# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1840620'
_audit_update_record             
;
2018-04-28 deposited with the CCDC.
2018-10-16 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         'C19 H16 Br O3 P'
_chemical_formula_sum            'C19 H16 Br O3 P'
_chemical_formula_weight         403.20

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'
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'
Br Br -0.2901 2.4595 '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                   14.870(3)
_cell_length_b                   8.1150(18)
_cell_length_c                   15.295(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.026(3)
_cell_angle_gamma                90
_cell_volume                     1773.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2620
_cell_measurement_theta_min      1.425
_cell_measurement_theta_max      25.004

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.421
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12190
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.425
_diffrn_reflns_theta_max         25.001
_diffrn_reflns_theta_full        25.001
_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             3127
_reflns_number_gt                2561
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0478P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3127
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.15737(2) 0.37962(3) 0.22065(2) 0.04659(12) Uani 1 1 d . . . . .
C1 C 0.34038(18) 0.6437(3) 0.16483(17) 0.0426(6) Uani 1 1 d . . . . .
H1A H 0.2783 0.6695 0.1360 0.051 Uiso 1 1 calc R U . . .
C2 C 0.4020(2) 0.6128(3) 0.11339(19) 0.0511(7) Uani 1 1 d . . . . .
H2B H 0.3815 0.6215 0.0504 0.061 Uiso 1 1 calc R U . . .
C3 C 0.4918(2) 0.5702(4) 0.1543(2) 0.0576(8) Uani 1 1 d . . . . .
H3A H 0.5320 0.5455 0.1192 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5239(2) 0.5631(4) 0.2480(2) 0.0632(8) Uani 1 1 d . . . . .
H4A H 0.5857 0.5349 0.2760 0.076 Uiso 1 1 calc R U . . .
C5 C 0.46358(19) 0.5983(4) 0.2997(2) 0.0538(7) Uani 1 1 d . . . . .
H5A H 0.4854 0.5965 0.3628 0.065 Uiso 1 1 calc R U . . .
C6 C 0.37017(17) 0.6364(3) 0.25798(17) 0.0374(6) Uani 1 1 d . . . . .
C7 C 0.29334(17) 0.5347(3) 0.40837(15) 0.0392(6) Uani 1 1 d . . . . .
C8 C 0.2428(2) 0.5649(4) 0.46979(19) 0.0580(8) Uani 1 1 d . . . . .
H8A H 0.2085 0.6617 0.4660 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2433(2) 0.4498(4) 0.5379(2) 0.0675(9) Uani 1 1 d . . . . .
H9A H 0.2083 0.4693 0.5788 0.081 Uiso 1 1 calc R U . . .
C10 C 0.2945(2) 0.3098(4) 0.5445(2) 0.0658(9) Uani 1 1 d . . . . .
H10A H 0.2959 0.2353 0.5911 0.079 Uiso 1 1 calc R U . . .
C11 C 0.3438(2) 0.2770(4) 0.4836(2) 0.0692(9) Uani 1 1 d . . . . .
H11A H 0.3772 0.1792 0.4875 0.083 Uiso 1 1 calc R U . . .
C12 C 0.3440(2) 0.3899(3) 0.4162(2) 0.0568(8) Uani 1 1 d . . . . .
H12A H 0.3787 0.3683 0.3754 0.068 Uiso 1 1 calc R U . . .
C13 C 0.17983(16) 0.7296(3) 0.25171(16) 0.0357(5) Uani 1 1 d . . . . .
C14 C 0.14835(18) 0.8930(3) 0.23476(18) 0.0453(7) Uani 1 1 d . . . . .
C15 C 0.0601(2) 0.9242(4) 0.1755(2) 0.0588(8) Uani 1 1 d . . . . .
H15A H 0.0399 1.0325 0.1642 0.071 Uiso 1 1 calc R U . . .
C16 C 0.00328(19) 0.7991(4) 0.1339(2) 0.0571(8) Uani 1 1 d . . . . .
H16A H -0.0556 0.8234 0.0957 0.069 Uiso 1 1 calc R U . . .
C17 C 0.03163(18) 0.6355(3) 0.14748(18) 0.0453(6) Uani 1 1 d . . . . .
C18 C 0.11964(18) 0.6028(3) 0.20613(17) 0.0378(6) Uani 1 1 d . . . . .
C19 C -0.1089(2) 0.5357(5) 0.0440(2) 0.0779(10) Uani 1 1 d . . . . .
H19A H -0.1383 0.4333 0.0208 0.117 Uiso 1 1 calc R U . . .
H19B H -0.1479 0.5945 0.0739 0.117 Uiso 1 1 calc R U . . .
H19C H -0.1000 0.6009 -0.0053 0.117 Uiso 1 1 calc R U . . .
O1 O 0.32790(13) 0.8524(2) 0.37835(12) 0.0476(4) Uani 1 1 d . . . . .
O2 O 0.20066(15) 1.0253(2) 0.27059(14) 0.0649(6) Uani 1 1 d . . . . .
H2A H 0.2478 0.9948 0.3091 0.097 Uiso 1 1 calc R U . . .
O3 O -0.01975(12) 0.5032(3) 0.10778(14) 0.0618(5) Uani 1 1 d . . . . .
P1 P 0.29532(4) 0.69571(8) 0.32733(4) 0.03599(17) 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
Br1 C18 1.891(2) . ?
C1 C6 1.372(3) . ?
C1 C2 1.385(4) . ?
C2 C3 1.354(4) . ?
C3 C4 1.380(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.394(4) . ?
C6 P1 1.802(2) . ?
C7 C8 1.377(4) . ?
C7 C12 1.383(4) . ?
C7 P1 1.807(2) . ?
C8 C9 1.398(4) . ?
C9 C10 1.356(5) . ?
C10 C11 1.361(4) . ?
C11 C12 1.380(4) . ?
C13 C14 1.406(3) . ?
C13 C18 1.415(3) . ?
C13 P1 1.807(2) . ?
C14 O2 1.350(3) . ?
C14 C15 1.396(4) . ?
C15 C16 1.362(4) . ?
C16 C17 1.391(4) . ?
C17 O3 1.359(3) . ?
C17 C18 1.393(4) . ?
C19 O3 1.436(3) . ?
O1 P1 1.5004(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
C6 C1 C2 120.5(2) . . ?
C3 C2 C1 120.4(3) . . ?
C2 C3 C4 120.3(3) . . ?
C5 C4 C3 119.6(3) . . ?
C4 C5 C6 120.4(3) . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 P1 121.68(19) . . ?
C5 C6 P1 119.3(2) . . ?
C8 C7 C12 118.6(2) . . ?
C8 C7 P1 117.1(2) . . ?
C12 C7 P1 124.2(2) . . ?
C7 C8 C9 119.9(3) . . ?
C10 C9 C8 120.1(3) . . ?
C9 C10 C11 120.7(3) . . ?
C10 C11 C12 119.6(3) . . ?
C11 C12 C7 121.1(3) . . ?
C14 C13 C18 117.5(2) . . ?
C14 C13 P1 118.06(19) . . ?
C18 C13 P1 124.40(18) . . ?
O2 C14 C15 116.9(2) . . ?
O2 C14 C13 123.4(2) . . ?
C15 C14 C13 119.7(2) . . ?
C16 C15 C14 121.3(3) . . ?
C15 C16 C17 121.2(3) . . ?
O3 C17 C16 125.2(2) . . ?
O3 C17 C18 116.7(2) . . ?
C16 C17 C18 118.1(2) . . ?
C17 C18 C13 122.2(2) . . ?
C17 C18 Br1 116.98(19) . . ?
C13 C18 Br1 120.80(18) . . ?
C17 O3 C19 117.3(2) . . ?
O1 P1 C6 111.68(11) . . ?
O1 P1 C13 108.50(11) . . ?
C6 P1 C13 107.23(11) . . ?
O1 P1 C7 108.66(11) . . ?
C6 P1 C7 109.90(11) . . ?
C13 P1 C7 110.88(11) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1840622'
_audit_update_record             
;
2018-04-28 deposited with the CCDC.
2018-10-16 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 H21 O3 P'
_chemical_formula_sum            'C21 H21 O3 P'
_chemical_formula_weight         352.35

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'
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           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -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'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   32.26(3)
_cell_length_b                   16.224(15)
_cell_length_c                   7.120(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3726(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2645
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.242

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13479
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.262
_diffrn_reflns_theta_max         26.848
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3537
_reflns_number_gt                3302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     0.812
_reflns_Friedel_fraction_full    0.916

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0504P)²+0.6507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1285 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3537
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
C1 C 0.42012(7) 0.80731(14) 0.6027(3) 0.0300(5) Uani 1 1 d . . . . .
C2 C 0.45520(7) 0.83902(16) 0.5102(4) 0.0373(6) Uani 1 1 d . . . . .
H2A H 0.4556 0.8424 0.3798 0.045 Uiso 1 1 calc R U . . .
C3 C 0.48932(8) 0.86536(19) 0.6136(4) 0.0481(7) Uani 1 1 d . . . . .
C4 C 0.48805(9) 0.8603(2) 0.8080(5) 0.0533(8) Uani 1 1 d . . . . .
H4A H 0.5106 0.8785 0.8778 0.064 Uiso 1 1 calc R U . . .
C5 C 0.45396(8) 0.82894(18) 0.8993(4) 0.0444(7) Uani 1 1 d . . . . .
H5A H 0.4539 0.8257 1.0297 0.053 Uiso 1 1 calc R U . . .
C6 C 0.41949(7) 0.80194(15) 0.7980(4) 0.0328(5) Uani 1 1 d . . . . .
C7 C 0.37621(7) 0.65797(15) 0.4954(4) 0.0347(6) Uani 1 1 d . . . . .
C8 C 0.35591(8) 0.62200(16) 0.6476(4) 0.0426(6) Uani 1 1 d . . . . .
H8A H 0.3415 0.6548 0.7325 0.051 Uiso 1 1 calc R U . . .
C9 C 0.35721(9) 0.53729(18) 0.6724(5) 0.0558(8) Uani 1 1 d . . . . .
H9A H 0.3432 0.5131 0.7724 0.067 Uiso 1 1 calc R U . . .
C10 C 0.37950(11) 0.4886(2) 0.5477(6) 0.0641(10) Uani 1 1 d . . . . .
H10A H 0.3808 0.4319 0.5657 0.077 Uiso 1 1 calc R U . . .
C11 C 0.39967(10) 0.52390(18) 0.3980(5) 0.0598(10) Uani 1 1 d . . . . .
H11A H 0.4147 0.4911 0.3153 0.072 Uiso 1 1 calc R U . . .
C12 C 0.39771(9) 0.60781(17) 0.3703(5) 0.0453(7) Uani 1 1 d . . . . .
H12A H 0.4109 0.6312 0.2670 0.054 Uiso 1 1 calc R U . . .
C13 C 0.33004(7) 0.81347(15) 0.5239(4) 0.0308(5) Uani 1 1 d . . . . .
C14 C 0.32910(8) 0.89456(16) 0.5870(4) 0.0381(6) Uani 1 1 d . . . . .
H14A H 0.3538 0.9232 0.6050 0.046 Uiso 1 1 calc R U . . .
C15 C 0.29096(8) 0.93331(18) 0.6237(4) 0.0458(7) Uani 1 1 d . . . . .
C16 C 0.25472(8) 0.88848(19) 0.5961(4) 0.0485(7) Uani 1 1 d . . . . .
H16A H 0.2294 0.9136 0.6209 0.058 Uiso 1 1 calc R U . . .
C17 C 0.25497(8) 0.80777(18) 0.5331(4) 0.0414(6) Uani 1 1 d . . . . .
C18 C 0.29324(8) 0.77055(16) 0.4968(3) 0.0366(6) Uani 1 1 d . . . . .
H18A H 0.2941 0.7164 0.4541 0.044 Uiso 1 1 calc R U . . .
C19 C 0.52914(11) 0.8960(2) 0.3379(6) 0.0678(10) Uani 1 1 d . . . . .
H19A H 0.5553 0.9197 0.3034 0.102 Uiso 1 1 calc R U . . .
H19B H 0.5278 0.8401 0.2937 0.102 Uiso 1 1 calc R U . . .
H19C H 0.5071 0.9274 0.2825 0.102 Uiso 1 1 calc R U . . .
C20 C 0.28928(11) 1.0211(2) 0.6932(7) 0.0743(10) Uani 1 1 d . . . . .
H20A H 0.3169 1.0424 0.7041 0.111 Uiso 1 1 calc R U . . .
H20B H 0.2738 1.0541 0.6059 0.111 Uiso 1 1 calc R U . . .
H20C H 0.2760 1.0226 0.8138 0.111 Uiso 1 1 calc R U . . .
C21 C 0.21491(9) 0.7611(2) 0.5024(5) 0.0609(9) Uani 1 1 d . . . . .
H21A H 0.2210 0.7064 0.4589 0.091 Uiso 1 1 calc R U . . .
H21B H 0.1999 0.7580 0.6186 0.091 Uiso 1 1 calc R U . . .
H21C H 0.1984 0.7892 0.4103 0.091 Uiso 1 1 calc R U . . .
O1 O 0.38917(6) 0.78583(12) 0.2524(3) 0.0423(5) Uani 1 1 d . . . . .
O2 O 0.38529(6) 0.76988(12) 0.8821(3) 0.0418(5) Uani 1 1 d . . . . .
H2B H 0.3872 0.7754 0.9962 0.063 Uiso 1 1 calc R U . . .
O3 O 0.52500(6) 0.89693(18) 0.5359(4) 0.0747(8) Uani 1 1 d . . . . .
P1 P 0.37897(2) 0.76806(4) 0.45333(9) 0.02926(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.394(4) . ?
C1 C2 1.407(3) . ?
C1 P1 1.816(3) . ?
C2 C3 1.391(4) . ?
C3 O3 1.376(3) . ?
C3 C4 1.388(5) . ?
C4 C5 1.375(4) . ?
C5 C6 1.396(4) . ?
C6 O2 1.359(3) . ?
C7 C12 1.392(4) . ?
C7 C8 1.394(4) . ?
C7 P1 1.813(3) . ?
C8 C9 1.386(4) . ?
C9 C10 1.388(5) . ?
C10 C11 1.374(5) . ?
C11 C12 1.377(4) . ?
C13 C18 1.390(4) . ?
C13 C14 1.390(4) . ?
C13 P1 1.813(3) . ?
C14 C15 1.406(4) . ?
C15 C16 1.391(4) . ?
C15 C20 1.508(5) . ?
C16 C17 1.384(4) . ?
C17 C18 1.399(4) . ?
C17 C21 1.514(4) . ?
C19 O3 1.416(5) . ?
O1 P1 1.496(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
C6 C1 C2 120.1(2) . . ?
C6 C1 P1 123.49(19) . . ?
C2 C1 P1 116.2(2) . . ?
C3 C2 C1 120.1(3) . . ?
O3 C3 C4 116.6(3) . . ?
O3 C3 C2 124.3(3) . . ?
C4 C3 C2 119.1(3) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 C6 120.6(3) . . ?
O2 C6 C1 118.4(2) . . ?
O2 C6 C5 122.6(2) . . ?
C1 C6 C5 119.0(2) . . ?
C12 C7 C8 119.1(3) . . ?
C12 C7 P1 116.5(2) . . ?
C8 C7 P1 124.3(2) . . ?
C9 C8 C7 120.0(3) . . ?
C8 C9 C10 119.8(3) . . ?
C11 C10 C9 120.3(3) . . ?
C10 C11 C12 120.1(3) . . ?
C11 C12 C7 120.6(3) . . ?
C18 C13 C14 120.0(2) . . ?
C18 C13 P1 120.1(2) . . ?
C14 C13 P1 119.54(18) . . ?
C13 C14 C15 120.1(2) . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 C20 120.7(3) . . ?
C14 C15 C20 121.0(3) . . ?
C17 C16 C15 122.4(2) . . ?
C16 C17 C18 118.3(2) . . ?
C16 C17 C21 121.0(3) . . ?
C18 C17 C21 120.7(3) . . ?
C13 C18 C17 120.8(2) . . ?
C3 O3 C19 118.3(3) . . ?
O1 P1 C13 112.23(11) . . ?
O1 P1 C7 111.02(11) . . ?
C13 P1 C7 108.16(12) . . ?
O1 P1 C1 109.36(12) . . ?
C13 P1 C1 109.36(13) . . ?
C7 P1 C1 106.53(11) . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_180315_zm_zju_1
_database_code_depnum_ccdc_archive 'CCDC 1854975'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;
_audit_creation_date             2018-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 O5 P'
_chemical_formula_sum            'C20 H19 O5 P'
_chemical_formula_weight         370.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o P'
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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                   12.4510(7)
_cell_length_b                   18.5872(10)
_cell_length_c                   7.9138(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1831.48(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7835
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3175
_cell_measurement_theta_min      3.2346
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25295
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_min         3.241
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -70.00    2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  126.0000   92.0000 72

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   77.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  -14.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega  -53.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -77.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  6 omega  -56.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -77.0000  -90.0000 102

#__ type_ start__ end____ width___ exp.time_
  7 omega  -13.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000  -30.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0173542000
_diffrn_orient_matrix_UB_12      0.0231741000
_diffrn_orient_matrix_UB_13      -0.0657460000
_diffrn_orient_matrix_UB_21      -0.0535779000
_diffrn_orient_matrix_UB_22      0.0026476000
_diffrn_orient_matrix_UB_23      -0.0298431000
_diffrn_orient_matrix_UB_31      -0.0086189000
_diffrn_orient_matrix_UB_32      0.0301988000
_diffrn_orient_matrix_UB_33      0.0530989000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3013
_reflns_number_total             3352
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.4196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.66969(6) 0.35533(4) 0.64989(12) 0.0329(2) Uani 1 1 d . . . . .
O1 O 0.67551(18) 0.45495(11) 0.3509(3) 0.0468(6) Uani 1 1 d . . . . .
O2 O 0.5100(2) 0.44394(13) 0.2285(5) 0.0706(9) Uani 1 1 d . . . . .
O3 O 0.71080(17) 0.37069(12) 0.1406(3) 0.0459(5) Uani 1 1 d . . . . .
O4 O 0.4796(2) 0.20277(14) 0.3996(4) 0.0658(8) Uani 1 1 d . . . . .
O5 O 0.55664(17) 0.37711(11) 0.6768(3) 0.0464(6) Uani 1 1 d . . . . .
C1 C 0.5964(3) 0.49371(19) 0.2598(7) 0.0651(12) Uani 1 1 d . . . . .
H1A H 0.625682 0.511386 0.154069 0.078 Uiso 1 1 calc R . . . .
H1B H 0.571071 0.534391 0.325416 0.078 Uiso 1 1 calc R . . . .
C2 C 0.6637(2) 0.38251(16) 0.2993(4) 0.0367(7) Uani 1 1 d . . . . .
C3 C 0.5448(3) 0.37818(18) 0.2703(5) 0.0465(8) Uani 1 1 d . . . . .
C4 C 0.4841(3) 0.3200(2) 0.2916(5) 0.0526(9) Uani 1 1 d . . . . .
H4 H 0.411718 0.320614 0.262730 0.063 Uiso 1 1 calc R . . . .
C5 C 0.5326(3) 0.25631(19) 0.3599(5) 0.0448(8) Uani 1 1 d . . . . .
C6 C 0.6534(3) 0.25509(17) 0.3835(4) 0.0393(8) Uani 1 1 d . . . . .
H6A H 0.686403 0.238718 0.279300 0.047 Uiso 1 1 calc R . . . .
H6B H 0.670922 0.220457 0.470903 0.047 Uiso 1 1 calc R . . . .
C7 C 0.7024(2) 0.32853(16) 0.4319(4) 0.0332(7) Uani 1 1 d . . . . .
H7 H 0.780712 0.324668 0.422613 0.040 Uiso 1 1 calc R . . . .
C8 C 0.8241(3) 0.3824(3) 0.1327(6) 0.0639(11) Uani 1 1 d . . . . .
H8A H 0.846808 0.382538 0.016762 0.096 Uiso 1 1 calc GR . . . .
H8B H 0.860492 0.344582 0.192349 0.096 Uiso 1 1 calc GR . . . .
H8C H 0.841116 0.427836 0.183622 0.096 Uiso 1 1 calc GR . . . .
C9 C 0.7652(3) 0.42497(16) 0.7061(4) 0.0367(7) Uani 1 1 d . . . . .
C10 C 0.7248(3) 0.48373(17) 0.7947(5) 0.0485(8) Uani 1 1 d . . . . .
H10 H 0.652139 0.485925 0.821350 0.058 Uiso 1 1 calc R . . . .
C11 C 0.7929(4) 0.53893(19) 0.8433(5) 0.0601(11) Uani 1 1 d . . . . .
H11 H 0.765563 0.578378 0.901423 0.072 Uiso 1 1 calc R . . . .
C12 C 0.9007(4) 0.5357(2) 0.8059(5) 0.0648(12) Uani 1 1 d . . . . .
H12 H 0.946141 0.572760 0.839124 0.078 Uiso 1 1 calc R . . . .
C13 C 0.9408(4) 0.4781(2) 0.7200(6) 0.0648(11) Uani 1 1 d . . . . .
H13 H 1.013871 0.475956 0.695876 0.078 Uiso 1 1 calc R . . . .
C14 C 0.8739(3) 0.42232(19) 0.6680(5) 0.0496(9) Uani 1 1 d . . . . .
H14 H 0.901833 0.383549 0.608172 0.060 Uiso 1 1 calc R . . . .
C15 C 0.7031(2) 0.27480(16) 0.7689(4) 0.0361(7) Uani 1 1 d . . . . .
C16 C 0.8035(3) 0.24201(19) 0.7613(6) 0.0509(9) Uani 1 1 d . . . . .
H16 H 0.858766 0.263576 0.700504 0.061 Uiso 1 1 calc R . . . .
C17 C 0.8215(3) 0.1776(2) 0.8436(6) 0.0604(11) Uani 1 1 d . . . . .
H17 H 0.888782 0.155946 0.838222 0.073 Uiso 1 1 calc R . . . .
C18 C 0.7400(3) 0.1452(2) 0.9338(5) 0.0601(11) Uani 1 1 d . . . . .
H18 H 0.752053 0.101794 0.988939 0.072 Uiso 1 1 calc R . . . .
C19 C 0.6410(3) 0.1774(2) 0.9417(6) 0.0588(10) Uani 1 1 d . . . . .
H19 H 0.585955 0.155484 1.002321 0.071 Uiso 1 1 calc R . . . .
C20 C 0.6221(3) 0.24200(19) 0.8604(5) 0.0472(9) Uani 1 1 d . . . . .
H20 H 0.554757 0.263460 0.867185 0.057 Uiso 1 1 calc R . . . .


_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 O5 1.480(2) . ?
P1 C7 1.842(3) . ?
P1 C9 1.813(3) . ?
P1 C15 1.817(3) . ?
O1 C1 1.417(4) . ?
O1 C2 1.415(4) . ?
O2 C1 1.440(5) . ?
O2 C3 1.338(4) . ?
O3 C2 1.403(4) . ?
O3 C8 1.429(4) . ?
O4 C5 1.235(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.501(4) . ?
C2 C7 1.529(4) . ?
C3 C4 1.329(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.435(5) . ?
C5 C6 1.515(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.544(4) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.392(5) . ?
C9 C14 1.388(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(5) . ?
C15 C20 1.384(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(5) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 P1 C7 114.81(14) . . ?
O5 P1 C9 113.14(14) . . ?
O5 P1 C15 111.63(14) . . ?
C9 P1 C7 106.13(15) . . ?
C9 P1 C15 108.11(14) . . ?
C15 P1 C7 102.24(14) . . ?
C2 O1 C1 105.4(3) . . ?
C3 O2 C1 107.6(3) . . ?
C2 O3 C8 115.3(3) . . ?
O1 C1 O2 106.3(3) . . ?
O1 C1 H1A 110.5 . . ?
O1 C1 H1B 110.5 . . ?
O2 C1 H1A 110.5 . . ?
O2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
O1 C2 C3 101.4(2) . . ?
O1 C2 C7 113.2(3) . . ?
O3 C2 O1 111.3(3) . . ?
O3 C2 C3 105.5(3) . . ?
O3 C2 C7 112.3(2) . . ?
C3 C2 C7 112.4(3) . . ?
O2 C3 C2 107.9(3) . . ?
C4 C3 O2 126.2(3) . . ?
C4 C3 C2 125.8(3) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
O4 C5 C4 122.4(3) . . ?
O4 C5 C6 119.2(3) . . ?
C4 C5 C6 118.4(3) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C5 C6 C7 114.2(3) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
P1 C7 H7 108.1 . . ?
C2 C7 P1 113.3(2) . . ?
C2 C7 C6 106.6(3) . . ?
C2 C7 H7 108.1 . . ?
C6 C7 P1 112.6(2) . . ?
C6 C7 H7 108.1 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 P1 116.6(3) . . ?
C14 C9 P1 124.1(2) . . ?
C14 C9 C10 119.3(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 119.6(4) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 P1 123.0(3) . . ?
C20 C15 P1 117.8(2) . . ?
C20 C15 C16 119.0(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.7(4) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.2(3) . . ?
C19 C20 H20 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1840623'
_audit_update_record             
;
2018-04-28 deposited with the CCDC.
2018-10-16 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         'C19 H16 Br O3 P'
_chemical_formula_sum            'C19 H16 Br O3 P'
_chemical_formula_weight         403.20

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'
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'
Br Br -0.2901 2.4595 '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                   11.472(9)
_cell_length_b                   17.116(13)
_cell_length_c                   18.240(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3582(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2625
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.004

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.398
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'multi-scan '
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23501
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.1182
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_full        25.004
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3164
_reflns_number_gt                1934
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0947P)²+0.9558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3164
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Br1 Br 0.14024(8) 0.05112(5) 0.27135(4) 0.0773(4) Uani 1 1 d . . . . .
C1 C 0.0850(5) 0.2565(4) 0.6328(3) 0.0603(17) Uani 1 1 d . . . . .
H1B H 0.0732 0.2967 0.5993 0.072 Uiso 1 1 calc R U . . .
C2 C 0.0031(6) 0.2407(5) 0.6856(4) 0.078(2) Uani 1 1 d . . . . .
H2A H -0.0653 0.2698 0.6873 0.094 Uiso 1 1 calc R U . . .
C3 C 0.0212(8) 0.1831(5) 0.7352(4) 0.086(2) Uani 1 1 d . . . . .
H3A H -0.0344 0.1738 0.7713 0.103 Uiso 1 1 calc R U . . .
C4 C 0.1195(8) 0.1386(5) 0.7333(4) 0.084(3) Uani 1 1 d . . . . .
H4A H 0.1308 0.0991 0.7675 0.101 Uiso 1 1 calc R U . . .
C5 C 0.2015(6) 0.1526(4) 0.6804(3) 0.0576(16) Uani 1 1 d . . . . .
H5A H 0.2684 0.1221 0.6785 0.069 Uiso 1 1 calc R U . . .
C6 C 0.1856(5) 0.2116(3) 0.6301(3) 0.0404(13) Uani 1 1 d . . . . .
C7 C 0.3192(4) 0.3290(3) 0.5517(3) 0.0425(14) Uani 1 1 d . . . . .
C8 C 0.3190(6) 0.3764(4) 0.6126(4) 0.0638(18) Uani 1 1 d . . . . .
H8A H 0.3049 0.3556 0.6589 0.077 Uiso 1 1 calc R U . . .
C9 C 0.3398(7) 0.4550(4) 0.6042(6) 0.088(3) Uani 1 1 d . . . . .
H9A H 0.3388 0.4875 0.6450 0.106 Uiso 1 1 calc R U . . .
C10 C 0.3618(6) 0.4859(5) 0.5366(7) 0.091(3) Uani 1 1 d . . . . .
H10A H 0.3755 0.5392 0.5313 0.109 Uiso 1 1 calc R U . . .
C11 C 0.3638(6) 0.4382(4) 0.4771(5) 0.082(3) Uani 1 1 d . . . . .
H11A H 0.3798 0.4591 0.4311 0.099 Uiso 1 1 calc R U . . .
C12 C 0.3423(5) 0.3593(4) 0.4839(4) 0.0573(17) Uani 1 1 d . . . . .
H12A H 0.3434 0.3271 0.4429 0.069 Uiso 1 1 calc R U . . .
C13 C 0.2592(4) 0.1837(3) 0.4793(3) 0.0361(12) Uani 1 1 d . . . . .
C14 C 0.3236(5) 0.1212(3) 0.4525(3) 0.0433(14) Uani 1 1 d . . . . .
H14A H 0.3893 0.1051 0.4783 0.052 Uiso 1 1 calc R U . . .
C15 C 0.2941(5) 0.0825(3) 0.3900(3) 0.0461(14) Uani 1 1 d . . . . .
C16 C 0.1929(6) 0.1065(3) 0.3531(3) 0.0469(15) Uani 1 1 d . . . . .
C17 C 0.1303(5) 0.1696(3) 0.3768(3) 0.0497(15) Uani 1 1 d . . . . .
H17A H 0.0659 0.1863 0.3500 0.060 Uiso 1 1 calc R U . . .
C18 C 0.1614(5) 0.2088(3) 0.4398(3) 0.0400(13) Uani 1 1 d . . . . .
C19 C 0.4455(7) -0.0096(4) 0.4017(4) 0.093(3) Uani 1 1 d . . . . .
H19A H 0.4794 -0.0529 0.3758 0.140 Uiso 1 1 calc R U . . .
H19B H 0.5032 0.0303 0.4085 0.140 Uiso 1 1 calc R U . . .
H19C H 0.4178 -0.0270 0.4486 0.140 Uiso 1 1 calc R U . . .
O1 O 0.4096(3) 0.18821(19) 0.59201(18) 0.0389(9) Uani 1 1 d . . . . .
O2 O 0.1040(3) 0.2716(2) 0.4660(2) 0.0543(11) Uani 1 1 d . . . . .
H2B H 0.0484 0.2815 0.4393 0.081 Uiso 1 1 calc R U . . .
O3 O 0.3517(4) 0.0207(3) 0.3608(2) 0.0729(14) Uani 1 1 d . . . . .
P1 P 0.30020(12) 0.22613(8) 0.56447(7) 0.0355(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
Br1 C16 1.867(5) . ?
C1 C2 1.372(9) . ?
C1 C6 1.387(8) . ?
C2 C3 1.355(10) . ?
C3 C4 1.361(11) . ?
C4 C5 1.368(9) . ?
C5 C6 1.376(8) . ?
C6 P1 1.795(5) . ?
C7 C12 1.366(8) . ?
C7 C8 1.376(8) . ?
C7 P1 1.790(6) . ?
C8 C9 1.374(9) . ?
C9 C10 1.366(13) . ?
C10 C11 1.358(13) . ?
C11 C12 1.379(9) . ?
C13 C14 1.389(7) . ?
C13 C18 1.401(7) . ?
C13 P1 1.779(5) . ?
C14 C15 1.361(8) . ?
C15 O3 1.357(7) . ?
C15 C16 1.403(8) . ?
C16 C17 1.368(8) . ?
C17 C18 1.377(8) . ?
C18 O2 1.349(6) . ?
C19 O3 1.409(8) . ?
O1 P1 1.499(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.0(6) . . ?
C3 C2 C1 120.5(7) . . ?
C2 C3 C4 121.1(7) . . ?
C3 C4 C5 119.3(7) . . ?
C4 C5 C6 120.5(7) . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 P1 116.7(4) . . ?
C1 C6 P1 123.8(4) . . ?
C12 C7 C8 120.5(6) . . ?
C12 C7 P1 121.0(5) . . ?
C8 C7 P1 118.3(5) . . ?
C9 C8 C7 119.1(8) . . ?
C10 C9 C8 120.8(8) . . ?
C11 C10 C9 119.5(7) . . ?
C10 C11 C12 120.9(8) . . ?
C7 C12 C11 119.2(7) . . ?
C14 C13 C18 118.8(5) . . ?
C14 C13 P1 118.7(4) . . ?
C18 C13 P1 122.4(4) . . ?
C15 C14 C13 122.4(5) . . ?
O3 C15 C14 126.0(5) . . ?
O3 C15 C16 116.2(5) . . ?
C14 C15 C16 117.8(5) . . ?
C17 C16 C15 120.9(5) . . ?
C17 C16 Br1 118.9(5) . . ?
C15 C16 Br1 120.2(4) . . ?
C16 C17 C18 120.8(5) . . ?
O2 C18 C17 123.8(5) . . ?
O2 C18 C13 117.0(5) . . ?
C17 C18 C13 119.2(5) . . ?
C15 O3 C19 116.8(5) . . ?
O1 P1 C13 109.7(2) . . ?
O1 P1 C7 111.6(2) . . ?
C13 P1 C7 108.7(3) . . ?
O1 P1 C6 109.3(2) . . ?
C13 P1 C6 109.4(2) . . ?
C7 P1 C6 108.2(2) . . ?

_refine_diff_density_max         0.850
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1840621'
_audit_update_record             
;
2018-04-28 deposited with the CCDC.
2018-10-16 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         'C20 H19 O3 P'
_chemical_formula_sum            'C20 H19 O3 P'
_chemical_formula_weight         338.32

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'
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                   18.086(10)
_cell_length_b                   11.245(6)
_cell_length_c                   17.491(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.109(7)
_cell_angle_gamma                90
_cell_volume                     3522(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2625
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      25.004

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   'multi-scan '
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12250
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_full        25.004
_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             3108
_reflns_number_gt                2121
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²+0.5568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3108
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25152(16) 0.5937(2) 0.35863(15) 0.0554(7) Uani 1 1 d . . . . .
H1A H 0.2949 0.6012 0.3360 0.066 Uiso 1 1 calc R U . . .
C2 C 0.25305(19) 0.6183(3) 0.43695(16) 0.0668(9) Uani 1 1 d . . . . .
H2A H 0.2975 0.6416 0.4666 0.080 Uiso 1 1 calc R U . . .
C3 C 0.1897(2) 0.6081(3) 0.47012(17) 0.0734(9) Uani 1 1 d . . . . .
H3A H 0.1910 0.6239 0.5225 0.088 Uiso 1 1 calc R U . . .
C4 C 0.1242(2) 0.5748(3) 0.42680(17) 0.0779(10) Uani 1 1 d . . . . .
H4A H 0.0808 0.5691 0.4495 0.093 Uiso 1 1 calc R U . . .
C5 C 0.12221(17) 0.5495(3) 0.34949(16) 0.0644(8) Uani 1 1 d . . . . .
H5A H 0.0775 0.5263 0.3205 0.077 Uiso 1 1 calc R U . . .
C6 C 0.18586(15) 0.5584(2) 0.31453(13) 0.0435(6) Uani 1 1 d . . . . .
C7 C 0.11846(13) 0.4143(2) 0.18619(14) 0.0431(6) Uani 1 1 d . . . . .
C8 C 0.12168(16) 0.3085(2) 0.22761(18) 0.0629(8) Uani 1 1 d . . . . .
H8A H 0.1547 0.3009 0.2732 0.075 Uiso 1 1 calc R U . . .
C9 C 0.07594(18) 0.2147(3) 0.2012(2) 0.0775(10) Uani 1 1 d . . . . .
H9A H 0.0787 0.1435 0.2285 0.093 Uiso 1 1 calc R U . . .
C10 C 0.02612(18) 0.2266(3) 0.1345(2) 0.0771(10) Uani 1 1 d . . . . .
H10A H -0.0047 0.1632 0.1167 0.093 Uiso 1 1 calc R U . . .
C11 C 0.02177(18) 0.3303(3) 0.09439(19) 0.0750(9) Uani 1 1 d . . . . .
H11A H -0.0122 0.3376 0.0495 0.090 Uiso 1 1 calc R U . . .
C12 C 0.06732(15) 0.4251(3) 0.11975(15) 0.0566(7) Uani 1 1 d . . . . .
H12A H 0.0636 0.4961 0.0922 0.068 Uiso 1 1 calc R U . . .
C13 C 0.26997(13) 0.4988(2) 0.18784(13) 0.0394(6) Uani 1 1 d . . . . .
C14 C 0.29434(14) 0.5561(2) 0.12470(13) 0.0429(6) Uani 1 1 d . . . . .
H14A H 0.2666 0.6190 0.1010 0.051 Uiso 1 1 calc R U . . .
C15 C 0.35858(14) 0.5210(2) 0.09732(14) 0.0447(6) Uani 1 1 d . . . . .
C16 C 0.40188(14) 0.4287(2) 0.13239(15) 0.0476(6) Uani 1 1 d . . . . .
C17 C 0.37899(14) 0.3738(2) 0.19618(14) 0.0478(7) Uani 1 1 d . . . . .
H17A H 0.4082 0.3134 0.2210 0.057 Uiso 1 1 calc R U . . .
C18 C 0.31370(14) 0.4067(2) 0.22392(13) 0.0426(6) Uani 1 1 d . . . . .
C19 C 0.34353(18) 0.6671(3) -0.00408(17) 0.0732(9) Uani 1 1 d . . . . .
H19A H 0.3676 0.6938 -0.0465 0.110 Uiso 1 1 calc R U . . .
H19B H 0.2939 0.6406 -0.0231 0.110 Uiso 1 1 calc R U . . .
H19C H 0.3411 0.7314 0.0316 0.110 Uiso 1 1 calc R U . . .
C20 C 0.47168(17) 0.3871(3) 0.10161(18) 0.0712(9) Uani 1 1 d . . . . .
H20A H 0.4793 0.4344 0.0577 0.107 Uiso 1 1 calc R U . . .
H20B H 0.5140 0.3953 0.1411 0.107 Uiso 1 1 calc R U . . .
H20C H 0.4661 0.3051 0.0865 0.107 Uiso 1 1 calc R U . . .
O1 O 0.15028(9) 0.64735(14) 0.16846(9) 0.0465(4) Uani 1 1 d . . . . .
O2 O 0.38498(10) 0.57150(18) 0.03415(10) 0.0596(5) Uani 1 1 d . . . . .
O3 O 0.28992(10) 0.35240(15) 0.28583(9) 0.0547(5) Uani 1 1 d . . . . .
H3B H 0.3123 0.2894 0.2947 0.082 Uiso 1 1 calc R U . . .
P1 P 0.17996(4) 0.53838(6) 0.21210(3) 0.0403(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
C1 C6 1.380(4) . ?
C1 C2 1.394(4) . ?
C2 C3 1.360(4) . ?
C3 C4 1.366(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.381(4) . ?
C6 P1 1.794(3) . ?
C7 C12 1.385(3) . ?
C7 C8 1.390(4) . ?
C7 P1 1.802(3) . ?
C8 C9 1.379(4) . ?
C9 C10 1.377(4) . ?
C10 C11 1.358(4) . ?
C11 C12 1.382(4) . ?
C13 C18 1.399(3) . ?
C13 C14 1.402(3) . ?
C13 P1 1.795(3) . ?
C14 C15 1.376(3) . ?
C15 O2 1.386(3) . ?
C15 C16 1.389(4) . ?
C16 C17 1.389(3) . ?
C16 C20 1.515(4) . ?
C17 C18 1.388(3) . ?
C18 O3 1.364(3) . ?
C19 O2 1.422(3) . ?
O1 P1 1.5023(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
C6 C1 C2 120.2(3) . . ?
C3 C2 C1 120.1(3) . . ?
C2 C3 C4 120.2(3) . . ?
C3 C4 C5 120.1(3) . . ?
C4 C5 C6 120.8(3) . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 P1 121.3(2) . . ?
C5 C6 P1 119.8(2) . . ?
C12 C7 C8 119.1(2) . . ?
C12 C7 P1 117.3(2) . . ?
C8 C7 P1 123.6(2) . . ?
C9 C8 C7 120.1(3) . . ?
C10 C9 C8 120.0(3) . . ?
C11 C10 C9 120.3(3) . . ?
C10 C11 C12 120.6(3) . . ?
C11 C12 C7 119.9(3) . . ?
C18 C13 C14 118.4(2) . . ?
C18 C13 P1 123.42(18) . . ?
C14 C13 P1 117.92(19) . . ?
C15 C14 C13 121.1(2) . . ?
C14 C15 O2 124.2(2) . . ?
C14 C15 C16 120.8(2) . . ?
O2 C15 C16 115.0(2) . . ?
C17 C16 C15 118.2(2) . . ?
C17 C16 C20 120.4(2) . . ?
C15 C16 C20 121.3(2) . . ?
C18 C17 C16 121.8(2) . . ?
O3 C18 C17 122.5(2) . . ?
O3 C18 C13 117.9(2) . . ?
C17 C18 C13 119.6(2) . . ?
C15 O2 C19 117.8(2) . . ?
O1 P1 C6 111.83(11) . . ?
O1 P1 C13 110.67(11) . . ?
C6 P1 C13 109.82(11) . . ?
O1 P1 C7 109.90(11) . . ?
C6 P1 C7 107.21(12) . . ?
C13 P1 C7 107.25(11) . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.044

