.7 . . ?
C37A C38A C39A 109.90(17) . . ?
C37A C38A H38A 109.7 . . ?
C39A C38A H38A 109.7 . . ?
C37A C38A H38B 109.7 . . ?
C39A C38A H38B 109.7 . . ?
H38A C38A H38B 108.2 . . ?
C40A C39A C38A 109.84(19) . . ?
C40A C39A C34A 109.73(18) . . ?
C38A C39A C34A 107.6(2) . . ?
C40A C39A H39A 109.9 . . ?
C38A C39A H39A 109.9 . . ?
C34A C39A H39A 109.9 . . ?
C35A C40A C39A 109.83(19) . . ?
C35A C40A H40A 109.7 . . ?
C39A C40A H40A 109.7 . . ?
C35A C40A H40B 109.7 . . ?
C39A C40A H40B 109.7 . . ?
H40A C40A H40B 108.2 . . ?
C31X N30X H30X 109.6(13) . . ?
C31X N30X H30Y 110.2(15) . . ?
H30X N30X H30Y 111(2) . . ?
C31X N30X H30Z 110.3(13) . . ?
H30X N30X H30Z 108(2) . . ?
H30Y N30X H30Z 107.4(19) . . ?
N30X C31X C33X 109.52(16) . . ?
N30X C31X C34X 108.65(15) . . ?
C33X C31X C34X 110.00(15) . . ?
N30X C31X C32X 109.42(15) . . ?
C33X C31X C32X 109.54(16) . . ?
C34X C31X C32X 109.69(16) . . ?
C35X C32X C31X 108.77(15) . . ?
C35X C32X H32X 109.9 . . ?
C31X C32X H32X 109.9 . . ?
C35X C32X H32Y 109.9 . . ?
C31X C32X H32Y 109.9 . . ?
H32X C32X H32Y 108.3 . . ?
C31X C33X C37X 109.16(16) . . ?
C31X C33X H33X 109.8 . . ?
C37X C33X H33X 109.8 . . ?
C31X C33X H33Y 109.8 . . ?
C37X C33X H33Y 109.8 . . ?
H33X C33X H33Y 108.3 . . ?
C31X C34X C39X 109.47(16) . . ?
C31X C34X H34X 109.8 . . ?
C39X C34X H34X 109.8 . . ?
C31X C34X H34Y 109.8 . . ?
C39X C34X H34Y 109.8 . . ?
H34X C34X H34Y 108.2 . . ?
C36X C35X C32X 110.16(18) . . ?
C36X C35X C40X 109.74(17) . . ?
C32X C35X C40X 109.13(17) . . ?
C36X C35X H35X 109.3 . . ?
C32X C35X H35X 109.3 . . ?
C40X C35X H35X 109.3 . . ?
C35X C36X C37X 109.55(17) . . ?
C35X C36X H36X 109.8 . . ?
C37X C36X H36X 109.8 . . ?
C35X C36X H36Y 109.8 . . ?
C37X C36X H36Y 109.8 . . ?
H36X C36X H36Y 108.2 . . ?
C38X C37X C36X 109.34(18) . . ?
C38X C37X C33X 109.88(16) . . ?
C36X C37X C33X 108.83(16) . . ?
C38X C37X H37X 109.6 . . ?
C36X C37X H37X 109.6 . . ?
C33X C37X H37X 109.6 . . ?
C37X C38X C39X 110.05(16) . . ?
C37X C38X H38X 109.7 . . ?
C39X C38X H38X 109.7 . . ?
C37X C38X H38Y 109.7 . . ?
C39X C38X H38Y 109.7 . . ?
H38X C38X H38Y 108.2 . . ?
C38X C39X C34X 108.55(18) . . ?
C38X C39X C40X 109.83(17) . . ?
C34X C39X C40X 109.75(17) . . ?
C38X C39X H39X 109.6 . . ?
C34X C39X H39X 109.6 . . ?
C40X C39X H39X 109.6 . . ?
C39X C40X C35X 109.02(17) . . ?
C39X C40X H40X 109.9 . . ?
C35X C40X H40X 109.9 . . ?
C39X C40X H40Y 109.9 . . ?
C35X C40X H40Y 109.9 . . ?
H40X C40X H40Y 108.3 . . ?
H11W O1W H12W 106(2) . . ?
H21W O2W H22W 111(3) . . ?

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_dbampin
_database_code_depnum_ccdc_archive 'CCDC 1984991'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N O2 P'
_chemical_formula_sum            'C15 H18 N O2 P'
_chemical_formula_weight         275.27

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      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                   10.2763(4)
_cell_length_b                   9.1700(3)
_cell_length_c                   15.3112(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.2290(10)
_cell_angle_gamma                90
_cell_volume                     1404.54(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.6078
_cell_measurement_theta_max      27.5233

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.193
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            27104
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3210
_reflns_number_gt                2966
_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 Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0375P)²+0.8661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3210
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
P1 P 0.19848(3) 0.83371(3) 0.64264(2) 0.01141(9) Uani 1 1 d . . . . .
H1 H 0.1454(15) 0.7837(16) 0.5616(10) 0.015(3) Uiso 1 1 d . . . . .
O11 O 0.08431(8) 0.88510(9) 0.68183(6) 0.01391(18) Uani 1 1 d . . . . .
O12 O 0.31084(9) 0.93453(10) 0.63985(6) 0.0203(2) Uani 1 1 d . . . . .
C2 C 0.25745(11) 0.66613(12) 0.70570(8) 0.0121(2) Uani 1 1 d . . . . .
H21 H 0.2382 0.6756 0.7659 0.015 Uiso 1 1 calc R U . . .
H22 H 0.2028 0.5841 0.6751 0.015 Uiso 1 1 calc R U . . .
N3 N 0.40205(9) 0.62392(11) 0.71854(6) 0.01066(19) Uani 1 1 d . . . . .
H31 H 0.4097(16) 0.5372(19) 0.7497(11) 0.023(4) Uiso 1 1 d . . . . .
C4 C 0.44603(11) 0.60427(13) 0.63174(8) 0.0136(2) Uani 1 1 d . . . . .
H41 H 0.4491 0.7006 0.6031 0.016 Uiso 1 1 calc R U . . .
H42 H 0.5374 0.5627 0.6448 0.016 Uiso 1 1 calc R U . . .
C5 C 0.35302(11) 0.50514(12) 0.56760(8) 0.0120(2) Uani 1 1 d . . . . .
C6 C 0.28873(12) 0.55468(13) 0.48293(8) 0.0161(2) Uani 1 1 d . . . . .
H61 H 0.3046 0.6509 0.4649 0.019 Uiso 1 1 calc R U . . .
C7 C 0.20100(13) 0.46350(14) 0.42444(8) 0.0199(3) Uani 1 1 d . . . . .
H71 H 0.1575 0.4980 0.3666 0.024 Uiso 1 1 calc R U . . .
C8 C 0.17671(13) 0.32280(14) 0.45003(8) 0.0179(3) Uani 1 1 d . . . . .
H81 H 0.1160 0.2614 0.4103 0.022 Uiso 1 1 calc R U . . .
C9 C 0.24206(13) 0.27242(13) 0.53440(8) 0.0169(2) Uani 1 1 d . . . . .
H91 H 0.2265 0.1760 0.5523 0.020 Uiso 1 1 calc R U . . .
C10 C 0.32989(12) 0.36279(13) 0.59246(8) 0.0147(2) Uani 1 1 d . . . . .
H101 H 0.3748 0.3274 0.6498 0.018 Uiso 1 1 calc R U . . .
C11 C 0.49073(11) 0.73028(13) 0.78110(8) 0.0143(2) Uani 1 1 d . . . . .
H111 H 0.4859 0.8267 0.7514 0.017 Uiso 1 1 calc R U . . .
H112 H 0.4561 0.7418 0.8360 0.017 Uiso 1 1 calc R U . . .
C12 C 0.63501(11) 0.68294(12) 0.80764(7) 0.0121(2) Uani 1 1 d . . . . .
C13 C 0.72798(12) 0.74117(14) 0.76387(8) 0.0166(2) Uani 1 1 d . . . . .
H131 H 0.6996 0.8087 0.7162 0.020 Uiso 1 1 calc R U . . .
C14 C 0.86204(12) 0.70136(15) 0.78927(8) 0.0195(3) Uani 1 1 d . . . . .
H141 H 0.9245 0.7410 0.7586 0.023 Uiso 1 1 calc R U . . .
C15 C 0.90457(12) 0.60387(14) 0.85937(8) 0.0184(3) Uani 1 1 d . . . . .
H151 H 0.9960 0.5763 0.8766 0.022 Uiso 1 1 calc R U . . .
C16 C 0.81291(12) 0.54691(13) 0.90423(8) 0.0174(2) Uani 1 1 d . . . . .
H161 H 0.8420 0.4814 0.9529 0.021 Uiso 1 1 calc R U . . .
C17 C 0.67837(12) 0.58538(13) 0.87826(8) 0.0142(2) Uani 1 1 d . . . . .
H171 H 0.6160 0.5451 0.9087 0.017 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 O12 1.4874(9) . ?
P1 O11 1.5103(8) . ?
P1 C2 1.8420(11) . ?
P1 H1 1.319(15) . ?
C2 N3 1.5043(14) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.5093(14) . ?
N3 C11 1.5165(14) . ?
N3 H31 0.922(17) . ?
C4 C5 1.5082(15) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.3897(16) . ?
C5 C10 1.3953(16) . ?
C6 C7 1.3944(17) . ?
C6 H61 0.9500 . ?
C7 C8 1.3874(18) . ?
C7 H71 0.9500 . ?
C8 C9 1.3914(17) . ?
C8 H81 0.9500 . ?
C9 C10 1.3873(17) . ?
C9 H91 0.9500 . ?
C10 H101 0.9500 . ?
C11 C12 1.5087(15) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C13 1.3928(16) . ?
C12 C17 1.3955(16) . ?
C13 C14 1.3919(17) . ?
C13 H131 0.9500 . ?
C14 C15 1.3884(19) . ?
C14 H141 0.9500 . ?
C15 C16 1.3885(18) . ?
C15 H151 0.9500 . ?
C16 C17 1.3937(17) . ?
C16 H161 0.9500 . ?
C17 H171 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 P1 O11 119.75(5) . . ?
O12 P1 C2 111.67(5) . . ?
O11 P1 C2 104.14(5) . . ?
O12 P1 H1 110.2(6) . . ?
O11 P1 H1 106.9(6) . . ?
C2 P1 H1 102.6(7) . . ?
N3 C2 P1 118.67(8) . . ?
N3 C2 H21 107.6 . . ?
P1 C2 H21 107.6 . . ?
N3 C2 H22 107.6 . . ?
P1 C2 H22 107.6 . . ?
H21 C2 H22 107.1 . . ?
C2 N3 C4 113.68(9) . . ?
C2 N3 C11 110.48(9) . . ?
C4 N3 C11 112.04(9) . . ?
C2 N3 H31 104.7(10) . . ?
C4 N3 H31 110.2(10) . . ?
C11 N3 H31 105.1(10) . . ?
C5 C4 N3 111.87(9) . . ?
C5 C4 H41 109.2 . . ?
N3 C4 H41 109.2 . . ?
C5 C4 H42 109.2 . . ?
N3 C4 H42 109.2 . . ?
H41 C4 H42 107.9 . . ?
C6 C5 C10 119.08(11) . . ?
C6 C5 C4 120.37(10) . . ?
C10 C5 C4 120.55(10) . . ?
C5 C6 C7 120.17(11) . . ?
C5 C6 H61 119.9 . . ?
C7 C6 H61 119.9 . . ?
C8 C7 C6 120.52(11) . . ?
C8 C7 H71 119.7 . . ?
C6 C7 H71 119.7 . . ?
C7 C8 C9 119.41(11) . . ?
C7 C8 H81 120.3 . . ?
C9 C8 H81 120.3 . . ?
C10 C9 C8 120.11(11) . . ?
C10 C9 H91 119.9 . . ?
C8 C9 H91 119.9 . . ?
C9 C10 C5 120.69(11) . . ?
C9 C10 H101 119.7 . . ?
C5 C10 H101 119.7 . . ?
C12 C11 N3 113.36(9) . . ?
C12 C11 H111 108.9 . . ?
N3 C11 H111 108.9 . . ?
C12 C11 H112 108.9 . . ?
N3 C11 H112 108.9 . . ?
H111 C11 H112 107.7 . . ?
C13 C12 C17 119.08(11) . . ?
C13 C12 C11 120.01(11) . . ?
C17 C12 C11 120.86(10) . . ?
C14 C13 C12 120.60(11) . . ?
C14 C13 H131 119.7 . . ?
C12 C13 H131 119.7 . . ?
C15 C14 C13 120.08(11) . . ?
C15 C14 H141 120.0 . . ?
C13 C14 H141 120.0 . . ?
C14 C15 C16 119.70(11) . . ?
C14 C15 H151 120.2 . . ?
C16 C15 H151 120.2 . . ?
C15 C16 C17 120.31(11) . . ?
C15 C16 H161 119.8 . . ?
C17 C16 H161 119.8 . . ?
C16 C17 C12 120.22(11) . . ?
C16 C17 H171 119.9 . . ?
C12 C17 H171 119.9 . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_diprampin
_database_code_depnum_ccdc_archive 'CCDC 1984990'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H18 N O2 P, 2(H2 O)'
_chemical_formula_sum            'C7 H22 N O4 P'
_chemical_formula_weight         215.22

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   13.3640(6)
_cell_length_b                   8.5851(4)
_cell_length_c                   20.1404(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.384(2)
_cell_angle_gamma                90
_cell_volume                     2310.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9998
_cell_measurement_theta_min      2.8202
_cell_measurement_theta_max      27.4702

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            16179
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.820
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2663
_reflns_number_gt                2425
_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 Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0386P)²+1.7367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2663
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
P1 P 0.51372(2) 0.35154(3) 0.59620(2) 0.01422(9) Uani 1 1 d . . . . .
H1 H 0.6085(10) 0.3355(16) 0.5789(7) 0.016(3) Uiso 1 1 d . . . . .
O11 O 0.44695(6) 0.35925(10) 0.53559(4) 0.02006(19) Uani 1 1 d . . . . .
O12 O 0.49424(7) 0.23103(10) 0.64827(4) 0.02268(19) Uani 1 1 d . . . . .
C2 C 0.51304(8) 0.53839(12) 0.63919(5) 0.0133(2) Uani 1 1 d . . . . .
H21 H 0.4481 0.5495 0.6613 0.016 Uiso 1 1 calc R U . . .
H22 H 0.5660 0.5363 0.6744 0.016 Uiso 1 1 calc R U . . .
N3 N 0.52890(7) 0.68082(11) 0.59674(4) 0.01232(18) Uani 1 1 d . . . . .
H31 H 0.5315(11) 0.6560(18) 0.5541(8) 0.026(4) Uiso 1 1 d . . . . .
C4 C 0.44196(8) 0.79505(13) 0.60064(6) 0.0166(2) Uani 1 1 d . . . . .
H41 H 0.4557 0.8833 0.5698 0.020 Uiso 1 1 calc R U . . .
C5 C 0.34563(9) 0.71695(15) 0.57659(6) 0.0225(3) Uani 1 1 d . . . . .
H51 H 0.2961 0.7968 0.5643 0.027 Uiso 1 1 calc R U . . .
H52 H 0.3195 0.6518 0.6122 0.027 Uiso 1 1 calc R U . . .
H53 H 0.3592 0.6520 0.5378 0.027 Uiso 1 1 calc R U . . .
C6 C 0.43301(10) 0.86214(14) 0.66995(6) 0.0225(3) Uani 1 1 d . . . . .
H61 H 0.4951 0.9164 0.6825 0.027 Uiso 1 1 calc R U . . .
H62 H 0.4211 0.7776 0.7015 0.027 Uiso 1 1 calc R U . . .
H63 H 0.3770 0.9357 0.6706 0.027 Uiso 1 1 calc R U . . .
C7 C 0.63089(8) 0.75497(14) 0.61198(6) 0.0187(2) Uani 1 1 d . . . . .
H71 H 0.6362 0.7774 0.6607 0.022 Uiso 1 1 calc R U . . .
C8 C 0.71264(9) 0.64001(16) 0.59435(7) 0.0249(3) Uani 1 1 d . . . . .
H81 H 0.7049 0.6105 0.5475 0.030 Uiso 1 1 calc R U . . .
H82 H 0.7074 0.5470 0.6222 0.030 Uiso 1 1 calc R U . . .
H83 H 0.7783 0.6885 0.6020 0.030 Uiso 1 1 calc R U . . .
C9 C 0.64328(10) 0.90715(16) 0.57417(7) 0.0288(3) Uani 1 1 d . . . . .
H91 H 0.6275 0.8901 0.5270 0.035 Uiso 1 1 calc R U . . .
H92 H 0.7125 0.9436 0.5795 0.035 Uiso 1 1 calc R U . . .
H93 H 0.5978 0.9857 0.5918 0.035 Uiso 1 1 calc R U . . .
O1W O 0.36135(7) 0.20470(11) 0.75028(5) 0.0258(2) Uani 1 1 d . . . . .
H11W H 0.3992(13) 0.208(2) 0.7162(9) 0.035(4) Uiso 1 1 d . . . . .
H12W H 0.3996(15) 0.209(2) 0.7831(11) 0.048(5) Uiso 1 1 d . . . . .
O2W O 0.18997(7) 0.02612(13) 0.76768(5) 0.0315(2) Uani 1 1 d . . . . .
H21W H 0.2494(17) 0.060(3) 0.7624(10) 0.056(6) Uiso 1 1 d . . . . .
H22W H 0.1945(14) -0.073(3) 0.7605(9) 0.047(5) Uiso 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
P1 O11 1.4960(9) . ?
P1 O12 1.5005(8) . ?
P1 C2 1.8230(11) . ?
P1 H1 1.329(13) . ?
C2 N3 1.5100(13) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.5238(14) . ?
N3 C7 1.5287(14) . ?
N3 H31 0.886(16) . ?
C4 C6 1.5176(16) . ?
C4 C5 1.5203(16) . ?
C4 H41 1.0000 . ?
C5 H51 0.9800 . ?
C5 H52 0.9800 . ?
C5 H53 0.9800 . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 C8 1.5207(17) . ?
C7 C9 1.5233(17) . ?
C7 H71 1.0000 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C9 H91 0.9800 . ?
C9 H92 0.9800 . ?
C9 H93 0.9800 . ?
O1W H11W 0.863(18) . ?
O1W H12W 0.83(2) . ?
O2W H21W 0.86(2) . ?
O2W H22W 0.86(2) . ?

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
O11 P1 O12 119.38(5) . . ?
O11 P1 C2 109.81(5) . . ?
O12 P1 C2 105.77(5) . . ?
O11 P1 H1 110.2(6) . . ?
O12 P1 H1 107.1(6) . . ?
C2 P1 H1 103.4(6) . . ?
N3 C2 P1 116.18(7) . . ?
N3 C2 H21 108.2 . . ?
P1 C2 H21 108.2 . . ?
N3 C2 H22 108.2 . . ?
P1 C2 H22 108.2 . . ?
H21 C2 H22 107.4 . . ?
C2 N3 C4 111.98(8) . . ?
C2 N3 C7 111.11(8) . . ?
C4 N3 C7 113.51(8) . . ?
C2 N3 H31 111.3(10) . . ?
C4 N3 H31 104.6(10) . . ?
C7 N3 H31 103.9(10) . . ?
C6 C4 C5 112.05(10) . . ?
C6 C4 N3 111.64(9) . . ?
C5 C4 N3 109.92(9) . . ?
C6 C4 H41 107.7 . . ?
C5 C4 H41 107.7 . . ?
N3 C4 H41 107.7 . . ?
C4 C5 H51 109.5 . . ?
C4 C5 H52 109.5 . . ?
H51 C5 H52 109.5 . . ?
C4 C5 H53 109.5 . . ?
H51 C5 H53 109.5 . . ?
H52 C5 H53 109.5 . . ?
C4 C6 H61 109.5 . . ?
C4 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
C4 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
C8 C7 C9 110.64(10) . . ?
C8 C7 N3 108.96(9) . . ?
C9 C7 N3 111.34(10) . . ?
C8 C7 H71 108.6 . . ?
C9 C7 H71 108.6 . . ?
N3 C7 H71 108.6 . . ?
C7 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C7 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
C7 C9 H91 109.5 . . ?
C7 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
C7 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
H11W O1W H12W 105.8(17) . . ?
H21W O2W H22W 104.2(18) . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_dbabnpin
_database_code_depnum_ccdc_archive 'CCDC 1984987'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N O2 P, C H4 O'
_chemical_formula_sum            'C23 H28 N O3 P'
_chemical_formula_weight         397.43

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7954(5)
_cell_length_b                   9.9645(5)
_cell_length_c                   11.1729(6)
_cell_angle_alpha                73.496(2)
_cell_angle_beta                 82.075(2)
_cell_angle_gamma                87.525(2)
_cell_volume                     1035.62(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.4340
_cell_measurement_theta_max      27.5371

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            19211
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.099
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4763
_reflns_number_gt                4190
_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 Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0407P)²+0.5483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4763
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
P1 P 0.69186(3) 0.47241(3) 0.31901(3) 0.01699(9) Uani 1 1 d . . . . .
H1 H 0.6460(15) 0.5051(15) 0.2066(13) 0.019(4) Uiso 1 1 d . . . . .
O11 O 0.57845(9) 0.40951(9) 0.42181(8) 0.0225(2) Uani 1 1 d . . . . .
O12 O 0.82437(10) 0.39503(10) 0.30759(9) 0.0272(2) Uani 1 1 d . . . . .
C2 C 0.72499(12) 0.64771(12) 0.33708(10) 0.0149(2) Uani 1 1 d . . . . .
H21 H 0.6586 0.7146 0.2902 0.018 Uiso 1 1 calc R U . . .
C21 C 0.87011(12) 0.70416(13) 0.28185(11) 0.0186(2) Uani 1 1 d . . . . .
H211 H 0.8870 0.7850 0.3127 0.022 Uiso 1 1 calc R U . . .
H212 H 0.9386 0.6306 0.3119 0.022 Uiso 1 1 calc R U . . .
C22 C 0.89016(12) 0.74958(13) 0.13884(11) 0.0185(2) Uani 1 1 d . . . . .
C23 C 0.82547(17) 0.86905(15) 0.07289(13) 0.0304(3) Uani 1 1 d . . . . .
H231 H 0.7640 0.9199 0.1175 0.036 Uiso 1 1 calc R U . . .
C24 C 0.8499(2) 0.91493(17) -0.05791(14) 0.0391(4) Uani 1 1 d . . . . .
H241 H 0.8060 0.9975 -0.1022 0.047 Uiso 1 1 calc R U . . .
C25 C 0.93804(17) 0.84046(17) -0.12360(13) 0.0343(3) Uani 1 1 d . . . . .
H251 H 0.9548 0.8718 -0.2129 0.041 Uiso 1 1 calc R U . . .
C26 C 1.00140(15) 0.72082(17) -0.05931(13) 0.0316(3) Uani 1 1 d . . . . .
H261 H 1.0612 0.6690 -0.1043 0.038 Uiso 1 1 calc R U . . .
C27 C 0.97794(14) 0.67571(15) 0.07162(12) 0.0250(3) Uani 1 1 d . . . . .
H271 H 1.0225 0.5934 0.1155 0.030 Uiso 1 1 calc R U . . .
N3 N 0.69054(10) 0.64261(10) 0.47482(9) 0.0145(2) Uani 1 1 d . . . . .
H31 H 0.6047(17) 0.6054(16) 0.5014(15) 0.024(4) Uiso 1 1 d . . . . .
C4 C 0.79028(13) 0.54830(13) 0.55416(11) 0.0188(2) Uani 1 1 d . . . . .
H41 H 0.8087 0.4635 0.5250 0.023 Uiso 1 1 calc R U . . .
H42 H 0.8787 0.5981 0.5415 0.023 Uiso 1 1 calc R U . . .
C5 C 0.73669(12) 0.50475(13) 0.69259(11) 0.0179(2) Uani 1 1 d . . . . .
C6 C 0.66384(15) 0.38038(14) 0.74415(12) 0.0252(3) Uani 1 1 d . . . . .
H61 H 0.6461 0.3250 0.6915 0.030 Uiso 1 1 calc R U . . .
C7 C 0.61682(16) 0.33656(15) 0.87223(13) 0.0298(3) Uani 1 1 d . . . . .
H71 H 0.5681 0.2509 0.9071 0.036 Uiso 1 1 calc R U . . .
C8 C 0.64118(14) 0.41812(15) 0.94910(12) 0.0258(3) Uani 1 1 d . . . . .
H81 H 0.6082 0.3888 1.0365 0.031 Uiso 1 1 calc R U . . .
C9 C 0.71333(14) 0.54196(14) 0.89875(12) 0.0234(3) Uani 1 1 d . . . . .
H91 H 0.7295 0.5979 0.9515 0.028 Uiso 1 1 calc R U . . .
C10 C 0.76232(13) 0.58478(13) 0.77084(11) 0.0203(3) Uani 1 1 d . . . . .
H101 H 0.8135 0.6690 0.7368 0.024 Uiso 1 1 calc R U . . .
C11 C 0.68310(13) 0.78530(12) 0.50083(11) 0.0170(2) Uani 1 1 d . . . . .
H111 H 0.6275 0.7763 0.5837 0.020 Uiso 1 1 calc R U . . .
H112 H 0.7774 0.8130 0.5064 0.020 Uiso 1 1 calc R U . . .
C12 C 0.62192(12) 0.89977(12) 0.40328(11) 0.0164(2) Uani 1 1 d . . . . .
C13 C 0.48552(13) 0.89395(13) 0.38308(12) 0.0197(2) Uani 1 1 d . . . . .
H131 H 0.4293 0.8171 0.4317 0.024 Uiso 1 1 calc R U . . .
C14 C 0.43157(14) 1.00050(14) 0.29174(12) 0.0240(3) Uani 1 1 d . . . . .
H141 H 0.3392 0.9948 0.2766 0.029 Uiso 1 1 calc R U . . .
C15 C 0.51162(15) 1.11515(14) 0.22259(13) 0.0259(3) Uani 1 1 d . . . . .
H151 H 0.4744 1.1874 0.1599 0.031 Uiso 1 1 calc R U . . .
C16 C 0.64585(15) 1.12390(14) 0.24520(13) 0.0265(3) Uani 1 1 d . . . . .
H161 H 0.7003 1.2034 0.1998 0.032 Uiso 1 1 calc R U . . .
C17 C 0.70059(13) 1.01596(13) 0.33464(12) 0.0224(3) Uani 1 1 d . . . . .
H171 H 0.7932 1.0216 0.3491 0.027 Uiso 1 1 calc R U . . .
O1M O 0.98315(11) 0.20877(13) 0.44355(12) 0.0430(3) Uani 1 1 d . . . . .
H1M H 0.934(2) 0.266(2) 0.398(2) 0.051(6) Uiso 1 1 d . . . . .
C1M C 0.89511(15) 0.13605(17) 0.55085(14) 0.0323(3) Uani 1 1 d . . . . .
H11M H 0.8061 0.1206 0.5263 0.049 Uiso 1 1 calc R U . . .
H12M H 0.8812 0.1913 0.6115 0.049 Uiso 1 1 calc R U . . .
H13M H 0.9367 0.0456 0.5895 0.049 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 O12 1.4898(10) . ?
P1 O11 1.4985(9) . ?
P1 C2 1.8613(12) . ?
P1 H1 1.340(14) . ?
C2 N3 1.5162(14) . ?
C2 C21 1.5323(16) . ?
C2 H21 1.0000 . ?
C21 C22 1.5187(16) . ?
C21 H211 0.9900 . ?
C21 H212 0.9900 . ?
C22 C27 1.3880(18) . ?
C22 C23 1.3882(19) . ?
C23 C24 1.391(2) . ?
C23 H231 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H241 0.9500 . ?
C25 C26 1.377(2) . ?
C25 H251 0.9500 . ?
C26 C27 1.3920(19) . ?
C26 H261 0.9500 . ?
C27 H271 0.9500 . ?
N3 C4 1.5198(15) . ?
N3 C11 1.5269(15) . ?
N3 H31 0.910(17) . ?
C4 C5 1.5068(16) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.3908(18) . ?
C5 C10 1.3919(18) . ?
C6 C7 1.3896(19) . ?
C6 H61 0.9500 . ?
C7 C8 1.387(2) . ?
C7 H71 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H81 0.9500 . ?
C9 C10 1.3917(17) . ?
C9 H91 0.9500 . ?
C10 H101 0.9500 . ?
C11 C12 1.5042(16) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C17 1.3900(17) . ?
C12 C13 1.3917(17) . ?
C13 C14 1.3902(18) . ?
C13 H131 0.9500 . ?
C14 C15 1.3877(19) . ?
C14 H141 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H151 0.9500 . ?
C16 C17 1.3893(19) . ?
C16 H161 0.9500 . ?
C17 H171 0.9500 . ?
O1M C1M 1.4077(18) . ?
O1M H1M 0.84(2) . ?
C1M H11M 0.9800 . ?
C1M H12M 0.9800 . ?
C1M H13M 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
O12 P1 O11 119.73(5) . . ?
O12 P1 C2 109.84(6) . . ?
O11 P1 C2 105.84(5) . . ?
O12 P1 H1 107.3(6) . . ?
O11 P1 H1 110.4(6) . . ?
C2 P1 H1 102.3(6) . . ?
N3 C2 C21 112.36(9) . . ?
N3 C2 P1 108.74(7) . . ?
C21 C2 P1 114.27(8) . . ?
N3 C2 H21 107.0 . . ?
C21 C2 H21 107.0 . . ?
P1 C2 H21 107.0 . . ?
C22 C21 C2 112.42(10) . . ?
C22 C21 H211 109.1 . . ?
C2 C21 H211 109.1 . . ?
C22 C21 H212 109.1 . . ?
C2 C21 H212 109.1 . . ?
H211 C21 H212 107.9 . . ?
C27 C22 C23 118.69(12) . . ?
C27 C22 C21 120.63(11) . . ?
C23 C22 C21 120.62(11) . . ?
C22 C23 C24 120.59(14) . . ?
C22 C23 H231 119.7 . . ?
C24 C23 H231 119.7 . . ?
C25 C24 C23 120.05(14) . . ?
C25 C24 H241 120.0 . . ?
C23 C24 H241 120.0 . . ?
C26 C25 C24 119.88(13) . . ?
C26 C25 H251 120.1 . . ?
C24 C25 H251 120.1 . . ?
C25 C26 C27 120.04(14) . . ?
C25 C26 H261 120.0 . . ?
C27 C26 H261 120.0 . . ?
C22 C27 C26 120.74(13) . . ?
C22 C27 H271 119.6 . . ?
C26 C27 H271 119.6 . . ?
C2 N3 C4 111.28(9) . . ?
C2 N3 C11 114.70(9) . . ?
C4 N3 C11 109.54(9) . . ?
C2 N3 H31 107.2(10) . . ?
C4 N3 H31 108.0(10) . . ?
C11 N3 H31 105.8(10) . . ?
C5 C4 N3 112.89(9) . . ?
C5 C4 H41 109.0 . . ?
N3 C4 H41 109.0 . . ?
C5 C4 H42 109.0 . . ?
N3 C4 H42 109.0 . . ?
H41 C4 H42 107.8 . . ?
C6 C5 C10 119.22(11) . . ?
C6 C5 C4 119.61(11) . . ?
C10 C5 C4 121.14(11) . . ?
C7 C6 C5 120.46(13) . . ?
C7 C6 H61 119.8 . . ?
C5 C6 H61 119.8 . . ?
C8 C7 C6 119.86(13) . . ?
C8 C7 H71 120.1 . . ?
C6 C7 H71 120.1 . . ?
C9 C8 C7 120.13(12) . . ?
C9 C8 H81 119.9 . . ?
C7 C8 H81 119.9 . . ?
C8 C9 C10 120.03(12) . . ?
C8 C9 H91 120.0 . . ?
C10 C9 H91 120.0 . . ?
C9 C10 C5 120.29(12) . . ?
C9 C10 H101 119.9 . . ?
C5 C10 H101 119.9 . . ?
C12 C11 N3 114.41(9) . . ?
C12 C11 H111 108.7 . . ?
N3 C11 H111 108.7 . . ?
C12 C11 H112 108.7 . . ?
N3 C11 H112 108.7 . . ?
H111 C11 H112 107.6 . . ?
C17 C12 C13 118.96(11) . . ?
C17 C12 C11 119.93(11) . . ?
C13 C12 C11 121.08(11) . . ?
C14 C13 C12 120.03(12) . . ?
C14 C13 H131 120.0 . . ?
C12 C13 H131 120.0 . . ?
C15 C14 C13 120.48(12) . . ?
C15 C14 H141 119.8 . . ?
C13 C14 H141 119.8 . . ?
C16 C15 C14 119.77(12) . . ?
C16 C15 H151 120.1 . . ?
C14 C15 H151 120.1 . . ?
C15 C16 C17 119.68(12) . . ?
C15 C16 H161 120.2 . . ?
C17 C16 H161 120.2 . . ?
C16 C17 C12 121.02(12) . . ?
C16 C17 H171 119.5 . . ?
C12 C17 H171 119.5 . . ?
C1M O1M H1M 106.5(14) . . ?
O1M C1M H11M 109.5 . . ?
O1M C1M H12M 109.5 . . ?
H11M C1M H12M 109.5 . . ?
O1M C1M H13M 109.5 . . ?
H11M C1M H13M 109.5 . . ?
H12M C1M H13M 109.5 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_morfpin
_database_code_depnum_ccdc_archive 'CCDC 1984994'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H12 N O3 P, H2 O'
_chemical_formula_sum            'C5 H14 N O4 P'
_chemical_formula_weight         183.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           61
_space_group_name_H-M_alt        'P b c a'
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.3557(4)
_cell_length_b                   12.4193(5)
_cell_length_c                   13.5892(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1747.71(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.9676
_cell_measurement_theta_max      27.4731

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.379
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.827
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            14505
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.968
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2003
_reflns_number_gt                1750
_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 Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0398P)²+1.2299P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2003
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
P1 P 0.42000(4) 0.34608(3) 0.39276(3) 0.01898(12) Uani 1 1 d . . . . .
H1 H 0.4634(19) 0.2488(15) 0.3805(13) 0.025(5) Uiso 1 1 d . . . . .
O11 O 0.44693(11) 0.37533(9) 0.49832(7) 0.0225(2) Uani 1 1 d . . . . .
O12 O 0.28570(11) 0.35327(10) 0.35391(9) 0.0331(3) Uani 1 1 d . . . . .
C2 C 0.52078(15) 0.43286(14) 0.31612(11) 0.0243(3) Uani 1 1 d . . . . .
H21 H 0.5518 0.3904 0.2592 0.029 Uiso 1 1 calc R U . . .
H22 H 0.4666 0.4921 0.2902 0.029 Uiso 1 1 calc R U . . .
N3 N 0.63491(11) 0.48076(10) 0.36715(8) 0.0170(3) Uani 1 1 d . . . . .
H31 H 0.6082(19) 0.5161(16) 0.4222(14) 0.028(5) Uiso 1 1 d . . . . .
C4 C 0.69819(15) 0.56346(12) 0.30247(11) 0.0232(3) Uani 1 1 d . . . . .
H41 H 0.6353 0.6206 0.2857 0.028 Uiso 1 1 calc R U . . .
H42 H 0.7275 0.5293 0.2405 0.028 Uiso 1 1 calc R U . . .
C5 C 0.81232(16) 0.61207(14) 0.35574(13) 0.0300(4) Uani 1 1 d . . . . .
H51 H 0.8545 0.6658 0.3126 0.036 Uiso 1 1 calc R U . . .
H52 H 0.7815 0.6498 0.4154 0.036 Uiso 1 1 calc R U . . .
O6 O 0.90408(11) 0.53239(11) 0.38317(9) 0.0323(3) Uani 1 1 d . . . . .
C7 C 0.84614(15) 0.45624(15) 0.44757(12) 0.0302(4) Uani 1 1 d . . . . .
H71 H 0.8152 0.4935 0.5075 0.036 Uiso 1 1 calc R U . . .
H72 H 0.9114 0.4023 0.4677 0.036 Uiso 1 1 calc R U . . .
C8 C 0.73370(14) 0.39949(12) 0.39822(11) 0.0225(3) Uani 1 1 d . . . . .
H81 H 0.7648 0.3592 0.3400 0.027 Uiso 1 1 calc R U . . .
H82 H 0.6943 0.3475 0.4446 0.027 Uiso 1 1 calc R U . . .
O1W O 0.06530(18) 0.22948(16) 0.34595(11) 0.0621(6) Uani 1 1 d . . . . .
H11W H 0.138(3) 0.257(2) 0.3580(18) 0.063(8) Uiso 1 1 d . . . . .
H12W H 0.039(3) 0.206(2) 0.401(2) 0.072(9) Uiso 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
P1 O12 1.4903(12) . ?
P1 O11 1.5059(11) . ?
P1 C2 1.8262(15) . ?
P1 H1 1.299(19) . ?
C2 N3 1.4939(18) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C8 1.4980(19) . ?
N3 C4 1.5023(18) . ?
N3 H31 0.91(2) . ?
C4 C5 1.512(2) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 O6 1.422(2) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
O6 C7 1.421(2) . ?
C7 C8 1.517(2) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
O1W H11W 0.85(3) . ?
O1W H12W 0.84(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
O12 P1 O11 119.72(7) . . ?
O12 P1 C2 107.21(7) . . ?
O11 P1 C2 107.17(7) . . ?
O12 P1 H1 109.5(8) . . ?
O11 P1 H1 106.4(8) . . ?
C2 P1 H1 106.1(8) . . ?
N3 C2 P1 114.98(10) . . ?
N3 C2 H21 108.5 . . ?
P1 C2 H21 108.5 . . ?
N3 C2 H22 108.5 . . ?
P1 C2 H22 108.5 . . ?
H21 C2 H22 107.5 . . ?
C2 N3 C8 113.75(12) . . ?
C2 N3 C4 110.23(11) . . ?
C8 N3 C4 109.13(11) . . ?
C2 N3 H31 109.4(12) . . ?
C8 N3 H31 107.5(12) . . ?
C4 N3 H31 106.5(12) . . ?
N3 C4 C5 109.51(12) . . ?
N3 C4 H41 109.8 . . ?
C5 C4 H41 109.8 . . ?
N3 C4 H42 109.8 . . ?
C5 C4 H42 109.8 . . ?
H41 C4 H42 108.2 . . ?
O6 C5 C4 111.72(13) . . ?
O6 C5 H51 109.3 . . ?
C4 C5 H51 109.3 . . ?
O6 C5 H52 109.3 . . ?
C4 C5 H52 109.3 . . ?
H51 C5 H52 107.9 . . ?
C7 O6 C5 110.03(12) . . ?
O6 C7 C8 111.16(13) . . ?
O6 C7 H71 109.4 . . ?
C8 C7 H71 109.4 . . ?
O6 C7 H72 109.4 . . ?
C8 C7 H72 109.4 . . ?
H71 C7 H72 108.0 . . ?
N3 C8 C7 109.62(12) . . ?
N3 C8 H81 109.7 . . ?
C7 C8 H81 109.7 . . ?
N3 C8 H82 109.7 . . ?
C7 C8 H82 109.7 . . ?
H81 C8 H82 108.2 . . ?
H11W O1W H12W 105(2) . . ?

_refine_diff_density_max         0.505
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_idampin
_database_code_depnum_ccdc_archive 'CCDC 1984992'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 N O6 P'
_chemical_formula_sum            'C5 H10 N O6 P'
_chemical_formula_weight         211.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1523(6)
_cell_length_b                   7.4078(9)
_cell_length_c                   11.8502(14)
_cell_angle_alpha                101.004(5)
_cell_angle_beta                 95.811(5)
_cell_angle_gamma                103.446(5)
_cell_volume                     426.75(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5555
_cell_measurement_theta_min      3.8451
_cell_measurement_theta_max      72.1061

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    2.968
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            7703
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.845
_diffrn_reflns_theta_max         72.255
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1679
_reflns_number_gt                1527
_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 Instrument Service V6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0453P)²+0.1673P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1679
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.58300(8) 0.17824(5) 0.22834(3) 0.01590(15) Uani 1 1 d . . . . .
H1 H 0.705(4) 0.108(3) 0.1474(17) 0.021(5) Uiso 1 1 d . . . . .
O11 O 0.3485(2) 0.24072(16) 0.17714(10) 0.0217(3) Uani 1 1 d . . . . .
O12 O 0.5359(2) 0.04538(16) 0.30954(10) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.8200(3) 0.3976(2) 0.31392(14) 0.0166(3) Uani 1 1 d . . . . .
H21 H 0.7923 0.4145 0.3964 0.020 Uiso 1 1 calc R U . . .
H22 H 1.0074 0.3878 0.3100 0.020 Uiso 1 1 calc R U . . .
N3 N 0.7796(3) 0.56718(18) 0.26866(11) 0.0134(3) Uani 1 1 d . . . . .
H31 H 0.605(4) 0.544(3) 0.2446(17) 0.022(5) Uiso 1 1 d . . . . .
C4 C 0.8589(3) 0.7462(2) 0.36096(13) 0.0155(3) Uani 1 1 d . . . . .
H41 H 0.8762 0.8572 0.3245 0.019 Uiso 1 1 calc R U . . .
H42 H 1.0364 0.7565 0.4060 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6499(3) 0.7475(2) 0.44185(13) 0.0149(3) Uani 1 1 d . . . . .
O51 O 0.7431(2) 0.87942(17) 0.53633(10) 0.0231(3) Uani 1 1 d . . . . .
H511 H 0.623(6) 0.891(4) 0.586(3) 0.072(10) Uiso 1 1 d . . . . .
O52 O 0.4256(2) 0.63988(16) 0.41687(10) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.9196(3) 0.5926(2) 0.16579(14) 0.0177(3) Uani 1 1 d . . . . .
H61 H 0.9311 0.4675 0.1220 0.021 Uiso 1 1 calc R U . . .
H62 H 1.1054 0.6745 0.1924 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7630(3) 0.6836(2) 0.08773(13) 0.0156(3) Uani 1 1 d . . . . .
O71 O 0.9064(2) 0.74559(17) 0.01093(10) 0.0202(3) Uani 1 1 d . . . . .
H711 H 0.806(5) 0.767(3) -0.043(2) 0.042(7) Uiso 1 1 d . . . . .
O72 O 0.5322(2) 0.68664(16) 0.09600(10) 0.0198(3) 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
P1 O12 1.5005(12) . ?
P1 O11 1.5034(12) . ?
P1 C2 1.8321(16) . ?
P1 H1 1.293(19) . ?
C2 N3 1.5054(19) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.4918(19) . ?
N3 C6 1.4982(19) . ?
N3 H31 0.88(2) . ?
C4 C5 1.513(2) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 O52 1.2129(19) . ?
C5 O51 1.3015(19) . ?
O51 H511 0.91(3) . ?
C6 C7 1.517(2) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 O72 1.2082(19) . ?
C7 O71 1.3125(19) . ?
O71 H711 0.85(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
O12 P1 O11 118.98(7) . . ?
O12 P1 C2 105.84(7) . . ?
O11 P1 C2 105.06(7) . . ?
O12 P1 H1 108.5(9) . . ?
O11 P1 H1 110.7(9) . . ?
C2 P1 H1 106.9(9) . . ?
N3 C2 P1 110.72(10) . . ?
N3 C2 H21 109.5 . . ?
P1 C2 H21 109.5 . . ?
N3 C2 H22 109.5 . . ?
P1 C2 H22 109.5 . . ?
H21 C2 H22 108.1 . . ?
C4 N3 C6 110.68(12) . . ?
C4 N3 C2 112.46(12) . . ?
C6 N3 C2 112.52(12) . . ?
C4 N3 H31 107.5(13) . . ?
C6 N3 H31 107.0(13) . . ?
C2 N3 H31 106.4(13) . . ?
N3 C4 C5 110.43(12) . . ?
N3 C4 H41 109.6 . . ?
C5 C4 H41 109.6 . . ?
N3 C4 H42 109.6 . . ?
C5 C4 H42 109.6 . . ?
H41 C4 H42 108.1 . . ?
O52 C5 O51 126.67(15) . . ?
O52 C5 C4 122.35(14) . . ?
O51 C5 C4 110.96(13) . . ?
C5 O51 H511 115(2) . . ?
N3 C6 C7 109.35(12) . . ?
N3 C6 H61 109.8 . . ?
C7 C6 H61 109.8 . . ?
N3 C6 H62 109.8 . . ?
C7 C6 H62 109.8 . . ?
H61 C6 H62 108.3 . . ?
O72 C7 O71 127.06(15) . . ?
O72 C7 C6 121.69(14) . . ?
O71 C7 C6 111.17(13) . . ?
C7 O71 H711 110.5(16) . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_dbampph
_database_code_depnum_ccdc_archive 'CCDC 1984989'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N O2 P, C6 H7 O3 P'
_chemical_formula_sum            'C27 H29 N O5 P2'
_chemical_formula_weight         509.45

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      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                   9.4746(4)
_cell_length_b                   11.3717(5)
_cell_length_c                   23.1551(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.9900(10)
_cell_angle_gamma                90
_cell_volume                     2493.28(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.5113
_cell_measurement_theta_max      27.5362

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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 8.3333
_diffrn_reflns_number            29936
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.511
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5741
_reflns_number_gt                4966
_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 Instrument Service V6.2.10'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0305P)²+1.7355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0062(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5741
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
P1 P 0.36134(4) 0.47913(3) 0.72904(2) 0.01728(9) Uani 1 1 d . . . . .
O11 O 0.45050(10) 0.51193(9) 0.67902(4) 0.0223(2) Uani 1 1 d . . . . .
O12 O 0.38730(10) 0.35800(9) 0.75332(4) 0.0222(2) Uani 1 1 d . . . . .
C2 C 0.38862(14) 0.58886(13) 0.78727(6) 0.0195(3) Uani 1 1 d . . . . .
H21 H 0.3938 0.6677 0.7693 0.023 Uiso 1 1 calc R U . . .
H22 H 0.3046 0.5881 0.8115 0.023 Uiso 1 1 calc R U . . .
N3 N 0.51710(11) 0.57240(10) 0.82592(5) 0.0167(2) Uani 1 1 d . . . . .
H31 H 0.503(2) 0.5063(17) 0.8487(8) 0.036(5) Uiso 1 1 d . . . . .
C4 C 0.54193(14) 0.67777(12) 0.86504(6) 0.0191(3) Uani 1 1 d . . . . .
H41 H 0.6289 0.6641 0.8890 0.023 Uiso 1 1 calc R U . . .
H42 H 0.5581 0.7478 0.8408 0.023 Uiso 1 1 calc R U . . .
C5 C 0.42242(14) 0.70363(12) 0.90436(6) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.33968(15) 0.80328(13) 0.89543(6) 0.0232(3) Uani 1 1 d . . . . .
H61 H 0.3547 0.8526 0.8631 0.028 Uiso 1 1 calc R U . . .
C7 C 0.23473(16) 0.83100(15) 0.93383(7) 0.0286(3) Uani 1 1 d . . . . .
H71 H 0.1779 0.8989 0.9274 0.034 Uiso 1 1 calc R U . . .
C8 C 0.21297(16) 0.76007(15) 0.98120(7) 0.0286(3) Uani 1 1 d . . . . .
H81 H 0.1412 0.7792 1.0073 0.034 Uiso 1 1 calc R U . . .
C9 C 0.29591(16) 0.66112(14) 0.99062(6) 0.0267(3) Uani 1 1 d . . . . .
H91 H 0.2812 0.6124 1.0232 0.032 Uiso 1 1 calc R U . . .
C10 C 0.40038(15) 0.63331(13) 0.95247(6) 0.0229(3) Uani 1 1 d . . . . .
H101 H 0.4575 0.5657 0.9592 0.028 Uiso 1 1 calc R U . . .
C11 C 0.64571(14) 0.54941(13) 0.79063(6) 0.0206(3) Uani 1 1 d . . . . .
H111 H 0.6312 0.4751 0.7690 0.025 Uiso 1 1 calc R U . . .
H112 H 0.6543 0.6135 0.7620 0.025 Uiso 1 1 calc R U . . .
C12 C 0.78220(14) 0.54091(12) 0.82588(6) 0.0191(3) Uani 1 1 d . . . . .
C13 C 0.88035(15) 0.63123(13) 0.82204(6) 0.0229(3) Uani 1 1 d . . . . .
H131 H 0.8567 0.6998 0.8004 0.028 Uiso 1 1 calc R U . . .
C14 C 1.01214(15) 0.62231(14) 0.84945(7) 0.0264(3) Uani 1 1 d . . . . .
H141 H 1.0787 0.6843 0.8464 0.032 Uiso 1 1 calc R U . . .
C15 C 1.04645(15) 0.52287(15) 0.88134(7) 0.0283(3) Uani 1 1 d . . . . .
H151 H 1.1372 0.5160 0.8998 0.034 Uiso 1 1 calc R U . . .
C16 C 0.94827(16) 0.43314(15) 0.88644(7) 0.0280(3) Uani 1 1 d . . . . .
H161 H 0.9714 0.3657 0.9090 0.034 Uiso 1 1 calc R U . . .
C17 C 0.81624(15) 0.44165(13) 0.85862(6) 0.0227(3) Uani 1 1 d . . . . .
H171 H 0.7495 0.3799 0.8620 0.027 Uiso 1 1 calc R U . . .
C18 C 0.17678(14) 0.49776(12) 0.70983(6) 0.0197(3) Uani 1 1 d . . . . .
C19 C 0.07729(15) 0.42137(13) 0.73234(6) 0.0225(3) Uani 1 1 d . . . . .
H191 H 0.1065 0.3625 0.7593 0.027 Uiso 1 1 calc R U . . .
C20 C -0.06440(15) 0.43117(14) 0.71542(7) 0.0265(3) Uani 1 1 d . . . . .
H201 H -0.1310 0.3768 0.7295 0.032 Uiso 1 1 calc R U . . .
C21 C -0.10866(15) 0.51961(15) 0.67821(7) 0.0290(3) Uani 1 1 d . . . . .
H211 H -0.2059 0.5268 0.6673 0.035 Uiso 1 1 calc R U . . .
C22 C -0.01145(17) 0.59785(16) 0.65672(7) 0.0322(4) Uani 1 1 d . . . . .
H221 H -0.0424 0.6595 0.6317 0.039 Uiso 1 1 calc R U . . .
C23 C 0.13130(16) 0.58629(14) 0.67174(7) 0.0274(3) Uani 1 1 d . . . . .
H231 H 0.1980 0.6387 0.6561 0.033 Uiso 1 1 calc R U . . .
P2 P 0.56588(4) 0.76708(3) 0.60744(2) 0.01816(10) Uani 1 1 d . . . . .
O21 O 0.43777(10) 0.68398(10) 0.61350(5) 0.0258(2) Uani 1 1 d . . . . .
H21O H 0.446(3) 0.623(2) 0.6389(11) 0.070(8) Uiso 1 1 d . . . . .
O22 O 0.67475(11) 0.74283(10) 0.65834(5) 0.0239(2) Uani 1 1 d . . . . .
H22O H 0.652(2) 0.785(2) 0.6893(10) 0.053(6) Uiso 1 1 d . . . . .
O23 O 0.52152(11) 0.89236(9) 0.60360(4) 0.0243(2) Uani 1 1 d . . . . .
C24 C 0.65672(14) 0.72310(12) 0.54438(6) 0.0187(3) Uani 1 1 d . . . . .
C25 C 0.64059(17) 0.61157(14) 0.52067(7) 0.0280(3) Uani 1 1 d . . . . .
H251 H 0.5785 0.5567 0.5375 0.034 Uiso 1 1 calc R U . . .
C26 C 0.71542(19) 0.57980(15) 0.47214(7) 0.0351(4) Uani 1 1 d . . . . .
H261 H 0.7028 0.5039 0.4556 0.042 Uiso 1 1 calc R U . . .
C27 C 0.80741(17) 0.65825(16) 0.44823(7) 0.0326(4) Uani 1 1 d . . . . .
H271 H 0.8594 0.6359 0.4156 0.039 Uiso 1 1 calc R U . . .
C28 C 0.82435(16) 0.76962(16) 0.47163(7) 0.0300(3) Uani 1 1 d . . . . .
H281 H 0.8880 0.8236 0.4551 0.036 Uiso 1 1 calc R U . . .
C29 C 0.74842(15) 0.80238(14) 0.51917(6) 0.0242(3) Uani 1 1 d . . . . .
H291 H 0.7590 0.8794 0.5347 0.029 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 O11 1.5039(10) . ?
P1 O12 1.5048(10) . ?
P1 C18 1.8018(14) . ?
P1 C2 1.8487(14) . ?
C2 N3 1.4974(17) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C11 1.5134(16) . ?
N3 C4 1.5155(17) . ?
N3 H31 0.93(2) . ?
C4 C5 1.5063(18) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.389(2) . ?
C5 C10 1.393(2) . ?
C6 C7 1.393(2) . ?
C6 H61 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H71 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H81 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H91 0.9500 . ?
C10 H101 0.9500 . ?
C11 C12 1.5082(19) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C13 1.390(2) . ?
C12 C17 1.391(2) . ?
C13 C14 1.385(2) . ?
C13 H131 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H141 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H151 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H161 0.9500 . ?
C17 H171 0.9500 . ?
C18 C19 1.396(2) . ?
C18 C23 1.397(2) . ?
C19 C20 1.390(2) . ?
C19 H191 0.9500 . ?
C20 C21 1.380(2) . ?
C20 H201 0.9500 . ?
C21 C22 1.385(2) . ?
C21 H211 0.9500 . ?
C22 C23 1.391(2) . ?
C22 H221 0.9500 . ?
C23 H231 0.9500 . ?
P2 O23 1.4871(11) . ?
P2 O21 1.5485(11) . ?
P2 O22 1.5634(10) . ?
P2 C24 1.7917(14) . ?
O21 H21O 0.91(3) . ?
O22 H22O 0.90(2) . ?
C24 C25 1.388(2) . ?
C24 C29 1.394(2) . ?
C25 C26 1.397(2) . ?
C25 H251 0.9500 . ?
C26 C27 1.377(3) . ?
C26 H261 0.9500 . ?
C27 C28 1.385(2) . ?
C27 H271 0.9500 . ?
C28 C29 1.387(2) . ?
C28 H281 0.9500 . ?
C29 H291 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 P1 O12 115.21(6) . . ?
O11 P1 C18 110.31(6) . . ?
O12 P1 C18 110.15(6) . . ?
O11 P1 C2 109.04(6) . . ?
O12 P1 C2 109.17(6) . . ?
C18 P1 C2 102.15(6) . . ?
N3 C2 P1 116.21(9) . . ?
N3 C2 H21 108.2 . . ?
P1 C2 H21 108.2 . . ?
N3 C2 H22 108.2 . . ?
P1 C2 H22 108.2 . . ?
H21 C2 H22 107.4 . . ?
C2 N3 C11 110.60(10) . . ?
C2 N3 C4 111.38(10) . . ?
C11 N3 C4 110.38(10) . . ?
C2 N3 H31 108.3(12) . . ?
C11 N3 H31 107.3(12) . . ?
C4 N3 H31 108.8(12) . . ?
C5 C4 N3 114.29(11) . . ?
C5 C4 H41 108.7 . . ?
N3 C4 H41 108.7 . . ?
C5 C4 H42 108.7 . . ?
N3 C4 H42 108.7 . . ?
H41 C4 H42 107.6 . . ?
C6 C5 C10 119.20(13) . . ?
C6 C5 C4 120.09(13) . . ?
C10 C5 C4 120.53(13) . . ?
C5 C6 C7 120.08(14) . . ?
C5 C6 H61 120.0 . . ?
C7 C6 H61 120.0 . . ?
C8 C7 C6 120.25(15) . . ?
C8 C7 H71 119.9 . . ?
C6 C7 H71 119.9 . . ?
C7 C8 C9 119.96(14) . . ?
C7 C8 H81 120.0 . . ?
C9 C8 H81 120.0 . . ?
C8 C9 C10 119.90(14) . . ?
C8 C9 H91 120.0 . . ?
C10 C9 H91 120.0 . . ?
C9 C10 C5 120.60(14) . . ?
C9 C10 H101 119.7 . . ?
C5 C10 H101 119.7 . . ?
C12 C11 N3 114.21(11) . . ?
C12 C11 H111 108.7 . . ?
N3 C11 H111 108.7 . . ?
C12 C11 H112 108.7 . . ?
N3 C11 H112 108.7 . . ?
H111 C11 H112 107.6 . . ?
C13 C12 C17 119.42(13) . . ?
C13 C12 C11 118.75(13) . . ?
C17 C12 C11 121.67(13) . . ?
C14 C13 C12 120.74(14) . . ?
C14 C13 H131 119.6 . . ?
C12 C13 H131 119.6 . . ?
C15 C14 C13 119.74(14) . . ?
C15 C14 H141 120.1 . . ?
C13 C14 H141 120.1 . . ?
C14 C15 C16 120.04(14) . . ?
C14 C15 H151 120.0 . . ?
C16 C15 H151 120.0 . . ?
C15 C16 C17 120.26(14) . . ?
C15 C16 H161 119.9 . . ?
C17 C16 H161 119.9 . . ?
C16 C17 C12 119.78(14) . . ?
C16 C17 H171 120.1 . . ?
C12 C17 H171 120.1 . . ?
C19 C18 C23 119.13(13) . . ?
C19 C18 P1 119.79(11) . . ?
C23 C18 P1 121.07(11) . . ?
C20 C19 C18 120.20(14) . . ?
C20 C19 H191 119.9 . . ?
C18 C19 H191 119.9 . . ?
C21 C20 C19 120.27(14) . . ?
C21 C20 H201 119.9 . . ?
C19 C20 H201 119.9 . . ?
C20 C21 C22 120.06(14) . . ?
C20 C21 H211 120.0 . . ?
C22 C21 H211 120.0 . . ?
C21 C22 C23 120.15(15) . . ?
C21 C22 H221 119.9 . . ?
C23 C22 H221 119.9 . . ?
C22 C23 C18 120.13(15) . . ?
C22 C23 H231 119.9 . . ?
C18 C23 H231 119.9 . . ?
O23 P2 O21 111.67(6) . . ?
O23 P2 O22 113.06(6) . . ?
O21 P2 O22 108.83(6) . . ?
O23 P2 C24 111.19(6) . . ?
O21 P2 C24 107.68(6) . . ?
O22 P2 C24 104.01(6) . . ?
P2 O21 H21O 118.2(16) . . ?
P2 O22 H22O 109.5(14) . . ?
C25 C24 C29 119.13(13) . . ?
C25 C24 P2 121.86(11) . . ?
C29 C24 P2 119.00(11) . . ?
C24 C25 C26 120.16(15) . . ?
C24 C25 H251 119.9 . . ?
C26 C25 H251 119.9 . . ?
C27 C26 C25 120.13(16) . . ?
C27 C26 H261 119.9 . . ?
C25 C26 H261 119.9 . . ?
C26 C27 C28 120.11(14) . . ?
C26 C27 H271 119.9 . . ?
C28 C27 H271 119.9 . . ?
C27 C28 C29 120.01(15) . . ?
C27 C28 H281 120.0 . . ?
C29 C28 H281 120.0 . . ?
C28 C29 C24 120.44(15) . . ?
C28 C29 H291 119.8 . . ?
C24 C29 H291 119.8 . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_sp1004
_database_code_depnum_ccdc_archive 'CCDC 1984996'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N O4 P'
_chemical_formula_sum            'C4 H10 N O4 P'
_chemical_formula_weight         167.10

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

_cell_length_a                   7.9050(4)
_cell_length_b                   7.9314(4)
_cell_length_c                   11.8753(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     744.55(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5034
_cell_measurement_theta_min      3.0886
_cell_measurement_theta_max      27.4874

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.222
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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 8.3333
_diffrn_reflns_number            6172
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.089
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1717
_reflns_number_gt                1690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_max     0.997
_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 Instrument Service V6.2.6'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0349P)²+0.1061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 686 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1717
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0552
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
P1 P 0.56520(4) 0.30931(5) 0.32648(3) 0.01331(11) Uani 1 1 d . . . . .
H1P H 0.585(2) 0.391(2) 0.2326(16) 0.017(5) Uiso 1 1 d . . . . .
O11 O 0.62008(14) 0.12952(13) 0.31072(9) 0.0163(2) Uani 1 1 d . . . . .
O12 O 0.64469(15) 0.40501(15) 0.42243(11) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.33602(18) 0.2957(2) 0.34622(12) 0.0141(3) Uani 1 1 d . . . . .
H21 H 0.2880 0.2333 0.2815 0.017 Uiso 1 1 calc R U . . .
H22 H 0.3142 0.2275 0.4145 0.017 Uiso 1 1 calc R U . . .
N3 N 0.24112(16) 0.45941(17) 0.35768(11) 0.0124(3) Uani 1 1 d . . . . .
H31 H 0.278(2) 0.525(3) 0.3014(17) 0.017(5) Uiso 1 1 d . . . . .
C4 C 0.2735(2) 0.5415(2) 0.46862(13) 0.0146(3) Uani 1 1 d . . . . .
H41 H 0.3962 0.5387 0.4850 0.017 Uiso 1 1 calc R U . . .
H42 H 0.2145 0.4777 0.5286 0.017 Uiso 1 1 calc R U . . .
C5 C 0.21274(18) 0.7225(2) 0.46930(13) 0.0149(3) Uani 1 1 d . . . . .
O51 O 0.23428(17) 0.79107(18) 0.56908(10) 0.0258(3) Uani 1 1 d . . . . .
H511 H 0.201(4) 0.894(4) 0.565(2) 0.052(8) Uiso 1 1 d . . . . .
O52 O 0.15458(16) 0.79354(16) 0.38817(10) 0.0247(3) Uani 1 1 d . . . . .
C6 C 0.0562(2) 0.4270(2) 0.33981(15) 0.0240(4) Uani 1 1 d . . . . .
H61 H -0.0069 0.5324 0.3494 0.029 Uiso 1 1 calc R U . . .
H62 H 0.0164 0.3439 0.3949 0.029 Uiso 1 1 calc R U . . .
H63 H 0.0381 0.3835 0.2635 0.029 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 O11 1.5022(11) . ?
P1 O12 1.5065(13) . ?
P1 C2 1.8299(15) . ?
P1 H1P 1.298(19) . ?
C2 N3 1.5060(19) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.4917(18) . ?
N3 C6 1.500(2) . ?
N3 H31 0.89(2) . ?
C4 C5 1.514(2) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 O52 1.2070(19) . ?
C5 O51 1.3147(19) . ?
O51 H511 0.86(3) . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 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
O11 P1 O12 116.87(7) . . ?
O11 P1 C2 104.23(7) . . ?
O12 P1 C2 110.23(7) . . ?
O11 P1 H1P 109.4(9) . . ?
O12 P1 H1P 110.4(8) . . ?
C2 P1 H1P 104.9(8) . . ?
N3 C2 P1 116.98(10) . . ?
N3 C2 H21 108.1 . . ?
P1 C2 H21 108.1 . . ?
N3 C2 H22 108.1 . . ?
P1 C2 H22 108.1 . . ?
H21 C2 H22 107.3 . . ?
C4 N3 C6 111.52(12) . . ?
C4 N3 C2 111.77(11) . . ?
C6 N3 C2 108.97(12) . . ?
C4 N3 H31 110.5(13) . . ?
C6 N3 H31 108.0(12) . . ?
C2 N3 H31 105.9(13) . . ?
N3 C4 C5 111.37(12) . . ?
N3 C4 H41 109.4 . . ?
C5 C4 H41 109.4 . . ?
N3 C4 H42 109.4 . . ?
C5 C4 H42 109.4 . . ?
H41 C4 H42 108.0 . . ?
O52 C5 O51 125.16(15) . . ?
O52 C5 C4 123.99(14) . . ?
O51 C5 C4 110.85(13) . . ?
C5 O51 H511 108(2) . . ?
N3 C6 H61 109.5 . . ?
N3 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
N3 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_prolinpin
_database_code_depnum_ccdc_archive 'CCDC 1985000'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N O4 P, 0.25(H2 O)'
_chemical_formula_sum            'C6 H12.50 N O4.25 P'
_chemical_formula_weight         197.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.5885(3)
_cell_length_b                   19.1273(12)
_cell_length_c                   8.3332(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.684(3)
_cell_angle_gamma                90
_cell_volume                     865.48(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5336
_cell_measurement_theta_min      4.6236
_cell_measurement_theta_max      72.0191

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             418
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.718
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    2.723
_shelx_estimated_absorpt_T_min   0.245
_shelx_estimated_absorpt_T_max   0.729
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            6469
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.623
_diffrn_reflns_theta_max         72.086
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1684
_reflns_number_gt                1545
_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 Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0264P)²+1.5989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1684
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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 0.59394(11) 0.19623(3) 0.34388(7) 0.0162(2) Uani 1 1 d . . . . .
H1 H 0.362(5) 0.2028(15) 0.299(4) 0.024(7) Uiso 1 1 d . . . . .
O11 O 0.6773(3) 0.21069(9) 0.5245(2) 0.0205(4) Uani 1 1 d . . . . .
O12 O 0.6670(3) 0.12723(9) 0.2803(2) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.7093(4) 0.26314(13) 0.2243(3) 0.0165(5) Uani 1 1 d . . . . .
H21 H 0.8907 0.2655 0.2636 0.020 Uiso 1 1 calc R U . . .
H22 H 0.6717 0.2484 0.1072 0.020 Uiso 1 1 calc R U . . .
N3 N 0.6069(4) 0.33454(11) 0.2334(2) 0.0164(4) Uani 1 1 d . . . . .
H31 H 0.440(6) 0.3297(16) 0.198(4) 0.027(8) Uiso 1 1 d . . . . .
C4 C 0.6680(4) 0.36763(13) 0.4038(3) 0.0179(5) Uani 1 1 d . . . . .
H41 H 0.8103 0.3426 0.4765 0.021 Uiso 1 1 calc R U . . .
C41 C 0.4449(4) 0.36299(13) 0.4775(3) 0.0180(5) Uani 1 1 d . . . . .
O411 O 0.4920(3) 0.38625(10) 0.6284(2) 0.0228(4) Uani 1 1 d . . . . .
H411 H 0.348(9) 0.380(3) 0.689(6) 0.080(15) Uiso 1 1 d . . . . .
O412 O 0.2472(3) 0.34036(10) 0.3992(2) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.7417(5) 0.44347(14) 0.3760(3) 0.0257(6) Uani 1 1 d . . . . .
H51 H 0.6661 0.4765 0.4410 0.031 Uiso 1 1 calc R U . . .
H52 H 0.9228 0.4492 0.4079 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6435(6) 0.45559(15) 0.1919(4) 0.0331(7) Uani 1 1 d . . . . .
H61 H 0.4661 0.4674 0.1655 0.040 Uiso 1 1 calc R U . . .
H62 H 0.7350 0.4935 0.1516 0.040 Uiso 1 1 calc R U . . .
C7 C 0.6876(5) 0.38590(14) 0.1187(3) 0.0232(5) Uani 1 1 d . . . . .
H71 H 0.8636 0.3796 0.1192 0.028 Uiso 1 1 calc R U . . .
H72 H 0.5872 0.3810 0.0042 0.028 Uiso 1 1 calc R U . . .
O1W O 0.363(3) 0.0210(9) 0.3271(19) 0.093(4) Uiso 0.25 1 d . . P . .
H11W H 0.4449 0.0632 0.3374 0.111 Uiso 0.25 1 d R U P . .
H12W H 0.3559 -0.0002 0.2459 0.111 Uiso 0.25 1 d R U P . .


_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 O11 1.4923(17) . ?
P1 O12 1.5137(19) . ?
P1 C2 1.830(2) . ?
P1 H1 1.27(3) . ?
C2 N3 1.490(3) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C7 1.512(3) . ?
N3 C4 1.518(3) . ?
N3 H31 0.92(3) . ?
C4 C41 1.517(3) . ?
C4 C5 1.540(4) . ?
C4 H41 1.0000 . ?
C41 O412 1.222(3) . ?
C41 O411 1.301(3) . ?
O411 H411 1.06(5) . ?
C5 C6 1.520(4) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.510(4) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
O1W H11W 0.9219 . ?
O1W H12W 0.7825 . ?

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
O11 P1 O12 117.97(10) . . ?
O11 P1 C2 110.68(10) . . ?
O12 P1 C2 105.09(10) . . ?
O11 P1 H1 109.5(13) . . ?
O12 P1 H1 108.9(13) . . ?
C2 P1 H1 103.7(13) . . ?
N3 C2 P1 115.12(16) . . ?
N3 C2 H21 108.5 . . ?
P1 C2 H21 108.5 . . ?
N3 C2 H22 108.5 . . ?
P1 C2 H22 108.5 . . ?
H21 C2 H22 107.5 . . ?
C2 N3 C7 112.83(19) . . ?
C2 N3 C4 115.19(18) . . ?
C7 N3 C4 106.61(18) . . ?
C2 N3 H31 105(2) . . ?
C7 N3 H31 107.4(19) . . ?
C4 N3 H31 109.2(19) . . ?
C41 C4 N3 109.27(18) . . ?
C41 C4 C5 113.0(2) . . ?
N3 C4 C5 105.15(19) . . ?
C41 C4 H41 109.8 . . ?
N3 C4 H41 109.8 . . ?
C5 C4 H41 109.8 . . ?
O412 C41 O411 126.0(2) . . ?
O412 C41 C4 122.0(2) . . ?
O411 C41 C4 111.9(2) . . ?
C41 O411 H411 115(3) . . ?
C6 C5 C4 104.5(2) . . ?
C6 C5 H51 110.9 . . ?
C4 C5 H51 110.9 . . ?
C6 C5 H52 110.9 . . ?
C4 C5 H52 110.9 . . ?
H51 C5 H52 108.9 . . ?
C7 C6 C5 102.6(2) . . ?
C7 C6 H61 111.2 . . ?
C5 C6 H61 111.2 . . ?
C7 C6 H62 111.2 . . ?
C5 C6 H62 111.2 . . ?
H61 C6 H62 109.2 . . ?
C6 C7 N3 102.5(2) . . ?
C6 C7 H71 111.3 . . ?
N3 C7 H71 111.3 . . ?
C6 C7 H72 111.3 . . ?
N3 C7 H72 111.3 . . ?
H71 C7 H72 109.2 . . ?
H11W O1W H12W 117.0 . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_2fteampin_sq
_database_code_depnum_ccdc_archive 'CCDC 1984995'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 N3 O6 P, 2(H2 O)'
_chemical_formula_sum            'C21 H24 N3 O8 P'
_chemical_formula_weight         477.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.6105(2)
_cell_length_b                   21.6543(9)
_cell_length_c                   8.9960(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.695(2)
_cell_angle_gamma                90
_cell_volume                     1089.27(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7365
_cell_measurement_theta_min      4.0831
_cell_measurement_theta_max      66.6248

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    1.604
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            8705
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.083
_diffrn_reflns_theta_max         66.621
_diffrn_reflns_theta_full        66.621
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1961
_reflns_number_gt                1822
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service V6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0386P)²+0.6276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1961
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.85992(17) 0.77171(4) 0.64538(14) 0.0488(3) Uani 0.5 1 d . . P . .
H1 H 0.853(6) 0.8318(18) 0.635(4) 0.041(10) Uiso 0.5 1 d . . P . .
O11 O 0.9934(3) 0.7500 0.5213(3) 0.0733(8) Uani 1 2 d S T P A .
O12A O 0.9782(10) 0.7500 0.7888(11) 0.069(2) Uani 0.5 2 d S T P A 1
O12B O 0.8778(11) 0.742(2) 0.8132(9) 0.065(8) Uani 0.25 1 d . . P A 2
C2 C 0.5459(4) 0.7500 0.6087(3) 0.0341(5) Uani 1 2 d S T P A .
H21 H 0.4899 0.7861 0.6586 0.041 Uiso 1 1 d R U . . .
N3 N 0.4373(3) 0.7500 0.4511(2) 0.0311(4) Uani 1 2 d S T P . .
H31 H 0.266(6) 0.7500 0.458(4) 0.064(10) Uiso 1 2 d S . P . .
C4 C 0.4931(3) 0.69316(8) 0.3666(2) 0.0378(4) Uani 1 1 d . . . . .
H41 H 0.6684 0.6868 0.3730 0.045 Uiso 1 1 calc R U . . .
H42 H 0.4364 0.6984 0.2602 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3734(3) 0.63709(8) 0.4296(2) 0.0413(4) Uani 1 1 d . . . . .
H51 H 0.4312 0.6316 0.5357 0.050 Uiso 1 1 calc R U . . .
H52 H 0.1983 0.6436 0.4240 0.050 Uiso 1 1 calc R U . . .
N6 N 0.4267(3) 0.58204(6) 0.34626(16) 0.0360(3) Uani 1 1 d . . . . .
C7 C 0.6325(3) 0.54675(8) 0.37869(19) 0.0366(4) Uani 1 1 d . . . . .
O71 O 0.7891(2) 0.56021(6) 0.47383(14) 0.0482(4) Uani 1 1 d . . . . .
C8 C 0.6078(3) 0.49223(8) 0.27836(17) 0.0333(4) Uani 1 1 d . . . . .
C9 C 0.7604(3) 0.44374(8) 0.2615(2) 0.0390(4) Uani 1 1 d . . . . .
H91 H 0.9115 0.4415 0.3171 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6850(3) 0.39781(8) 0.1591(2) 0.0410(4) Uani 1 1 d . . . . .
H101 H 0.7869 0.3637 0.1443 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4632(3) 0.40132(8) 0.07890(19) 0.0392(4) Uani 1 1 d . . . . .
H111 H 0.4145 0.3690 0.0116 0.047 Uiso 1 1 calc R U . . .
C12 C 0.3109(3) 0.45105(8) 0.09502(19) 0.0371(4) Uani 1 1 d . . . . .
H121 H 0.1603 0.4537 0.0389 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3872(3) 0.49643(8) 0.19571(18) 0.0334(4) Uani 1 1 d . . . . .
C14 C 0.2701(3) 0.55440(8) 0.23677(19) 0.0359(4) Uani 1 1 d . . . . .
O141 O 0.0797(2) 0.57628(6) 0.18944(15) 0.0475(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
P1 P1 0.9404(19) 4_575 ?
P1 O11 1.471(3) . ?
P1 O12A 1.478(9) . ?
P1 O12B 1.534(13) 4_575 ?
P1 O12B 1.64(2) . ?
P1 C2 1.827(2) . ?
P1 H1 1.30(4) . ?
O11 P1 1.471(3) 4_575 ?
O12A P1 1.478(9) 4_575 ?
O12B O12B 0.34(10) 4_575 ?
O12B P1 1.534(13) 4_575 ?
C2 N3 1.497(3) . ?
C2 P1 1.827(2) 4_575 ?
C2 H21 0.9663 . ?
N3 C4 1.493(2) . ?
N3 C4 1.493(2) 4_575 ?
N3 H31 0.97(4) . ?
C4 C5 1.519(2) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 N6 1.452(2) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
N6 C7 1.396(2) . ?
N6 C14 1.399(2) . ?
C7 O71 1.211(2) . ?
C7 C8 1.486(2) . ?
C8 C9 1.371(3) . ?
C8 C13 1.394(2) . ?
C9 C10 1.397(3) . ?
C9 H91 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H101 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H111 0.9500 . ?
C12 C13 1.380(2) . ?
C12 H121 0.9500 . ?
C13 C14 1.478(2) . ?
C14 O141 1.214(2) . ?

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
P1 P1 O11 71.36(5) 4_575 . ?
P1 P1 O12A 71.45(12) 4_575 . ?
O11 P1 O12A 109.9(3) . . ?
P1 P1 O12B 78.8(18) 4_575 4_575 ?
O11 P1 O12B 133.5(11) . 4_575 ?
P1 P1 O12B 66.9(16) 4_575 . ?
O11 P1 O12B 125.3(12) . . ?
O12B P1 O12B 12(3) 4_575 . ?
P1 P1 C2 75.09(4) 4_575 . ?
O11 P1 C2 108.92(12) . . ?
O12A P1 C2 115.7(3) . . ?
O12B P1 C2 96.4(6) 4_575 . ?
O12B P1 C2 92.9(5) . . ?
P1 P1 H1 175.7(16) 4_575 . ?
O11 P1 H1 106.2(16) . . ?
O12A P1 H1 112.8(16) . . ?
O12B P1 H1 105(2) 4_575 . ?
O12B P1 H1 117(2) . . ?
C2 P1 H1 102.8(16) . . ?
P1 O11 P1 37.28(10) 4_575 . ?
P1 O12A P1 37.1(2) . 4_575 ?
O12B O12B P1 101.2(18) 4_575 4_575 ?
O12B O12B P1 66.9(16) 4_575 . ?
P1 O12B P1 34.3(3) 4_575 . ?
N3 C2 P1 118.85(16) . 4_575 ?
N3 C2 P1 118.85(16) . . ?
P1 C2 P1 29.82(7) 4_575 . ?
N3 C2 H21 108.5 . . ?
P1 C2 H21 118.0 4_575 . ?
P1 C2 H21 93.1 . . ?
C4 N3 C4 111.02(18) . 4_575 ?
C4 N3 C2 113.34(12) . . ?
C4 N3 C2 113.34(12) 4_575 . ?
C4 N3 H31 106.4(10) . . ?
C4 N3 H31 106.4(10) 4_575 . ?
C2 N3 H31 106(2) . . ?
N3 C4 C5 110.58(14) . . ?
N3 C4 H41 109.5 . . ?
C5 C4 H41 109.5 . . ?
N3 C4 H42 109.5 . . ?
C5 C4 H42 109.5 . . ?
H41 C4 H42 108.1 . . ?
N6 C5 C4 110.36(14) . . ?
N6 C5 H51 109.6 . . ?
C4 C5 H51 109.6 . . ?
N6 C5 H52 109.6 . . ?
C4 C5 H52 109.6 . . ?
H51 C5 H52 108.1 . . ?
C7 N6 C14 111.96(14) . . ?
C7 N6 C5 122.90(15) . . ?
C14 N6 C5 124.80(15) . . ?
O71 C7 N6 123.79(17) . . ?
O71 C7 C8 130.31(17) . . ?
N6 C7 C8 105.88(14) . . ?
C9 C8 C13 121.74(16) . . ?
C9 C8 C7 130.37(16) . . ?
C13 C8 C7 107.89(15) . . ?
C8 C9 C10 117.39(17) . . ?
C8 C9 H91 121.3 . . ?
C10 C9 H91 121.3 . . ?
C11 C10 C9 120.91(18) . . ?
C11 C10 H101 119.5 . . ?
C9 C10 H101 119.5 . . ?
C10 C11 C12 121.37(17) . . ?
C10 C11 H111 119.3 . . ?
C12 C11 H111 119.3 . . ?
C13 C12 C11 117.38(17) . . ?
C13 C12 H121 121.3 . . ?
C11 C12 H121 121.3 . . ?
C12 C13 C8 121.18(17) . . ?
C12 C13 C14 130.42(17) . . ?
C8 C13 C14 108.39(15) . . ?
O141 C14 N6 124.32(17) . . ?
O141 C14 C13 129.83(16) . . ?
N6 C14 C13 105.85(15) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_mpoll
_database_code_depnum_ccdc_archive 'CCDC 1984999'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 N O4 P2, H2 O'
_chemical_formula_sum            'C9 H17 N O5 P2'
_chemical_formula_weight         281.17

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      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                   7.0189(3)
_cell_length_b                   5.7569(2)
_cell_length_c                   15.9662(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.694(2)
_cell_angle_gamma                90
_cell_volume                     637.73(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1584
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.350
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            2908
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.290
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_full        25.242
_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 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2908
_reflns_number_gt                2630
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.997

_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       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0435P)²+0.1163P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2908
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.43014(10) 0.78959(11) 0.69949(4) 0.02173(17) Uani 1 1 d . . . . .
H1 H 0.394(4) 0.798(6) 0.6207(18) 0.023(7) Uiso 1 1 d . . . . .
O11 O 0.6478(3) 0.8149(4) 0.72539(13) 0.0334(5) Uani 1 1 d . . . . .
H11O H 0.725(7) 0.958(10) 0.710(3) 0.079(16) Uiso 1 1 d . . . . .
O12 O 0.3010(3) 0.9494(3) 0.73767(14) 0.0341(5) Uani 1 1 d . . . . .
C2 C 0.3973(4) 0.4883(5) 0.72952(18) 0.0205(5) Uani 1 1 d . . . . .
H21 H 0.4678 0.3883 0.6941 0.025 Uiso 1 1 calc R U . . .
H22 H 0.4590 0.4682 0.7891 0.025 Uiso 1 1 calc R U . . .
N3 N 0.1949(3) 0.4002(4) 0.72213(14) 0.0193(5) Uani 1 1 d . . . . .
H31 H 0.209(4) 0.260(6) 0.7299(16) 0.010(7) Uiso 1 1 d . . . . .
C4 C 0.0843(4) 0.4314(5) 0.63451(17) 0.0240(6) Uani 1 1 d . . . . .
H41 H 0.1762 0.4289 0.5932 0.029 Uiso 1 1 calc R U . . .
H42 H 0.0219 0.5860 0.6310 0.029 Uiso 1 1 calc R U . . .
P2 P -0.10022(11) 0.21073(12) 0.60422(5) 0.02588(19) Uani 1 1 d . . . . .
H2 H -0.003(4) 0.043(6) 0.580(2) 0.027(8) Uiso 1 1 d . . . . .
O21 O -0.1819(3) 0.1482(4) 0.68345(14) 0.0403(6) Uani 1 1 d . . . . .
O22 O -0.2298(3) 0.3029(4) 0.52954(14) 0.0403(5) Uani 1 1 d . . . . .
C5 C 0.0832(4) 0.5055(5) 0.78721(17) 0.0230(6) Uani 1 1 d . . . . .
H51 H 0.0858 0.6769 0.7822 0.028 Uiso 1 1 calc R U . . .
H52 H -0.0529 0.4551 0.7745 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1620(4) 0.4385(5) 0.87659(18) 0.0214(6) Uani 1 1 d . . . . .
C7 C 0.2719(4) 0.5937(5) 0.93022(19) 0.0262(6) Uani 1 1 d . . . . .
H71 H 0.3091 0.7378 0.9086 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3281(4) 0.5401(6) 1.0156(2) 0.0317(7) Uani 1 1 d . . . . .
H81 H 0.4026 0.6477 1.0520 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2753(4) 0.3303(6) 1.04698(18) 0.0320(7) Uani 1 1 d . . . . .
H91 H 0.3111 0.2948 1.1053 0.038 Uiso 1 1 calc R U . . .
C10 C 0.1704(4) 0.1717(5) 0.99380(19) 0.0293(7) Uani 1 1 d . . . . .
H101 H 0.1370 0.0262 1.0156 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1133(4) 0.2229(6) 0.90871(18) 0.0267(6) Uani 1 1 d . . . . .
H111 H 0.0417 0.1127 0.8724 0.032 Uiso 1 1 calc R U . . .
O1W O 0.6335(5) 0.7418(5) 0.4811(2) 0.0675(10) Uani 1 1 d . . . . .
H11W H 0.519(7) 0.723(8) 0.477(2) 0.048(12) Uiso 1 1 d . . . . .
H12W H 0.666(7) 0.619(9) 0.500(3) 0.060(14) Uiso 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
P1 O12 1.485(2) . ?
P1 O11 1.528(2) . ?
P1 C2 1.824(3) . ?
P1 H1 1.25(3) . ?
O11 H11O 1.04(6) . ?
C2 N3 1.496(3) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.505(3) . ?
N3 C5 1.519(4) . ?
N3 H31 0.82(3) . ?
C4 P2 1.826(3) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
P2 O22 1.484(2) . ?
P2 O21 1.509(2) . ?
P2 H2 1.28(3) . ?
C5 C6 1.501(4) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.388(4) . ?
C6 C11 1.404(4) . ?
C7 C8 1.395(4) . ?
C7 H71 0.9500 . ?
C8 C9 1.380(5) . ?
C8 H81 0.9500 . ?
C9 C10 1.381(4) . ?
C9 H91 0.9500 . ?
C10 C11 1.389(4) . ?
C10 H101 0.9500 . ?
C11 H111 0.9500 . ?
O1W H11W 0.80(4) . ?
O1W H12W 0.79(5) . ?

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
O12 P1 O11 118.51(14) . . ?
O12 P1 C2 111.82(13) . . ?
O11 P1 C2 100.40(12) . . ?
O12 P1 H1 110.3(14) . . ?
O11 P1 H1 108.2(13) . . ?
C2 P1 H1 106.7(16) . . ?
P1 O11 H11O 123(3) . . ?
N3 C2 P1 117.25(19) . . ?
N3 C2 H21 108.0 . . ?
P1 C2 H21 108.0 . . ?
N3 C2 H22 108.0 . . ?
P1 C2 H22 108.0 . . ?
H21 C2 H22 107.2 . . ?
C2 N3 C4 112.6(2) . . ?
C2 N3 C5 113.1(2) . . ?
C4 N3 C5 109.9(2) . . ?
C2 N3 H31 103.5(19) . . ?
C4 N3 H31 106.9(19) . . ?
C5 N3 H31 110.5(19) . . ?
N3 C4 P2 114.14(19) . . ?
N3 C4 H41 108.7 . . ?
P2 C4 H41 108.7 . . ?
N3 C4 H42 108.7 . . ?
P2 C4 H42 108.7 . . ?
H41 C4 H42 107.6 . . ?
O22 P2 O21 119.63(14) . . ?
O22 P2 C4 106.73(13) . . ?
O21 P2 C4 106.72(13) . . ?
O22 P2 H2 108.8(15) . . ?
O21 P2 H2 111.0(15) . . ?
C4 P2 H2 102.4(14) . . ?
C6 C5 N3 113.2(2) . . ?
C6 C5 H51 108.9 . . ?
N3 C5 H51 108.9 . . ?
C6 C5 H52 108.9 . . ?
N3 C5 H52 108.9 . . ?
H51 C5 H52 107.8 . . ?
C7 C6 C11 119.1(3) . . ?
C7 C6 C5 120.7(3) . . ?
C11 C6 C5 120.0(3) . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 H71 119.7 . . ?
C8 C7 H71 119.7 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H81 120.1 . . ?
C7 C8 H81 120.1 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H91 119.9 . . ?
C10 C9 H91 119.9 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H101 119.7 . . ?
C11 C10 H101 119.7 . . ?
C10 C11 C6 119.7(3) . . ?
C10 C11 H111 120.2 . . ?
C6 C11 H111 120.2 . . ?
H11W O1W H12W 98(5) . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_spo15
_database_code_depnum_ccdc_archive 'CCDC 1984997'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 N O4 P'
_chemical_formula_sum            'C10 H14 N O4 P'
_chemical_formula_weight         243.19

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6610(2)
_cell_length_b                   8.5501(3)
_cell_length_c                   12.0035(4)
_cell_angle_alpha                78.8540(10)
_cell_angle_beta                 79.1710(10)
_cell_angle_gamma                78.1390(10)
_cell_volume                     551.19(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4441
_cell_measurement_theta_min      3.2466
_cell_measurement_theta_max      27.5333

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.236
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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 8.3333
_diffrn_reflns_number            7035
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2526
_reflns_number_gt                2333
_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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0319P)²+0.3273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2526
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
P1 P 1.30560(5) 0.57790(4) 0.36831(3) 0.01297(10) Uani 1 1 d . . . . .
H1 H 1.259(3) 0.645(2) 0.4609(14) 0.021(4) Uiso 1 1 d . . . . .
O11 O 1.47976(17) 0.66228(12) 0.27981(9) 0.0237(2) Uani 1 1 d . . . . .
O12 O 1.36048(18) 0.39790(11) 0.40463(9) 0.0239(2) Uani 1 1 d . . . . .
C2 C 1.0084(2) 0.61092(14) 0.32097(11) 0.0122(2) Uani 1 1 d . . . . .
H21 H 1.0287 0.5541 0.2544 0.015 Uiso 1 1 calc R U . . .
H22 H 0.8970 0.5574 0.3836 0.015 Uiso 1 1 calc R U . . .
N3 N 0.88250(18) 0.78145(12) 0.28716(9) 0.0115(2) Uani 1 1 d . . . . .
H31 H 0.734(3) 0.769(2) 0.2803(15) 0.027(4) Uiso 1 1 d . . . . .
C4 C 0.8581(2) 0.88262(15) 0.37828(11) 0.0156(3) Uani 1 1 d . . . . .
H41 H 1.0156 0.9172 0.3762 0.019 Uiso 1 1 calc R U . . .
H42 H 0.8157 0.8182 0.4548 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6598(2) 1.03086(15) 0.35913(11) 0.0171(3) Uani 1 1 d . . . . .
O51 O 0.68056(19) 1.14325(12) 0.41508(9) 0.0232(2) Uani 1 1 d . . . . .
H511 H 0.573(3) 1.230(2) 0.4037(15) 0.028 Uiso 1 1 d . U . . .
O52 O 0.50539(19) 1.03759(12) 0.30071(10) 0.0287(3) Uani 1 1 d . . . . .
C6 C 1.0064(2) 0.86377(15) 0.17478(11) 0.0147(2) Uani 1 1 d . . . . .
H61 H 0.9314 0.9798 0.1633 0.018 Uiso 1 1 calc R U . . .
H62 H 1.1807 0.8569 0.1802 0.018 Uiso 1 1 calc R U . . .
C7 C 0.9910(2) 0.79304(15) 0.07171(11) 0.0158(3) Uani 1 1 d . . . . .
C8 C 1.1955(3) 0.70018(17) 0.01749(14) 0.0293(3) Uani 1 1 d . . . . .
H81 H 1.3401 0.6679 0.0515 0.035 Uiso 1 1 calc R U . . .
C9 C 1.1878(4) 0.6546(2) -0.08699(16) 0.0475(6) Uani 1 1 d . . . . .
H91 H 1.3272 0.5911 -0.1242 0.057 Uiso 1 1 calc R U . . .
C10 C 0.9774(5) 0.7018(2) -0.13631(14) 0.0483(6) Uani 1 1 d . . . . .
H101 H 0.9749 0.6744 -0.2091 0.058 Uiso 1 1 calc R U . . .
C11 C 0.7713(4) 0.7880(2) -0.08086(14) 0.0381(4) Uani 1 1 d . . . . .
H111 H 0.6251 0.8162 -0.1138 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7772(3) 0.83384(18) 0.02315(12) 0.0239(3) Uani 1 1 d . . . . .
H121 H 0.6348 0.8933 0.0614 0.029 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 O11 1.4911(10) . ?
P1 O12 1.5001(9) . ?
P1 C2 1.8264(12) . ?
P1 H1 1.307(16) . ?
C2 N3 1.5003(14) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.4912(16) . ?
N3 C6 1.5125(15) . ?
N3 H31 0.887(19) . ?
C4 C5 1.5228(16) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 O52 1.2057(17) . ?
C5 O51 1.3091(16) . ?
O51 H511 0.865(19) . ?
C6 C7 1.5020(18) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 C8 1.3904(19) . ?
C7 C12 1.3923(19) . ?
C8 C9 1.394(3) . ?
C8 H81 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H91 0.9500 . ?
C10 C11 1.376(3) . ?
C10 H101 0.9500 . ?
C11 C12 1.387(2) . ?
C11 H111 0.9500 . ?
C12 H121 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 P1 O12 120.56(6) . . ?
O11 P1 C2 110.42(6) . . ?
O12 P1 C2 103.35(6) . . ?
O11 P1 H1 109.5(7) . . ?
O12 P1 H1 107.9(7) . . ?
C2 P1 H1 103.7(7) . . ?
N3 C2 P1 118.74(8) . . ?
N3 C2 H21 107.6 . . ?
P1 C2 H21 107.6 . . ?
N3 C2 H22 107.6 . . ?
P1 C2 H22 107.6 . . ?
H21 C2 H22 107.1 . . ?
C4 N3 C2 112.39(9) . . ?
C4 N3 C6 109.59(9) . . ?
C2 N3 C6 112.61(9) . . ?
C4 N3 H31 108.3(11) . . ?
C2 N3 H31 103.2(11) . . ?
C6 N3 H31 110.5(11) . . ?
N3 C4 C5 109.79(10) . . ?
N3 C4 H41 109.7 . . ?
C5 C4 H41 109.7 . . ?
N3 C4 H42 109.7 . . ?
C5 C4 H42 109.7 . . ?
H41 C4 H42 108.2 . . ?
O52 C5 O51 126.47(12) . . ?
O52 C5 C4 122.48(12) . . ?
O51 C5 C4 111.04(11) . . ?
C5 O51 H511 113.0(12) . . ?
C7 C6 N3 114.18(10) . . ?
C7 C6 H61 108.7 . . ?
N3 C6 H61 108.7 . . ?
C7 C6 H62 108.7 . . ?
N3 C6 H62 108.7 . . ?
H61 C6 H62 107.6 . . ?
C8 C7 C12 119.44(14) . . ?
C8 C7 C6 120.56(13) . . ?
C12 C7 C6 119.69(12) . . ?
C7 C8 C9 119.81(17) . . ?
C7 C8 H81 120.1 . . ?
C9 C8 H81 120.1 . . ?
C10 C9 C8 119.97(17) . . ?
C10 C9 H91 120.0 . . ?
C8 C9 H91 120.0 . . ?
C11 C10 C9 120.49(16) . . ?
C11 C10 H101 119.8 . . ?
C9 C10 H101 119.8 . . ?
C10 C11 C12 119.89(18) . . ?
C10 C11 H111 120.1 . . ?
C12 C11 H111 120.1 . . ?
C11 C12 C7 120.30(15) . . ?
C11 C12 H121 119.9 . . ?
C7 C12 H121 119.9 . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_tbun_2pin
_database_code_depnum_ccdc_archive 'CCDC 1985002'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H17 N O4 P2'
_chemical_formula_sum            'C6 H17 N O4 P2'
_chemical_formula_weight         229.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   8.6777(3)
_cell_length_b                   11.9197(3)
_cell_length_c                   10.7504(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.4590(10)
_cell_angle_gamma                90
_cell_volume                     1076.75(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.5977
_cell_measurement_theta_max      27.4920

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.546
_exptl_crystal_size_mid          0.379
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.390
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            16205
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.598
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2457
_reflns_number_gt                2387
_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 Instrument Service V6.2.12'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0328P)²+0.5958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2457
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
P1 P 0.33113(3) 0.50647(2) 0.78850(3) 0.01476(9) Uani 1 1 d . . . . .
H1 H 0.2889(18) 0.5377(13) 0.6684(15) 0.023(4) Uiso 1 1 d . . . . .
O11 O 0.24542(10) 0.39268(7) 0.78689(8) 0.01910(18) Uani 1 1 d . . . . .
H11O H 0.281(3) 0.353(2) 0.866(3) 0.086(9) Uiso 1 1 d . . . . .
O12 O 0.29978(10) 0.59361(7) 0.87696(8) 0.02072(18) Uani 1 1 d . . . . .
C2 C 0.54486(13) 0.48104(10) 0.82511(11) 0.0159(2) Uani 1 1 d . . . . .
H21 H 0.5998 0.5537 0.8483 0.019 Uiso 1 1 calc R U . . .
H22 H 0.5737 0.4324 0.9021 0.019 Uiso 1 1 calc R U . . .
N3 N 0.60945(11) 0.42799(8) 0.72178(9) 0.01414(19) Uani 1 1 d . . . . .
H31 H 0.5905(19) 0.4785(14) 0.6618(16) 0.025(4) Uiso 1 1 d . . . . .
C4 C 0.52713(13) 0.31879(9) 0.67429(11) 0.0157(2) Uani 1 1 d . . . . .
H41 H 0.4710 0.2920 0.7383 0.019 Uiso 1 1 calc R U . . .
H42 H 0.6093 0.2624 0.6698 0.019 Uiso 1 1 calc R U . . .
P2 P 0.38449(3) 0.32536(2) 0.51790(3) 0.01647(9) Uani 1 1 d . . . . .
H2 H 0.2642(19) 0.3866(14) 0.5343(16) 0.028(4) Uiso 1 1 d . . . . .
O21 O 0.32796(11) 0.20596(7) 0.49188(8) 0.0237(2) Uani 1 1 d . . . . .
O22 O 0.45870(11) 0.38377(8) 0.42449(8) 0.02306(19) Uani 1 1 d . . . . .
C5 C 0.79505(13) 0.41575(10) 0.76222(11) 0.0175(2) Uani 1 1 d . . . . .
C6 C 0.84289(15) 0.32642(11) 0.86588(12) 0.0240(3) Uani 1 1 d . . . . .
H61 H 0.7979 0.2540 0.8319 0.029 Uiso 1 1 calc R U . . .
H62 H 0.8024 0.3470 0.9401 0.029 Uiso 1 1 calc R U . . .
H63 H 0.9592 0.3208 0.8924 0.029 Uiso 1 1 calc R U . . .
C7 C 0.86696(15) 0.52918(11) 0.81184(13) 0.0247(3) Uani 1 1 d . . . . .
H71 H 0.9825 0.5268 0.8231 0.030 Uiso 1 1 calc R U . . .
H72 H 0.8433 0.5456 0.8945 0.030 Uiso 1 1 calc R U . . .
H73 H 0.8211 0.5879 0.7498 0.030 Uiso 1 1 calc R U . . .
C8 C 0.84637(15) 0.38342(12) 0.64092(12) 0.0236(3) Uani 1 1 d . . . . .
H81 H 0.8059 0.3084 0.6129 0.028 Uiso 1 1 calc R U . . .
H82 H 0.9628 0.3833 0.6593 0.028 Uiso 1 1 calc R U . . .
H83 H 0.8033 0.4378 0.5727 0.028 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 O12 1.4787(9) . ?
P1 O11 1.5449(9) . ?
P1 C2 1.8227(11) . ?
P1 H1 1.305(16) . ?
O11 H11O 0.95(3) . ?
C2 N3 1.5030(14) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.5109(14) . ?
N3 C5 1.5668(14) . ?
N3 H31 0.868(17) . ?
C4 P2 1.8236(11) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
P2 O22 1.4936(9) . ?
P2 O21 1.5086(9) . ?
P2 H2 1.321(16) . ?
C5 C6 1.5222(17) . ?
C5 C7 1.5283(17) . ?
C5 C8 1.5288(16) . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 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
O12 P1 O11 117.29(5) . . ?
O12 P1 C2 108.58(5) . . ?
O11 P1 C2 108.52(5) . . ?
O12 P1 H1 112.6(7) . . ?
O11 P1 H1 102.9(7) . . ?
C2 P1 H1 106.3(7) . . ?
P1 O11 H11O 112.0(17) . . ?
N3 C2 P1 117.22(7) . . ?
N3 C2 H21 108.0 . . ?
P1 C2 H21 108.0 . . ?
N3 C2 H22 108.0 . . ?
P1 C2 H22 108.0 . . ?
H21 C2 H22 107.2 . . ?
C2 N3 C4 112.34(9) . . ?
C2 N3 C5 112.41(8) . . ?
C4 N3 C5 112.34(8) . . ?
C2 N3 H31 102.7(11) . . ?
C4 N3 H31 111.2(11) . . ?
C5 N3 H31 105.2(11) . . ?
N3 C4 P2 115.42(8) . . ?
N3 C4 H41 108.4 . . ?
P2 C4 H41 108.4 . . ?
N3 C4 H42 108.4 . . ?
P2 C4 H42 108.4 . . ?
H41 C4 H42 107.5 . . ?
O22 P2 O21 119.33(5) . . ?
O22 P2 C4 109.42(5) . . ?
O21 P2 C4 104.17(5) . . ?
O22 P2 H2 108.7(7) . . ?
O21 P2 H2 108.3(7) . . ?
C4 P2 H2 106.1(7) . . ?
C6 C5 C7 110.51(10) . . ?
C6 C5 C8 111.34(10) . . ?
C7 C5 C8 109.89(10) . . ?
C6 C5 N3 109.99(9) . . ?
C7 C5 N3 108.44(9) . . ?
C8 C5 N3 106.56(9) . . ?
C5 C6 H61 109.5 . . ?
C5 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
C5 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
C5 C7 H71 109.5 . . ?
C5 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
C5 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
C5 C8 H81 109.5 . . ?
C5 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C5 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_bampin
_database_code_depnum_ccdc_archive 'CCDC 1984998'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 N O2 P'
_chemical_formula_sum            'C8 H12 N O2 P'
_chemical_formula_weight         185.16

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

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

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

_cell_length_a                   10.4097(4)
_cell_length_b                   6.3878(3)
_cell_length_c                   27.1688(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1806.59(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6643
_cell_measurement_theta_min      3.1891
_cell_measurement_theta_max      25.9374

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.784
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.254
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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 8.3333
_diffrn_reflns_number            8771
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_max         25.960
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3454
_reflns_number_gt                3301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_max     0.998
_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 Instrument Service v2014.11.0.1'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+1.4753P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3454
_refine_ls_number_parameters     241
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
P1A P 0.68370(10) 1.03607(16) 0.35081(4) 0.0150(3) Uani 1 1 d D . . . .
H1A H 0.752(4) 0.887(5) 0.3304(15) 0.014(11) Uiso 1 1 d D . . . .
O11A O 0.5510(3) 0.9509(4) 0.35800(11) 0.0153(6) Uani 1 1 d . . . . .
O12A O 0.7011(3) 1.2420(4) 0.32496(12) 0.0189(6) Uani 1 1 d . . . . .
C2A C 0.7588(4) 1.0601(7) 0.41130(16) 0.0158(8) Uani 1 1 d . . . . .
H21A H 0.8456 0.9968 0.4102 0.019 Uiso 1 1 calc R U . . .
H22A H 0.7688 1.2102 0.4195 0.019 Uiso 1 1 calc R U . . .
N3A N 0.6819(3) 0.9554(5) 0.45064(13) 0.0153(8) Uani 1 1 d . . . . .
H31A H 0.655(6) 0.797(11) 0.449(2) 0.06(2) Uiso 1 1 d . . . . .
H32A H 0.594(5) 1.033(7) 0.4514(18) 0.015(12) Uiso 1 1 d . . . . .
C4A C 0.7396(4) 0.9760(7) 0.50083(17) 0.0193(9) Uani 1 1 d . . . . .
H41A H 0.7366 1.1242 0.5114 0.023 Uiso 1 1 calc R U . . .
H42A H 0.8306 0.9314 0.4999 0.023 Uiso 1 1 calc R U . . .
C5A C 0.6667(4) 0.8428(8) 0.53688(16) 0.0203(9) Uani 1 1 d . . . . .
C6A C 0.7108(5) 0.6418(8) 0.54832(17) 0.0283(10) Uani 1 1 d . . . . .
H61A H 0.7897 0.5939 0.5348 0.034 Uiso 1 1 calc R U . . .
C7A C 0.6416(6) 0.5131(9) 0.5789(2) 0.0365(12) Uani 1 1 d . . . . .
H71A H 0.6730 0.3775 0.5867 0.044 Uiso 1 1 calc R U . . .
C8A C 0.5256(6) 0.5815(11) 0.5982(2) 0.0413(14) Uani 1 1 d . . . . .
H81A H 0.4767 0.4917 0.6189 0.050 Uiso 1 1 calc R U . . .
C9A C 0.4811(5) 0.7805(10) 0.58752(19) 0.0365(13) Uani 1 1 d . . . . .
H91A H 0.4018 0.8270 0.6009 0.044 Uiso 1 1 calc R U . . .
C10A C 0.5524(4) 0.9135(8) 0.55704(17) 0.0260(10) Uani 1 1 d . . . . .
H10A H 0.5226 1.0511 0.5502 0.031 Uiso 1 1 calc R U . . .
P1X P 0.51345(9) 0.45965(15) 0.43697(4) 0.0138(3) Uani 1 1 d . . . . .
H1X H 0.430(4) 0.582(7) 0.4579(17) 0.015(11) Uiso 1 1 d . . . . .
O11X O 0.6460(3) 0.5439(4) 0.42956(11) 0.0149(7) Uani 1 1 d . . . . .
O12X O 0.4963(3) 0.2547(5) 0.46288(12) 0.0188(6) Uani 1 1 d . . . . .
C2X C 0.4364(4) 0.4370(6) 0.37636(15) 0.0155(8) Uani 1 1 d . . . . .
H21X H 0.4245 0.2870 0.3684 0.019 Uiso 1 1 calc R U . . .
H22X H 0.3505 0.5030 0.3777 0.019 Uiso 1 1 calc R U . . .
N3X N 0.5130(3) 0.5375(6) 0.33685(14) 0.0137(8) Uani 1 1 d . . . . .
H31X H 0.528(4) 0.669(7) 0.3423(15) 0.002(10) Uiso 1 1 d . . . . .
H32X H 0.592(4) 0.474(6) 0.3359(16) 0.003 Uiso 1 1 d . U . . .
C4X C 0.4523(4) 0.5117(7) 0.28698(17) 0.0193(9) Uani 1 1 d . . . . .
H41X H 0.3634 0.5665 0.2876 0.023 Uiso 1 1 calc R U . . .
H42X H 0.4488 0.3614 0.2782 0.023 Uiso 1 1 calc R U . . .
C5X C 0.5303(4) 0.6292(8) 0.24917(16) 0.0246(10) Uani 1 1 d . . . . .
C6X C 0.4927(6) 0.8282(9) 0.2344(2) 0.0386(13) Uani 1 1 d . . . . .
H61X H 0.4160 0.8880 0.2471 0.046 Uiso 1 1 calc R U . . .
C7X C 0.5671(8) 0.9398(10) 0.2011(3) 0.0573(19) Uani 1 1 d . . . . .
H71X H 0.5407 1.0753 0.1909 0.069 Uiso 1 1 calc R U . . .
C8X C 0.6786(7) 0.8558(13) 0.1829(2) 0.0547(19) Uani 1 1 d . . . . .
H81X H 0.7300 0.9347 0.1607 0.066 Uiso 1 1 calc R U . . .
C9X C 0.7165(5) 0.6559(12) 0.19662(19) 0.0444(15) Uani 1 1 d . . . . .
H91X H 0.7928 0.5966 0.1834 0.053 Uiso 1 1 calc R U . . .
C10X C 0.6421(5) 0.5429(9) 0.22978(18) 0.0300(11) Uani 1 1 d . . . . .
H10X H 0.6677 0.4060 0.2393 0.036 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
P1A O11A 1.498(3) . ?
P1A O12A 1.502(3) . ?
P1A C2A 1.827(5) . ?
P1A H1A 1.313(14) . ?
C2A N3A 1.493(5) . ?
C2A H21A 0.9900 . ?
C2A H22A 0.9900 . ?
N3A C4A 1.496(6) . ?
N3A H31A 1.05(7) . ?
N3A H32A 1.04(5) . ?
C4A C5A 1.503(6) . ?
C4A H41A 0.9900 . ?
C4A H42A 0.9900 . ?
C5A C10A 1.385(6) . ?
C5A C6A 1.399(7) . ?
C6A C7A 1.373(8) . ?
C6A H61A 0.9500 . ?
C7A C8A 1.388(9) . ?
C7A H71A 0.9500 . ?
C8A C9A 1.383(9) . ?
C8A H81A 0.9500 . ?
C9A C10A 1.399(7) . ?
C9A H91A 0.9500 . ?
C10A H10A 0.9500 . ?
P1X O11X 1.495(3) . ?
P1X O12X 1.497(3) . ?
P1X C2X 1.837(4) . ?
P1X H1X 1.30(4) . ?
C2X N3X 1.483(5) . ?
C2X H21X 0.9900 . ?
C2X H22X 0.9900 . ?
N3X C4X 1.504(6) . ?
N3X H31X 0.87(5) . ?
N3X H32X 0.92(5) . ?
C4X C5X 1.509(7) . ?
C4X H41X 0.9900 . ?
C4X H42X 0.9900 . ?
C5X C6X 1.390(7) . ?
C5X C10X 1.391(7) . ?
C6X C7X 1.388(9) . ?
C6X H61X 0.9500 . ?
C7X C8X 1.371(10) . ?
C7X H71X 0.9500 . ?
C8X C9X 1.388(11) . ?
C8X H81X 0.9500 . ?
C9X C10X 1.390(8) . ?
C9X H91X 0.9500 . ?
C10X H10X 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11A P1A O12A 119.36(16) . . ?
O11A P1A C2A 107.95(18) . . ?
O12A P1A C2A 107.20(19) . . ?
O11A P1A H1A 107(2) . . ?
O12A P1A H1A 112(2) . . ?
C2A P1A H1A 102(2) . . ?
N3A C2A P1A 112.1(3) . . ?
N3A C2A H21A 109.2 . . ?
P1A C2A H21A 109.2 . . ?
N3A C2A H22A 109.2 . . ?
P1A C2A H22A 109.2 . . ?
H21A C2A H22A 107.9 . . ?
C2A N3A C4A 113.5(3) . . ?
C2A N3A H31A 123(4) . . ?
C4A N3A H31A 103(4) . . ?
C2A N3A H32A 106(3) . . ?
C4A N3A H32A 107(3) . . ?
H31A N3A H32A 103(4) . . ?
N3A C4A C5A 110.0(3) . . ?
N3A C4A H41A 109.7 . . ?
C5A C4A H41A 109.7 . . ?
N3A C4A H42A 109.7 . . ?
C5A C4A H42A 109.7 . . ?
H41A C4A H42A 108.2 . . ?
C10A C5A C6A 119.6(4) . . ?
C10A C5A C4A 120.4(4) . . ?
C6A C5A C4A 119.9(4) . . ?
C7A C6A C5A 120.8(5) . . ?
C7A C6A H61A 119.6 . . ?
C5A C6A H61A 119.6 . . ?
C6A C7A C8A 119.8(5) . . ?
C6A C7A H71A 120.1 . . ?
C8A C7A H71A 120.1 . . ?
C9A C8A C7A 120.1(5) . . ?
C9A C8A H81A 120.0 . . ?
C7A C8A H81A 120.0 . . ?
C8A C9A C10A 120.3(5) . . ?
C8A C9A H91A 119.8 . . ?
C10A C9A H91A 119.8 . . ?
C5A C10A C9A 119.4(5) . . ?
C5A C10A H10A 120.3 . . ?
C9A C10A H10A 120.3 . . ?
O11X P1X O12X 119.20(16) . . ?
O11X P1X C2X 108.08(18) . . ?
O12X P1X C2X 107.49(19) . . ?
O11X P1X H1X 117(2) . . ?
O12X P1X H1X 104(2) . . ?
C2X P1X H1X 99(2) . . ?
N3X C2X P1X 112.3(3) . . ?
N3X C2X H21X 109.1 . . ?
P1X C2X H21X 109.1 . . ?
N3X C2X H22X 109.1 . . ?
P1X C2X H22X 109.1 . . ?
H21X C2X H22X 107.9 . . ?
C2X N3X C4X 112.3(3) . . ?
C2X N3X H31X 113(3) . . ?
C4X N3X H31X 110(3) . . ?
C2X N3X H32X 108(3) . . ?
C4X N3X H32X 108(3) . . ?
H31X N3X H32X 106(4) . . ?
N3X C4X C5X 109.4(3) . . ?
N3X C4X H41X 109.8 . . ?
C5X C4X H41X 109.8 . . ?
N3X C4X H42X 109.8 . . ?
C5X C4X H42X 109.8 . . ?
H41X C4X H42X 108.2 . . ?
C6X C5X C10X 119.3(5) . . ?
C6X C5X C4X 120.0(4) . . ?
C10X C5X C4X 120.7(4) . . ?
C7X C6X C5X 120.0(6) . . ?
C7X C6X H61X 120.0 . . ?
C5X C6X H61X 120.0 . . ?
C8X C7X C6X 120.5(6) . . ?
C8X C7X H71X 119.7 . . ?
C6X C7X H71X 119.7 . . ?
C7X C8X C9X 120.2(6) . . ?
C7X C8X H81X 119.9 . . ?
C9X C8X H81X 119.9 . . ?
C8X C9X C10X 119.6(6) . . ?
C8X C9X H91X 120.2 . . ?
C10X C9X H91X 120.2 . . ?
C9X C10X C5X 120.4(5) . . ?
C9X C10X H10X 119.8 . . ?
C5X C10X H10X 119.8 . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_dcampin
_database_code_depnum_ccdc_archive 'CCDC 1985003'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H26 N O2 P'
_chemical_formula_sum            'C13 H26 N O2 P'
_chemical_formula_weight         259.32

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5485(2)
_cell_length_b                   8.7247(2)
_cell_length_c                   10.3439(2)
_cell_angle_alpha                71.4180(10)
_cell_angle_beta                 68.6890(10)
_cell_angle_gamma                81.2800(10)
_cell_volume                     680.70(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4913
_cell_measurement_theta_min      2.4649
_cell_measurement_theta_max      27.5063

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.828
_exptl_crystal_size_mid          0.486
_exptl_crystal_size_min          0.370
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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 8.3333
_diffrn_reflns_number            7152
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.206
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3105
_reflns_number_gt                2803
_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 Instrument Service V6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0434P)²+0.2845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3105
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
P1 P 0.33630(4) 0.23698(4) 0.60086(3) 0.01501(10) Uani 1 1 d . . . . .
H1 H 0.256(2) 0.265(2) 0.7304(18) 0.029(4) Uiso 1 1 d . . . . .
O11 O 0.36298(11) 0.39851(10) 0.48901(10) 0.0216(2) Uani 1 1 d . . . . .
O12 O 0.25028(11) 0.10701(11) 0.59137(11) 0.0235(2) Uani 1 1 d . . . . .
C2 C 0.54243(14) 0.15056(13) 0.61017(12) 0.0135(2) Uani 1 1 d . . . . .
H21 H 0.5263 0.0764 0.7086 0.016 Uiso 1 1 calc R U . . .
H22 H 0.5884 0.0848 0.5413 0.016 Uiso 1 1 calc R U . . .
N3 N 0.67213(12) 0.27083(12) 0.57737(10) 0.01170(19) Uani 1 1 d . . . . .
H31 H 0.634(2) 0.371(2) 0.5480(17) 0.021(4) Uiso 1 1 d . . . . .
C4 C 0.71139(14) 0.26742(14) 0.71064(12) 0.0132(2) Uani 1 1 d . . . . .
H41 H 0.7920 0.3547 0.6797 0.016 Uiso 1 1 calc R U . . .
C5 C 0.79788(15) 0.10790(14) 0.76981(13) 0.0162(2) Uani 1 1 d . . . . .
H51 H 0.9051 0.0910 0.6947 0.019 Uiso 1 1 calc R U . . .
H52 H 0.7253 0.0171 0.7951 0.019 Uiso 1 1 calc R U . . .
C6 C 0.83236(17) 0.11040(16) 0.90447(14) 0.0208(3) Uani 1 1 d . . . . .
H61 H 0.8829 0.0044 0.9448 0.025 Uiso 1 1 calc R U . . .
H62 H 0.9137 0.1945 0.8770 0.025 Uiso 1 1 calc R U . . .
C7 C 0.67077(16) 0.14540(16) 1.01922(13) 0.0200(3) Uani 1 1 d . . . . .
H71 H 0.6962 0.1475 1.1047 0.024 Uiso 1 1 calc R U . . .
H72 H 0.5917 0.0582 1.0507 0.024 Uiso 1 1 calc R U . . .
C8 C 0.58919(16) 0.30738(15) 0.95959(13) 0.0193(3) Uani 1 1 d . . . . .
H81 H 0.6651 0.3954 0.9347 0.023 Uiso 1 1 calc R U . . .
H82 H 0.4831 0.3267 1.0348 0.023 Uiso 1 1 calc R U . . .
C9 C 0.55206(15) 0.31012(14) 0.82446(13) 0.0164(2) Uani 1 1 d . . . . .
H91 H 0.4652 0.2315 0.8517 0.020 Uiso 1 1 calc R U . . .
H92 H 0.5077 0.4191 0.7832 0.020 Uiso 1 1 calc R U . . .
C10 C 0.82617(14) 0.24975(14) 0.44863(12) 0.0125(2) Uani 1 1 d . . . . .
H101 H 0.8596 0.1320 0.4660 0.015 Uiso 1 1 calc R U . . .
C11 C 0.97681(14) 0.34194(14) 0.42582(12) 0.0146(2) Uani 1 1 d . . . . .
H111 H 1.0089 0.3051 0.5141 0.018 Uiso 1 1 calc R U . . .
H112 H 0.9468 0.4592 0.4072 0.018 Uiso 1 1 calc R U . . .
C12 C 1.12473(15) 0.31178(15) 0.29682(13) 0.0181(2) Uani 1 1 d . . . . .
H121 H 1.2213 0.3738 0.2807 0.022 Uiso 1 1 calc R U . . .
H122 H 1.1592 0.1954 0.3190 0.022 Uiso 1 1 calc R U . . .
C13 C 1.07839(17) 0.36204(18) 0.15936(14) 0.0239(3) Uani 1 1 d . . . . .
H131 H 1.0572 0.4807 0.1304 0.029 Uiso 1 1 calc R U . . .
H132 H 1.1735 0.3339 0.0799 0.029 Uiso 1 1 calc R U . . .
C14 C 0.92263(16) 0.27792(16) 0.18317(13) 0.0190(3) Uani 1 1 d . . . . .
H141 H 0.9487 0.1602 0.1997 0.023 Uiso 1 1 calc R U . . .
H142 H 0.8903 0.3188 0.0951 0.023 Uiso 1 1 calc R U . . .
C15 C 0.77558(15) 0.30687(14) 0.31260(12) 0.0155(2) Uani 1 1 d . . . . .
H151 H 0.6778 0.2470 0.3279 0.019 Uiso 1 1 calc R U . . .
H152 H 0.7427 0.4236 0.2931 0.019 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 O12 1.4874(9) . ?
P1 O11 1.4978(9) . ?
P1 C2 1.8322(11) . ?
P1 H1 1.346(16) . ?
C2 N3 1.5158(14) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.5236(14) . ?
N3 C10 1.5327(14) . ?
N3 H31 0.883(16) . ?
C4 C5 1.5271(16) . ?
C4 C9 1.5298(15) . ?
C4 H41 1.0000 . ?
C5 C6 1.5321(16) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.5237(18) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 C8 1.5239(18) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 C9 1.5343(17) . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 C11 1.5274(15) . ?
C10 C15 1.5314(15) . ?
C10 H101 1.0000 . ?
C11 C12 1.5314(16) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C13 1.5266(17) . ?
C12 H121 0.9900 . ?
C12 H122 0.9900 . ?
C13 C14 1.5215(18) . ?
C13 H131 0.9900 . ?
C13 H132 0.9900 . ?
C14 C15 1.5272(16) . ?
C14 H141 0.9900 . ?
C14 H142 0.9900 . ?
C15 H151 0.9900 . ?
C15 H152 0.9900 . ?

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
O12 P1 O11 121.79(5) . . ?
O12 P1 C2 106.39(5) . . ?
O11 P1 C2 107.68(5) . . ?
O12 P1 H1 108.6(7) . . ?
O11 P1 H1 107.1(7) . . ?
C2 P1 H1 103.9(7) . . ?
N3 C2 P1 116.03(7) . . ?
N3 C2 H21 108.3 . . ?
P1 C2 H21 108.3 . . ?
N3 C2 H22 108.3 . . ?
P1 C2 H22 108.3 . . ?
H21 C2 H22 107.4 . . ?
C2 N3 C4 112.93(8) . . ?
C2 N3 C10 109.44(8) . . ?
C4 N3 C10 114.66(8) . . ?
C2 N3 H31 110.8(10) . . ?
C4 N3 H31 103.9(10) . . ?
C10 N3 H31 104.7(10) . . ?
N3 C4 C5 112.41(9) . . ?
N3 C4 C9 109.90(9) . . ?
C5 C4 C9 112.98(9) . . ?
N3 C4 H41 107.1 . . ?
C5 C4 H41 107.1 . . ?
C9 C4 H41 107.1 . . ?
C4 C5 C6 110.16(10) . . ?
C4 C5 H51 109.6 . . ?
C6 C5 H51 109.6 . . ?
C4 C5 H52 109.6 . . ?
C6 C5 H52 109.6 . . ?
H51 C5 H52 108.1 . . ?
C7 C6 C5 110.92(10) . . ?
C7 C6 H61 109.5 . . ?
C5 C6 H61 109.5 . . ?
C7 C6 H62 109.5 . . ?
C5 C6 H62 109.5 . . ?
H61 C6 H62 108.0 . . ?
C6 C7 C8 110.62(10) . . ?
C6 C7 H71 109.5 . . ?
C8 C7 H71 109.5 . . ?
C6 C7 H72 109.5 . . ?
C8 C7 H72 109.5 . . ?
H71 C7 H72 108.1 . . ?
C7 C8 C9 111.00(10) . . ?
C7 C8 H81 109.4 . . ?
C9 C8 H81 109.4 . . ?
C7 C8 H82 109.4 . . ?
C9 C8 H82 109.4 . . ?
H81 C8 H82 108.0 . . ?
C4 C9 C8 110.66(10) . . ?
C4 C9 H91 109.5 . . ?
C8 C9 H91 109.5 . . ?
C4 C9 H92 109.5 . . ?
C8 C9 H92 109.5 . . ?
H91 C9 H92 108.1 . . ?
C11 C10 C15 109.97(9) . . ?
C11 C10 N3 113.22(9) . . ?
C15 C10 N3 108.14(9) . . ?
C11 C10 H101 108.5 . . ?
C15 C10 H101 108.5 . . ?
N3 C10 H101 108.5 . . ?
C10 C11 C12 109.46(9) . . ?
C10 C11 H111 109.8 . . ?
C12 C11 H111 109.8 . . ?
C10 C11 H112 109.8 . . ?
C12 C11 H112 109.8 . . ?
H111 C11 H112 108.2 . . ?
C13 C12 C11 111.38(10) . . ?
C13 C12 H121 109.4 . . ?
C11 C12 H121 109.4 . . ?
C13 C12 H122 109.4 . . ?
C11 C12 H122 109.4 . . ?
H121 C12 H122 108.0 . . ?
C14 C13 C12 110.96(10) . . ?
C14 C13 H131 109.4 . . ?
C12 C13 H131 109.4 . . ?
C14 C13 H132 109.4 . . ?
C12 C13 H132 109.4 . . ?
H131 C13 H132 108.0 . . ?
C13 C14 C15 111.54(10) . . ?
C13 C14 H141 109.3 . . ?
C15 C14 H141 109.3 . . ?
C13 C14 H142 109.3 . . ?
C15 C14 H142 109.3 . . ?
H141 C14 H142 108.0 . . ?
C14 C15 C10 109.85(9) . . ?
C14 C15 H151 109.7 . . ?
C10 C15 H151 109.7 . . ?
C14 C15 H152 109.7 . . ?
C10 C15 H152 109.7 . . ?
H151 C15 H152 108.2 . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_ftmpin_dba
_database_code_depnum_ccdc_archive 'CCDC 1985001'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-02-19 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N2 O4 P'
_chemical_formula_sum            'C24 H23 N2 O4 P'
_chemical_formula_weight         434.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9559(5)
_cell_length_b                   10.8993(5)
_cell_length_c                   11.2372(5)
_cell_angle_alpha                110.8480(10)
_cell_angle_beta                 92.5530(10)
_cell_angle_gamma                110.0000(10)
_cell_volume                     1051.45(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      4.7004
_cell_measurement_theta_max      70.1680

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    1.448
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            17202
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.700
_diffrn_reflns_theta_max         70.162
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3984
_reflns_number_gt                3629
_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 Instrument Service V6.2.10'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0369P)²+0.4762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3984
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.67957(3) 0.27047(3) 0.66347(3) 0.01442(10) Uani 1 1 d . . . . .
O11 O 0.65600(10) 0.12206(10) 0.57369(9) 0.0175(2) Uani 1 1 d . . . . .
O12 O 0.69680(11) 0.31141(11) 0.80590(9) 0.0228(2) Uani 1 1 d . . . . .
C2 C 0.52104(14) 0.29796(14) 0.60198(13) 0.0168(3) Uani 1 1 d . . . . .
H21 H 0.5011 0.3719 0.6720 0.020 Uiso 1 1 calc R U . . .
H22 H 0.5412 0.3295 0.5299 0.020 Uiso 1 1 calc R U . . .
N3 N 0.39249(12) 0.15948(12) 0.55541(11) 0.0150(2) Uani 1 1 d . . . . .
H31 H 0.4216(19) 0.0877(19) 0.5117(16) 0.023(4) Uiso 1 1 d . . . . .
C4 C 0.27208(15) 0.15146(15) 0.46340(13) 0.0194(3) Uani 1 1 d . . . . .
H41 H 0.2374 0.2280 0.5077 0.023 Uiso 1 1 calc R U . . .
H42 H 0.1895 0.0592 0.4389 0.023 Uiso 1 1 calc R U . . .
C5 C 0.32166(15) 0.16624(15) 0.34236(13) 0.0195(3) Uani 1 1 d . . . . .
C6 C 0.2983(2) 0.26525(19) 0.30314(16) 0.0335(4) Uani 1 1 d . . . . .
H61 H 0.2545 0.3256 0.3542 0.040 Uiso 1 1 calc R U . . .
C7 C 0.3383(2) 0.2771(2) 0.18963(18) 0.0401(4) Uani 1 1 d . . . . .
H71 H 0.3194 0.3437 0.1624 0.048 Uiso 1 1 calc R U . . .
C8 C 0.40542(19) 0.19293(18) 0.11639(16) 0.0328(4) Uani 1 1 d . . . . .
H81 H 0.4338 0.2018 0.0393 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4309(2) 0.09548(19) 0.15617(16) 0.0360(4) Uani 1 1 d . . . . .
H91 H 0.4786 0.0382 0.1068 0.043 Uiso 1 1 calc R U . . .
C10 C 0.38772(19) 0.08029(17) 0.26723(15) 0.0297(4) Uani 1 1 d . . . . .
H101 H 0.4033 0.0109 0.2922 0.036 Uiso 1 1 calc R U . . .
C11 C 0.33710(15) 0.11808(14) 0.66527(13) 0.0174(3) Uani 1 1 d . . . . .
H111 H 0.2691 0.0172 0.6275 0.021 Uiso 1 1 calc R U . . .
H112 H 0.4208 0.1254 0.7222 0.021 Uiso 1 1 calc R U . . .
C12 C 0.26094(15) 0.20531(14) 0.74740(13) 0.0166(3) Uani 1 1 d . . . . .
C13 C 0.33812(16) 0.32794(15) 0.85756(14) 0.0212(3) Uani 1 1 d . . . . .
H131 H 0.4410 0.3599 0.8793 0.025 Uiso 1 1 calc R U . . .
C14 C 0.26494(18) 0.40353(16) 0.93563(14) 0.0268(3) Uani 1 1 d . . . . .
H141 H 0.3178 0.4874 1.0103 0.032 Uiso 1 1 calc R U . . .
C15 C 0.11480(19) 0.35653(17) 0.90446(15) 0.0277(3) Uani 1 1 d . . . . .
H151 H 0.0650 0.4084 0.9579 0.033 Uiso 1 1 calc R U . . .
C16 C 0.03704(17) 0.23450(17) 0.79596(15) 0.0262(3) Uani 1 1 d . . . . .
H161 H -0.0659 0.2024 0.7751 0.031 Uiso 1 1 calc R U . . .
C17 C 0.11001(15) 0.15915(16) 0.71776(14) 0.0215(3) Uani 1 1 d . . . . .
H171 H 0.0565 0.0753 0.6433 0.026 Uiso 1 1 calc R U . . .
C18 C 0.83784(15) 0.39427(15) 0.63214(14) 0.0199(3) Uani 1 1 d . . . . .
H181 H 0.8340 0.4899 0.6666 0.024 Uiso 1 1 calc R U . . .
H182 H 0.9273 0.4004 0.6801 0.024 Uiso 1 1 calc R U . . .
N19 N 0.84767(13) 0.35494(12) 0.49586(12) 0.0200(3) Uani 1 1 d . . . . .
C20 C 0.79030(16) 0.40213(15) 0.41303(15) 0.0230(3) Uani 1 1 d . . . . .
O201 O 0.73243(13) 0.48701(12) 0.44622(12) 0.0329(3) Uani 1 1 d . . . . .
C21 C 0.81562(15) 0.32719(16) 0.28255(15) 0.0229(3) Uani 1 1 d . . . . .
C22 C 0.78000(17) 0.33494(18) 0.16603(16) 0.0300(4) Uani 1 1 d . . . . .
H221 H 0.7332 0.3960 0.1604 0.036 Uiso 1 1 calc R U . . .
C23 C 0.81527(19) 0.2500(2) 0.05723(17) 0.0348(4) Uani 1 1 d . . . . .
H231 H 0.7926 0.2530 -0.0245 0.042 Uiso 1 1 calc R U . . .
C24 C 0.8834(2) 0.1606(2) 0.06632(17) 0.0358(4) Uani 1 1 d . . . . .
H241 H 0.9056 0.1030 -0.0097 0.043 Uiso 1 1 calc R U . . .
C25 C 0.91992(18) 0.15369(18) 0.18432(16) 0.0289(3) Uani 1 1 d . . . . .
H251 H 0.9669 0.0930 0.1905 0.035 Uiso 1 1 calc R U . . .
C26 C 0.88461(15) 0.23919(15) 0.29204(14) 0.0218(3) Uani 1 1 d . . . . .
C27 C 0.90834(14) 0.25703(15) 0.42982(14) 0.0194(3) Uani 1 1 d . . . . .
O271 O 0.96708(11) 0.20202(11) 0.47923(10) 0.0244(2) 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
P1 O12 1.4849(10) . ?
P1 O11 1.4991(9) . ?
P1 C18 1.8332(14) . ?
P1 C2 1.8526(14) . ?
C2 N3 1.4989(17) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
N3 C4 1.5057(17) . ?
N3 C11 1.5228(17) . ?
N3 H31 0.912(18) . ?
C4 C5 1.5103(19) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C6 1.384(2) . ?
C5 C10 1.390(2) . ?
C6 C7 1.389(2) . ?
C6 H61 0.9500 . ?
C7 C8 1.377(3) . ?
C7 H71 0.9500 . ?
C8 C9 1.380(2) . ?
C8 H81 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H91 0.9500 . ?
C10 H101 0.9500 . ?
C11 C12 1.5039(18) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C17 1.393(2) . ?
C12 C13 1.3944(19) . ?
C13 C14 1.390(2) . ?
C13 H131 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H141 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H151 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H161 0.9500 . ?
C17 H171 0.9500 . ?
C18 N19 1.4537(18) . ?
C18 H181 0.9900 . ?
C18 H182 0.9900 . ?
N19 C20 1.3969(19) . ?
N19 C27 1.4041(18) . ?
C20 O201 1.2104(18) . ?
C20 C21 1.484(2) . ?
C21 C22 1.380(2) . ?
C21 C26 1.386(2) . ?
C22 C23 1.389(2) . ?
C22 H221 0.9500 . ?
C23 C24 1.391(3) . ?
C23 H231 0.9500 . ?
C24 C25 1.394(2) . ?
C24 H241 0.9500 . ?
C25 C26 1.384(2) . ?
C25 H251 0.9500 . ?
C26 C27 1.487(2) . ?
C27 O271 1.2074(18) . ?

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
O12 P1 O11 120.81(6) . . ?
O12 P1 C18 107.82(6) . . ?
O11 P1 C18 108.42(6) . . ?
O12 P1 C2 110.48(6) . . ?
O11 P1 C2 103.21(6) . . ?
C18 P1 C2 105.01(6) . . ?
N3 C2 P1 107.91(9) . . ?
N3 C2 H21 110.1 . . ?
P1 C2 H21 110.1 . . ?
N3 C2 H22 110.1 . . ?
P1 C2 H22 110.1 . . ?
H21 C2 H22 108.4 . . ?
C2 N3 C4 113.27(11) . . ?
C2 N3 C11 113.09(10) . . ?
C4 N3 C11 112.15(10) . . ?
C2 N3 H31 108.9(11) . . ?
C4 N3 H31 106.9(11) . . ?
C11 N3 H31 101.6(11) . . ?
N3 C4 C5 111.90(11) . . ?
N3 C4 H41 109.2 . . ?
C5 C4 H41 109.2 . . ?
N3 C4 H42 109.2 . . ?
C5 C4 H42 109.2 . . ?
H41 C4 H42 107.9 . . ?
C6 C5 C10 118.86(14) . . ?
C6 C5 C4 119.60(13) . . ?
C10 C5 C4 121.52(13) . . ?
C5 C6 C7 120.54(15) . . ?
C5 C6 H61 119.7 . . ?
C7 C6 H61 119.7 . . ?
C8 C7 C6 120.36(16) . . ?
C8 C7 H71 119.8 . . ?
C6 C7 H71 119.8 . . ?
C7 C8 C9 119.28(15) . . ?
C7 C8 H81 120.4 . . ?
C9 C8 H81 120.4 . . ?
C8 C9 C10 120.70(16) . . ?
C8 C9 H91 119.7 . . ?
C10 C9 H91 119.7 . . ?
C9 C10 C5 120.23(15) . . ?
C9 C10 H101 119.9 . . ?
C5 C10 H101 119.9 . . ?
C12 C11 N3 115.49(11) . . ?
C12 C11 H111 108.4 . . ?
N3 C11 H111 108.4 . . ?
C12 C11 H112 108.4 . . ?
N3 C11 H112 108.4 . . ?
H111 C11 H112 107.5 . . ?
C17 C12 C13 119.14(13) . . ?
C17 C12 C11 119.77(12) . . ?
C13 C12 C11 120.99(13) . . ?
C14 C13 C12 120.16(14) . . ?
C14 C13 H131 119.9 . . ?
C12 C13 H131 119.9 . . ?
C15 C14 C13 119.98(14) . . ?
C15 C14 H141 120.0 . . ?
C13 C14 H141 120.0 . . ?
C16 C15 C14 120.35(13) . . ?
C16 C15 H151 119.8 . . ?
C14 C15 H151 119.8 . . ?
C15 C16 C17 119.72(14) . . ?
C15 C16 H161 120.1 . . ?
C17 C16 H161 120.1 . . ?
C16 C17 C12 120.64(14) . . ?
C16 C17 H171 119.7 . . ?
C12 C17 H171 119.7 . . ?
N19 C18 P1 114.18(9) . . ?
N19 C18 H181 108.7 . . ?
P1 C18 H181 108.7 . . ?
N19 C18 H182 108.7 . . ?
P1 C18 H182 108.7 . . ?
H181 C18 H182 107.6 . . ?
C20 N19 C27 111.83(12) . . ?
C20 N19 C18 124.54(12) . . ?
C27 N19 C18 123.51(12) . . ?
O201 C20 N19 124.74(14) . . ?
O201 C20 C21 129.36(14) . . ?
N19 C20 C21 105.90(12) . . ?
C22 C21 C26 121.83(15) . . ?
C22 C21 C20 129.77(14) . . ?
C26 C21 C20 108.40(13) . . ?
C21 C22 C23 117.39(15) . . ?
C21 C22 H221 121.3 . . ?
C23 C22 H221 121.3 . . ?
C22 C23 C24 120.88(16) . . ?
C22 C23 H231 119.6 . . ?
C24 C23 H231 119.6 . . ?
C23 C24 C25 121.56(16) . . ?
C23 C24 H241 119.2 . . ?
C25 C24 H241 119.2 . . ?
C26 C25 C24 116.99(15) . . ?
C26 C25 H251 121.5 . . ?
C24 C25 H251 121.5 . . ?
C25 C26 C21 121.35(14) . . ?
C25 C26 C27 130.41(14) . . ?
C21 C26 C27 108.24(13) . . ?
O271 C27 N19 125.12(13) . . ?
O271 C27 C26 129.26(13) . . ?
N19 C27 C26 105.61(12) . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.044

