# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1511454'
_audit_update_record             
;
2016-10-23 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Br N0 O3 P'
_chemical_formula_weight         431.25

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'
Br Br -0.6763 1.2805 '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                   5.4900(2)
_cell_length_b                   19.9165(6)
_cell_length_c                   18.1684(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.993(4)
_cell_angle_gamma                90
_cell_volume                     1979.02(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.738
_shelx_estimated_absorpt_T_min   0.257
_shelx_estimated_absorpt_T_max   0.522
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10571
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.299
_diffrn_reflns_theta_max         59.995
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.817
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.817
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.817
_reflns_number_total             2938
_reflns_number_gt                2417
_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-2013 (Sheldrick, 2013)'
_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)+(0.0794P)²+2.9374P]
 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         2938
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.55072(19) 0.45649(4) 0.63258(4) 0.1197(4) Uani 1 1 d . . . . .
P1 P 0.1691(2) 0.67622(7) 0.65857(8) 0.0651(4) Uani 1 1 d . . . . .
O1 O 0.2284(7) 0.74898(18) 0.6863(2) 0.0813(11) Uani 1 1 d . . . . .
O2 O -0.0935(7) 0.6650(2) 0.6465(3) 0.0914(12) Uani 1 1 d . . . . .
O3 O 0.3055(7) 0.63294(17) 0.72274(19) 0.0712(9) Uani 1 1 d . . . . .
C1 C 0.4674(13) 0.7693(4) 0.7180(4) 0.106(2) Uani 1 1 d . . . . .
H1A H 0.5878 0.7576 0.6850 0.158 Uiso 1 1 calc R U . . .
H1B H 0.5040 0.7469 0.7644 0.158 Uiso 1 1 calc R U . . .
H1C H 0.4692 0.8170 0.7258 0.158 Uiso 1 1 calc R U . . .
C2 C 0.3385(9) 0.6575(3) 0.5803(3) 0.0648(12) Uani 1 1 d . . . . .
H2 H 0.5037 0.6755 0.5915 0.078 Uiso 1 1 calc R U . . .
C3 C 0.3630(12) 0.5807(3) 0.5749(3) 0.0795(15) Uani 1 1 d . . . . .
H3A H 0.2023 0.5608 0.5649 0.095 Uiso 1 1 calc R U . . .
H3B H 0.4594 0.5694 0.5344 0.095 Uiso 1 1 calc R U . . .
C4 C 0.4848(11) 0.5522(3) 0.6464(3) 0.0736(14) Uani 1 1 d . . . . .
H4 H 0.6418 0.5752 0.6571 0.088 Uiso 1 1 calc R U . . .
C5 C 0.3365(10) 0.5612(3) 0.7123(3) 0.0695(13) Uani 1 1 d . . . . .
H5 H 0.1762 0.5398 0.7023 0.083 Uiso 1 1 calc R U . . .
C6 C 0.4615(10) 0.5348(3) 0.7855(3) 0.0714(14) Uani 1 1 d . . . . .
C7 C 0.6639(11) 0.5683(3) 0.8155(3) 0.0794(15) Uani 1 1 d . . . . .
H7 H 0.7254 0.6044 0.7904 0.095 Uiso 1 1 calc R U . . .
C8 C 0.7797(15) 0.5483(4) 0.8842(4) 0.108(2) Uani 1 1 d . . . . .
H8 H 0.9152 0.5718 0.9047 0.130 Uiso 1 1 calc R U . . .
C9 C 0.6954(17) 0.4954(4) 0.9202(4) 0.108(2) Uani 1 1 d . . . . .
H9 H 0.7741 0.4823 0.9654 0.130 Uiso 1 1 calc R U . . .
C10 C 0.4874(14) 0.4593(3) 0.8900(4) 0.0889(19) Uani 1 1 d . . . . .
C11 C 0.3694(11) 0.4795(3) 0.8211(3) 0.0797(16) Uani 1 1 d . . . . .
C12 C 0.1604(12) 0.4422(3) 0.7913(5) 0.0944(19) Uani 1 1 d . . . . .
H12 H 0.0791 0.4535 0.7459 0.113 Uiso 1 1 calc R U . . .
C13 C 0.0842(18) 0.3893(4) 0.8317(7) 0.128(3) Uani 1 1 d . . . . .
H13 H -0.0494 0.3644 0.8120 0.154 Uiso 1 1 calc R U . . .
C14 C 0.192(2) 0.3709(4) 0.8989(7) 0.140(4) Uani 1 1 d . . . . .
H14 H 0.1295 0.3354 0.9247 0.168 Uiso 1 1 calc R U . . .
C15 C 0.392(2) 0.4051(4) 0.9279(5) 0.125(3) Uani 1 1 d . . . . .
H15 H 0.4679 0.3924 0.9736 0.150 Uiso 1 1 calc R U . . .
C16 C 0.2346(10) 0.6906(3) 0.5096(3) 0.0715(14) Uani 1 1 d . . . . .
C17 C 0.3512(14) 0.7441(4) 0.4819(4) 0.104(2) Uani 1 1 d . . . . .
H17 H 0.4941 0.7600 0.5072 0.125 Uiso 1 1 calc R U . . .
C18 C 0.2616(19) 0.7757(5) 0.4165(5) 0.132(3) Uani 1 1 d . . . . .
H18 H 0.3438 0.8125 0.3991 0.159 Uiso 1 1 calc R U . . .
C19 C 0.0563(18) 0.7530(5) 0.3785(4) 0.119(3) Uani 1 1 d . . . . .
H19 H -0.0062 0.7747 0.3356 0.143 Uiso 1 1 calc R U . . .
C20 C -0.0592(16) 0.6980(5) 0.4035(5) 0.128(3) Uani 1 1 d . . . . .
H20 H -0.1970 0.6810 0.3764 0.154 Uiso 1 1 calc R U . . .
C21 C 0.0275(13) 0.6672(4) 0.4691(4) 0.109(2) Uani 1 1 d . . . . .
H21 H -0.0551 0.6302 0.4860 0.131 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
Br1 C4 1.960(5) . ?
P1 O2 1.456(4) . ?
P1 O1 1.559(4) . ?
P1 O3 1.584(4) . ?
P1 C2 1.805(5) . ?
O1 C1 1.445(8) . ?
O3 C5 1.454(6) . ?
C2 C16 1.509(7) . ?
C2 C3 1.540(8) . ?
C3 C4 1.518(8) . ?
C4 C5 1.516(8) . ?
C5 C6 1.536(8) . ?
C6 C7 1.367(8) . ?
C6 C11 1.394(8) . ?
C7 C8 1.407(9) . ?
C8 C9 1.344(11) . ?
C9 C10 1.419(11) . ?
C10 C15 1.406(11) . ?
C10 C11 1.417(9) . ?
C11 C12 1.434(9) . ?
C12 C13 1.370(10) . ?
C13 C14 1.360(14) . ?
C14 C15 1.361(14) . ?
C16 C17 1.363(9) . ?
C16 C21 1.381(9) . ?
C17 C18 1.397(11) . ?
C18 C19 1.348(12) . ?
C19 C20 1.364(12) . ?
C20 C21 1.387(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O1 111.5(2) . . ?
O2 P1 O3 115.2(2) . . ?
O1 P1 O3 101.3(2) . . ?
O2 P1 C2 114.9(3) . . ?
O1 P1 C2 109.8(2) . . ?
O3 P1 C2 103.0(2) . . ?
C1 O1 P1 123.1(4) . . ?
C5 O3 P1 119.5(3) . . ?
C16 C2 C3 114.1(5) . . ?
C16 C2 P1 113.4(4) . . ?
C3 C2 P1 108.0(4) . . ?
C4 C3 C2 110.6(5) . . ?
C5 C4 C3 113.9(5) . . ?
C5 C4 Br1 109.5(4) . . ?
C3 C4 Br1 109.1(4) . . ?
O3 C5 C4 107.2(4) . . ?
O3 C5 C6 105.7(4) . . ?
C4 C5 C6 114.4(4) . . ?
C7 C6 C11 121.0(6) . . ?
C7 C6 C5 117.7(5) . . ?
C11 C6 C5 121.2(5) . . ?
C6 C7 C8 120.3(7) . . ?
C9 C8 C7 120.4(7) . . ?
C8 C9 C10 120.5(7) . . ?
C15 C10 C11 119.4(8) . . ?
C15 C10 C9 121.3(8) . . ?
C11 C10 C9 119.3(6) . . ?
C6 C11 C10 118.5(6) . . ?
C6 C11 C12 123.1(6) . . ?
C10 C11 C12 118.4(6) . . ?
C13 C12 C11 117.9(8) . . ?
C14 C13 C12 124.0(10) . . ?
C13 C14 C15 119.2(8) . . ?
C14 C15 C10 121.1(9) . . ?
C17 C16 C21 117.2(6) . . ?
C17 C16 C2 120.1(5) . . ?
C21 C16 C2 122.6(5) . . ?
C16 C17 C18 121.8(7) . . ?
C19 C18 C17 120.1(8) . . ?
C18 C19 C20 119.4(7) . . ?
C19 C20 C21 120.5(8) . . ?
C16 C21 C20 120.9(7) . . ?

_refine_diff_density_max         0.964
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-2

