# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_cd16694
_database_code_depnum_ccdc_archive 'CCDC 1518992'
_audit_update_record             
;
2016-11-24 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Br N O4'
_chemical_formula_weight         470.35

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.1087(12)
_cell_length_b                   9.6236(13)
_cell_length_c                   13.9209(18)
_cell_angle_alpha                106.948(3)
_cell_angle_beta                 95.031(3)
_cell_angle_gamma                99.718(3)
_cell_volume                     1138.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1466
_cell_measurement_theta_min      4.520
_cell_measurement_theta_max      43.012

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.834
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6592
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4230
_reflns_number_gt                2665
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.3237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4230
_refine_ls_number_parameters     277
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Br1 Br 0.91938(5) 0.81676(6) 0.62096(3) 0.0985(2) Uani 1 1 d . . . . .
N1 N 0.3374(3) 0.6077(3) 0.1006(2) 0.0502(7) Uani 1 1 d D . . . .
O1 O 0.6099(3) 0.5200(3) 0.11539(18) 0.0726(7) Uani 1 1 d . . . . .
O2 O 0.5574(2) 0.4359(2) 0.24394(17) 0.0534(6) Uani 1 1 d . . . . .
O3 O 0.0020(3) 0.3583(4) 0.1592(3) 0.1077(11) Uani 1 1 d . . . . .
O4 O 0.1828(3) 0.3026(3) 0.06633(19) 0.0673(7) Uani 1 1 d . . . . .
C1 C 0.3590(3) 0.7606(4) 0.1257(2) 0.0477(8) Uani 1 1 d . . . . .
C2 C 0.3482(4) 0.8449(5) 0.0618(3) 0.0666(10) Uani 1 1 d . . . . .
H2 H 0.3301 0.8010 -0.0083 0.080 Uiso 1 1 calc R U . . .
C3 C 0.3647(5) 0.9955(5) 0.1040(3) 0.0771(12) Uani 1 1 d . . . . .
H3 H 0.3566 1.0537 0.0617 0.093 Uiso 1 1 calc R U . . .
C4 C 0.3929(5) 1.0620(4) 0.2070(3) 0.0766(11) Uani 1 1 d . . . . .
H4 H 0.4031 1.1643 0.2337 0.092 Uiso 1 1 calc R U . . .
C5 C 0.4062(4) 0.9780(4) 0.2715(3) 0.0638(9) Uani 1 1 d . . . . .
H5 H 0.4254 1.0226 0.3415 0.077 Uiso 1 1 calc R U . . .
C6 C 0.3905(3) 0.8272(4) 0.2301(2) 0.0486(8) Uani 1 1 d . . . . .
C7 C 0.3916(3) 0.7086(3) 0.2802(2) 0.0444(7) Uani 1 1 d . . . . .
C8 C 0.3864(3) 0.5633(3) 0.1866(2) 0.0403(7) Uani 1 1 d . . . . .
C9 C 0.2551(3) 0.4815(3) 0.2261(2) 0.0468(7) Uani 1 1 d . . . . .
H9 H 0.2955 0.4289 0.2697 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2327(3) 0.6313(4) 0.2919(2) 0.0505(8) Uani 1 1 d . . . . .
C11 C 0.0952(4) 0.6950(5) 0.2835(3) 0.0725(11) Uani 1 1 d . . . . .
H11A H 0.1090 0.7972 0.2837 0.087 Uiso 1 1 calc R U . . .
H11B H 0.0051 0.6297 0.2412 0.087 Uiso 1 1 calc R U . . .
C12 C 0.1471(4) 0.6669(5) 0.3794(3) 0.0781(12) Uani 1 1 d . . . . .
H12A H 0.0883 0.5847 0.3953 0.094 Uiso 1 1 calc R U . . .
H12B H 0.1922 0.7521 0.4378 0.094 Uiso 1 1 calc R U . . .
C13 C 0.5171(3) 0.7405(3) 0.3669(2) 0.0452(7) Uani 1 1 d . . . . .
C14 C 0.6562(4) 0.8218(4) 0.3659(3) 0.0637(10) Uani 1 1 d . . . . .
H14 H 0.6695 0.8626 0.3136 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7769(4) 0.8446(5) 0.4401(3) 0.0702(10) Uani 1 1 d . . . . .
H15 H 0.8704 0.8987 0.4373 0.084 Uiso 1 1 calc R U . . .
C16 C 0.7566(4) 0.7865(4) 0.5178(3) 0.0629(9) Uani 1 1 d . . . . .
C17 C 0.6199(4) 0.7058(4) 0.5215(3) 0.0615(9) Uani 1 1 d . . . . .
H17 H 0.6072 0.6661 0.5743 0.074 Uiso 1 1 calc R U . . .
C18 C 0.5012(4) 0.6834(4) 0.4467(2) 0.0530(8) Uani 1 1 d . . . . .
H18 H 0.4083 0.6288 0.4499 0.064 Uiso 1 1 calc R U . . .
C19 C 0.5285(3) 0.5033(3) 0.1762(2) 0.0454(7) Uani 1 1 d . . . . .
C20 C 0.7010(4) 0.3896(5) 0.2474(3) 0.0815(13) Uani 1 1 d . . . . .
H20A H 0.6947 0.2976 0.1933 0.098 Uiso 1 1 calc R U . . .
H20B H 0.7786 0.4645 0.2375 0.098 Uiso 1 1 calc R U . . .
C21 C 0.7393(5) 0.3688(6) 0.3441(4) 0.1012(15) Uani 1 1 d . . . . .
H21A H 0.7448 0.4599 0.3973 0.152 Uiso 1 1 calc R U . . .
H21B H 0.8350 0.3398 0.3465 0.152 Uiso 1 1 calc R U . . .
H21C H 0.6636 0.2927 0.3527 0.152 Uiso 1 1 calc R U . . .
C22 C 0.1311(4) 0.3770(4) 0.1482(3) 0.0597(9) Uani 1 1 d . . . . .
C23 C 0.0723(5) 0.2065(6) -0.0193(4) 0.1084(17) Uani 1 1 d . . . . .
H23A H 0.0029 0.2630 -0.0389 0.130 Uiso 1 1 calc R U . . .
H23B H 0.0150 0.1269 -0.0001 0.130 Uiso 1 1 calc R U . . .
C24 C 0.1491(7) 0.1446(7) -0.1046(4) 0.1256(19) Uani 1 1 d . . . . .
H24A H 0.2028 0.2237 -0.1249 0.188 Uiso 1 1 calc R U . . .
H24B H 0.0763 0.0795 -0.1604 0.188 Uiso 1 1 calc R U . . .
H24C H 0.2187 0.0901 -0.0846 0.188 Uiso 1 1 calc R U . . .
H1 H 0.358(3) 0.561(3) 0.0478(17) 0.046(10) Uiso 1 1 d 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 1.893(3) . ?
N1 C1 1.384(4) . ?
N1 C8 1.443(4) . ?
N1 H1 0.801(17) . ?
O1 C19 1.200(3) . ?
O2 C19 1.323(4) . ?
O2 C20 1.452(4) . ?
O3 C22 1.189(4) . ?
O4 C22 1.329(4) . ?
O4 C23 1.457(5) . ?
C1 C2 1.376(5) . ?
C1 C6 1.388(4) . ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.502(4) . ?
C7 C13 1.510(4) . ?
C7 C10 1.557(4) . ?
C7 C8 1.599(4) . ?
C8 C19 1.505(4) . ?
C8 C9 1.551(4) . ?
C9 C22 1.493(4) . ?
C9 C10 1.524(4) . ?
C9 H9 0.9800 . ?
C10 C12 1.492(4) . ?
C10 C11 1.494(5) . ?
C11 C12 1.491(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.376(4) . ?
C13 C18 1.384(4) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C17 C18 1.376(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 C21 1.440(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 C24 1.459(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 111.2(3) . . ?
C1 N1 H1 120(2) . . ?
C8 N1 H1 114(2) . . ?
C19 O2 C20 116.7(2) . . ?
C22 O4 C23 117.4(3) . . ?
C2 C1 N1 128.3(3) . . ?
C2 C1 C6 120.6(3) . . ?
N1 C1 C6 111.1(3) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 C7 130.5(3) . . ?
C1 C6 C7 108.8(3) . . ?
C6 C7 C13 115.9(3) . . ?
C6 C7 C10 114.3(2) . . ?
C13 C7 C10 117.5(2) . . ?
C6 C7 C8 102.9(2) . . ?
C13 C7 C8 115.5(2) . . ?
C10 C7 C8 86.1(2) . . ?
N1 C8 C19 112.8(2) . . ?
N1 C8 C9 113.2(2) . . ?
C19 C8 C9 119.1(2) . . ?
N1 C8 C7 102.5(2) . . ?
C19 C8 C7 117.3(2) . . ?
C9 C8 C7 88.7(2) . . ?
C22 C9 C10 121.1(3) . . ?
C22 C9 C8 116.9(3) . . ?
C10 C9 C8 89.0(2) . . ?
C22 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C12 C10 C11 59.9(2) . . ?
C12 C10 C9 129.7(3) . . ?
C11 C10 C9 126.2(3) . . ?
C12 C10 C7 129.3(3) . . ?
C11 C10 C7 123.4(3) . . ?
C9 C10 C7 91.3(2) . . ?
C12 C11 C10 60.0(2) . . ?
C12 C11 H11A 117.8 . . ?
C10 C11 H11A 117.8 . . ?
C12 C11 H11B 117.8 . . ?
C10 C11 H11B 117.8 . . ?
H11A C11 H11B 114.9 . . ?
C11 C12 C10 60.1(2) . . ?
C11 C12 H12A 117.8 . . ?
C10 C12 H12A 117.8 . . ?
C11 C12 H12B 117.8 . . ?
C10 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C14 C13 C18 117.3(3) . . ?
C14 C13 C7 120.3(3) . . ?
C18 C13 C7 122.4(3) . . ?
C13 C14 C15 122.0(3) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 Br1 119.5(3) . . ?
C15 C16 Br1 119.9(3) . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
O1 C19 O2 123.6(3) . . ?
O1 C19 C8 123.5(3) . . ?
O2 C19 C8 112.9(3) . . ?
C21 C20 O2 109.6(3) . . ?
C21 C20 H20A 109.7 . . ?
O2 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
O2 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
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 . . ?
O3 C22 O4 123.8(3) . . ?
O3 C22 C9 124.3(4) . . ?
O4 C22 C9 111.9(3) . . ?
O4 C23 C24 109.6(4) . . ?
O4 C23 H23A 109.8 . . ?
C24 C23 H23A 109.8 . . ?
O4 C23 H23B 109.8 . . ?
C24 C23 H23B 109.8 . . ?
H23A C23 H23B 108.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 169.1(3) . . . . ?
C8 N1 C1 C6 -13.0(4) . . . . ?
N1 C1 C2 C3 175.7(3) . . . . ?
C6 C1 C2 C3 -1.9(5) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C4 C5 C6 C7 -176.7(3) . . . . ?
C2 C1 C6 C5 2.2(5) . . . . ?
N1 C1 C6 C5 -175.8(3) . . . . ?
C2 C1 C6 C7 178.6(3) . . . . ?
N1 C1 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C13 -46.8(4) . . . . ?
C1 C6 C7 C13 137.3(3) . . . . ?
C5 C6 C7 C10 94.7(4) . . . . ?
C1 C6 C7 C10 -81.2(3) . . . . ?
C5 C6 C7 C8 -173.8(3) . . . . ?
C1 C6 C7 C8 10.3(3) . . . . ?
C1 N1 C8 C19 -108.6(3) . . . . ?
C1 N1 C8 C9 112.4(3) . . . . ?
C1 N1 C8 C7 18.4(3) . . . . ?
C6 C7 C8 N1 -16.8(3) . . . . ?
C13 C7 C8 N1 -144.1(2) . . . . ?
C10 C7 C8 N1 97.2(2) . . . . ?
C6 C7 C8 C19 107.3(3) . . . . ?
C13 C7 C8 C19 -20.0(4) . . . . ?
C10 C7 C8 C19 -138.7(3) . . . . ?
C6 C7 C8 C9 -130.3(2) . . . . ?
C13 C7 C8 C9 102.4(3) . . . . ?
C10 C7 C8 C9 -16.3(2) . . . . ?
N1 C8 C9 C22 38.3(4) . . . . ?
C19 C8 C9 C22 -97.8(3) . . . . ?
C7 C8 C9 C22 141.4(3) . . . . ?
N1 C8 C9 C10 -86.5(3) . . . . ?
C19 C8 C9 C10 137.4(3) . . . . ?
C7 C8 C9 C10 16.6(2) . . . . ?
C22 C9 C10 C12 74.4(5) . . . . ?
C8 C9 C10 C12 -164.4(4) . . . . ?
C22 C9 C10 C11 -4.0(5) . . . . ?
C8 C9 C10 C11 117.2(3) . . . . ?
C22 C9 C10 C7 -138.2(3) . . . . ?
C8 C9 C10 C7 -17.1(2) . . . . ?
C6 C7 C10 C12 -93.5(4) . . . . ?
C13 C7 C10 C12 47.3(5) . . . . ?
C8 C7 C10 C12 164.1(3) . . . . ?
C6 C7 C10 C11 -17.2(4) . . . . ?
C13 C7 C10 C11 123.6(3) . . . . ?
C8 C7 C10 C11 -119.6(3) . . . . ?
C6 C7 C10 C9 118.9(3) . . . . ?
C13 C7 C10 C9 -100.2(3) . . . . ?
C8 C7 C10 C9 16.6(2) . . . . ?
C9 C10 C11 C12 119.4(4) . . . . ?
C7 C10 C11 C12 -119.7(4) . . . . ?
C9 C10 C12 C11 -113.9(4) . . . . ?
C7 C10 C12 C11 110.3(4) . . . . ?
C6 C7 C13 C14 -33.2(4) . . . . ?
C10 C7 C13 C14 -173.4(3) . . . . ?
C8 C7 C13 C14 87.2(4) . . . . ?
C6 C7 C13 C18 150.6(3) . . . . ?
C10 C7 C13 C18 10.4(4) . . . . ?
C8 C7 C13 C18 -89.0(3) . . . . ?
C18 C13 C14 C15 1.0(5) . . . . ?
C7 C13 C14 C15 -175.4(3) . . . . ?
C13 C14 C15 C16 -1.0(6) . . . . ?
C14 C15 C16 C17 0.7(6) . . . . ?
C14 C15 C16 Br1 -179.7(3) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
Br1 C16 C17 C18 180.0(3) . . . . ?
C16 C17 C18 C13 0.4(5) . . . . ?
C14 C13 C18 C17 -0.7(5) . . . . ?
C7 C13 C18 C17 175.7(3) . . . . ?
C20 O2 C19 O1 4.2(5) . . . . ?
C20 O2 C19 C8 -173.1(3) . . . . ?
N1 C8 C19 O1 15.3(4) . . . . ?
C9 C8 C19 O1 151.6(3) . . . . ?
C7 C8 C19 O1 -103.4(3) . . . . ?
N1 C8 C19 O2 -167.4(2) . . . . ?
C9 C8 C19 O2 -31.1(4) . . . . ?
C7 C8 C19 O2 73.8(3) . . . . ?
C19 O2 C20 C21 159.5(4) . . . . ?
C23 O4 C22 O3 7.9(6) . . . . ?
C23 O4 C22 C9 -174.7(3) . . . . ?
C10 C9 C22 O3 -38.1(5) . . . . ?
C8 C9 C22 O3 -144.6(4) . . . . ?
C10 C9 C22 O4 144.5(3) . . . . ?
C8 C9 C22 O4 38.0(4) . . . . ?
C22 O4 C23 C24 175.1(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
N1 H1 O1 0.801(17) 2.24(2) 3.014(4) 163(3) 2_665
C21 H21B Br1 0.96 2.97 3.900(4) 162.7 2_766
C20 H20B O3 0.97 2.61 3.126(4) 113.4 1_655
N1 H1 O1 0.801(17) 2.24(2) 3.014(4) 163(3) 2_665
C21 H21B Br1 0.96 2.97 3.900(4) 162.7 2_766
C20 H20B O3 0.97 2.61 3.126(4) 113.4 1_655
C20 H20B O3 0.97 2.61 3.126(4) 113.4 1_655
C21 H21B Br1 0.96 2.97 3.900(4) 162.7 2_766
N1 H1 O1 0.801(17) 2.24(2) 3.014(4) 163(3) 2_665

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v17461
_database_code_depnum_ccdc_archive 'CCDC 1580815'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N O4'
_chemical_formula_weight         363.40

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

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

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

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

_cell_length_a                   17.5019(5)
_cell_length_b                   8.4032(3)
_cell_length_c                   12.4676(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1833.63(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4984
_cell_measurement_theta_min      10.108
_cell_measurement_theta_max      139.773

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.737
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10486
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.054
_diffrn_reflns_theta_max         65.467
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.908
_reflns_number_total             3013
_reflns_number_gt                2787
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_max     0.910
_reflns_Friedel_fraction_full    0.866

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

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.2332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0107(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1160 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3013
_refine_ls_number_parameters     260
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.052
_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
N1 N 0.52688(16) 0.4718(3) 0.6193(3) 0.0488(7) Uani 1 1 d . . . . .
O1 O 0.87906(17) 0.7319(5) 0.4710(3) 0.0845(11) Uani 1 1 d . . . . .
H1 H 0.9200 0.7534 0.4996 0.127 Uiso 1 1 calc R U . . .
O2 O 0.8599(3) 0.6263(10) 0.6279(5) 0.079(2) Uani 0.6 1 d . U P A 1
O2' O 0.8347(7) 0.7304(18) 0.6304(9) 0.100(3) Uani 0.4 1 d . U P A 2
O3 O 0.51061(13) 0.1561(3) 0.5598(3) 0.0587(7) Uani 1 1 d . . . . .
O4 O 0.62134(14) 0.0959(3) 0.6365(2) 0.0547(6) Uani 1 1 d . . . . .
C1 C 0.52023(18) 0.5644(4) 0.5277(3) 0.0443(7) Uani 1 1 d . . . . .
C2 C 0.4620(2) 0.6702(4) 0.5024(4) 0.0571(9) Uani 1 1 d . . . . .
H2 H 0.4186 0.6784 0.5452 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4705(2) 0.7635(5) 0.4111(4) 0.0636(11) Uani 1 1 d . . . . .
H3 H 0.4327 0.8367 0.3936 0.076 Uiso 1 1 calc R U . . .
C4 C 0.5336(2) 0.7503(5) 0.3463(4) 0.0624(10) Uani 1 1 d . . . . .
H4 H 0.5379 0.8140 0.2856 0.075 Uiso 1 1 calc R U . . .
C5 C 0.5912(2) 0.6417(4) 0.3712(3) 0.0523(8) Uani 1 1 d . . . . .
H5 H 0.6336 0.6317 0.3268 0.063 Uiso 1 1 calc R U . . .
C6 C 0.58456(18) 0.5495(4) 0.4619(3) 0.0409(7) Uani 1 1 d . . . . .
C7 C 0.64072(17) 0.4332(4) 0.5119(2) 0.0395(7) Uani 1 1 d . . . . .
C8 C 0.59396(17) 0.3697(3) 0.6152(3) 0.0406(7) Uani 1 1 d . . . . .
C9 C 0.6466(2) 0.3997(4) 0.7125(3) 0.0480(8) Uani 1 1 d . . . . .
H9A H 0.6190 0.4522 0.7699 0.058 Uiso 1 1 calc R U . . .
H9B H 0.6676 0.3006 0.7393 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7084(2) 0.5048(4) 0.6692(3) 0.0509(9) Uani 1 1 d . . . . .
H10 H 0.7447 0.5536 0.7126 0.061 Uiso 1 1 calc R U . . .
C11 C 0.70701(17) 0.5223(4) 0.5641(3) 0.0423(7) Uani 1 1 d . . . . .
C12 C 0.7604(2) 0.6141(5) 0.4927(3) 0.0517(8) Uani 1 1 d . . . . .
H12A H 0.7730 0.5474 0.4317 0.062 Uiso 1 1 calc R U . . .
H12B H 0.7331 0.7059 0.4654 0.062 Uiso 1 1 calc R U . . .
C13 C 0.8334(2) 0.6711(5) 0.5412(3) 0.0540(9) Uani 1 1 d . . . . .
C14 C 0.66773(19) 0.3008(4) 0.4367(3) 0.0469(8) Uani 1 1 d . . . . .
C15 C 0.6277(2) 0.2593(5) 0.3447(3) 0.0608(9) Uani 1 1 d . . . . .
H15 H 0.5849 0.3178 0.3249 0.073 Uiso 1 1 calc R U . . .
C16 C 0.6507(3) 0.1320(6) 0.2823(4) 0.0838(15) Uani 1 1 d . . . . .
H16 H 0.6233 0.1059 0.2209 0.101 Uiso 1 1 calc R U . . .
C17 C 0.7135(3) 0.0442(6) 0.3102(5) 0.0865(17) Uani 1 1 d . . . . .
H17 H 0.7285 -0.0417 0.2681 0.104 Uiso 1 1 calc R U . . .
C18 C 0.7540(3) 0.0829(5) 0.3997(5) 0.0772(14) Uani 1 1 d . . . . .
H18 H 0.7966 0.0231 0.4185 0.093 Uiso 1 1 calc R U . . .
C19 C 0.7320(2) 0.2110(5) 0.4631(4) 0.0595(10) Uani 1 1 d . . . . .
H19 H 0.7604 0.2370 0.5237 0.071 Uiso 1 1 calc R U . . .
C20 C 0.56984(17) 0.1971(4) 0.6007(3) 0.0415(7) Uani 1 1 d . . . . .
C21 C 0.6076(3) -0.0734(4) 0.6223(4) 0.0652(10) Uani 1 1 d . . . . .
H21A H 0.5730 -0.0900 0.5626 0.078 Uiso 1 1 calc R U . . .
H21B H 0.6553 -0.1270 0.6063 0.078 Uiso 1 1 calc R U . . .
C22 C 0.5746(4) -0.1396(5) 0.7194(5) 0.0920(17) Uani 1 1 d . . . . .
H22A H 0.6084 -0.1208 0.7787 0.138 Uiso 1 1 calc R U . . .
H22B H 0.5672 -0.2520 0.7105 0.138 Uiso 1 1 calc R U . . .
H22C H 0.5263 -0.0896 0.7333 0.138 Uiso 1 1 calc R U . . .
H1A H 0.484(3) 0.442(6) 0.660(4) 0.066(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.386(5) . ?
N1 C8 1.455(4) . ?
N1 H1A 0.94(5) . ?
O1 C13 1.290(5) . ?
O1 H1 0.8200 . ?
O2 C13 1.235(7) . ?
O2' C13 1.218(11) . ?
O3 C20 1.206(4) . ?
O4 C20 1.317(4) . ?
O4 C21 1.454(4) . ?
C1 C2 1.389(5) . ?
C1 C6 1.399(5) . ?
C2 C3 1.390(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.520(4) . ?
C7 C11 1.526(4) . ?
C7 C14 1.530(5) . ?
C7 C8 1.617(4) . ?
C8 C20 1.521(4) . ?
C8 C9 1.544(4) . ?
C9 C10 1.497(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.318(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.504(4) . ?
C12 C13 1.492(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.388(5) . ?
C14 C19 1.395(5) . ?
C15 C16 1.382(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C21 C22 1.452(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 111.7(3) . . ?
C1 N1 H1A 122(3) . . ?
C8 N1 H1A 120(3) . . ?
C13 O1 H1 109.5 . . ?
C20 O4 C21 118.5(3) . . ?
N1 C1 C2 127.4(3) . . ?
N1 C1 C6 111.4(3) . . ?
C2 C1 C6 121.0(3) . . ?
C1 C2 C3 117.9(4) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 130.2(3) . . ?
C1 C6 C7 109.7(3) . . ?
C6 C7 C11 110.6(2) . . ?
C6 C7 C14 114.6(3) . . ?
C11 C7 C14 112.5(3) . . ?
C6 C7 C8 102.2(2) . . ?
C11 C7 C8 101.9(2) . . ?
C14 C7 C8 113.9(3) . . ?
N1 C8 C20 110.0(2) . . ?
N1 C8 C9 111.0(3) . . ?
C20 C8 C9 114.5(3) . . ?
N1 C8 C7 104.0(2) . . ?
C20 C8 C7 111.2(3) . . ?
C9 C8 C7 105.7(2) . . ?
C10 C9 C8 104.1(3) . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C9 114.3(3) . . ?
C11 C10 H10 122.9 . . ?
C9 C10 H10 122.9 . . ?
C10 C11 C12 129.3(3) . . ?
C10 C11 C7 112.5(3) . . ?
C12 C11 C7 118.1(3) . . ?
C13 C12 C11 117.2(3) . . ?
C13 C12 H12A 108.0 . . ?
C11 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C11 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
O2' C13 O1 116.4(6) . . ?
O2 C13 O1 118.8(4) . . ?
O2' C13 C12 121.2(6) . . ?
O2 C13 C12 125.3(4) . . ?
O1 C13 C12 112.5(3) . . ?
C15 C14 C19 117.8(3) . . ?
C15 C14 C7 122.2(3) . . ?
C19 C14 C7 119.9(3) . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.5(5) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 120.5(5) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
O3 C20 O4 123.2(3) . . ?
O3 C20 C8 124.1(3) . . ?
O4 C20 C8 112.7(3) . . ?
C22 C21 O4 109.8(4) . . ?
C22 C21 H21A 109.7 . . ?
O4 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
O4 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 177.3(3) . . . . ?
C8 N1 C1 C6 -7.3(4) . . . . ?
N1 C1 C2 C3 173.5(4) . . . . ?
C6 C1 C2 C3 -1.6(5) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C4 C5 C6 C7 -174.6(3) . . . . ?
N1 C1 C6 C5 -175.1(3) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
N1 C1 C6 C7 1.0(4) . . . . ?
C2 C1 C6 C7 176.7(3) . . . . ?
C5 C6 C7 C11 72.4(4) . . . . ?
C1 C6 C7 C11 -103.0(3) . . . . ?
C5 C6 C7 C14 -56.0(4) . . . . ?
C1 C6 C7 C14 128.5(3) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C1 C6 C7 C8 4.8(3) . . . . ?
C1 N1 C8 C20 -109.2(3) . . . . ?
C1 N1 C8 C9 123.0(3) . . . . ?
C1 N1 C8 C7 9.9(3) . . . . ?
C6 C7 C8 N1 -8.6(3) . . . . ?
C11 C7 C8 N1 105.9(3) . . . . ?
C14 C7 C8 N1 -132.7(3) . . . . ?
C6 C7 C8 C20 109.8(3) . . . . ?
C11 C7 C8 C20 -135.8(3) . . . . ?
C14 C7 C8 C20 -14.4(3) . . . . ?
C6 C7 C8 C9 -125.5(3) . . . . ?
C11 C7 C8 C9 -11.1(3) . . . . ?
C14 C7 C8 C9 110.4(3) . . . . ?
N1 C8 C9 C10 -100.2(3) . . . . ?
C20 C8 C9 C10 134.5(3) . . . . ?
C7 C8 C9 C10 11.9(3) . . . . ?
C8 C9 C10 C11 -8.8(4) . . . . ?
C9 C10 C11 C12 -178.2(3) . . . . ?
C9 C10 C11 C7 1.4(5) . . . . ?
C6 C7 C11 C10 114.4(3) . . . . ?
C14 C7 C11 C10 -116.1(4) . . . . ?
C8 C7 C11 C10 6.3(4) . . . . ?
C6 C7 C11 C12 -66.0(4) . . . . ?
C14 C7 C11 C12 63.6(4) . . . . ?
C8 C7 C11 C12 -174.1(3) . . . . ?
C10 C11 C12 C13 12.2(6) . . . . ?
C7 C11 C12 C13 -167.4(3) . . . . ?
C11 C12 C13 O2' -43.2(10) . . . . ?
C11 C12 C13 O2 13.7(8) . . . . ?
C11 C12 C13 O1 172.4(4) . . . . ?
C6 C7 C14 C15 -19.5(4) . . . . ?
C11 C7 C14 C15 -146.9(3) . . . . ?
C8 C7 C14 C15 97.7(4) . . . . ?
C6 C7 C14 C19 164.5(3) . . . . ?
C11 C7 C14 C19 37.0(4) . . . . ?
C8 C7 C14 C19 -78.4(4) . . . . ?
C19 C14 C15 C16 0.6(6) . . . . ?
C7 C14 C15 C16 -175.5(4) . . . . ?
C14 C15 C16 C17 0.1(7) . . . . ?
C15 C16 C17 C18 -0.4(8) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
C17 C18 C19 C14 0.7(6) . . . . ?
C15 C14 C19 C18 -1.0(5) . . . . ?
C7 C14 C19 C18 175.3(4) . . . . ?
C21 O4 C20 O3 2.4(5) . . . . ?
C21 O4 C20 C8 -176.6(3) . . . . ?
N1 C8 C20 O3 25.4(4) . . . . ?
C9 C8 C20 O3 151.2(3) . . . . ?
C7 C8 C20 O3 -89.2(4) . . . . ?
N1 C8 C20 O4 -155.6(3) . . . . ?
C9 C8 C20 O4 -29.8(4) . . . . ?
C7 C8 C20 O4 89.8(3) . . . . ?
C20 O4 C21 C22 -96.6(5) . . . . ?

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
N1 H1A O2 0.94(5) 2.27(5) 3.038(6) 138(4) 3_465
C22 H22B N1 0.96 2.68 3.595(5) 159.6 1_545
O1 H1 O3 0.82 1.91 2.722(4) 169.3 3_565
N1 H1A O2 0.94(5) 2.27(5) 3.038(6) 138(4) 3_465
C22 H22B N1 0.96 2.68 3.595(5) 159.6 1_545
O1 H1 O3 0.82 1.91 2.722(4) 169.3 3_565
N1 H1A O2 0.94(5) 2.27(5) 3.038(6) 138(4) 3_465
C22 H22B N1 0.96 2.68 3.595(5) 159.6 1_545
O1 H1 O3 0.82 1.91 2.722(4) 169.3 3_565
N1 H1A O2 0.94(5) 2.27(5) 3.038(6) 138(4) 3_465
C22 H22B N1 0.96 2.68 3.595(5) 159.6 1_545
O1 H1 O3 0.82 1.91 2.722(4) 169.3 3_565
O1 H1 O3 0.82 1.91 2.722(4) 169.3 3_565
C22 H22B N1 0.96 2.68 3.595(5) 159.6 1_545
N1 H1A O2 0.94(5) 2.27(5) 3.038(6) 138(4) 3_465
O1 H1 O3 0.82 1.91 2.722(4) 169.3 3_565
C22 H22B N1 0.96 2.68 3.595(5) 159.6 1_545
N1 H1A O2 0.94(5) 2.27(5) 3.038(6) 138(4) 3_465

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dm16863_0m
_database_code_depnum_ccdc_archive 'CCDC 1522872'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_audit_creation_date             2016-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 Br N O4'
_chemical_formula_sum            'C24 H24 Br N O4'
_chemical_formula_weight         470.35
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.8749(12)
_cell_length_b                   13.1162(14)
_cell_length_c                   14.6639(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.809(2)
_cell_angle_gamma                90
_cell_volume                     2186.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3164
_cell_measurement_temperature    130
_cell_measurement_theta_max      25.069
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.7689.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.640
_diffrn_reflns_theta_min         1.791
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4120
_reflns_number_total             6683
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.5140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C20(H20A,H20B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 0.81695(2) 0.28406(2) 0.53623(2) 0.03733(10) Uani 1 1 d . . . . .
O1 O 0.32241(15) 0.20173(14) 0.19735(12) 0.0272(4) Uani 1 1 d . . . . .
O2 O 0.38023(15) 0.10998(13) 0.33201(12) 0.0251(4) Uani 1 1 d . . . . .
O3 O 0.06362(14) 0.37459(13) 0.57459(12) 0.0233(4) Uani 1 1 d . . . . .
O4 O 0.17396(14) 0.51429(13) 0.62306(12) 0.0229(4) Uani 1 1 d . . . . .
N1 N 0.12291(17) 0.26793(16) 0.24222(15) 0.0238(5) Uani 1 1 d . . . . .
H1 H 0.059329 0.233085 0.213181 0.029 Uiso 1 1 calc R . . . .
C1 C 0.1444(2) 0.36908(19) 0.22399(17) 0.0222(5) Uani 1 1 d . . . . .
C2 C 0.0853(2) 0.4287(2) 0.14594(19) 0.0314(6) Uani 1 1 d . . . . .
H2 H 0.023824 0.400860 0.095440 0.038 Uiso 1 1 calc R . . . .
C3 C 0.1189(3) 0.5293(2) 0.1442(2) 0.0353(7) Uani 1 1 d . . . . .
H3 H 0.080397 0.570693 0.091218 0.042 Uiso 1 1 calc R . . . .
C4 C 0.2074(3) 0.5712(2) 0.2181(2) 0.0332(6) Uani 1 1 d . . . . .
H4 H 0.228244 0.640886 0.215525 0.040 Uiso 1 1 calc R . . . .
C5 C 0.2660(2) 0.51134(19) 0.29620(18) 0.0255(5) Uani 1 1 d . . . . .
H5 H 0.326752 0.539513 0.347053 0.031 Uiso 1 1 calc R . . . .
C6 C 0.2338(2) 0.41071(18) 0.29800(16) 0.0183(5) Uani 1 1 d . . . . .
C7 C 0.27642(19) 0.32997(18) 0.37440(16) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.2235(2) 0.22886(18) 0.31770(17) 0.0195(5) Uani 1 1 d . . . . .
C9 C 0.1864(2) 0.16401(19) 0.39104(18) 0.0238(5) Uani 1 1 d . . . . .
H9A H 0.254593 0.126785 0.432637 0.029 Uiso 1 1 calc R . . . .
H9B H 0.125064 0.114168 0.359146 0.029 Uiso 1 1 calc R . . . .
C10 C 0.1382(2) 0.24144(18) 0.44857(18) 0.0232(5) Uani 1 1 d . . . . .
H10A H 0.053214 0.253259 0.418544 0.028 Uiso 1 1 calc R . . . .
H10B H 0.149967 0.217010 0.514550 0.028 Uiso 1 1 calc R . . . .
C11 C 0.20734(19) 0.33749(18) 0.44795(16) 0.0179(5) Uani 1 1 d . . . . .
C12 C 0.4090(2) 0.32416(17) 0.41898(16) 0.0180(5) Uani 1 1 d . . . . .
C13 C 0.4590(2) 0.28998(18) 0.51183(17) 0.0217(5) Uani 1 1 d . . . . .
H13 H 0.410013 0.275538 0.551260 0.026 Uiso 1 1 calc R . . . .
C14 C 0.5805(2) 0.2768(2) 0.54739(18) 0.0262(5) Uani 1 1 d . . . . .
H14 H 0.614280 0.253384 0.610736 0.031 Uiso 1 1 calc R . . . .
C15 C 0.6514(2) 0.29806(18) 0.48954(19) 0.0231(5) Uani 1 1 d . . . . .
C16 C 0.6041(2) 0.33384(19) 0.39841(19) 0.0247(5) Uani 1 1 d . . . . .
H16 H 0.653712 0.349579 0.359844 0.030 Uiso 1 1 calc R . . . .
C17 C 0.4836(2) 0.34679(19) 0.36321(17) 0.0218(5) Uani 1 1 d . . . . .
H17 H 0.451016 0.371445 0.300148 0.026 Uiso 1 1 calc R . . . .
C18 C 0.2108(2) 0.42021(18) 0.50057(17) 0.0203(5) Uani 1 1 d . . . . .
H18 H 0.260742 0.474758 0.494455 0.024 Uiso 1 1 calc R . . . .
C19 C 0.1410(2) 0.43147(18) 0.56793(16) 0.0193(5) Uani 1 1 d . . . . .
C20 C 0.1017(2) 0.5398(2) 0.68468(18) 0.0252(5) Uani 1 1 d . . . . .
H20A H 0.091457 0.479340 0.721881 0.030 Uiso 1 1 calc R . . . .
H20B H 0.023151 0.563436 0.646266 0.030 Uiso 1 1 calc R . . . .
C21 C 0.1633(3) 0.6218(3) 0.7492(3) 0.0559(10) Uani 1 1 d . . . . .
H21A H 0.174474 0.680562 0.711473 0.084 Uiso 1 1 calc GR . . . .
H21B H 0.240123 0.596907 0.787850 0.084 Uiso 1 1 calc GR . . . .
H21C H 0.116201 0.642218 0.791065 0.084 Uiso 1 1 calc GR . . . .
C22 C 0.3128(2) 0.17912(19) 0.27424(18) 0.0219(5) Uani 1 1 d . . . . .
C23 C 0.4752(2) 0.0671(2) 0.3003(2) 0.0319(6) Uani 1 1 d . . . . .
H23A H 0.525840 0.122138 0.287827 0.038 Uiso 1 1 calc R . . . .
H23B H 0.443065 0.027682 0.240910 0.038 Uiso 1 1 calc R . . . .
C24 C 0.5449(3) -0.0013(2) 0.3784(2) 0.0431(8) Uani 1 1 d . . . . .
H24A H 0.607459 -0.034611 0.357953 0.065 Uiso 1 1 calc GR . . . .
H24B H 0.492966 -0.053180 0.392435 0.065 Uiso 1 1 calc GR . . . .
H24C H 0.579954 0.039275 0.435703 0.065 Uiso 1 1 calc GR . . . .


_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 C15 1.894(2) . ?
O1 C22 1.203(3) . ?
O2 C22 1.337(3) . ?
O2 C23 1.452(3) . ?
O3 C19 1.209(3) . ?
O4 C19 1.343(3) . ?
O4 C20 1.453(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.391(3) . ?
N1 C8 1.466(3) . ?
C1 C2 1.396(4) . ?
C1 C6 1.392(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.398(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(3) . ?
C6 C7 1.518(3) . ?
C7 C8 1.595(3) . ?
C7 C11 1.536(3) . ?
C7 C12 1.522(3) . ?
C8 C9 1.532(3) . ?
C8 C22 1.532(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.533(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.505(3) . ?
C11 C18 1.325(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.401(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 C16 1.374(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.469(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.479(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.500(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O2 C23 115.99(19) . . ?
C19 O4 C20 116.03(18) . . ?
C1 N1 H1 125.5 . . ?
C1 N1 C8 108.90(19) . . ?
C8 N1 H1 125.5 . . ?
N1 C1 C2 128.0(2) . . ?
N1 C1 C6 111.4(2) . . ?
C6 C1 C2 120.6(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C7 108.5(2) . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 C7 130.4(2) . . ?
C6 C7 C8 101.44(18) . . ?
C6 C7 C11 109.99(18) . . ?
C6 C7 C12 115.75(19) . . ?
C11 C7 C8 102.10(17) . . ?
C12 C7 C8 112.65(19) . . ?
C12 C7 C11 113.44(18) . . ?
N1 C8 C7 102.42(18) . . ?
N1 C8 C9 112.78(19) . . ?
N1 C8 C22 110.22(19) . . ?
C9 C8 C7 104.22(18) . . ?
C22 C8 C7 110.80(18) . . ?
C22 C8 C9 115.4(2) . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C8 C9 C10 104.32(19) . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 C9 105.08(19) . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C10 C11 C7 110.70(19) . . ?
C18 C11 C7 121.9(2) . . ?
C18 C11 C10 127.4(2) . . ?
C13 C12 C7 122.1(2) . . ?
C13 C12 C17 118.4(2) . . ?
C17 C12 C7 119.3(2) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 Br1 120.68(19) . . ?
C16 C15 Br1 118.34(18) . . ?
C16 C15 C14 120.9(2) . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.4 . . ?
C11 C18 H18 118.5 . . ?
C11 C18 C19 123.1(2) . . ?
C19 C18 H18 118.5 . . ?
O3 C19 O4 123.1(2) . . ?
O3 C19 C18 125.6(2) . . ?
O4 C19 C18 111.3(2) . . ?
O4 C20 H20A 110.3 . . ?
O4 C20 H20B 110.3 . . ?
O4 C20 C21 107.1(2) . . ?
H20A C20 H20B 108.6 . . ?
C21 C20 H20A 110.3 . . ?
C21 C20 H20B 110.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 O2 124.0(2) . . ?
O1 C22 C8 123.3(2) . . ?
O2 C22 C8 112.6(2) . . ?
O2 C23 H23A 110.3 . . ?
O2 C23 H23B 110.3 . . ?
O2 C23 C24 107.2(2) . . ?
H23A C23 H23B 108.5 . . ?
C24 C23 H23A 110.3 . . ?
C24 C23 H23B 110.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_shelx_SHELXL_version_number     2016/6
_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_mo_d8v17426_0m
_database_code_depnum_ccdc_archive 'CCDC 1579530'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 Br Cl N2 O2'
_chemical_formula_weight         533.83

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   32.328(10)
_cell_length_b                   10.078(3)
_cell_length_c                   15.161(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.440(8)
_cell_angle_gamma                90
_cell_volume                     4658(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      5.345
_cell_measurement_theta_max      53.883

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             2176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.910
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5646
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38239
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4570
_reflns_number_gt                3545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+13.6395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00054(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4570
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
Br1 Br 0.50273(2) 1.32089(5) 0.39159(4) 0.0767(2) Uani 1 1 d . . . . .
Cl1 Cl 0.24018(4) 0.41384(12) 0.42938(8) 0.0704(3) Uani 1 1 d . . . . .
N1 N 0.27354(11) 0.6459(3) 0.3413(2) 0.0470(7) Uani 1 1 d . . . . .
N2 N 0.44469(9) 0.7186(3) 0.2896(2) 0.0464(7) Uani 1 1 d . . . . .
O1 O 0.38990(9) 0.8702(3) 0.2194(2) 0.0644(8) Uani 1 1 d . . . . .
O2 O 0.51084(9) 0.6247(3) 0.3755(2) 0.0643(7) Uani 1 1 d . . . . .
C1 C 0.30561(12) 0.6677(3) 0.4276(2) 0.0443(8) Uani 1 1 d . . . . .
C2 C 0.30703(14) 0.7699(4) 0.4905(3) 0.0545(9) Uani 1 1 d . . . . .
H2 H 0.2843 0.8309 0.4793 0.065 Uiso 1 1 calc R U . . .
C3 C 0.34363(16) 0.7770(4) 0.5700(3) 0.0634(11) Uani 1 1 d . . . . .
H3 H 0.3454 0.8447 0.6128 0.076 Uiso 1 1 calc R U . . .
C4 C 0.37774(14) 0.6865(4) 0.5880(2) 0.0562(10) Uani 1 1 d . . . . .
H4 H 0.4018 0.6935 0.6425 0.067 Uiso 1 1 calc R U . . .
C5 C 0.37591(12) 0.5852(4) 0.5244(2) 0.0482(8) Uani 1 1 d . . . . .
H5 H 0.3988 0.5248 0.5356 0.058 Uiso 1 1 calc R U . . .
C6 C 0.33963(11) 0.5755(3) 0.4446(2) 0.0396(7) Uani 1 1 d . . . . .
C7 C 0.33040(10) 0.4849(3) 0.3605(2) 0.0367(7) Uani 1 1 d . . . . .
C8 C 0.27995(11) 0.5138(3) 0.3060(2) 0.0418(8) Uani 1 1 d . . . . .
C9 C 0.27646(12) 0.5203(4) 0.2027(2) 0.0521(9) Uani 1 1 d . . . . .
H9A H 0.2726 0.4323 0.1754 0.063 Uiso 1 1 calc R U . . .
H9B H 0.2518 0.5752 0.1676 0.063 Uiso 1 1 calc R U . . .
C10 C 0.31916(12) 0.5805(4) 0.2018(3) 0.0561(10) Uani 1 1 d . . . . .
H10A H 0.3169 0.6765 0.1976 0.067 Uiso 1 1 calc R U . . .
H10B H 0.3267 0.5476 0.1490 0.067 Uiso 1 1 calc R U . . .
C11 C 0.35328(11) 0.5388(3) 0.2931(2) 0.0380(7) Uani 1 1 d . . . . .
C12 C 0.39598(11) 0.5460(4) 0.3153(2) 0.0446(8) Uani 1 1 d . . . . .
H12 H 0.4129 0.5170 0.3746 0.054 Uiso 1 1 calc R U . . .
C13 C 0.42000(12) 0.5981(4) 0.2521(3) 0.0498(9) Uani 1 1 d . . . . .
H13A H 0.4400 0.5305 0.2448 0.060 Uiso 1 1 calc R U . . .
H13B H 0.3990 0.6167 0.1908 0.060 Uiso 1 1 calc R U . . .
C14 C 0.33959(10) 0.3369(3) 0.3798(2) 0.0385(7) Uani 1 1 d . . . . .
C15 C 0.34490(11) 0.2543(4) 0.3110(2) 0.0448(8) Uani 1 1 d . . . . .
H15 H 0.3449 0.2911 0.2547 0.054 Uiso 1 1 calc R U . . .
C16 C 0.35017(12) 0.1195(4) 0.3240(3) 0.0501(9) Uani 1 1 d . . . . .
H16 H 0.3532 0.0664 0.2764 0.060 Uiso 1 1 calc R U . . .
C17 C 0.35094(11) 0.0626(4) 0.4071(3) 0.0528(9) Uani 1 1 d . . . . .
H17 H 0.3546 -0.0286 0.4159 0.063 Uiso 1 1 calc R U . . .
C18 C 0.34626(12) 0.1424(4) 0.4768(3) 0.0512(9) Uani 1 1 d . . . . .
H18 H 0.3469 0.1048 0.5333 0.061 Uiso 1 1 calc R U . . .
C19 C 0.34056(11) 0.2782(4) 0.4636(2) 0.0449(8) Uani 1 1 d . . . . .
H19 H 0.3374 0.3308 0.5114 0.054 Uiso 1 1 calc R U . . .
C20 C 0.24662(12) 0.4142(4) 0.3171(3) 0.0512(9) Uani 1 1 d . . . . .
H20A H 0.2554 0.3261 0.3047 0.061 Uiso 1 1 calc R U . . .
H20B H 0.2184 0.4330 0.2703 0.061 Uiso 1 1 calc R U . . .
C21 C 0.42677(12) 0.8445(4) 0.2694(2) 0.0481(9) Uani 1 1 d . . . . .
C22 C 0.48811(12) 0.7238(4) 0.3493(3) 0.0471(8) Uani 1 1 d . . . . .
C23 C 0.49890(11) 0.8645(4) 0.3703(2) 0.0467(8) Uani 1 1 d . . . . .
C24 C 0.46246(11) 0.9384(4) 0.3219(2) 0.0459(8) Uani 1 1 d . . . . .
C25 C 0.46259(12) 1.0731(4) 0.3265(3) 0.0527(9) Uani 1 1 d . . . . .
H25 H 0.4380 1.1224 0.2936 0.063 Uiso 1 1 calc R U . . .
C26 C 0.50114(13) 1.1348(4) 0.3825(3) 0.0541(9) Uani 1 1 d . . . . .
C27 C 0.53762(13) 1.0613(4) 0.4311(3) 0.0580(10) Uani 1 1 d . . . . .
H27 H 0.5629 1.1044 0.4681 0.070 Uiso 1 1 calc R U . . .
C28 C 0.53716(12) 0.9237(4) 0.4254(3) 0.0572(10) Uani 1 1 d . . . . .
H28 H 0.5617 0.8735 0.4576 0.069 Uiso 1 1 calc R U . . .
H1 H 0.2488(12) 0.665(4) 0.337(2) 0.041(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C26 1.880(4) . ?
Cl1 C20 1.783(4) . ?
N1 C1 1.391(5) . ?
N1 C8 1.475(5) . ?
N1 H1 0.80(4) . ?
N2 C21 1.386(5) . ?
N2 C22 1.395(5) . ?
N2 C13 1.461(4) . ?
O1 C21 1.209(4) . ?
O2 C22 1.224(5) . ?
C1 C2 1.394(5) . ?
C1 C6 1.397(5) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(4) . ?
C7 C14 1.529(5) . ?
C7 C11 1.545(4) . ?
C7 C8 1.591(4) . ?
C8 C20 1.522(5) . ?
C8 C9 1.534(5) . ?
C9 C10 1.512(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.515(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.309(5) . ?
C12 C13 1.515(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.389(5) . ?
C14 C19 1.393(5) . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C24 1.500(5) . ?
C22 C23 1.470(5) . ?
C23 C28 1.377(5) . ?
C23 C24 1.380(5) . ?
C24 C25 1.359(5) . ?
C25 C26 1.399(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.380(6) . ?
C27 C28 1.389(6) . ?
C27 H27 0.9300 . ?
C28 H28 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
C1 N1 C8 109.5(3) . . ?
C1 N1 H1 117(3) . . ?
C8 N1 H1 116(3) . . ?
C21 N2 C22 111.4(3) . . ?
C21 N2 C13 122.8(3) . . ?
C22 N2 C13 125.8(3) . . ?
N1 C1 C2 127.2(3) . . ?
N1 C1 C6 111.3(3) . . ?
C2 C1 C6 121.4(3) . . ?
C3 C2 C1 117.3(4) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 122.2(4) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.1(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 C7 130.7(3) . . ?
C1 C6 C7 108.9(3) . . ?
C6 C7 C14 117.1(3) . . ?
C6 C7 C11 109.9(3) . . ?
C14 C7 C11 111.3(3) . . ?
C6 C7 C8 102.0(3) . . ?
C14 C7 C8 112.2(3) . . ?
C11 C7 C8 103.0(2) . . ?
N1 C8 C20 111.4(3) . . ?
N1 C8 C9 111.1(3) . . ?
C20 C8 C9 109.1(3) . . ?
N1 C8 C7 102.7(3) . . ?
C20 C8 C7 117.6(3) . . ?
C9 C8 C7 104.6(3) . . ?
C10 C9 C8 105.6(3) . . ?
C10 C9 H9A 110.6 . . ?
C8 C9 H9A 110.6 . . ?
C10 C9 H9B 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
C9 C10 C11 105.6(3) . . ?
C9 C10 H10A 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C12 C11 C10 127.2(3) . . ?
C12 C11 C7 123.0(3) . . ?
C10 C11 C7 109.8(3) . . ?
C11 C12 C13 125.1(3) . . ?
C11 C12 H12 117.4 . . ?
C13 C12 H12 117.4 . . ?
N2 C13 C12 111.7(3) . . ?
N2 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C19 117.4(3) . . ?
C15 C14 C7 120.4(3) . . ?
C19 C14 C7 122.2(3) . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 120.4(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 119.1(4) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C8 C20 Cl1 114.8(3) . . ?
C8 C20 H20A 108.6 . . ?
Cl1 C20 H20A 108.6 . . ?
C8 C20 H20B 108.6 . . ?
Cl1 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
O1 C21 N2 125.9(3) . . ?
O1 C21 C24 128.4(4) . . ?
N2 C21 C24 105.6(3) . . ?
O2 C22 N2 123.1(3) . . ?
O2 C22 C23 130.0(3) . . ?
N2 C22 C23 106.9(3) . . ?
C28 C23 C24 121.6(4) . . ?
C28 C23 C22 130.5(4) . . ?
C24 C23 C22 107.9(3) . . ?
C25 C24 C23 121.6(3) . . ?
C25 C24 C21 130.2(4) . . ?
C23 C24 C21 108.2(3) . . ?
C24 C25 C26 117.5(4) . . ?
C24 C25 H25 121.3 . . ?
C26 C25 H25 121.3 . . ?
C27 C26 C25 121.1(4) . . ?
C27 C26 Br1 119.9(3) . . ?
C25 C26 Br1 119.0(3) . . ?
C26 C27 C28 120.9(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C23 C28 C27 117.3(4) . . ?
C23 C28 H28 121.3 . . ?
C27 C28 H28 121.3 . . ?

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
C8 N1 C1 C2 -169.0(3) . . . . ?
C8 N1 C1 C6 14.2(4) . . . . ?
N1 C1 C2 C3 -176.0(3) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C4 C5 C6 C7 174.1(3) . . . . ?
N1 C1 C6 C5 176.3(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
N1 C1 C6 C7 1.8(4) . . . . ?
C2 C1 C6 C7 -175.2(3) . . . . ?
C5 C6 C7 C14 48.2(5) . . . . ?
C1 C6 C7 C14 -138.1(3) . . . . ?
C5 C6 C7 C11 -80.2(4) . . . . ?
C1 C6 C7 C11 93.5(3) . . . . ?
C5 C6 C7 C8 171.0(3) . . . . ?
C1 C6 C7 C8 -15.3(3) . . . . ?
C1 N1 C8 C20 104.0(3) . . . . ?
C1 N1 C8 C9 -134.2(3) . . . . ?
C1 N1 C8 C7 -22.8(3) . . . . ?
C6 C7 C8 N1 22.3(3) . . . . ?
C14 C7 C8 N1 148.4(3) . . . . ?
C11 C7 C8 N1 -91.7(3) . . . . ?
C6 C7 C8 C20 -100.4(3) . . . . ?
C14 C7 C8 C20 25.7(4) . . . . ?
C11 C7 C8 C20 145.6(3) . . . . ?
C6 C7 C8 C9 138.4(3) . . . . ?
C14 C7 C8 C9 -95.5(3) . . . . ?
C11 C7 C8 C9 24.4(3) . . . . ?
N1 C8 C9 C10 76.0(4) . . . . ?
C20 C8 C9 C10 -160.8(3) . . . . ?
C7 C8 C9 C10 -34.2(4) . . . . ?
C8 C9 C10 C11 30.2(4) . . . . ?
C9 C10 C11 C12 166.0(4) . . . . ?
C9 C10 C11 C7 -14.4(4) . . . . ?
C6 C7 C11 C12 65.2(4) . . . . ?
C14 C7 C11 C12 -66.3(4) . . . . ?
C8 C7 C11 C12 173.2(3) . . . . ?
C6 C7 C11 C10 -114.4(3) . . . . ?
C14 C7 C11 C10 114.1(3) . . . . ?
C8 C7 C11 C10 -6.4(4) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
C7 C11 C12 C13 -179.9(3) . . . . ?
C21 N2 C13 C12 -89.4(4) . . . . ?
C22 N2 C13 C12 90.2(4) . . . . ?
C11 C12 C13 N2 115.4(4) . . . . ?
C6 C7 C14 C15 -160.5(3) . . . . ?
C11 C7 C14 C15 -32.8(4) . . . . ?
C8 C7 C14 C15 82.1(4) . . . . ?
C6 C7 C14 C19 23.1(4) . . . . ?
C11 C7 C14 C19 150.8(3) . . . . ?
C8 C7 C14 C19 -94.3(4) . . . . ?
C19 C14 C15 C16 1.1(5) . . . . ?
C7 C14 C15 C16 -175.4(3) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 C14 -0.2(5) . . . . ?
C15 C14 C19 C18 -0.5(5) . . . . ?
C7 C14 C19 C18 175.9(3) . . . . ?
N1 C8 C20 Cl1 -47.4(4) . . . . ?
C9 C8 C20 Cl1 -170.4(3) . . . . ?
C7 C8 C20 Cl1 70.8(4) . . . . ?
C22 N2 C21 O1 179.7(3) . . . . ?
C13 N2 C21 O1 -0.7(5) . . . . ?
C22 N2 C21 C24 -0.2(4) . . . . ?
C13 N2 C21 C24 179.4(3) . . . . ?
C21 N2 C22 O2 -178.8(3) . . . . ?
C13 N2 C22 O2 1.6(5) . . . . ?
C21 N2 C22 C23 0.7(4) . . . . ?
C13 N2 C22 C23 -178.9(3) . . . . ?
O2 C22 C23 C28 -0.6(7) . . . . ?
N2 C22 C23 C28 179.9(4) . . . . ?
O2 C22 C23 C24 178.5(4) . . . . ?
N2 C22 C23 C24 -1.0(4) . . . . ?
C28 C23 C24 C25 0.0(6) . . . . ?
C22 C23 C24 C25 -179.2(3) . . . . ?
C28 C23 C24 C21 -179.9(3) . . . . ?
C22 C23 C24 C21 0.9(4) . . . . ?
O1 C21 C24 C25 -0.3(6) . . . . ?
N2 C21 C24 C25 179.6(4) . . . . ?
O1 C21 C24 C23 179.6(4) . . . . ?
N2 C21 C24 C23 -0.5(4) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C21 C24 C25 C26 179.7(3) . . . . ?
C24 C25 C26 C27 0.1(6) . . . . ?
C24 C25 C26 Br1 -179.6(3) . . . . ?
C25 C26 C27 C28 0.2(6) . . . . ?
Br1 C26 C27 C28 180.0(3) . . . . ?
C24 C23 C28 C27 0.4(6) . . . . ?
C22 C23 C28 C27 179.3(4) . . . . ?
C26 C27 C28 C23 -0.5(6) . . . . ?

_refine_diff_density_max         0.505
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cu_d8v17419_0m
_database_code_depnum_ccdc_archive 'CCDC 1579529'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38

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'

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

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

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

_cell_length_a                   14.0718(2)
_cell_length_b                   7.93280(10)
_cell_length_c                   14.6162(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.8680(10)
_cell_angle_gamma                90
_cell_volume                     1629.55(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8147
_cell_measurement_theta_min      6.054
_cell_measurement_theta_max      132.837

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.636
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29472
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.027
_diffrn_reflns_theta_max         65.497
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             5544
_reflns_number_gt                4427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.925

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

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+0.7050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1670 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5544
_refine_ls_number_parameters     430
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.052
_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
N1 N 0.2820(3) 0.3777(5) 0.8111(3) 0.0516(9) Uani 1 1 d . . . . .
N2 N 0.1398(3) 0.7199(6) 0.4153(3) 0.0582(11) Uani 1 1 d . . . . .
O1 O 0.1196(4) 0.5922(6) 0.7872(3) 0.1000(16) Uani 1 1 d . . . . .
H1 H 0.0955 0.5175 0.7550 0.150 Uiso 1 1 calc R U . . .
O2 O 0.0786(3) 0.2593(6) 0.6930(2) 0.0814(12) Uani 1 1 d . . . . .
H2 H 0.0910 0.2471 0.6392 0.122 Uiso 1 1 calc R U . . .
O3 O 0.0457(3) 0.6439(7) 0.5870(3) 0.0904(14) Uani 1 1 d D . . . .
H3 H 0.0496 0.5610 0.5429 0.108 Uiso 1 1 d DR U . . .
O4 O 0.0947(3) 0.3047(6) 0.5063(3) 0.0875(14) Uani 1 1 d . . . . .
C1 C 0.3652(3) 0.3438(5) 0.8652(3) 0.0478(11) Uani 1 1 d . . . . .
C2 C 0.4586(3) 0.3574(6) 0.8392(4) 0.0564(12) Uani 1 1 d . . . . .
H2A H 0.4723 0.4011 0.7823 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5307(4) 0.3038(7) 0.9008(4) 0.0667(15) Uani 1 1 d . . . . .
H3A H 0.5936 0.3100 0.8843 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5110(4) 0.2414(7) 0.9861(4) 0.0698(15) Uani 1 1 d . . . . .
H4A H 0.5604 0.2070 1.0264 0.084 Uiso 1 1 calc R U . . .
C5 C 0.4181(3) 0.2301(6) 1.0116(3) 0.0572(12) Uani 1 1 d . . . . .
H5 H 0.4047 0.1874 1.0688 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3453(3) 0.2828(5) 0.9515(3) 0.0481(11) Uani 1 1 d . . . . .
C7 C 0.2383(3) 0.2741(5) 0.9592(3) 0.0428(10) Uani 1 1 d . . . . .
C8 C 0.1979(3) 0.3620(6) 0.8674(3) 0.0450(10) Uani 1 1 d . . . . .
C9 C 0.1359(3) 0.2025(6) 0.8451(3) 0.0469(11) Uani 1 1 d . . . . .
H9 H 0.0712 0.2212 0.8648 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1938(3) 0.1074(5) 0.9200(3) 0.0455(10) Uani 1 1 d . . . . .
C11 C 0.2482(4) -0.0508(6) 0.9060(4) 0.0585(13) Uani 1 1 d . . . . .
H11A H 0.3133 -0.0560 0.9310 0.070 Uiso 1 1 calc R U . . .
H11B H 0.2365 -0.1110 0.8488 0.070 Uiso 1 1 calc R U . . .
C12 C 0.1703(4) -0.0468(6) 0.9719(3) 0.0582(13) Uani 1 1 d . . . . .
H12A H 0.1114 -0.1048 0.9545 0.070 Uiso 1 1 calc R U . . .
H12B H 0.1882 -0.0498 1.0368 0.070 Uiso 1 1 calc R U . . .
C13 C 0.1995(3) 0.3447(6) 1.0454(3) 0.0459(10) Uani 1 1 d . . . . .
C14 C 0.2481(4) 0.4714(7) 1.0934(3) 0.0632(14) Uani 1 1 d . . . . .
H14 H 0.3076 0.5058 1.0754 0.076 Uiso 1 1 calc R U . . .
C15 C 0.2086(4) 0.5475(8) 1.1683(4) 0.0754(16) Uani 1 1 d . . . . .
H15 H 0.2411 0.6339 1.1994 0.090 Uiso 1 1 calc R U . . .
C16 C 0.1217(5) 0.4959(8) 1.1967(4) 0.0735(16) Uani 1 1 d . . . . .
H16 H 0.0958 0.5464 1.2472 0.088 Uiso 1 1 calc R U . . .
C17 C 0.0734(4) 0.3703(8) 1.1505(3) 0.0673(14) Uani 1 1 d . . . . .
H17 H 0.0147 0.3349 1.1698 0.081 Uiso 1 1 calc R U . . .
C18 C 0.1115(3) 0.2957(6) 1.0753(3) 0.0549(12) Uani 1 1 d . . . . .
H18 H 0.0776 0.2111 1.0440 0.066 Uiso 1 1 calc R U . . .
C19 C 0.1460(4) 0.5266(6) 0.8742(4) 0.0628(14) Uani 1 1 d . . . . .
H19A H 0.0894 0.5100 0.9084 0.075 Uiso 1 1 calc R U . . .
H19B H 0.1864 0.6072 0.9074 0.075 Uiso 1 1 calc R U . . .
C20 C 0.1317(4) 0.1385(7) 0.7485(3) 0.0586(13) Uani 1 1 d . . . . .
H20A H 0.1954 0.1263 0.7270 0.070 Uiso 1 1 calc R U . . .
H20B H 0.1006 0.0294 0.7452 0.070 Uiso 1 1 calc R U . . .
C21 C 0.1929(3) 0.8401(6) 0.3704(3) 0.0473(11) Uani 1 1 d . . . . .
C22 C 0.1661(4) 0.9343(6) 0.2938(3) 0.0577(13) Uani 1 1 d . . . . .
H22 H 0.1043 0.9292 0.2684 0.069 Uiso 1 1 calc R U . . .
C23 C 0.2336(4) 1.0366(7) 0.2557(3) 0.0623(14) Uani 1 1 d . . . . .
H23 H 0.2164 1.1010 0.2044 0.075 Uiso 1 1 calc R U . . .
C24 C 0.3244(4) 1.0446(7) 0.2919(3) 0.0634(14) Uani 1 1 d . . . . .
H24 H 0.3686 1.1128 0.2644 0.076 Uiso 1 1 calc R U . . .
C25 C 0.3518(4) 0.9519(6) 0.3694(3) 0.0536(12) Uani 1 1 d . . . . .
H25 H 0.4140 0.9575 0.3940 0.064 Uiso 1 1 calc R U . . .
C26 C 0.2854(3) 0.8513(6) 0.4095(3) 0.0446(10) Uani 1 1 d . . . . .
C27 C 0.2937(3) 0.7363(5) 0.4918(3) 0.0430(10) Uani 1 1 d . . . . .
C28 C 0.1879(3) 0.6733(6) 0.5036(3) 0.0520(12) Uani 1 1 d . . . . .
C29 C 0.2259(4) 0.4864(6) 0.5057(3) 0.0562(12) Uani 1 1 d . . . . .
H29 H 0.2383 0.4517 0.5695 0.067 Uiso 1 1 calc R U . . .
C30 C 0.3171(3) 0.5497(6) 0.4678(3) 0.0516(11) Uani 1 1 d . . . . .
C31 C 0.3553(4) 0.4941(7) 0.3785(4) 0.0690(15) Uani 1 1 d . . . . .
H31A H 0.3775 0.5805 0.3377 0.083 Uiso 1 1 calc R U . . .
H31B H 0.3256 0.3976 0.3480 0.083 Uiso 1 1 calc R U . . .
C32 C 0.4124(4) 0.4634(8) 0.4669(4) 0.0743(16) Uani 1 1 d . . . . .
H32A H 0.4169 0.3486 0.4895 0.089 Uiso 1 1 calc R U . . .
H32B H 0.4689 0.5316 0.4792 0.089 Uiso 1 1 calc R U . . .
C33 C 0.3439(3) 0.8088(6) 0.5772(3) 0.0443(10) Uani 1 1 d . . . . .
C34 C 0.3420(4) 0.9803(6) 0.5932(3) 0.0550(12) Uani 1 1 d . . . . .
H34 H 0.3130 1.0512 0.5495 0.066 Uiso 1 1 calc R U . . .
C35 C 0.3825(4) 1.0484(7) 0.6728(3) 0.0641(14) Uani 1 1 d . . . . .
H35 H 0.3811 1.1645 0.6818 0.077 Uiso 1 1 calc R U . . .
C36 C 0.4249(4) 0.9462(7) 0.7393(3) 0.0634(14) Uani 1 1 d . . . . .
H36 H 0.4523 0.9923 0.7929 0.076 Uiso 1 1 calc R U . . .
C37 C 0.4261(4) 0.7756(7) 0.7251(3) 0.0624(14) Uani 1 1 d . . . . .
H37 H 0.4536 0.7051 0.7698 0.075 Uiso 1 1 calc R U . . .
C38 C 0.3870(3) 0.7074(6) 0.6451(3) 0.0539(12) Uani 1 1 d . . . . .
H38 H 0.3894 0.5914 0.6363 0.065 Uiso 1 1 calc R U . . .
C39 C 0.1358(3) 0.7314(8) 0.5837(3) 0.0676(14) Uani 1 1 d . . . . .
H39A H 0.1739 0.7099 0.6396 0.081 Uiso 1 1 calc R U . . .
H39B H 0.1247 0.8518 0.5792 0.081 Uiso 1 1 calc R U . . .
C40 C 0.1715(3) 0.3503(7) 0.4555(4) 0.0646(13) Uani 1 1 d . . . . .
H40A H 0.1490 0.3904 0.3955 0.077 Uiso 1 1 calc R U . . .
H40B H 0.2122 0.2535 0.4472 0.077 Uiso 1 1 calc R U . . .
H4 H 0.049(5) 0.232(11) 0.466(5) 0.13(3) Uiso 1 1 d . . . . .
H1B H 0.280(4) 0.483(9) 0.770(4) 0.10(2) Uiso 1 1 d . . . . .
H2B H 0.078(4) 0.755(8) 0.422(4) 0.09(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.407(6) . ?
N1 C8 1.480(5) . ?
N1 H1B 1.03(7) . ?
N2 C21 1.396(6) . ?
N2 C28 1.474(5) . ?
N2 H2B 0.92(6) . ?
O1 C19 1.406(6) . ?
O1 H1 0.8200 . ?
O2 C20 1.439(6) . ?
O2 H2 0.8200 . ?
O3 C39 1.449(6) . ?
O3 H3 0.9248 . ?
O4 C40 1.390(6) . ?
O4 H4 1.03(8) . ?
C1 C2 1.390(6) . ?
C1 C6 1.393(6) . ?
C2 C3 1.389(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.382(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.517(6) . ?
C7 C13 1.505(6) . ?
C7 C10 1.560(6) . ?
C7 C8 1.592(6) . ?
C8 C19 1.503(6) . ?
C8 C9 1.562(6) . ?
C9 C20 1.499(6) . ?
C9 C10 1.530(6) . ?
C9 H9 0.9800 . ?
C10 C12 1.485(6) . ?
C10 C11 1.489(6) . ?
C11 C12 1.496(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.390(6) . ?
C13 C14 1.387(7) . ?
C14 C15 1.391(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.383(6) . ?
C21 C26 1.398(6) . ?
C22 C23 1.386(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.359(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.510(6) . ?
C27 C33 1.516(6) . ?
C27 C30 1.560(6) . ?
C27 C28 1.588(6) . ?
C28 C39 1.486(7) . ?
C28 C29 1.576(7) . ?
C29 C40 1.495(7) . ?
C29 C30 1.509(7) . ?
C29 H29 0.9800 . ?
C30 C31 1.503(7) . ?
C30 C32 1.506(7) . ?
C31 C32 1.507(7) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.381(7) . ?
C33 C38 1.393(6) . ?
C34 C35 1.380(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.378(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.370(8) . ?
C36 H36 0.9300 . ?
C37 C38 1.378(6) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?

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
C1 N1 C8 109.7(3) . . ?
C1 N1 H1B 119(3) . . ?
C8 N1 H1B 113(3) . . ?
C21 N2 C28 110.5(4) . . ?
C21 N2 H2B 112(4) . . ?
C28 N2 H2B 112(4) . . ?
C19 O1 H1 109.5 . . ?
C20 O2 H2 109.5 . . ?
C39 O3 H3 103.6 . . ?
C40 O4 H4 109(4) . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 N1 127.1(4) . . ?
C6 C1 N1 112.1(4) . . ?
C3 C2 C1 118.0(5) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C4 C3 C2 121.4(5) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 C7 130.3(4) . . ?
C1 C6 C7 109.2(4) . . ?
C13 C7 C6 116.6(4) . . ?
C13 C7 C10 117.9(4) . . ?
C6 C7 C10 113.1(3) . . ?
C13 C7 C8 114.4(3) . . ?
C6 C7 C8 103.4(3) . . ?
C10 C7 C8 86.6(3) . . ?
N1 C8 C19 111.6(4) . . ?
N1 C8 C9 113.9(4) . . ?
C19 C8 C9 116.7(4) . . ?
N1 C8 C7 104.2(3) . . ?
C19 C8 C7 118.6(4) . . ?
C9 C8 C7 89.6(3) . . ?
C20 C9 C10 120.1(4) . . ?
C20 C9 C8 117.8(4) . . ?
C10 C9 C8 88.8(3) . . ?
C20 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C8 C9 H9 109.5 . . ?
C12 C10 C11 60.4(3) . . ?
C12 C10 C9 130.3(4) . . ?
C11 C10 C9 125.2(4) . . ?
C12 C10 C7 127.3(4) . . ?
C11 C10 C7 124.4(4) . . ?
C9 C10 C7 92.0(3) . . ?
C10 C11 C12 59.7(3) . . ?
C10 C11 H11A 117.8 . . ?
C12 C11 H11A 117.8 . . ?
C10 C11 H11B 117.8 . . ?
C12 C11 H11B 117.8 . . ?
H11A C11 H11B 114.9 . . ?
C10 C12 C11 59.9(3) . . ?
C10 C12 H12A 117.8 . . ?
C11 C12 H12A 117.8 . . ?
C10 C12 H12B 117.8 . . ?
C11 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C18 C13 C14 117.9(4) . . ?
C18 C13 C7 121.7(4) . . ?
C14 C13 C7 120.2(4) . . ?
C13 C14 C15 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.4(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.8(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.2(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 121.2(5) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
O1 C19 C8 111.7(4) . . ?
O1 C19 H19A 109.3 . . ?
C8 C19 H19A 109.3 . . ?
O1 C19 H19B 109.3 . . ?
C8 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
O2 C20 C9 107.5(4) . . ?
O2 C20 H20A 110.2 . . ?
C9 C20 H20A 110.2 . . ?
O2 C20 H20B 110.2 . . ?
C9 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C22 C21 N2 128.3(4) . . ?
C22 C21 C26 120.4(4) . . ?
N2 C21 C26 111.1(4) . . ?
C21 C22 C23 118.5(5) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C24 C23 C22 121.4(5) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 120.6(5) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 119.0(5) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C21 120.0(4) . . ?
C25 C26 C27 131.3(4) . . ?
C21 C26 C27 108.7(4) . . ?
C26 C27 C33 116.2(4) . . ?
C26 C27 C30 113.8(4) . . ?
C33 C27 C30 116.7(4) . . ?
C26 C27 C28 103.9(3) . . ?
C33 C27 C28 115.5(3) . . ?
C30 C27 C28 86.3(3) . . ?
N2 C28 C39 112.9(4) . . ?
N2 C28 C29 113.2(4) . . ?
C39 C28 C29 117.1(4) . . ?
N2 C28 C27 102.6(4) . . ?
C39 C28 C27 119.4(4) . . ?
C29 C28 C27 88.8(3) . . ?
C40 C29 C30 119.0(4) . . ?
C40 C29 C28 120.4(4) . . ?
C30 C29 C28 88.5(4) . . ?
C40 C29 H29 109.1 . . ?
C30 C29 H29 109.1 . . ?
C28 C29 H29 109.1 . . ?
C31 C30 C32 60.1(3) . . ?
C31 C30 C29 124.7(4) . . ?
C32 C30 C29 128.8(5) . . ?
C31 C30 C27 124.2(4) . . ?
C32 C30 C27 129.1(4) . . ?
C29 C30 C27 92.3(4) . . ?
C30 C31 C32 60.1(3) . . ?
C30 C31 H31A 117.8 . . ?
C32 C31 H31A 117.8 . . ?
C30 C31 H31B 117.8 . . ?
C32 C31 H31B 117.8 . . ?
H31A C31 H31B 114.9 . . ?
C30 C32 C31 59.8(3) . . ?
C30 C32 H32A 117.8 . . ?
C31 C32 H32A 117.8 . . ?
C30 C32 H32B 117.8 . . ?
C31 C32 H32B 117.8 . . ?
H32A C32 H32B 114.9 . . ?
C34 C33 C38 117.4(4) . . ?
C34 C33 C27 120.1(4) . . ?
C38 C33 C27 122.4(4) . . ?
C33 C34 C35 121.2(5) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C36 C35 C34 120.7(5) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C37 C36 C35 118.9(5) . . ?
C37 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
C36 C37 C38 120.6(5) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C33 121.3(5) . . ?
C37 C38 H38 119.4 . . ?
C33 C38 H38 119.4 . . ?
O3 C39 C28 110.2(5) . . ?
O3 C39 H39A 109.6 . . ?
C28 C39 H39A 109.6 . . ?
O3 C39 H39B 109.6 . . ?
C28 C39 H39B 109.6 . . ?
H39A C39 H39B 108.1 . . ?
O4 C40 C29 108.6(4) . . ?
O4 C40 H40A 110.0 . . ?
C29 C40 H40A 110.0 . . ?
O4 C40 H40B 110.0 . . ?
C29 C40 H40B 110.0 . . ?
H40A C40 H40B 108.4 . . ?

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
C8 N1 C1 C2 -175.0(4) . . . . ?
C8 N1 C1 C6 8.4(5) . . . . ?
C6 C1 C2 C3 1.9(7) . . . . ?
N1 C1 C2 C3 -174.5(4) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C4 C5 C6 C1 1.2(7) . . . . ?
C4 C5 C6 C7 175.6(5) . . . . ?
C2 C1 C6 C5 -2.0(7) . . . . ?
N1 C1 C6 C5 175.0(4) . . . . ?
C2 C1 C6 C7 -177.4(4) . . . . ?
N1 C1 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C13 51.9(7) . . . . ?
C1 C6 C7 C13 -133.3(4) . . . . ?
C5 C6 C7 C10 -89.6(6) . . . . ?
C1 C6 C7 C10 85.2(4) . . . . ?
C5 C6 C7 C8 178.4(5) . . . . ?
C1 C6 C7 C8 -6.8(5) . . . . ?
C1 N1 C8 C19 117.2(4) . . . . ?
C1 N1 C8 C9 -108.0(4) . . . . ?
C1 N1 C8 C7 -12.0(5) . . . . ?
C13 C7 C8 N1 139.0(4) . . . . ?
C6 C7 C8 N1 11.1(4) . . . . ?
C10 C7 C8 N1 -101.8(4) . . . . ?
C13 C7 C8 C19 14.2(6) . . . . ?
C6 C7 C8 C19 -113.7(4) . . . . ?
C10 C7 C8 C19 133.4(4) . . . . ?
C13 C7 C8 C9 -106.4(4) . . . . ?
C6 C7 C8 C9 125.8(3) . . . . ?
C10 C7 C8 C9 12.8(3) . . . . ?
N1 C8 C9 C20 -31.5(5) . . . . ?
C19 C8 C9 C20 100.9(5) . . . . ?
C7 C8 C9 C20 -136.8(4) . . . . ?
N1 C8 C9 C10 92.3(4) . . . . ?
C19 C8 C9 C10 -135.3(4) . . . . ?
C7 C8 C9 C10 -13.1(3) . . . . ?
C20 C9 C10 C12 -79.4(6) . . . . ?
C8 C9 C10 C12 158.9(5) . . . . ?
C20 C9 C10 C11 -0.6(7) . . . . ?
C8 C9 C10 C11 -122.4(5) . . . . ?
C20 C9 C10 C7 135.1(4) . . . . ?
C8 C9 C10 C7 13.3(3) . . . . ?
C13 C7 C10 C12 -44.3(6) . . . . ?
C6 C7 C10 C12 96.7(5) . . . . ?
C8 C7 C10 C12 -160.2(4) . . . . ?
C13 C7 C10 C11 -120.9(5) . . . . ?
C6 C7 C10 C11 20.0(6) . . . . ?
C8 C7 C10 C11 123.2(4) . . . . ?
C13 C7 C10 C9 102.9(4) . . . . ?
C6 C7 C10 C9 -116.2(4) . . . . ?
C8 C7 C10 C9 -13.1(3) . . . . ?
C9 C10 C11 C12 -120.7(5) . . . . ?
C7 C10 C11 C12 117.1(5) . . . . ?
C9 C10 C12 C11 112.8(5) . . . . ?
C7 C10 C12 C11 -112.6(5) . . . . ?
C6 C7 C13 C18 -157.8(4) . . . . ?
C10 C7 C13 C18 -18.2(6) . . . . ?
C8 C7 C13 C18 81.4(5) . . . . ?
C6 C7 C13 C14 27.3(6) . . . . ?
C10 C7 C13 C14 166.9(4) . . . . ?
C8 C7 C13 C14 -93.5(5) . . . . ?
C18 C13 C14 C15 -0.8(7) . . . . ?
C7 C13 C14 C15 174.2(5) . . . . ?
C13 C14 C15 C16 1.2(9) . . . . ?
C14 C15 C16 C17 -0.7(9) . . . . ?
C15 C16 C17 C18 -0.3(8) . . . . ?
C16 C17 C18 C13 0.7(8) . . . . ?
C14 C13 C18 C17 -0.1(7) . . . . ?
C7 C13 C18 C17 -175.1(4) . . . . ?
N1 C8 C19 O1 55.6(6) . . . . ?
C9 C8 C19 O1 -77.9(5) . . . . ?
C7 C8 C19 O1 176.6(4) . . . . ?
C10 C9 C20 O2 -175.8(4) . . . . ?
C8 C9 C20 O2 -69.7(5) . . . . ?
C28 N2 C21 C22 -169.2(5) . . . . ?
C28 N2 C21 C26 14.6(6) . . . . ?
N2 C21 C22 C23 -174.5(5) . . . . ?
C26 C21 C22 C23 1.5(7) . . . . ?
C21 C22 C23 C24 0.4(8) . . . . ?
C22 C23 C24 C25 -1.1(8) . . . . ?
C23 C24 C25 C26 -0.1(7) . . . . ?
C24 C25 C26 C21 1.9(7) . . . . ?
C24 C25 C26 C27 179.1(5) . . . . ?
C22 C21 C26 C25 -2.6(7) . . . . ?
N2 C21 C26 C25 174.0(4) . . . . ?
C22 C21 C26 C27 179.6(4) . . . . ?
N2 C21 C26 C27 -3.8(5) . . . . ?
C25 C26 C27 C33 47.2(6) . . . . ?
C21 C26 C27 C33 -135.3(4) . . . . ?
C25 C26 C27 C30 -92.7(6) . . . . ?
C21 C26 C27 C30 84.8(4) . . . . ?
C25 C26 C27 C28 175.2(5) . . . . ?
C21 C26 C27 C28 -7.3(5) . . . . ?
C21 N2 C28 C39 111.8(5) . . . . ?
C21 N2 C28 C29 -112.2(5) . . . . ?
C21 N2 C28 C27 -18.0(5) . . . . ?
C26 C27 C28 N2 14.8(5) . . . . ?
C33 C27 C28 N2 143.3(4) . . . . ?
C30 C27 C28 N2 -98.8(4) . . . . ?
C26 C27 C28 C39 -110.9(5) . . . . ?
C33 C27 C28 C39 17.6(6) . . . . ?
C30 C27 C28 C39 135.5(5) . . . . ?
C26 C27 C28 C29 128.3(4) . . . . ?
C33 C27 C28 C29 -103.2(4) . . . . ?
C30 C27 C28 C29 14.7(3) . . . . ?
N2 C28 C29 C40 -35.1(6) . . . . ?
C39 C28 C29 C40 98.9(5) . . . . ?
C27 C28 C29 C40 -138.3(5) . . . . ?
N2 C28 C29 C30 88.0(4) . . . . ?
C39 C28 C29 C30 -138.0(4) . . . . ?
C27 C28 C29 C30 -15.2(3) . . . . ?
C40 C29 C30 C31 4.4(7) . . . . ?
C28 C29 C30 C31 -119.9(5) . . . . ?
C40 C29 C30 C32 -72.8(6) . . . . ?
C28 C29 C30 C32 162.9(5) . . . . ?
C40 C29 C30 C27 139.8(4) . . . . ?
C28 C29 C30 C27 15.5(3) . . . . ?
C26 C27 C30 C31 16.7(6) . . . . ?
C33 C27 C30 C31 -122.9(5) . . . . ?
C28 C27 C30 C31 120.3(5) . . . . ?
C26 C27 C30 C32 93.8(6) . . . . ?
C33 C27 C30 C32 -45.9(7) . . . . ?
C28 C27 C30 C32 -162.6(5) . . . . ?
C26 C27 C30 C29 -119.0(4) . . . . ?
C33 C27 C30 C29 101.3(4) . . . . ?
C28 C27 C30 C29 -15.4(3) . . . . ?
C29 C30 C31 C32 -118.7(6) . . . . ?
C27 C30 C31 C32 119.3(5) . . . . ?
C29 C30 C32 C31 112.3(6) . . . . ?
C27 C30 C32 C31 -111.6(6) . . . . ?
C26 C27 C33 C34 28.4(6) . . . . ?
C30 C27 C33 C34 167.1(4) . . . . ?
C28 C27 C33 C34 -93.7(5) . . . . ?
C26 C27 C33 C38 -156.4(4) . . . . ?
C30 C27 C33 C38 -17.7(6) . . . . ?
C28 C27 C33 C38 81.5(5) . . . . ?
C38 C33 C34 C35 0.9(7) . . . . ?
C27 C33 C34 C35 176.3(4) . . . . ?
C33 C34 C35 C36 -0.9(8) . . . . ?
C34 C35 C36 C37 -0.1(8) . . . . ?
C35 C36 C37 C38 1.1(9) . . . . ?
C36 C37 C38 C33 -1.1(8) . . . . ?
C34 C33 C38 C37 0.1(7) . . . . ?
C27 C33 C38 C37 -175.3(4) . . . . ?
N2 C28 C39 O3 66.1(6) . . . . ?
C29 C28 C39 O3 -68.0(5) . . . . ?
C27 C28 C39 O3 -173.2(4) . . . . ?
C30 C29 C40 O4 175.7(4) . . . . ?
C28 C29 C40 O4 -77.5(6) . . . . ?

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
O4 H4 O3 1.03(8) 1.66(8) 2.669(5) 166(7) 2_546
C39 H39A O1 0.97 2.50 3.191(6) 127.7 .
O2 H2 O4 0.82 2.00 2.773(5) 157.3 .
O1 H1 O2 0.82 2.25 3.021(7) 157.3 .
O4 H4 O3 1.03(8) 1.66(8) 2.669(5) 166(7) 2_546
C39 H39A O1 0.97 2.50 3.191(6) 127.7 .
O2 H2 O4 0.82 2.00 2.773(5) 157.3 .
O1 H1 O2 0.82 2.25 3.021(7) 157.3 .
O1 H1 O2 0.82 2.25 3.021(7) 157.3 .
O2 H2 O4 0.82 2.00 2.773(5) 157.3 .
C39 H39A O1 0.97 2.50 3.191(6) 127.7 .
O4 H4 O3 1.03(8) 1.66(8) 2.669(5) 166(7) 2_546
O1 H1 O2 0.82 2.25 3.021(7) 157.3 .
O2 H2 O4 0.82 2.00 2.773(5) 157.3 .
C39 H39A O1 0.97 2.50 3.191(6) 127.7 .
O4 H4 O3 1.03(8) 1.66(8) 2.669(5) 166(7) 2_546
O1 H1 O2 0.82 2.25 3.021(7) 157.3 .
O2 H2 O4 0.82 2.00 2.773(5) 157.3 .
C39 H39A O1 0.97 2.50 3.191(6) 127.7 .
O4 H4 O3 1.03(8) 1.66(8) 2.669(5) 166(7) 2_546

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4

