# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_m22_05_beucher_23-1_a1
_database_code_depnum_ccdc_archive 'CCDC 2177765'
loop_
_audit_author_name
_audit_author_address
'Emmanuel Wenger'
;University of Lorraine, Faculty of Sciences et Technologies
France
;
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2022-06-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H32 N2 O8'
_chemical_formula_sum            'C21 H32 N2 O8'
_chemical_formula_weight         440.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H32N2O8
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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   8.9833(2)
_cell_length_b                   13.0769(2)
_cell_length_c                   20.1678(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2369.19(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16339
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.4680
_cell_measurement_theta_min      3.9690
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0533
0 1 0 0.0533
1 0 0 0.1971
-1 0 0 0.1971
0 0 1 0.0494
0 0 -1 0.0314
0 -5 11 0.0457
0 5 -11 0.0457

_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.081
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0005 -1.0016 -0.0109 -0.0423 0.0703 0.0848
-0.0005 1.0016 0.0109 0.0423 -0.0703 -0.0848
0.9998 0.0010 -0.0080 0.0832 -0.0924 0.1180
-0.9998 -0.0010 0.0080 -0.0832 0.0924 -0.1180
0.0018 -0.0047 0.9990 0.0609 0.0454 -0.0073
-0.0018 0.0047 -0.9990 -0.0609 -0.0454 0.0073
0.0221 -5.0592 10.9347 0.4587 0.8513 0.3439
-0.0221 5.0592 -10.9347 -0.4587 -0.8513 -0.3439

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22611
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.509
_diffrn_reflns_theta_min         4.029
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4508
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -11.00   1.00   10.00    --  -40.72 -57.00 120.00  104
  2  ω    -33.00  70.00   1.00   10.00    --   40.72 -58.00-129.00  103
  3  ω    -33.00  70.00   1.00   10.00    --   40.72 -57.00   0.00  103
  4  ω     38.00 141.00   1.00   20.00    --  113.00 -47.00 -13.87  103
  5  ω     85.00 178.00   1.00   20.00    --  113.00  45.00-150.00   93
  6  ω     85.00 178.00   1.00   20.00    --  113.00  45.00 -90.00   93
  7  ω     37.00 145.00   1.00   20.00    --  113.00 -70.00 -54.32  108
  8  ω     83.00 178.00   1.00   20.00    --  113.00  61.00-150.00   95
  9  ω     85.00 178.00   1.00   20.00    --  113.00  45.00 -60.00   93
 10  ω     85.00 178.00   1.00   20.00    --  113.00  45.00 120.00   93
 11  ω     85.00 178.00   1.00   20.00    --  113.00  45.00 -30.00   93
 12  ω     37.00 145.00   1.00   20.00    --  113.00 -70.00 108.93  108
 13  ω     38.00 141.00   1.00   20.00    --  113.00 -45.00-180.00  103
 14  ω   -115.00 -11.00   1.00   10.00    --  -40.72 -57.00 -30.00  104
 15  ω   -115.00 -11.00   1.00   10.00    --  -40.72 -58.00-129.00  104
 16  ω    -33.00  70.00   1.00   10.00    --   40.72 -57.00 120.00  103
 17  ω     85.00 150.00   1.00   20.00    --  113.00  45.00  60.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0836543000
_diffrn_orient_matrix_UB_12      0.0415888000
_diffrn_orient_matrix_UB_13      0.0610218000
_diffrn_orient_matrix_UB_21      -0.0919564000
_diffrn_orient_matrix_UB_22      -0.0707575000
_diffrn_orient_matrix_UB_23      0.0453014000
_diffrn_orient_matrix_UB_31      0.1180837000
_diffrn_orient_matrix_UB_32      -0.0845042000
_diffrn_orient_matrix_UB_33      -0.0078822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                4848
_reflns_number_total             4942
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.00112(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         4942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.023
_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)+(0.0406P)²+0.3233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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
O1 O 0.15582(12) 0.53932(8) 0.48651(5) 0.0225(2) Uani 1 1 d . . . . .
O5 O 0.45829(11) 0.47507(7) 0.38233(5) 0.0194(2) Uani 1 1 d . . . . .
O3 O 0.67852(11) 0.63630(8) 0.39983(5) 0.0226(2) Uani 1 1 d . . . . .
O8 O 0.54850(12) 0.64984(8) 0.56790(5) 0.0223(2) Uani 1 1 d . . . . .
O7 O 0.48627(12) 0.48322(8) 0.58154(5) 0.0220(2) Uani 1 1 d . . . . .
O2 O 0.10882(13) 0.52080(9) 0.37694(5) 0.0282(2) Uani 1 1 d . . . . .
O6 O 0.55322(13) 0.38647(8) 0.46944(5) 0.0269(2) Uani 1 1 d . . . . .
O4 O 0.54312(14) 0.77623(9) 0.37686(6) 0.0322(3) Uani 1 1 d . . . . .
N2 N 0.47269(13) 0.55353(8) 0.47962(5) 0.0160(2) Uani 1 1 d . . . . .
C10 C 0.55681(17) 0.69404(10) 0.40296(7) 0.0198(3) Uani 1 1 d . . . . .
C17 C 0.50900(14) 0.56758(10) 0.54757(7) 0.0171(3) Uani 1 1 d . . . . .
C12 C 0.50011(15) 0.46169(10) 0.44504(7) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.16999(15) 0.56130(11) 0.42288(7) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.43560(15) 0.64471(10) 0.44360(6) 0.0166(3) Uani 1 1 d . . . . .
C4 C 0.32103(16) 0.71616(10) 0.47088(7) 0.0197(3) Uani 1 1 d . . . . .
H4A H 0.276(2) 0.6963(15) 0.5137(9) 0.024 Uiso 1 1 d . U . . .
H4B H 0.338(2) 0.7874(15) 0.4613(9) 0.024 Uiso 1 1 d . U . . .
N1 N 0.2422(2) 0.72635(13) 0.29566(8) 0.0412(4) Uani 1 1 d . . . . .
C2 C 0.27550(15) 0.65077(11) 0.41301(7) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.25993(18) 0.69448(12) 0.34762(8) 0.0250(3) Uani 1 1 d . . . . .
C18 C 0.53189(17) 0.47505(13) 0.65245(7) 0.0249(3) Uani 1 1 d . . . . .
C6 C 0.06840(17) 0.44880(12) 0.50957(8) 0.0261(3) Uani 1 1 d . . . . .
C13 C 0.50220(18) 0.40039(12) 0.33010(7) 0.0256(3) Uani 1 1 d . . . . .
C20 C 0.69965(19) 0.48683(16) 0.65715(8) 0.0323(4) Uani 1 1 d . . . . .
H20A H 0.746(3) 0.436(2) 0.6292(12) 0.048 Uiso 1 1 d . U . . .
H20B H 0.731(3) 0.555(2) 0.6419(12) 0.048 Uiso 1 1 d . U . . .
H20C H 0.731(3) 0.478(2) 0.7033(13) 0.048 Uiso 1 1 d . U . . .
C11 C 0.79650(19) 0.67599(14) 0.35773(8) 0.0291(3) Uani 1 1 d . . . . .
H11A H 0.753(3) 0.6947(19) 0.3134(12) 0.044 Uiso 1 1 d . U . . .
H11B H 0.840(3) 0.7369(18) 0.3776(11) 0.044 Uiso 1 1 d . U . . .
H11C H 0.869(3) 0.6180(19) 0.3545(12) 0.044 Uiso 1 1 d . U . . .
C21 C 0.4501(2) 0.55387(16) 0.69426(8) 0.0339(4) Uani 1 1 d . . . . .
H21A H 0.493(3) 0.624(2) 0.6873(12) 0.051 Uiso 1 1 d . U . . .
H21B H 0.342(3) 0.554(2) 0.6837(13) 0.051 Uiso 1 1 d . U . . .
H21C H 0.460(3) 0.535(2) 0.7387(13) 0.051 Uiso 1 1 d . U . . .
C14 C 0.4594(2) 0.45724(14) 0.26746(8) 0.0314(4) Uani 1 1 d . . . . .
H14A H 0.353(3) 0.477(2) 0.2684(12) 0.047 Uiso 1 1 d . U . . .
H14B H 0.516(3) 0.521(2) 0.2608(12) 0.047 Uiso 1 1 d . U . . .
H14C H 0.479(3) 0.4144(19) 0.2274(12) 0.047 Uiso 1 1 d . U . . .
C7 C -0.09276(19) 0.46093(18) 0.48911(9) 0.0369(4) Uani 1 1 d . . . . .
H7A H -0.138(3) 0.530(2) 0.5065(13) 0.055 Uiso 1 1 d . U . . .
H7B H -0.104(3) 0.457(2) 0.4414(14) 0.055 Uiso 1 1 d . U . . .
H7C H -0.149(3) 0.406(2) 0.5100(13) 0.055 Uiso 1 1 d . U . . .
C9 C 0.0852(2) 0.45755(16) 0.58425(9) 0.0362(4) Uani 1 1 d . . . . .
H9A H 0.189(3) 0.454(2) 0.5967(13) 0.054 Uiso 1 1 d . U . . .
H9B H 0.037(3) 0.526(2) 0.6023(13) 0.054 Uiso 1 1 d . U . . .
H9C H 0.036(3) 0.401(2) 0.6068(13) 0.054 Uiso 1 1 d . U . . .
C16 C 0.6687(2) 0.38131(16) 0.33321(9) 0.0367(4) Uani 1 1 d . . . . .
H16A H 0.725(3) 0.446(2) 0.3336(12) 0.055 Uiso 1 1 d . U . . .
H16B H 0.693(3) 0.340(2) 0.3725(14) 0.055 Uiso 1 1 d . U . . .
H16C H 0.700(3) 0.341(2) 0.2924(13) 0.055 Uiso 1 1 d . U . . .
C19 C 0.4840(2) 0.36669(16) 0.66916(9) 0.0395(4) Uani 1 1 d . . . . .
H19A H 0.372(3) 0.363(2) 0.6682(14) 0.059 Uiso 1 1 d . U . . .
H19B H 0.535(3) 0.316(2) 0.6376(14) 0.059 Uiso 1 1 d . U . . .
H19C H 0.514(3) 0.351(2) 0.7166(14) 0.059 Uiso 1 1 d . U . . .
C15 C 0.4100(3) 0.30389(14) 0.33826(10) 0.0404(4) Uani 1 1 d . . . . .
H15A H 0.428(3) 0.271(2) 0.3822(14) 0.061 Uiso 1 1 d . U . . .
H15B H 0.294(4) 0.322(2) 0.3329(13) 0.061 Uiso 1 1 d . U . . .
H15C H 0.437(3) 0.257(2) 0.3019(14) 0.061 Uiso 1 1 d . U . . .
C8 C 0.1412(3) 0.35338(16) 0.48324(13) 0.0494(6) Uani 1 1 d . . . . .
H8A H 0.130(4) 0.351(2) 0.4361(17) 0.074 Uiso 1 1 d . U . . .
H8B H 0.249(4) 0.352(2) 0.4949(15) 0.074 Uiso 1 1 d . U . . .
H8C H 0.087(4) 0.296(2) 0.4996(15) 0.074 Uiso 1 1 d . 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
O1 C5 1.3211(17) . ?
O1 C6 1.4947(17) . ?
O5 C12 1.3310(17) . ?
O5 C13 1.4895(16) . ?
O3 C10 1.3303(18) . ?
O3 C11 1.4538(18) . ?
O8 C17 1.2046(17) . ?
O7 C17 1.3146(17) . ?
O7 C18 1.4915(16) . ?
O2 C5 1.2003(18) . ?
O6 C12 1.1989(18) . ?
O4 C10 1.2030(18) . ?
N2 C17 1.4205(17) . ?
N2 C12 1.4105(17) . ?
N2 C3 1.4355(17) . ?
C10 C3 1.5078(19) . ?
C5 C2 1.5189(19) . ?
C3 C4 1.4950(19) . ?
C3 C2 1.5669(18) . ?
C4 H4A 0.990(19) . ?
C4 H4B 0.96(2) . ?
C4 C2 1.5035(19) . ?
N1 C1 1.139(2) . ?
C2 C1 1.444(2) . ?
C18 C20 1.518(2) . ?
C18 C21 1.521(2) . ?
C18 C19 1.519(2) . ?
C6 C7 1.514(2) . ?
C6 C9 1.518(2) . ?
C6 C8 1.506(3) . ?
C13 C14 1.515(2) . ?
C13 C16 1.518(2) . ?
C13 C15 1.518(2) . ?
C20 H20A 0.97(3) . ?
C20 H20B 0.98(3) . ?
C20 H20C 0.98(3) . ?
C11 H11A 1.00(2) . ?
C11 H11B 0.97(2) . ?
C11 H11C 1.00(3) . ?
C21 H21A 1.00(3) . ?
C21 H21B 1.00(3) . ?
C21 H21C 0.93(3) . ?
C14 H14A 0.99(3) . ?
C14 H14B 0.98(3) . ?
C14 H14C 1.00(3) . ?
C7 H7A 1.05(3) . ?
C7 H7B 0.97(3) . ?
C7 H7C 0.97(3) . ?
C9 H9A 0.97(3) . ?
C9 H9B 1.06(3) . ?
C9 H9C 0.97(3) . ?
C16 H16A 0.98(3) . ?
C16 H16B 0.98(3) . ?
C16 H16C 1.01(3) . ?
C19 H19A 1.01(3) . ?
C19 H19B 1.03(3) . ?
C19 H19C 1.02(3) . ?
C15 H15A 1.00(3) . ?
C15 H15B 1.07(3) . ?
C15 H15C 0.98(3) . ?
C8 H8A 0.96(3) . ?
C8 H8B 1.00(3) . ?
C8 H8C 0.96(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
C5 O1 C6 121.68(12) . . ?
C12 O5 C13 120.74(11) . . ?
C10 O3 C11 115.10(12) . . ?
C17 O7 C18 121.15(11) . . ?
C17 N2 C3 115.73(11) . . ?
C12 N2 C17 123.16(11) . . ?
C12 N2 C3 119.84(10) . . ?
O3 C10 C3 112.12(12) . . ?
O4 C10 O3 124.77(14) . . ?
O4 C10 C3 123.11(14) . . ?
O8 C17 O7 128.15(13) . . ?
O8 C17 N2 120.76(12) . . ?
O7 C17 N2 111.01(11) . . ?
O5 C12 N2 107.98(11) . . ?
O6 C12 O5 127.60(13) . . ?
O6 C12 N2 124.42(12) . . ?
O1 C5 C2 110.80(12) . . ?
O2 C5 O1 127.56(14) . . ?
O2 C5 C2 121.63(13) . . ?
N2 C3 C10 117.57(12) . . ?
N2 C3 C4 119.52(11) . . ?
N2 C3 C2 117.02(11) . . ?
C10 C3 C2 115.29(11) . . ?
C4 C3 C10 115.45(12) . . ?
C4 C3 C2 58.76(9) . . ?
C3 C4 H4A 116.2(11) . . ?
C3 C4 H4B 114.8(12) . . ?
C3 C4 C2 63.01(9) . . ?
H4A C4 H4B 119.7(16) . . ?
C2 C4 H4A 114.6(11) . . ?
C2 C4 H4B 115.9(11) . . ?
C5 C2 C3 118.83(11) . . ?
C4 C2 C5 120.40(12) . . ?
C4 C2 C3 58.23(9) . . ?
C1 C2 C5 111.35(12) . . ?
C1 C2 C3 117.94(12) . . ?
C1 C2 C4 120.67(13) . . ?
N1 C1 C2 176.96(18) . . ?
O7 C18 C20 108.99(12) . . ?
O7 C18 C21 110.50(12) . . ?
O7 C18 C19 101.64(12) . . ?
C20 C18 C21 112.11(15) . . ?
C20 C18 C19 111.23(15) . . ?
C19 C18 C21 111.87(15) . . ?
O1 C6 C7 109.55(13) . . ?
O1 C6 C9 101.34(12) . . ?
O1 C6 C8 108.56(13) . . ?
C7 C6 C9 110.97(14) . . ?
C8 C6 C7 113.97(18) . . ?
C8 C6 C9 111.66(17) . . ?
O5 C13 C14 101.59(12) . . ?
O5 C13 C16 109.85(13) . . ?
O5 C13 C15 108.90(13) . . ?
C14 C13 C16 111.40(15) . . ?
C14 C13 C15 111.10(15) . . ?
C16 C13 C15 113.34(16) . . ?
C18 C20 H20A 108.9(15) . . ?
C18 C20 H20B 111.1(15) . . ?
C18 C20 H20C 109.5(15) . . ?
H20A C20 H20B 108(2) . . ?
H20A C20 H20C 110(2) . . ?
H20B C20 H20C 109(2) . . ?
O3 C11 H11A 109.0(14) . . ?
O3 C11 H11B 110.0(14) . . ?
O3 C11 H11C 104.0(14) . . ?
H11A C11 H11B 109(2) . . ?
H11A C11 H11C 112.2(19) . . ?
H11B C11 H11C 112.8(19) . . ?
C18 C21 H21A 110.9(15) . . ?
C18 C21 H21B 111.0(15) . . ?
C18 C21 H21C 108.3(16) . . ?
H21A C21 H21B 110(2) . . ?
H21A C21 H21C 109(2) . . ?
H21B C21 H21C 107(2) . . ?
C13 C14 H14A 110.8(14) . . ?
C13 C14 H14B 113.3(14) . . ?
C13 C14 H14C 110.8(14) . . ?
H14A C14 H14B 107(2) . . ?
H14A C14 H14C 109(2) . . ?
H14B C14 H14C 106(2) . . ?
C6 C7 H7A 111.6(15) . . ?
C6 C7 H7B 111.4(16) . . ?
C6 C7 H7C 107.4(15) . . ?
H7A C7 H7B 110(2) . . ?
H7A C7 H7C 107(2) . . ?
H7B C7 H7C 109(2) . . ?
C6 C9 H9A 110.5(15) . . ?
C6 C9 H9B 111.4(15) . . ?
C6 C9 H9C 111.2(16) . . ?
H9A C9 H9B 110(2) . . ?
H9A C9 H9C 106(2) . . ?
H9B C9 H9C 107(2) . . ?
C13 C16 H16A 111.5(16) . . ?
C13 C16 H16B 109.9(17) . . ?
C13 C16 H16C 108.7(16) . . ?
H16A C16 H16B 111(2) . . ?
H16A C16 H16C 108(2) . . ?
H16B C16 H16C 108(2) . . ?
C18 C19 H19A 109.1(17) . . ?
C18 C19 H19B 109.9(16) . . ?
C18 C19 H19C 109.0(16) . . ?
H19A C19 H19B 114(2) . . ?
H19A C19 H19C 106(2) . . ?
H19B C19 H19C 109(2) . . ?
C13 C15 H15A 111.3(17) . . ?
C13 C15 H15B 109.8(16) . . ?
C13 C15 H15C 107.6(16) . . ?
H15A C15 H15B 110(2) . . ?
H15A C15 H15C 111(2) . . ?
H15B C15 H15C 107(2) . . ?
C6 C8 H8A 109.3(19) . . ?
C6 C8 H8B 110.5(19) . . ?
C6 C8 H8C 108.0(19) . . ?
H8A C8 H8B 110(3) . . ?
H8A C8 H8C 105(3) . . ?
H8B C8 H8C 114(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C2 C3 54.45(16) . . . . ?
O1 C5 C2 C4 -13.60(18) . . . . ?
O1 C5 C2 C1 -163.42(12) . . . . ?
O3 C10 C3 N2 8.35(16) . . . . ?
O3 C10 C3 C4 158.13(12) . . . . ?
O3 C10 C3 C2 -136.10(12) . . . . ?
O2 C5 C2 C3 -127.00(15) . . . . ?
O2 C5 C2 C4 164.95(13) . . . . ?
O2 C5 C2 C1 15.13(19) . . . . ?
O4 C10 C3 N2 -171.53(13) . . . . ?
O4 C10 C3 C4 -21.8(2) . . . . ?
O4 C10 C3 C2 44.02(19) . . . . ?
N2 C3 C4 C2 -105.50(13) . . . . ?
N2 C3 C2 C5 -0.07(18) . . . . ?
N2 C3 C2 C4 109.72(13) . . . . ?
N2 C3 C2 C1 -139.74(13) . . . . ?
C10 C3 C4 C2 105.34(13) . . . . ?
C10 C3 C2 C5 144.58(13) . . . . ?
C10 C3 C2 C4 -105.63(13) . . . . ?
C10 C3 C2 C1 4.91(18) . . . . ?
C17 O7 C18 C20 -62.38(18) . . . . ?
C17 O7 C18 C21 61.23(17) . . . . ?
C17 O7 C18 C19 -179.89(14) . . . . ?
C17 N2 C12 O5 -177.80(11) . . . . ?
C17 N2 C12 O6 1.6(2) . . . . ?
C17 N2 C3 C10 97.36(14) . . . . ?
C17 N2 C3 C4 -51.16(17) . . . . ?
C17 N2 C3 C2 -118.81(13) . . . . ?
C12 O5 C13 C14 -168.69(13) . . . . ?
C12 O5 C13 C16 -50.65(19) . . . . ?
C12 O5 C13 C15 74.02(17) . . . . ?
C12 N2 C17 O8 146.15(13) . . . . ?
C12 N2 C17 O7 -36.79(17) . . . . ?
C12 N2 C3 C10 -70.17(16) . . . . ?
C12 N2 C3 C4 141.31(13) . . . . ?
C12 N2 C3 C2 73.66(16) . . . . ?
C5 O1 C6 C7 -62.43(18) . . . . ?
C5 O1 C6 C9 -179.73(14) . . . . ?
C5 O1 C6 C8 62.6(2) . . . . ?
C3 N2 C17 O8 -20.91(19) . . . . ?
C3 N2 C17 O7 156.15(11) . . . . ?
C3 N2 C12 O5 -11.24(17) . . . . ?
C3 N2 C12 O6 168.17(14) . . . . ?
C3 C4 C2 C5 107.11(14) . . . . ?
C3 C4 C2 C1 -105.87(15) . . . . ?
C4 C3 C2 C5 -109.79(14) . . . . ?
C4 C3 C2 C1 110.54(15) . . . . ?
C18 O7 C17 O8 -10.0(2) . . . . ?
C18 O7 C17 N2 173.19(11) . . . . ?
C6 O1 C5 O2 6.8(2) . . . . ?
C6 O1 C5 C2 -174.75(12) . . . . ?
C13 O5 C12 O6 -12.5(2) . . . . ?
C13 O5 C12 N2 166.93(11) . . . . ?
C11 O3 C10 O4 -4.1(2) . . . . ?
C11 O3 C10 C3 176.06(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2350766'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_date             2024-01-19T11:28:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         C24H29BrNO7P
_chemical_formula_sum            'C24 H29 Br N O7 P'
_chemical_formula_weight         554.36
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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                   8.6898(2)
_cell_length_b                   14.0318(4)
_cell_length_c                   22.1254(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2697.83(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9838
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      77.3
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.989
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.010796
_diffrn_orient_matrix_ub_12      -0.070838
_diffrn_orient_matrix_ub_13      -0.002555
_diffrn_orient_matrix_ub_21      0.006782
_diffrn_orient_matrix_ub_22      -0.003644
_diffrn_orient_matrix_ub_23      0.045059
_diffrn_orient_matrix_ub_31      -0.114369
_diffrn_orient_matrix_ub_32      -0.006903
_diffrn_orient_matrix_ub_33      0.002431
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_number            5848
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         81.236
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_coverage         0.759
_reflns_number_total             5848
_reflns_number_gt                5023
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1215P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5848
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1953 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.044(9)
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0311 0.018 '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'

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 0.7559(4) 0.0866(3) 0.57489(19) 0.0592(8) Uani 1 1 d . . . . .
C2 C 0.7772(4) 0.1164(3) 0.5106(2) 0.0620(8) Uani 1 1 d . . . . .
H2A H 0.77802 0.066619 0.480153 0.074 Uiso 1 1 calc R U . . .
H2B H 0.847265 0.168702 0.502703 0.074 Uiso 1 1 calc R U . . .
C3 C 0.6254(4) 0.1400(3) 0.53953(16) 0.0548(7) Uani 1 1 d . . . . .
C4 C 0.8359(4) 0.1419(3) 0.62407(19) 0.0625(8) Uani 1 1 d . . . . .
C5 C 0.7691(5) 0.1534(5) 0.6806(2) 0.0780(12) Uani 1 1 d . . . . .
H5 H 0.674781 0.124976 0.688991 0.094 Uiso 1 1 calc R U . . .
C6 C 0.8428(6) 0.2071(5) 0.7246(2) 0.0887(15) Uani 1 1 d . . . . .
H6 H 0.797779 0.215297 0.762355 0.106 Uiso 1 1 calc R U . . .
C7 C 0.9819(6) 0.2480(5) 0.7120(3) 0.0857(14) Uani 1 1 d . . . . .
C8 C 1.0521(5) 0.2339(5) 0.6575(3) 0.0873(14) Uani 1 1 d . . . . .
H8 H 1.149007 0.259504 0.650084 0.105 Uiso 1 1 calc R U . . .
C9 C 0.9784(5) 0.1814(4) 0.6136(2) 0.0743(11) Uani 1 1 d . . . . .
H9 H 1.025621 0.172449 0.576281 0.089 Uiso 1 1 calc R U . . .
C10 C 0.5196(4) 0.2639(3) 0.60187(17) 0.0556(7) Uani 1 1 d . . . . .
C11 C 0.4392(9) 0.3962(4) 0.6597(3) 0.102(2) Uani 1 1 d . . . . .
H11A H 0.456923 0.359563 0.696211 0.123 Uiso 1 1 calc R U . . .
H11B H 0.330979 0.391523 0.649325 0.123 Uiso 1 1 calc R U . . .
C12 C 0.4819(8) 0.4978(4) 0.6698(3) 0.0896(16) Uani 1 1 d . . . . .
C13 C 0.4286(12) 0.5662(6) 0.6292(5) 0.126(3) Uani 1 1 d . . . . .
H13 H 0.370347 0.548114 0.595845 0.151 Uiso 1 1 calc R U . . .
C14 C 0.4629(15) 0.6608(7) 0.6389(6) 0.152(4) Uani 1 1 d . . . . .
H14 H 0.426827 0.706749 0.612154 0.182 Uiso 1 1 calc R U . . .
C15 C 0.5478(12) 0.6870(7) 0.6865(5) 0.131(3) Uani 1 1 d . . . . .
H15 H 0.569692 0.751247 0.69211 0.158 Uiso 1 1 calc R U . . .
C16 C 0.6021(13) 0.6236(8) 0.7264(5) 0.140(4) Uani 1 1 d . . . . .
H16 H 0.661017 0.643617 0.759083 0.168 Uiso 1 1 calc R U . . .
C17 C 0.5694(13) 0.5268(6) 0.7183(4) 0.123(3) Uani 1 1 d . . . . .
H17 H 0.606837 0.482127 0.745609 0.147 Uiso 1 1 calc R U . . .
C18 C 0.7315(6) -0.0169(3) 0.5898(3) 0.0757(12) Uani 1 1 d . . . . .
C19A C 0.716(3) -0.1719(14) 0.5559(13) 0.120(7) Uani 0.63(4) 1 d . . P A 1
H19A H 0.786565 -0.19262 0.587133 0.143 Uiso 0.63(4) 1 calc R U P A 1
H19B H 0.611267 -0.180963 0.570152 0.143 Uiso 0.63(4) 1 calc R U P A 1
C20A C 0.740(5) -0.2223(11) 0.5027(15) 0.200(18) Uani 0.63(4) 1 d . . P A 1
H20A H 0.842905 -0.210381 0.488424 0.299 Uiso 0.63(4) 1 calc R U P A 1
H20B H 0.667458 -0.202211 0.472763 0.299 Uiso 0.63(4) 1 calc R U P A 1
H20C H 0.727919 -0.289258 0.510298 0.299 Uiso 0.63(4) 1 calc R U P A 1
C19B C 0.691(4) -0.166(3) 0.5320(18) 0.102(9) Uani 0.37(4) 1 d . . P A 2
H19C H 0.658605 -0.176245 0.490593 0.123 Uiso 0.37(4) 1 calc R U P A 2
H19D H 0.604526 -0.178948 0.558632 0.123 Uiso 0.37(4) 1 calc R U P A 2
C20B C 0.825(4) -0.2272(16) 0.5475(15) 0.124(11) Uani 0.37(4) 1 d . . P A 2
H20D H 0.905144 -0.217975 0.518223 0.186 Uiso 0.37(4) 1 calc R U P A 2
H20E H 0.793879 -0.292867 0.54746 0.186 Uiso 0.37(4) 1 calc R U P A 2
H20F H 0.862756 -0.210469 0.586929 0.186 Uiso 0.37(4) 1 calc R U P A 2
C22 C 0.183(2) -0.0587(10) 0.5970(12) 0.270(14) Uani 1 1 d . . . . .
H22A H 0.12616 -0.036961 0.562545 0.405 Uiso 1 1 calc R U . . .
H22B H 0.11958 -0.055222 0.632399 0.405 Uiso 1 1 calc R U . . .
H22C H 0.215043 -0.123476 0.590675 0.405 Uiso 1 1 calc R U . . .
C21 C 0.3133(10) -0.0011(5) 0.6050(4) 0.110(2) Uani 1 1 d . . . . .
H21A H 0.368624 -0.021644 0.640739 0.132 Uiso 1 1 calc R U . . .
H21B H 0.280895 0.064334 0.611262 0.132 Uiso 1 1 calc R U . . .
C23 C 0.3961(10) 0.0027(7) 0.4088(4) 0.125(3) Uani 1 1 d . . . . .
H23A H 0.333898 0.055352 0.394334 0.15 Uiso 1 1 calc R U . . .
H23B H 0.328368 -0.04364 0.427569 0.15 Uiso 1 1 calc R U . . .
C24 C 0.4781(17) -0.0413(11) 0.3582(5) 0.177(6) Uani 1 1 d . . . . .
H24A H 0.57225 -0.069043 0.372567 0.265 Uiso 1 1 calc R U . . .
H24B H 0.500918 0.006298 0.328381 0.265 Uiso 1 1 calc R U . . .
H24C H 0.414911 -0.090016 0.340556 0.265 Uiso 1 1 calc R U . . .
Br1 Br 1.08192(9) 0.32625(7) 0.77057(4) 0.1182(4) Uani 1 1 d . . . . .
N1 N 0.6054(4) 0.2383(2) 0.55446(14) 0.0561(6) Uani 1 1 d . . . . .
H1 H 0.649006 0.281397 0.532744 0.067 Uiso 1 1 calc R U . . .
O1 O 0.4389(4) 0.2119(2) 0.63183(14) 0.0681(7) Uani 1 1 d . . . . .
O2 O 0.5322(4) 0.3593(2) 0.61103(15) 0.0693(7) Uani 1 1 d . . . . .
O3 O 0.7053(7) -0.0471(3) 0.6390(2) 0.1052(14) Uani 1 1 d . . . . .
O4 O 0.7433(5) -0.0709(3) 0.5400(2) 0.0959(12) Uani 1 1 d . . . . .
O5 O 0.3209(4) 0.1494(2) 0.50737(18) 0.0757(8) Uani 1 1 d . . . . .
O6 O 0.5058(5) 0.0364(3) 0.45203(18) 0.0875(10) Uani 1 1 d . . . . .
O7 O 0.4149(4) -0.0055(2) 0.55317(19) 0.0767(8) Uani 1 1 d . . . . .
P1 P 0.45029(11) 0.08312(7) 0.51266(5) 0.0624(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.494(6) . ?
C1 C18 1.504(6) . ?
C1 C4 1.507(6) . ?
C1 C3 1.568(5) . ?
C2 C3 1.503(5) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 N1 1.430(5) . ?
C3 P1 1.818(4) . ?
C4 C9 1.376(6) . ?
C4 C5 1.388(6) . ?
C5 C6 1.388(8) . ?
C5 H5 0.93 . ?
C6 C7 1.366(9) . ?
C6 H6 0.93 . ?
C7 C8 1.367(8) . ?
C7 Br1 1.908(5) . ?
C8 C9 1.377(7) . ?
C8 H8 0.93 . ?
C9 H9 0.93 . ?
C10 O1 1.210(5) . ?
C10 N1 1.336(5) . ?
C10 O2 1.359(5) . ?
C11 O2 1.443(6) . ?
C11 C12 1.491(7) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C17 1.376(11) . ?
C12 C13 1.394(12) . ?
C13 C14 1.377(12) . ?
C13 H13 0.93 . ?
C14 C15 1.337(16) . ?
C14 H14 0.93 . ?
C15 C16 1.339(16) . ?
C15 H15 0.93 . ?
C16 C17 1.398(13) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
C18 O3 1.190(8) . ?
C18 O4 1.341(8) . ?
C19A C20A 1.39(4) . ?
C19A O4 1.48(2) . ?
C19A H19A 0.97 . ?
C19A H19B 0.97 . ?
C20A H20A 0.9893 . ?
C20A H20B 0.9905 . ?
C20A H20C 0.9905 . ?
C19B O4 1.42(4) . ?
C19B C20B 1.49(5) . ?
C19B H19C 0.97 . ?
C19B H19D 0.97 . ?
C20B H20D 0.96 . ?
C20B H20E 0.96 . ?
C20B H20F 0.96 . ?
C22 C21 1.400(17) . ?
C22 H22A 0.9601 . ?
C22 H22B 0.9601 . ?
C22 H22C 0.9601 . ?
C21 O7 1.448(9) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C23 O6 1.431(8) . ?
C23 C24 1.463(15) . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?
N1 H1 0.86 . ?
O5 P1 1.463(3) . ?
O6 P1 1.569(4) . ?
O7 P1 1.563(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
C2 C1 C18 119.7(4) . . ?
C2 C1 C4 119.1(3) . . ?
C18 C1 C4 113.8(4) . . ?
C2 C1 C3 58.7(3) . . ?
C18 C1 C3 117.9(3) . . ?
C4 C1 C3 116.6(3) . . ?
C1 C2 C3 63.1(3) . . ?
C1 C2 H2A 117.4 . . ?
C3 C2 H2A 117.4 . . ?
C1 C2 H2B 117.4 . . ?
C3 C2 H2B 117.4 . . ?
H2A C2 H2B 114.5 . . ?
N1 C3 C2 114.7(3) . . ?
N1 C3 C1 115.7(3) . . ?
C2 C3 C1 58.2(3) . . ?
N1 C3 P1 113.4(3) . . ?
C2 C3 P1 119.9(3) . . ?
C1 C3 P1 124.0(3) . . ?
C9 C4 C5 118.8(4) . . ?
C9 C4 C1 120.0(4) . . ?
C5 C4 C1 121.1(4) . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 119.6(5) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.9(5) . . ?
C6 C7 Br1 120.5(4) . . ?
C8 C7 Br1 118.6(4) . . ?
C7 C8 C9 119.5(5) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.2 . . ?
C4 C9 C8 121.0(5) . . ?
C4 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
O1 C10 N1 126.3(4) . . ?
O1 C10 O2 124.0(4) . . ?
N1 C10 O2 109.7(3) . . ?
O2 C11 C12 108.4(4) . . ?
O2 C11 H11A 110 . . ?
C12 C11 H11A 110 . . ?
O2 C11 H11B 110 . . ?
C12 C11 H11B 110 . . ?
H11A C11 H11B 108.4 . . ?
C17 C12 C13 118.9(7) . . ?
C17 C12 C11 122.5(8) . . ?
C13 C12 C11 118.6(7) . . ?
C14 C13 C12 119.4(9) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 120.5(11) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 122.0(8) . . ?
C14 C15 H15 119 . . ?
C16 C15 H15 119 . . ?
C15 C16 C17 119.3(9) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.3 . . ?
C12 C17 C16 120.0(10) . . ?
C12 C17 H17 120 . . ?
C16 C17 H17 120 . . ?
O3 C18 O4 124.4(5) . . ?
O3 C18 C1 124.8(5) . . ?
O4 C18 C1 110.8(4) . . ?
C20A C19A O4 105(2) . . ?
C20A C19A H19A 110.9 . . ?
O4 C19A H19A 110.7 . . ?
C20A C19A H19B 110.5 . . ?
O4 C19A H19B 110.7 . . ?
H19A C19A H19B 108.8 . . ?
C19A C20A H20A 112.5 . . ?
C19A C20A H20B 112.9 . . ?
H20A C20A H20B 106.1 . . ?
C19A C20A H20C 112.9 . . ?
H20A C20A H20C 105.9 . . ?
H20B C20A H20C 105.9 . . ?
O4 C19B C20B 105(2) . . ?
O4 C19B H19C 110.8 . . ?
C20B C19B H19C 110.8 . . ?
O4 C19B H19D 110.7 . . ?
C20B C19B H19D 110.6 . . ?
H19C C19B H19D 108.8 . . ?
C19B C20B H20D 109.4 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.6 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C22 C21 O7 111.6(10) . . ?
C22 C21 H21A 109.3 . . ?
O7 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
O7 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
O6 C23 C24 109.0(8) . . ?
O6 C23 H23A 109.8 . . ?
C24 C23 H23A 109.9 . . ?
O6 C23 H23B 109.9 . . ?
C24 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 N1 C3 120.6(3) . . ?
C10 N1 H1 119.7 . . ?
C3 N1 H1 119.7 . . ?
C10 O2 C11 114.8(3) . . ?
C18 O4 C19B 127.4(18) . . ?
C18 O4 C19A 109.5(12) . . ?
C23 O6 P1 120.3(5) . . ?
C21 O7 P1 122.7(4) . . ?
O5 P1 O7 113.6(2) . . ?
O5 P1 O6 115.7(2) . . ?
O7 P1 O6 102.6(2) . . ?
O5 P1 C3 112.98(19) . . ?
O7 P1 C3 109.02(18) . . ?
O6 P1 C3 101.87(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 C1 C2 C3 106.5(4) . . . . ?
C4 C1 C2 C3 -105.2(4) . . . . ?
C1 C2 C3 N1 106.0(4) . . . . ?
C1 C2 C3 P1 -113.7(3) . . . . ?
C2 C1 C3 N1 -104.3(4) . . . . ?
C18 C1 C3 N1 146.1(4) . . . . ?
C4 C1 C3 N1 5.1(5) . . . . ?
C18 C1 C3 C2 -109.6(5) . . . . ?
C4 C1 C3 C2 109.4(4) . . . . ?
C2 C1 C3 P1 106.8(3) . . . . ?
C18 C1 C3 P1 -2.8(5) . . . . ?
C4 C1 C3 P1 -143.8(3) . . . . ?
C2 C1 C4 C9 -33.8(6) . . . . ?
C18 C1 C4 C9 116.2(5) . . . . ?
C3 C1 C4 C9 -101.2(5) . . . . ?
C2 C1 C4 C5 146.8(4) . . . . ?
C18 C1 C4 C5 -63.2(5) . . . . ?
C3 C1 C4 C5 79.4(5) . . . . ?
C9 C4 C5 C6 2.6(8) . . . . ?
C1 C4 C5 C6 -178.0(5) . . . . ?
C4 C5 C6 C7 -0.5(9) . . . . ?
C5 C6 C7 C8 -2.4(10) . . . . ?
C5 C6 C7 Br1 177.6(5) . . . . ?
C6 C7 C8 C9 3.0(10) . . . . ?
Br1 C7 C8 C9 -176.9(5) . . . . ?
C5 C4 C9 C8 -2.0(8) . . . . ?
C1 C4 C9 C8 178.6(5) . . . . ?
C7 C8 C9 C4 -0.8(9) . . . . ?
O2 C11 C12 C17 -105.1(8) . . . . ?
O2 C11 C12 C13 76.2(9) . . . . ?
C17 C12 C13 C14 -0.8(14) . . . . ?
C11 C12 C13 C14 178.0(9) . . . . ?
C12 C13 C14 C15 0.6(19) . . . . ?
C13 C14 C15 C16 -0.1(19) . . . . ?
C14 C15 C16 C17 -0.1(17) . . . . ?
C13 C12 C17 C16 0.6(13) . . . . ?
C11 C12 C17 C16 -178.1(7) . . . . ?
C15 C16 C17 C12 -0.2(15) . . . . ?
C2 C1 C18 O3 -175.7(5) . . . . ?
C4 C1 C18 O3 34.4(7) . . . . ?
C3 C1 C18 O3 -107.7(6) . . . . ?
C2 C1 C18 O4 4.2(5) . . . . ?
C4 C1 C18 O4 -145.6(4) . . . . ?
C3 C1 C18 O4 72.3(5) . . . . ?
O1 C10 N1 C3 -8.7(6) . . . . ?
O2 C10 N1 C3 173.0(3) . . . . ?
C2 C3 N1 C10 -149.1(3) . . . . ?
C1 C3 N1 C10 -84.1(4) . . . . ?
P1 C3 N1 C10 68.1(4) . . . . ?
O1 C10 O2 C11 -0.8(7) . . . . ?
N1 C10 O2 C11 177.5(5) . . . . ?
C12 C11 O2 C10 172.0(5) . . . . ?
O3 C18 O4 C19B 17(2) . . . . ?
C1 C18 O4 C19B -163(2) . . . . ?
O3 C18 O4 C19A 1.1(14) . . . . ?
C1 C18 O4 C19A -178.9(12) . . . . ?
C20B C19B O4 C18 -93(3) . . . . ?
C20A C19A O4 C18 -176(2) . . . . ?
C24 C23 O6 P1 -177.3(9) . . . . ?
C22 C21 O7 P1 116.3(12) . . . . ?
C21 O7 P1 O5 -32.8(6) . . . . ?
C21 O7 P1 O6 -158.4(5) . . . . ?
C21 O7 P1 C3 94.1(5) . . . . ?
C23 O6 P1 O5 -42.5(7) . . . . ?
C23 O6 P1 O7 81.7(7) . . . . ?
C23 O6 P1 C3 -165.4(6) . . . . ?
N1 C3 P1 O5 3.5(3) . . . . ?
C2 C3 P1 O5 -137.2(3) . . . . ?
C1 C3 P1 O5 153.1(3) . . . . ?
N1 C3 P1 O7 -123.7(3) . . . . ?
C2 C3 P1 O7 95.5(3) . . . . ?
C1 C3 P1 O7 25.8(4) . . . . ?
N1 C3 P1 O6 128.3(3) . . . . ?
C2 C3 P1 O6 -12.4(4) . . . . ?
C1 C3 P1 O6 -82.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O5 0.86 1.99 2.804(4) 157.3 4_556 yes

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2350765'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_date             2024-01-18T16:42:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C23 H27 Br N O7 P'
_chemical_formula_sum            'C23 H27 Br N O7 P'
_chemical_formula_weight         540.33
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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                   8.6222(2)
_cell_length_b                   13.3983(3)
_cell_length_c                   22.3429(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2581.12(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9792
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      80.17
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.39
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.11
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.001346
_diffrn_orient_matrix_ub_12      0.074336
_diffrn_orient_matrix_ub_13      0.003976
_diffrn_orient_matrix_ub_21      0.00163
_diffrn_orient_matrix_ub_22      0.006618
_diffrn_orient_matrix_ub_23      -0.044576
_diffrn_orient_matrix_ub_31      -0.11596
_diffrn_orient_matrix_ub_32      0.000956
_diffrn_orient_matrix_ub_33      -0.00058
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.035
_diffrn_reflns_number            5510
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.847
_diffrn_reflns_theta_max         80.173
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.979
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.97
_reflns_Friedel_coverage         0.754
_reflns_number_total             5510
_reflns_number_gt                5249
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0989P)²+0.5040P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5510
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(5)
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0311 0.018 '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'

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 0.2421(3) 0.9219(2) 0.57069(14) 0.0450(6) Uani 1 1 d . . . . .
C2 C 0.3753(4) 0.8657(2) 0.53684(13) 0.0420(6) Uani 1 1 d . . . . .
C3 C 0.2207(4) 0.8867(3) 0.50776(16) 0.0486(7) Uani 1 1 d . . . . .
H3A H 0.217894 0.936851 0.476496 0.058 Uiso 1 1 calc R U . . .
H3B H 0.151716 0.830491 0.501296 0.058 Uiso 1 1 calc R U . . .
C4 C 0.1651(4) 0.8667(3) 0.62093(15) 0.0486(7) Uani 1 1 d . . . . .
C5 C 0.0234(4) 0.8209(3) 0.61180(19) 0.0603(9) Uani 1 1 d . . . . .
H5 H -0.025746 0.827202 0.574945 0.072 Uiso 1 1 calc R U . . .
C6 C -0.0461(5) 0.7659(4) 0.6567(2) 0.0734(12) Uani 1 1 d . . . . .
H6 H -0.142476 0.736557 0.650557 0.088 Uiso 1 1 calc R U . . .
C7 C 0.0281(5) 0.7552(4) 0.7102(2) 0.0700(11) Uani 1 1 d . . . . .
C8 C 0.1674(5) 0.8018(5) 0.72137(19) 0.0732(12) Uani 1 1 d . . . . .
H8 H 0.215295 0.79526 0.758453 0.088 Uiso 1 1 calc R U . . .
C9 C 0.2352(4) 0.8585(4) 0.67672(17) 0.0635(10) Uani 1 1 d . . . . .
H9 H 0.328294 0.891239 0.684085 0.076 Uiso 1 1 calc R U . . .
C10 C 0.4852(4) 0.7388(2) 0.60067(14) 0.0449(6) Uani 1 1 d . . . . .
C11 C 0.5656(8) 0.6029(4) 0.6599(3) 0.0908(18) Uani 1 1 d . . . . .
H11A H 0.546068 0.641351 0.695935 0.109 Uiso 1 1 calc R U . . .
H11B H 0.67476 0.60855 0.649971 0.109 Uiso 1 1 calc R U . . .
C12 C 0.5229(6) 0.4950(4) 0.6698(2) 0.0777(15) Uani 1 1 d . . . . .
C13 C 0.5737(9) 0.4235(5) 0.6298(3) 0.0972(17) Uani 1 1 d . . . . .
H13 H 0.634372 0.442411 0.597267 0.117 Uiso 1 1 calc R U . . .
C14 C 0.5355(11) 0.3249(6) 0.6376(4) 0.115(2) Uani 1 1 d . . . . .
H14 H 0.567759 0.278023 0.60952 0.138 Uiso 1 1 calc R U . . .
C15 C 0.4534(9) 0.2955(5) 0.6846(3) 0.0967(19) Uani 1 1 d . . . . .
H15 H 0.431012 0.228062 0.6894 0.116 Uiso 1 1 calc R U . . .
C16 C 0.4021(10) 0.3613(6) 0.7252(3) 0.108(2) Uani 1 1 d . . . . .
H16 H 0.34351 0.339693 0.757714 0.129 Uiso 1 1 calc R U . . .
C17 C 0.4378(9) 0.4646(5) 0.7184(3) 0.0953(18) Uani 1 1 d . . . . .
H17 H 0.403864 0.510847 0.746551 0.114 Uiso 1 1 calc R U . . .
C18 C 0.2610(4) 1.0324(3) 0.5823(2) 0.0571(8) Uani 1 1 d . . . . .
C19 C 0.2678(13) 1.1906(4) 0.5383(4) 0.128(3) Uani 1 1 d . . . . .
H19A H 0.180293 1.220133 0.558129 0.192 Uiso 1 1 calc R U . . .
H19B H 0.280239 1.220525 0.499517 0.192 Uiso 1 1 calc R U . . .
H19C H 0.359616 1.201715 0.561626 0.192 Uiso 1 1 calc R U . . .
C20 C 0.6881(7) 1.0198(4) 0.5988(3) 0.0839(14) Uani 1 1 d . . . . .
H20A H 0.710832 0.951356 0.60984 0.101 Uiso 1 1 calc R U . . .
H20B H 0.641539 1.05286 0.632965 0.101 Uiso 1 1 calc R U . . .
C21 C 0.8353(9) 1.0726(6) 0.5811(6) 0.136(4) Uani 1 1 d . . . . .
H21A H 0.889724 1.033428 0.551928 0.205 Uiso 1 1 calc R U . . .
H21B H 0.899592 1.081404 0.615809 0.205 Uiso 1 1 calc R U . . .
H21C H 0.810396 1.13663 0.564414 0.205 Uiso 1 1 calc R U . . .
C22 C 0.6018(8) 1.0171(7) 0.4073(4) 0.114(3) Uani 1 1 d . . . . .
H22A H 0.660573 1.068688 0.427632 0.137 Uiso 1 1 calc R U . . .
H22B H 0.67412 0.966524 0.393609 0.137 Uiso 1 1 calc R U . . .
C23 C 0.5252(14) 1.0583(12) 0.3583(5) 0.187(6) Uani 1 1 d . . . . .
H23A H 0.457947 1.009102 0.340886 0.28 Uiso 1 1 calc R U . . .
H23B H 0.599945 1.07948 0.329092 0.28 Uiso 1 1 calc R U . . .
H23C H 0.464969 1.114587 0.371124 0.28 Uiso 1 1 calc R U . . .
Br1 Br -0.06521(9) 0.67357(6) 0.76998(3) 0.1034(3) Uani 1 1 d . . . . .
N1 N 0.3970(3) 0.7638(2) 0.55315(12) 0.0444(5) Uani 1 1 d . . . . .
H1 H 0.353148 0.717705 0.532412 0.053 Uiso 1 1 calc R U . . .
O1 O 0.5661(3) 0.79464(19) 0.62926(12) 0.0564(6) Uani 1 1 d . . . . .
O2 O 0.4716(3) 0.63961(19) 0.61132(12) 0.0568(6) Uani 1 1 d . . . . .
O3 O 0.2872(5) 1.0683(3) 0.62984(17) 0.0849(10) Uani 1 1 d . . . . .
O4 O 0.2424(5) 1.0848(2) 0.53158(18) 0.0785(9) Uani 1 1 d . . . . .
O5 O 0.6826(3) 0.8586(2) 0.50530(14) 0.0616(7) Uani 1 1 d . . . . .
O6 O 0.4922(4) 0.9727(3) 0.44874(14) 0.0702(8) Uani 1 1 d . . . . .
O7 O 0.5818(3) 1.02162(19) 0.54848(15) 0.0622(7) Uani 1 1 d . . . . .
P002 P 0.54976(10) 0.92661(6) 0.50935(4) 0.0476(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C3 1.495(5) . ?
C1 C4 1.499(5) . ?
C1 C18 1.512(5) . ?
C1 C2 1.568(4) . ?
C2 N1 1.425(4) . ?
C2 C3 1.509(4) . ?
C2 P002 1.818(3) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 C5 1.382(5) . ?
C4 C9 1.390(5) . ?
C5 C6 1.382(6) . ?
C5 H5 0.93 . ?
C6 C7 1.364(7) . ?
C6 H6 0.93 . ?
C7 C8 1.376(7) . ?
C7 Br1 1.904(4) . ?
C8 C9 1.383(7) . ?
C8 H8 0.93 . ?
C9 H9 0.93 . ?
C10 O1 1.206(4) . ?
C10 N1 1.349(4) . ?
C10 O2 1.355(4) . ?
C11 O2 1.442(5) . ?
C11 C12 1.508(6) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C17 1.372(9) . ?
C12 C13 1.381(10) . ?
C13 C14 1.373(10) . ?
C13 H13 0.93 . ?
C14 C15 1.326(12) . ?
C14 H14 0.93 . ?
C15 C16 1.341(12) . ?
C15 H15 0.93 . ?
C16 C17 1.426(9) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
C18 O3 1.188(6) . ?
C18 O4 1.342(6) . ?
C19 O4 1.442(7) . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 O7 1.450(7) . ?
C20 C21 1.505(10) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C22 C23 1.393(13) . ?
C22 O6 1.450(6) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
N1 H1 0.86 . ?
O5 P002 1.467(3) . ?
O6 P002 1.569(3) . ?
O7 P002 1.569(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
C3 C1 C4 119.6(3) . . ?
C3 C1 C18 119.0(3) . . ?
C4 C1 C18 113.7(3) . . ?
C3 C1 C2 59.0(2) . . ?
C4 C1 C2 116.6(3) . . ?
C18 C1 C2 118.3(3) . . ?
N1 C2 C3 113.9(3) . . ?
N1 C2 C1 115.7(3) . . ?
C3 C2 C1 58.1(2) . . ?
N1 C2 P002 114.1(2) . . ?
C3 C2 P002 120.1(2) . . ?
C1 C2 P002 123.6(2) . . ?
C1 C3 C2 62.9(2) . . ?
C1 C3 H3A 117.5 . . ?
C2 C3 H3A 117.5 . . ?
C1 C3 H3B 117.5 . . ?
C2 C3 H3B 117.5 . . ?
H3A C3 H3B 114.5 . . ?
C5 C4 C9 118.8(3) . . ?
C5 C4 C1 120.0(3) . . ?
C9 C4 C1 121.2(3) . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.3(4) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.3(4) . . ?
C6 C7 Br1 118.5(4) . . ?
C8 C7 Br1 120.2(4) . . ?
C7 C8 C9 119.2(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C4 120.5(4) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
O1 C10 N1 126.1(3) . . ?
O1 C10 O2 124.5(3) . . ?
N1 C10 O2 109.5(3) . . ?
O2 C11 C12 107.5(4) . . ?
O2 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O2 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C17 C12 C13 118.4(5) . . ?
C17 C12 C11 122.1(6) . . ?
C13 C12 C11 119.5(6) . . ?
C14 C13 C12 120.6(7) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 121.0(8) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.1(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 119.6(7) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 119.2(7) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
O3 C18 O4 124.5(4) . . ?
O3 C18 C1 124.7(4) . . ?
O4 C18 C1 110.8(3) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O7 C20 C21 108.8(6) . . ?
O7 C20 H20A 109.9 . . ?
C21 C20 H20A 109.9 . . ?
O7 C20 H20B 109.9 . . ?
C21 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 O6 110.8(7) . . ?
C23 C22 H22A 109.5 . . ?
O6 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 N1 C2 120.9(3) . . ?
C10 N1 H1 119.5 . . ?
C2 N1 H1 119.5 . . ?
C10 O2 C11 114.7(3) . . ?
C18 O4 C19 114.1(5) . . ?
C22 O6 P002 120.4(4) . . ?
C20 O7 P002 122.0(3) . . ?
O5 P002 O6 115.99(18) . . ?
O5 P002 O7 113.65(17) . . ?
O6 P002 O7 102.55(18) . . ?
O5 P002 C2 112.83(16) . . ?
O6 P002 C2 101.93(16) . . ?
O7 P002 C2 108.77(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 N1 -103.2(3) . . . . ?
C4 C1 C2 N1 6.8(4) . . . . ?
C18 C1 C2 N1 148.2(3) . . . . ?
C4 C1 C2 C3 110.0(3) . . . . ?
C18 C1 C2 C3 -108.5(4) . . . . ?
C3 C1 C2 P002 107.2(3) . . . . ?
C4 C1 C2 P002 -142.7(3) . . . . ?
C18 C1 C2 P002 -1.3(4) . . . . ?
C4 C1 C3 C2 -105.1(3) . . . . ?
C18 C1 C3 C2 107.5(3) . . . . ?
N1 C2 C3 C1 106.4(3) . . . . ?
P002 C2 C3 C1 -113.1(3) . . . . ?
C3 C1 C4 C5 -32.5(5) . . . . ?
C18 C1 C4 C5 116.5(4) . . . . ?
C2 C1 C4 C5 -100.3(4) . . . . ?
C3 C1 C4 C9 145.9(4) . . . . ?
C18 C1 C4 C9 -65.0(5) . . . . ?
C2 C1 C4 C9 78.2(4) . . . . ?
C9 C4 C5 C6 -1.4(6) . . . . ?
C1 C4 C5 C6 177.1(4) . . . . ?
C4 C5 C6 C7 -1.4(8) . . . . ?
C5 C6 C7 C8 3.1(8) . . . . ?
C5 C6 C7 Br1 -176.9(4) . . . . ?
C6 C7 C8 C9 -1.8(8) . . . . ?
Br1 C7 C8 C9 178.2(4) . . . . ?
C7 C8 C9 C4 -1.2(8) . . . . ?
C5 C4 C9 C8 2.8(7) . . . . ?
C1 C4 C9 C8 -175.7(4) . . . . ?
O2 C11 C12 C17 -107.1(6) . . . . ?
O2 C11 C12 C13 74.6(7) . . . . ?
C17 C12 C13 C14 2.1(10) . . . . ?
C11 C12 C13 C14 -179.6(7) . . . . ?
C12 C13 C14 C15 -2.2(13) . . . . ?
C13 C14 C15 C16 1.5(13) . . . . ?
C14 C15 C16 C17 -0.8(11) . . . . ?
C13 C12 C17 C16 -1.4(9) . . . . ?
C11 C12 C17 C16 -179.7(6) . . . . ?
C15 C16 C17 C12 0.7(10) . . . . ?
C3 C1 C18 O3 -175.6(4) . . . . ?
C4 C1 C18 O3 35.1(5) . . . . ?
C2 C1 C18 O3 -107.4(5) . . . . ?
C3 C1 C18 O4 5.1(5) . . . . ?
C4 C1 C18 O4 -144.2(3) . . . . ?
C2 C1 C18 O4 73.3(4) . . . . ?
O1 C10 N1 C2 -8.7(5) . . . . ?
O2 C10 N1 C2 172.3(3) . . . . ?
C3 C2 N1 C10 -149.5(3) . . . . ?
C1 C2 N1 C10 -84.9(4) . . . . ?
P002 C2 N1 C10 67.6(3) . . . . ?
O1 C10 O2 C11 -1.3(6) . . . . ?
N1 C10 O2 C11 177.8(4) . . . . ?
C12 C11 O2 C10 173.8(5) . . . . ?
O3 C18 O4 C19 4.2(8) . . . . ?
C1 C18 O4 C19 -176.5(6) . . . . ?
C23 C22 O6 P002 -176.6(9) . . . . ?
C21 C20 O7 P002 105.4(6) . . . . ?
C22 O6 P002 O5 -48.3(6) . . . . ?
C22 O6 P002 O7 76.1(6) . . . . ?
C22 O6 P002 C2 -171.3(5) . . . . ?
C20 O7 P002 O5 -30.6(4) . . . . ?
C20 O7 P002 O6 -156.6(4) . . . . ?
C20 O7 P002 C2 96.0(4) . . . . ?
N1 C2 P002 O5 3.3(3) . . . . ?
C3 C2 P002 O5 -137.1(3) . . . . ?
C1 C2 P002 O5 153.3(3) . . . . ?
N1 C2 P002 O6 128.4(2) . . . . ?
C3 C2 P002 O6 -12.0(3) . . . . ?
C1 C2 P002 O6 -81.6(3) . . . . ?
N1 C2 P002 O7 -123.8(2) . . . . ?
C3 C2 P002 O7 95.8(3) . . . . ?
C1 C2 P002 O7 26.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O5 0.86 1.98 2.795(4) 158 4_466 yes

