# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

data_str1326
_audit_creation_date             2013-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
;
_shelxl_version_number           2013-4
_publ_contact_author_address     ?
_publ_contact_author_email       ?
_publ_contact_author_phone       ?
_publ_section_references         
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H16 N O4, B F4, H2 O'
_chemical_formula_sum            'C23 H18 B F4 N O5'
_chemical_formula_weight         475.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H16 N O2 B F4'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.16287(15)
_cell_length_b                   14.4364(2)
_cell_length_c                   20.3056(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.7873(18)
_cell_angle_gamma                90
_cell_volume                     2085.01(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7804
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.9887
_cell_measurement_theta_min      3.0586
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.041
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20025
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.136
_diffrn_reflns_theta_min         3.766
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0050976000
_diffrn_orient_matrix_UB_12      -0.0867870000
_diffrn_orient_matrix_UB_13      0.0439350000
_diffrn_orient_matrix_UB_21      0.1414994000
_diffrn_orient_matrix_UB_22      -0.0483501000
_diffrn_orient_matrix_UB_23      -0.0401884000
_diffrn_orient_matrix_UB_31      0.1637467000
_diffrn_orient_matrix_UB_32      0.0389618000
_diffrn_orient_matrix_UB_33      0.0479292000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3457
_reflns_number_total             4053
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²+1.5571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.053) H6(0.028) H21(0.029) H13(0.031) H9(0.029) H10(0.034)
 H18(0.035) H3(0.029) H11(0.037) H23(0.035) H22(0.033) H14(0.038) H15(0.047)
 H12(0.036) H17(0.043) H5A(0.082) H5B(0.082) H16(0.046)
 Fixed X: H2(0.0455) H6(0.1702) H21(-0.0058) H13(0.2133) H9(0.2461)
 H10(0.3556) H18(0.0332) H3(-0.011) H11(0.3974) H23(0.1071) H22(0.1197) H14(-
 0.0531) H15(-0.1285) H12(0.3273) H17(-0.0424) H5A(0.5958) H5B(0.5287) H16(-
 0.1222)
 Fixed Y: H2(1.2025) H6(1.0662) H21(0.8644) H13(0.8192) H9(1.0941) H10(1.1156)
 H18(0.7067) H3(1.1583) H11(0.9893) H23(1.0546) H22(0.9533) H14(0.7089)
 H15(0.5529) H12(0.8415) H17(0.5508) H5A(0.4037) H5B(0.3497) H16(0.4741)
 Fixed Z: H2(0.434) H6(0.122) H21(0.2376) H13(-0.0124) H9(0.0219) H10(-0.0795)
 H18(0.2474) H3(0.1868) H11(-0.1469) H23(0.4042) H22(0.3184) H14(0.0475)
 H15(0.048) H12(-0.1132) H17(0.2464) H5A(-0.006) H5B(0.0426) H16(0.1474)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.0234(2) 1.22928(10) 0.39833(8) 0.0352(4) Uani 1 1 d . . . . .
H2 H 0.0455 1.2025 0.4340 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1392(3) 1.00470(13) 0.12906(9) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.1702 1.0662 0.1220 0.028 Uiso 1 1 calc R U . . .
O4 O -0.1879(2) 1.30221(11) 0.21950(9) 0.0407(4) Uani 1 1 d . . . . .
C19 C -0.0018(3) 0.72391(13) 0.14746(10) 0.0251(4) Uani 1 1 d . . . . .
N1 N -0.0637(3) 1.29185(12) 0.26641(9) 0.0304(4) Uani 1 1 d . . . . .
O3 O 0.0091(3) 1.35565(11) 0.29967(9) 0.0458(5) Uani 1 1 d . . . . .
C7 C 0.1531(3) 0.93981(12) 0.08035(9) 0.0217(4) Uani 1 1 d . . . . .
C20 C 0.0468(3) 0.82232(13) 0.14771(9) 0.0227(4) Uani 1 1 d . . . . .
C5 C 0.0781(3) 0.97809(13) 0.18948(10) 0.0232(4) Uani 1 1 d . . . . .
C21 C 0.0332(3) 0.88430(13) 0.19789(10) 0.0245(4) Uani 1 1 d . . . . .
H21 H -0.0058 0.8644 0.2376 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2187(3) 0.95419(13) 0.01553(9) 0.0219(4) Uani 1 1 d . . . . .
C13 C 0.2427(3) 0.87858(14) -0.02561(10) 0.0258(4) Uani 1 1 d . . . . .
H13 H 0.2133 0.8192 -0.0124 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2619(3) 1.04346(13) -0.00519(10) 0.0243(4) Uani 1 1 d . . . . .
H9 H 0.2461 1.0941 0.0219 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3277(3) 1.05629(15) -0.06573(10) 0.0281(4) Uani 1 1 d . . . . .
H10 H 0.3556 1.1156 -0.0795 0.034 Uiso 1 1 calc R U . . .
C18 C 0.0011(3) 0.67611(14) 0.20731(11) 0.0295(4) Uani 1 1 d . . . . .
H18 H 0.0332 0.7067 0.2474 0.035 Uiso 1 1 calc R U . . .
C4 C 0.0595(3) 1.04452(13) 0.24291(10) 0.0247(4) Uani 1 1 d . . . . .
C3 C 0.0117(3) 1.13700(13) 0.23026(10) 0.0242(4) Uani 1 1 d . . . . .
H3 H -0.0110 1.1583 0.1868 0.029 Uiso 1 1 calc R U . . .
C1 C 0.0358(3) 1.16913(14) 0.34890(10) 0.0271(4) Uani 1 1 d . . . . .
C11 C 0.3524(3) 0.98047(16) -0.10624(10) 0.0307(5) Uani 1 1 d . . . . .
H11 H 0.3974 0.9893 -0.1469 0.037 Uiso 1 1 calc R U . . .
C23 C 0.0823(3) 1.07575(14) 0.36078(10) 0.0295(4) Uani 1 1 d . . . . .
H23 H 0.1071 1.0546 0.4042 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0017(3) 1.19692(13) 0.28258(10) 0.0248(4) Uani 1 1 d . . . . .
C22 C 0.0915(3) 1.01518(14) 0.30922(10) 0.0276(4) Uani 1 1 d . . . . .
H22 H 0.1197 0.9533 0.3184 0.033 Uiso 1 1 calc R U . . .
C14 C -0.0508(3) 0.67729(15) 0.08748(11) 0.0320(5) Uani 1 1 d . . . . .
H14 H -0.0531 0.7089 0.0475 0.038 Uiso 1 1 calc R U . . .
C15 C -0.0958(4) 0.58390(15) 0.08784(13) 0.0394(5) Uani 1 1 d . . . . .
H15 H -0.1285 0.5529 0.0480 0.047 Uiso 1 1 calc R U . . .
C12 C 0.3103(3) 0.89201(15) -0.08608(10) 0.0302(4) Uani 1 1 d . . . . .
H12 H 0.3273 0.8415 -0.1132 0.036 Uiso 1 1 calc R U . . .
C17 C -0.0443(3) 0.58278(15) 0.20660(12) 0.0360(5) Uani 1 1 d . . . . .
H17 H -0.0424 0.5508 0.2464 0.043 Uiso 1 1 calc R U . . .
F1 F 0.1973(3) 0.31532(11) 0.17047(7) 0.0529(4) Uani 1 1 d . . . . .
F2 F 0.2743(3) 0.37120(11) 0.07319(8) 0.0586(5) Uani 1 1 d . . . . .
F3 F -0.0209(3) 0.32233(19) 0.08128(11) 0.0855(7) Uani 1 1 d . . . . .
F4 F 0.2097(4) 0.22027(13) 0.08305(14) 0.1043(10) Uani 1 1 d . . . . .
O5 O 0.6108(3) 0.35350(15) 0.01579(10) 0.0545(5) Uani 1 1 d G . . . .
H5A H 0.5958 0.4037 -0.0060 0.082 Uiso 1 1 d G U . . .
H5B H 0.5287 0.3497 0.0426 0.082 Uiso 1 1 d G U . . .
C16 C -0.0923(4) 0.53679(15) 0.14729(13) 0.0385(5) Uani 1 1 d . . . . .
H16 H -0.1222 0.4741 0.1474 0.046 Uiso 1 1 calc R U . . .
B1 B 0.1689(5) 0.30653(18) 0.10268(14) 0.0398(6) Uani 1 1 d . . . . .
O1 O 0.10582(18) 0.85104(9) 0.09059(6) 0.0227(3) 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
O2 C1 1.338(2) . ?
C6 C7 1.375(3) . ?
C6 C5 1.404(3) . ?
O4 N1 1.233(3) . ?
C19 C20 1.463(3) . ?
C19 C18 1.395(3) . ?
C19 C14 1.399(3) . ?
N1 O3 1.222(3) . ?
N1 C2 1.466(3) . ?
C7 C8 1.463(3) . ?
C7 O1 1.348(2) . ?
C20 C21 1.368(3) . ?
C20 O1 1.346(2) . ?
C5 C21 1.407(3) . ?
C5 C4 1.466(3) . ?
C8 C13 1.397(3) . ?
C8 C9 1.402(3) . ?
C13 C12 1.386(3) . ?
C9 C10 1.380(3) . ?
C10 C11 1.393(3) . ?
C18 C17 1.386(3) . ?
C4 C3 1.394(3) . ?
C4 C22 1.404(3) . ?
C3 C2 1.382(3) . ?
C1 C23 1.403(3) . ?
C1 C2 1.400(3) . ?
C11 C12 1.385(3) . ?
C23 C22 1.372(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.383(3) . ?
C17 C16 1.382(4) . ?
F1 B1 1.373(3) . ?
F2 B1 1.381(3) . ?
F3 B1 1.396(4) . ?
F4 B1 1.350(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C6 C5 119.93(17) . . ?
C18 C19 C20 119.89(19) . . ?
C18 C19 C14 119.76(18) . . ?
C14 C19 C20 120.35(18) . . ?
O4 N1 C2 117.27(17) . . ?
O3 N1 O4 123.86(19) . . ?
O3 N1 C2 118.86(19) . . ?
C6 C7 C8 127.51(17) . . ?
O1 C7 C6 119.73(17) . . ?
O1 C7 C8 112.76(16) . . ?
C21 C20 C19 126.87(18) . . ?
O1 C20 C19 113.27(16) . . ?
O1 C20 C21 119.84(17) . . ?
C6 C5 C21 117.96(17) . . ?
C6 C5 C4 122.18(17) . . ?
C21 C5 C4 119.86(17) . . ?
C20 C21 C5 120.11(18) . . ?
C13 C8 C7 120.15(17) . . ?
C13 C8 C9 119.44(18) . . ?
C9 C8 C7 120.40(17) . . ?
C12 C13 C8 120.08(19) . . ?
C10 C9 C8 120.10(18) . . ?
C9 C10 C11 120.08(19) . . ?
C17 C18 C19 119.5(2) . . ?
C3 C4 C5 122.13(18) . . ?
C3 C4 C22 118.31(18) . . ?
C22 C4 C5 119.56(17) . . ?
C2 C3 C4 119.69(18) . . ?
O2 C1 C23 122.02(19) . . ?
O2 C1 C2 120.88(18) . . ?
C2 C1 C23 117.09(18) . . ?
C12 C11 C10 120.16(19) . . ?
C22 C23 C1 120.89(19) . . ?
C3 C2 N1 117.37(18) . . ?
C3 C2 C1 122.48(18) . . ?
C1 C2 N1 120.12(17) . . ?
C23 C22 C4 121.49(18) . . ?
C15 C14 C19 119.8(2) . . ?
C16 C15 C14 120.2(2) . . ?
C11 C12 C13 120.14(19) . . ?
C16 C17 C18 120.7(2) . . ?
C17 C16 C15 120.1(2) . . ?
F1 B1 F2 110.4(2) . . ?
F1 B1 F3 108.7(2) . . ?
F2 B1 F3 108.5(2) . . ?
F4 B1 F1 111.7(3) . . ?
F4 B1 F2 110.3(2) . . ?
F4 B1 F3 107.2(3) . . ?
C20 O1 C7 122.42(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C23 C22 179.1(2) . . . . ?
O2 C1 C2 N1 -2.8(3) . . . . ?
O2 C1 C2 C3 179.28(19) . . . . ?
C6 C7 C8 C13 173.3(2) . . . . ?
C6 C7 C8 C9 -5.3(3) . . . . ?
C6 C7 O1 C20 -0.9(3) . . . . ?
C6 C5 C21 C20 -1.0(3) . . . . ?
C6 C5 C4 C3 31.5(3) . . . . ?
C6 C5 C4 C22 -148.1(2) . . . . ?
O4 N1 C2 C3 38.3(3) . . . . ?
O4 N1 C2 C1 -139.7(2) . . . . ?
C19 C20 C21 C5 -177.3(2) . . . . ?
C19 C20 O1 C7 178.46(17) . . . . ?
C19 C18 C17 C16 0.0(3) . . . . ?
C19 C14 C15 C16 -0.1(4) . . . . ?
O3 N1 C2 C3 -141.8(2) . . . . ?
O3 N1 C2 C1 40.2(3) . . . . ?
C7 C6 C5 C21 0.1(3) . . . . ?
C7 C6 C5 C4 -179.58(18) . . . . ?
C7 C8 C13 C12 -178.02(19) . . . . ?
C7 C8 C9 C10 178.52(18) . . . . ?
C20 C19 C18 C17 -179.7(2) . . . . ?
C20 C19 C14 C15 179.7(2) . . . . ?
C5 C6 C7 C8 -178.15(19) . . . . ?
C5 C6 C7 O1 0.8(3) . . . . ?
C5 C4 C3 C2 -179.22(18) . . . . ?
C5 C4 C22 C23 177.6(2) . . . . ?
C21 C20 O1 C7 0.0(3) . . . . ?
C21 C5 C4 C3 -148.2(2) . . . . ?
C21 C5 C4 C22 32.2(3) . . . . ?
C8 C7 O1 C20 178.20(16) . . . . ?
C8 C13 C12 C11 -0.6(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C18 C19 C20 C21 -24.9(3) . . . . ?
C18 C19 C20 O1 156.76(18) . . . . ?
C18 C19 C14 C15 -0.1(3) . . . . ?
C18 C17 C16 C15 -0.1(4) . . . . ?
C4 C5 C21 C20 178.72(18) . . . . ?
C4 C3 C2 N1 -176.29(18) . . . . ?
C4 C3 C2 C1 1.7(3) . . . . ?
C3 C4 C22 C23 -2.0(3) . . . . ?
C1 C23 C22 C4 1.5(3) . . . . ?
C23 C1 C2 N1 175.80(19) . . . . ?
C23 C1 C2 C3 -2.1(3) . . . . ?
C2 C1 C23 C22 0.5(3) . . . . ?
C22 C4 C3 C2 0.4(3) . . . . ?
C14 C19 C20 C21 155.3(2) . . . . ?
C14 C19 C20 O1 -23.1(3) . . . . ?
C14 C19 C18 C17 0.1(3) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
O1 C7 C8 C13 -5.7(3) . . . . ?
O1 C7 C8 C9 175.75(17) . . . . ?
O1 C20 C21 C5 1.0(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 977073'
data_str1331
_audit_creation_date             2013-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-4
_publ_contact_author_address     ?
_publ_contact_author_email       ?
_publ_contact_author_phone       ?
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H17 N O2'
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H18 Cl N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4285(3)
_cell_length_b                   19.3666(4)
_cell_length_c                   11.1086(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.364(4)
_cell_angle_gamma                90
_cell_volume                     1699.93(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4464
_cell_measurement_temperature    298
_cell_measurement_theta_max      73.1603
_cell_measurement_theta_min      4.2410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.023
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.326
_diffrn_reflns_theta_min         4.566
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0444802000
_diffrn_orient_matrix_UB_12      -0.0465969000
_diffrn_orient_matrix_UB_13      -0.1196257000
_diffrn_orient_matrix_UB_21      -0.0263091000
_diffrn_orient_matrix_UB_22      0.0644705000
_diffrn_orient_matrix_UB_23      -0.0859865000
_diffrn_orient_matrix_UB_31      0.1879437000
_diffrn_orient_matrix_UB_32      -0.0019954000
_diffrn_orient_matrix_UB_33      0.0130385000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2532
_reflns_number_total             3362
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0922P)²+0.4646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1682
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C3(H3), C6(H6), C22(H22), C23(H23), C14(H14), C17(H17), C16(H16),
 C15(H15), C18(H18), C13(H13), C9(H9), C12(H12), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42781(17) 0.06985(6) 0.08200(12) 0.0403(3) Uani 1 1 d . . . . .
C20 C 0.3046(2) 0.07199(9) -0.03733(17) 0.0372(4) Uani 1 1 d . . . . .
C4 C 0.0810(2) -0.09514(9) -0.04784(18) 0.0375(4) Uani 1 1 d . . . . .
C21 C 0.1943(2) 0.01962(9) -0.08032(18) 0.0389(4) Uani 1 1 d . . . . .
H21 H 0.1143 0.0224 -0.1626 0.047 Uiso 1 1 calc R U . . .
C5 C 0.1955(2) -0.04015(9) -0.00420(18) 0.0375(4) Uani 1 1 d . . . . .
C3 C 0.0894(2) -0.15599(9) 0.02721(19) 0.0401(4) Uani 1 1 d . . . . .
H3 H 0.1743 -0.1593 0.1073 0.048 Uiso 1 1 calc R U . . .
C1 C -0.1620(3) -0.20473(10) -0.1367(2) 0.0437(5) Uani 1 1 d . . . . .
C7 C 0.4338(2) 0.01438(9) 0.16035(18) 0.0378(4) Uani 1 1 d . . . . .
C6 C 0.3231(2) -0.03818(9) 0.12071(18) 0.0387(4) Uani 1 1 d . . . . .
H6 H 0.3298 -0.0746 0.1768 0.046 Uiso 1 1 calc R U . . .
C22 C -0.0529(3) -0.09211(10) -0.16985(19) 0.0426(4) Uani 1 1 d . . . . .
H22 H -0.0606 -0.0539 -0.2222 0.051 Uiso 1 1 calc R U . . .
C23 C -0.1688(3) -0.14338(10) -0.2114(2) 0.0453(5) Uani 1 1 d . . . . .
H23 H -0.2552 -0.1387 -0.2905 0.054 Uiso 1 1 calc R U . . .
O2 O -0.2686(2) -0.25222(8) -0.17281(15) 0.0587(4) Uani 1 1 d . . . . .
C2 C -0.0222(3) -0.20924(9) -0.0140(2) 0.0425(5) Uani 1 1 d . . . . .
C19 C 0.3134(3) 0.13478(9) -0.10877(18) 0.0395(4) Uani 1 1 d . . . . .
C14 C 0.4606(3) 0.17451(10) -0.0734(2) 0.0442(5) Uani 1 1 d . . . . .
H14 H 0.5532 0.1621 -0.0020 0.053 Uiso 1 1 calc R U . . .
N1 N -0.0101(3) -0.26948(10) 0.0537(2) 0.0584(5) Uani 1 1 d . . . . .
C8 C 0.5683(3) 0.02115(10) 0.2853(2) 0.0456(5) Uani 1 1 d . . . . .
C17 C 0.1847(3) 0.21370(11) -0.2842(2) 0.0546(6) Uani 1 1 d . . . . .
H17 H 0.0920 0.2271 -0.3546 0.066 Uiso 1 1 calc R U . . .
C16 C 0.3327(3) 0.25167(11) -0.2495(2) 0.0527(5) Uani 1 1 d . . . . .
H16 H 0.3401 0.2902 -0.2972 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4693(3) 0.23226(10) -0.1441(2) 0.0503(5) Uani 1 1 d . . . . .
H15 H 0.5683 0.2582 -0.1204 0.060 Uiso 1 1 calc R U . . .
C18 C 0.1741(3) 0.15546(11) -0.2138(2) 0.0486(5) Uani 1 1 d . . . . .
H18 H 0.0740 0.1303 -0.2370 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6578(3) 0.08212(11) 0.3216(2) 0.0567(6) Uani 1 1 d . . . . .
H13 H 0.6323 0.1193 0.2651 0.068 Uiso 1 1 calc R U . . .
C9 C 0.6135(4) -0.03473(14) 0.3685(3) 0.0831(10) Uani 1 1 d . . . . .
H9 H 0.5585 -0.0768 0.3443 0.100 Uiso 1 1 calc R U . . .
C12 C 0.7837(4) 0.08894(14) 0.4398(3) 0.0774(9) Uani 1 1 d . . . . .
H12 H 0.8420 0.1304 0.4629 0.093 Uiso 1 1 calc R U . . .
C10 C 0.7391(6) -0.02818(19) 0.4865(3) 0.135(2) Uani 1 1 d . . . . .
H10 H 0.7684 -0.0657 0.5421 0.163 Uiso 1 1 calc R U . . .
C11 C 0.8223(6) 0.03431(19) 0.5227(3) 0.1228(18) Uani 1 1 d . . . . .
H11 H 0.9045 0.0391 0.6037 0.147 Uiso 1 1 calc R U . . .
H1A H -0.110(5) -0.2955(19) 0.014(4) 0.113(13) Uiso 1 1 d . . . . .
H1B H 0.055(4) -0.2667(17) 0.147(4) 0.095(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
O1 C20 1.371(2) . ?
O1 C7 1.372(2) . ?
C20 C21 1.346(3) . ?
C20 C19 1.468(2) . ?
C4 C5 1.405(3) . ?
C4 C3 1.431(3) . ?
C4 C22 1.432(3) . ?
C21 C5 1.432(3) . ?
C5 C6 1.430(3) . ?
C3 C2 1.363(3) . ?
C1 C23 1.439(3) . ?
C1 O2 1.250(2) . ?
C1 C2 1.462(3) . ?
C7 C6 1.347(3) . ?
C7 C8 1.460(3) . ?
C22 C23 1.356(3) . ?
C2 N1 1.372(3) . ?
C19 C14 1.396(3) . ?
C19 C18 1.395(3) . ?
C14 C15 1.384(3) . ?
C8 C13 1.384(3) . ?
C8 C9 1.388(3) . ?
C17 C16 1.382(3) . ?
C17 C18 1.393(3) . ?
C16 C15 1.378(3) . ?
C13 C12 1.377(3) . ?
C9 C10 1.374(4) . ?
C12 C11 1.366(4) . ?
C10 C11 1.386(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 C7 119.02(14) . . ?
O1 C20 C19 112.59(16) . . ?
C21 C20 O1 121.17(16) . . ?
C21 C20 C19 126.22(17) . . ?
C5 C4 C3 122.32(17) . . ?
C5 C4 C22 121.07(17) . . ?
C3 C4 C22 116.60(17) . . ?
C20 C21 C5 122.54(17) . . ?
C4 C5 C21 123.11(17) . . ?
C4 C5 C6 123.31(17) . . ?
C6 C5 C21 113.57(17) . . ?
C2 C3 C4 122.65(18) . . ?
C23 C1 C2 116.40(17) . . ?
O2 C1 C23 122.87(19) . . ?
O2 C1 C2 120.73(18) . . ?
O1 C7 C8 112.17(16) . . ?
C6 C7 O1 121.05(17) . . ?
C6 C7 C8 126.78(17) . . ?
C7 C6 C5 122.60(17) . . ?
C23 C22 C4 121.97(18) . . ?
C22 C23 C1 121.93(18) . . ?
C3 C2 C1 120.37(17) . . ?
C3 C2 N1 123.26(19) . . ?
N1 C2 C1 116.36(18) . . ?
C14 C19 C20 120.78(17) . . ?
C18 C19 C20 120.27(18) . . ?
C18 C19 C14 118.95(18) . . ?
C15 C14 C19 120.2(2) . . ?
C13 C8 C7 121.20(18) . . ?
C13 C8 C9 118.4(2) . . ?
C9 C8 C7 120.37(19) . . ?
C16 C17 C18 120.2(2) . . ?
C15 C16 C17 119.85(19) . . ?
C16 C15 C14 120.6(2) . . ?
C17 C18 C19 120.2(2) . . ?
C12 C13 C8 121.4(2) . . ?
C10 C9 C8 120.4(2) . . ?
C11 C12 C13 119.5(2) . . ?
C9 C10 C11 120.1(3) . . ?
C12 C11 C10 120.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C20 C21 C5 1.6(3) . . . . ?
O1 C20 C19 C14 18.5(3) . . . . ?
O1 C20 C19 C18 -161.82(18) . . . . ?
O1 C7 C6 C5 0.9(3) . . . . ?
O1 C7 C8 C13 9.0(3) . . . . ?
O1 C7 C8 C9 -168.5(3) . . . . ?
C20 O1 C7 C6 1.3(3) . . . . ?
C20 O1 C7 C8 -178.02(16) . . . . ?
C20 C21 C5 C4 179.92(18) . . . . ?
C20 C21 C5 C6 0.5(3) . . . . ?
C20 C19 C14 C15 177.78(18) . . . . ?
C20 C19 C18 C17 -177.76(19) . . . . ?
C4 C5 C6 C7 178.82(18) . . . . ?
C4 C3 C2 C1 -2.7(3) . . . . ?
C4 C3 C2 N1 176.2(2) . . . . ?
C4 C22 C23 C1 -1.5(3) . . . . ?
C21 C20 C19 C14 -159.59(19) . . . . ?
C21 C20 C19 C18 20.1(3) . . . . ?
C21 C5 C6 C7 -1.8(3) . . . . ?
C5 C4 C3 C2 179.36(19) . . . . ?
C5 C4 C22 C23 -177.23(19) . . . . ?
C3 C4 C5 C21 176.88(18) . . . . ?
C3 C4 C5 C6 -3.8(3) . . . . ?
C3 C4 C22 C23 1.6(3) . . . . ?
C7 O1 C20 C21 -2.6(3) . . . . ?
C7 O1 C20 C19 179.25(15) . . . . ?
C7 C8 C13 C12 179.4(3) . . . . ?
C7 C8 C9 C10 -179.5(4) . . . . ?
C6 C7 C8 C13 -170.3(2) . . . . ?
C6 C7 C8 C9 12.2(4) . . . . ?
C22 C4 C5 C21 -4.4(3) . . . . ?
C22 C4 C5 C6 174.96(18) . . . . ?
C22 C4 C3 C2 0.6(3) . . . . ?
C23 C1 C2 C3 2.7(3) . . . . ?
C23 C1 C2 N1 -176.3(2) . . . . ?
O2 C1 C23 C22 179.3(2) . . . . ?
O2 C1 C2 C3 -177.2(2) . . . . ?
O2 C1 C2 N1 3.8(3) . . . . ?
C2 C1 C23 C22 -0.6(3) . . . . ?
C19 C20 C21 C5 179.55(18) . . . . ?
C19 C14 C15 C16 0.6(3) . . . . ?
C14 C19 C18 C17 2.0(3) . . . . ?
C8 C7 C6 C5 -179.86(19) . . . . ?
C8 C13 C12 C11 0.5(5) . . . . ?
C8 C9 C10 C11 -0.4(8) . . . . ?
C17 C16 C15 C14 0.8(4) . . . . ?
C16 C17 C18 C19 -0.6(4) . . . . ?
C18 C19 C14 C15 -1.9(3) . . . . ?
C18 C17 C16 C15 -0.8(4) . . . . ?
C13 C8 C9 C10 3.0(6) . . . . ?
C13 C12 C11 C10 2.1(8) . . . . ?
C9 C8 C13 C12 -3.0(4) . . . . ?
C9 C10 C11 C12 -2.2(9) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 977074'
data_str1386
_audit_creation_date             2013-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-4
_publ_contact_author_address     ?
_publ_contact_author_email       ?
_publ_contact_author_phone       ?
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H16 O2, 0.25(C1.61 O), 0.25(C1.58 O)'
_chemical_formula_sum            'C23.80 H17.87 O2.50'
_chemical_formula_weight         343.81
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H16 O2'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   26.9819(14)
_cell_length_b                   19.5048(6)
_cell_length_c                   7.1392(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3757.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3311
_cell_measurement_temperature    150.05(10)
_cell_measurement_theta_max      73.1075
_cell_measurement_theta_min      3.2732
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1445
_exptl_crystal_size_max          0.2817
_exptl_crystal_size_mid          0.0459
_exptl_crystal_size_min          0.0339
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            20164
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.28
_diffrn_reflns_theta_min         3.28
_diffrn_ambient_temperature      150.05(10)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0563597000
_diffrn_orient_matrix_UB_12      -0.0067830000
_diffrn_orient_matrix_UB_13      0.0316172000
_diffrn_orient_matrix_UB_21      0.0048141000
_diffrn_orient_matrix_UB_22      0.0786332000
_diffrn_orient_matrix_UB_23      0.0023972000
_diffrn_orient_matrix_UB_31      -0.0081103000
_diffrn_orient_matrix_UB_32      0.0001807000
_diffrn_orient_matrix_UB_33      0.2134398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.878
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                4705
_reflns_number_total             6941
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6941
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1689P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2359
_refine_ls_wR_factor_ref         0.2602
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O5-C48
 1.3 with sigma of 0.02
 O6-C49
 1.3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C49) = Uanis(C50)
Uanis(C48) = Uanis(C47)
4. Others
 Fixed Sof: C49(0.19558) C50(0.60885) C48(0.21095) C47(0.5781)
5.a Aromatic/amide H refined with riding coordinates:
 C44(H44), C6(H6), C26(H26), C21(H21), C3(H3), C29(H29), C23(H23), C25(H25),
 C13(H13), C46(H46), C45(H45), C41(H41), C18(H18), C37(H37), C14(H14), C2(H2),
 C15(H15), C9(H9), C10(H10), C11(H11), C22(H22), C36(H36), C39(H39), C40(H40),
 C12(H12), C32(H32), C33(H33), C34(H34), C16(H16), C38(H38), C17(H17), C35(H35)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36285(15) 0.90729(17) 0.0899(6) 0.0575(9) Uani 1 1 d . . . . .
C28 C 0.2371(2) 0.9018(2) -0.4748(8) 0.0552(13) Uani 1 1 d . . . . .
O3 O 0.13510(16) 0.90879(16) -0.5475(6) 0.0623(10) Uani 1 1 d . . . . .
C27 C 0.2901(2) 0.8982(2) -0.4399(8) 0.0525(12) Uani 1 1 d . . . . .
C44 C 0.2132(2) 0.9638(2) -0.5331(9) 0.0578(13) Uani 1 1 d . . . . .
H44 H 0.2319 1.0036 -0.5464 0.069 Uiso 1 1 calc R U . . .
C5 C 0.2605(2) 0.8977(2) 0.0434(8) 0.0518(12) Uani 1 1 d . . . . .
C6 C 0.2900(2) 0.8418(2) 0.0999(7) 0.0521(12) Uani 1 1 d . . . . .
H6 H 0.2747 0.7999 0.1229 0.063 Uiso 1 1 calc R U . . .
C26 C 0.3122(3) 0.8376(2) -0.3786(8) 0.0590(14) Uani 1 1 d . . . . .
H26 H 0.2927 0.7989 -0.3607 0.071 Uiso 1 1 calc R U . . .
C20 C 0.3368(2) 0.9636(2) 0.0351(8) 0.0530(12) Uani 1 1 d . . . . .
C19 C 0.3697(2) 1.0226(2) 0.0024(10) 0.0622(14) Uani 1 1 d . . . . .
C21 C 0.2873(2) 0.9609(2) 0.0111(9) 0.0563(13) Uani 1 1 d . . . . .
H21 H 0.2702 1.0000 -0.0265 0.068 Uiso 1 1 calc R U . . .
C3 C 0.1819(2) 0.8317(3) 0.0445(9) 0.0625(14) Uani 1 1 d . . . . .
H3 H 0.1994 0.7934 0.0841 0.075 Uiso 1 1 calc R U . . .
C29 C 0.2052(2) 0.8445(2) -0.4567(9) 0.0574(13) Uani 1 1 d . . . . .
H29 H 0.2184 0.8025 -0.4205 0.069 Uiso 1 1 calc R U . . .
C7 C 0.3394(2) 0.8465(2) 0.1218(7) 0.0513(12) Uani 1 1 d . . . . .
C31 C 0.1194(2) 0.7936(3) -0.4803(10) 0.0639(15) Uani 1 1 d . . . . .
C4 C 0.2075(2) 0.8935(3) 0.0114(8) 0.0566(13) Uani 1 1 d . . . . .
C23 C 0.1290(3) 0.9455(3) -0.0724(10) 0.0695(16) Uani 1 1 d . . . . .
H23 H 0.1110 0.9836 -0.1113 0.083 Uiso 1 1 calc R U . . .
C43 C 0.1640(2) 0.9654(2) -0.5693(8) 0.0573(14) Uani 1 1 d . . . . .
C30 C 0.1558(2) 0.8493(2) -0.4908(9) 0.0610(14) Uani 1 1 d . . . . .
C25 C 0.3623(3) 0.8337(3) -0.3440(9) 0.0634(15) Uani 1 1 d . . . . .
H25 H 0.3761 0.7926 -0.3034 0.076 Uiso 1 1 calc R U . . .
C42 C 0.1348(3) 1.0245(3) -0.6379(9) 0.0627(15) Uani 1 1 d . . . . .
C13 C 0.4247(3) 0.7981(3) 0.1288(10) 0.0658(16) Uani 1 1 d . . . . .
H13 H 0.4367 0.8382 0.0750 0.079 Uiso 1 1 calc R U . . .
O4 O 0.44054(19) 0.8853(3) -0.3270(10) 0.0920(17) Uani 1 1 d . . . . .
C8 C 0.3743(2) 0.7914(3) 0.1652(9) 0.0571(13) Uani 1 1 d . . . . .
O2 O 0.0547(2) 0.8761(3) -0.0473(12) 0.108(2) Uani 1 1 d . . . . .
C46 C 0.3708(3) 0.9523(3) -0.4364(10) 0.0665(15) Uani 1 1 d . . . . .
H46 H 0.3905 0.9905 -0.4590 0.080 Uiso 1 1 calc R U . . .
C45 C 0.3208(2) 0.9554(2) -0.4685(8) 0.0582(13) Uani 1 1 d . . . . .
H45 H 0.3068 0.9963 -0.5100 0.070 Uiso 1 1 calc R U . . .
C41 C 0.1593(3) 1.0806(3) -0.7177(11) 0.0700(16) Uani 1 1 d . . . . .
H41 H 0.1937 1.0814 -0.7239 0.084 Uiso 1 1 calc R U . . .
C18 C 0.3517(3) 1.0813(3) -0.0909(13) 0.080(2) Uani 1 1 d . . . . .
H18 H 0.3186 1.0834 -0.1259 0.097 Uiso 1 1 calc R U . . .
C37 C 0.0834(3) 1.0244(3) -0.6308(13) 0.081(2) Uani 1 1 d . . . . .
H37 H 0.0667 0.9874 -0.5787 0.098 Uiso 1 1 calc R U . . .
C14 C 0.4186(3) 1.0212(3) 0.0510(14) 0.081(2) Uani 1 1 d . . . . .
H14 H 0.4311 0.9830 0.1128 0.097 Uiso 1 1 calc R U . . .
C2 C 0.1319(3) 0.8271(3) 0.0196(11) 0.0714(16) Uani 1 1 d . . . . .
H2 H 0.1161 0.7853 0.0393 0.086 Uiso 1 1 calc R U . . .
C24 C 0.3926(2) 0.8914(3) -0.3696(11) 0.0670(16) Uani 1 1 d . . . . .
C15 C 0.4504(3) 1.0765(3) 0.0095(16) 0.095(3) Uani 1 1 d . . . . .
H15 H 0.4836 1.0751 0.0445 0.113 Uiso 1 1 calc R U . . .
C9 C 0.3560(3) 0.7309(3) 0.2433(10) 0.0653(15) Uani 1 1 d . . . . .
H9 H 0.3223 0.7254 0.2662 0.078 Uiso 1 1 calc R U . . .
C10 C 0.3893(3) 0.6791(3) 0.2857(11) 0.0731(17) Uani 1 1 d . . . . .
H10 H 0.3778 0.6390 0.3411 0.088 Uiso 1 1 calc R U . . .
C11 C 0.4391(3) 0.6857(3) 0.2476(12) 0.0769(19) Uani 1 1 d . . . . .
H11 H 0.4604 0.6495 0.2735 0.092 Uiso 1 1 calc R U . . .
C22 C 0.1788(2) 0.9495(3) -0.0521(9) 0.0594(13) Uani 1 1 d . . . . .
H22 H 0.1946 0.9905 -0.0809 0.071 Uiso 1 1 calc R U . . .
C36 C 0.0710(3) 0.8017(3) -0.5479(12) 0.0736(18) Uani 1 1 d . . . . .
H36 H 0.0611 0.8430 -0.6012 0.088 Uiso 1 1 calc R U . . .
C39 C 0.0815(4) 1.1339(4) -0.7787(14) 0.095(3) Uani 1 1 d . . . . .
H39 H 0.0637 1.1708 -0.8261 0.114 Uiso 1 1 calc R U . . .
C40 C 0.1319(4) 1.1346(3) -0.7871(13) 0.090(2) Uani 1 1 d . . . . .
H40 H 0.1480 1.1720 -0.8402 0.109 Uiso 1 1 calc R U . . .
C12 C 0.4574(3) 0.7449(3) 0.1723(12) 0.0767(19) Uani 1 1 d . . . . .
H12 H 0.4912 0.7497 0.1503 0.092 Uiso 1 1 calc R U . . .
C32 C 0.1328(3) 0.7310(3) -0.3971(11) 0.0693(16) Uani 1 1 d . . . . .
H32 H 0.1644 0.7250 -0.3475 0.083 Uiso 1 1 calc R U . . .
C33 C 0.0984(3) 0.6783(3) -0.3899(13) 0.083(2) Uani 1 1 d . . . . .
H33 H 0.1079 0.6360 -0.3417 0.099 Uiso 1 1 calc R U . . .
C1 C 0.1044(3) 0.8829(4) -0.0340(11) 0.0759(18) Uani 1 1 d . . . . .
C34 C 0.0515(3) 0.6865(3) -0.4507(15) 0.090(2) Uani 1 1 d . . . . .
H34 H 0.0284 0.6516 -0.4368 0.108 Uiso 1 1 calc R U . . .
C16 C 0.4320(3) 1.1313(3) -0.0817(14) 0.089(2) Uani 1 1 d . . . . .
H16 H 0.4530 1.1675 -0.1127 0.107 Uiso 1 1 calc R U . . .
C38 C 0.0569(3) 1.0797(4) -0.7018(15) 0.092(2) Uani 1 1 d . . . . .
H38 H 0.0225 1.0798 -0.6968 0.111 Uiso 1 1 calc R U . . .
C17 C 0.3820(4) 1.1345(3) -0.1302(13) 0.091(2) Uani 1 1 d . . . . .
H17 H 0.3695 1.1733 -0.1896 0.109 Uiso 1 1 calc R U . . .
C35 C 0.0382(3) 0.7482(3) -0.5346(12) 0.0788(19) Uani 1 1 d . . . . .
H35 H 0.0064 0.7532 -0.5828 0.095 Uiso 1 1 calc R U . . .
O6 O 0.0000 1.0000 -0.2285(11) 0.0661(17) Uani 1 2 d DS T P . .
C49 C 0.0000 1.0000 -0.059(3) 0.058(2) Uani 0.3912 2 d DS T P A 3
C50 C -0.0171(3) 1.0499(4) -0.3330(15) 0.058(2) Uani 0.6089 1 d . . P A 4
O5 O 0.5000 1.0000 -0.5202(11) 0.0600(17) Uani 1 2 d DS T P . .
C48 C 0.5000 1.0000 -0.364(3) 0.060(2) Uani 0.4219 2 d DS T P B 5
C47 C 0.4806(4) 0.9512(4) -0.6459(16) 0.060(2) Uani 0.5781 1 d . . P B 6


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.360(6) . ?
O1 C7 1.363(6) . ?
C28 C27 1.455(9) . ?
C28 C44 1.432(7) . ?
C28 C29 1.416(8) . ?
O3 C43 1.360(6) . ?
O3 C30 1.350(7) . ?
C27 C26 1.394(8) . ?
C27 C45 1.405(7) . ?
C44 C43 1.354(9) . ?
C5 C6 1.410(8) . ?
C5 C21 1.448(7) . ?
C5 C4 1.448(8) . ?
C6 C7 1.344(8) . ?
C26 C25 1.376(10) . ?
C20 C19 1.472(8) . ?
C20 C21 1.349(8) . ?
C19 C18 1.411(9) . ?
C19 C14 1.363(10) . ?
C3 C4 1.409(8) . ?
C3 C2 1.364(10) . ?
C29 C30 1.358(9) . ?
C7 C8 1.463(8) . ?
C31 C30 1.466(8) . ?
C31 C36 1.402(10) . ?
C31 C32 1.405(8) . ?
C4 C22 1.415(8) . ?
C23 C22 1.353(10) . ?
C23 C1 1.417(9) . ?
C43 C42 1.479(8) . ?
C25 C24 1.403(9) . ?
C42 C41 1.400(9) . ?
C42 C37 1.388(10) . ?
C13 C8 1.390(9) . ?
C13 C12 1.397(9) . ?
O4 C24 1.335(9) . ?
C8 C9 1.397(8) . ?
O2 C1 1.349(9) . ?
C46 C45 1.372(9) . ?
C46 C24 1.408(9) . ?
C41 C40 1.380(9) . ?
C18 C17 1.351(10) . ?
C37 C38 1.390(10) . ?
C14 C15 1.411(9) . ?
C2 C1 1.371(10) . ?
C15 C16 1.346(11) . ?
C9 C10 1.385(9) . ?
C10 C11 1.376(11) . ?
C11 C12 1.367(10) . ?
C36 C35 1.370(9) . ?
C39 C40 1.360(14) . ?
C39 C38 1.364(12) . ?
C32 C33 1.386(9) . ?
C33 C34 1.348(12) . ?
C34 C35 1.390(11) . ?
C16 C17 1.395(13) . ?
O6 C49 1.212(19) . ?
O6 C50 1.310(10) . ?
O6 C50 1.310(10) 2_575 ?
O5 C48 1.116(18) . ?
O5 C47 1.409(11) . ?
O5 C47 1.409(11) 2_675 ?

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
C20 O1 C7 120.7(5) . . ?
C44 C28 C27 122.2(5) . . ?
C29 C28 C27 122.9(5) . . ?
C29 C28 C44 114.9(5) . . ?
C30 O3 C43 119.7(5) . . ?
C26 C27 C28 121.1(5) . . ?
C26 C27 C45 117.9(5) . . ?
C45 C27 C28 121.0(5) . . ?
C43 C44 C28 121.0(5) . . ?
C6 C5 C21 114.9(5) . . ?
C6 C5 C4 124.0(5) . . ?
C4 C5 C21 121.1(5) . . ?
C7 C6 C5 122.7(5) . . ?
C25 C26 C27 121.6(5) . . ?
O1 C20 C19 111.5(5) . . ?
C21 C20 O1 121.1(5) . . ?
C21 C20 C19 127.4(5) . . ?
C18 C19 C20 120.2(6) . . ?
C14 C19 C20 121.8(5) . . ?
C14 C19 C18 118.0(6) . . ?
C20 C21 C5 120.6(5) . . ?
C2 C3 C4 121.4(6) . . ?
C30 C29 C28 121.7(5) . . ?
O1 C7 C8 112.0(5) . . ?
C6 C7 O1 120.0(5) . . ?
C6 C7 C8 127.8(5) . . ?
C36 C31 C30 121.5(6) . . ?
C36 C31 C32 118.9(6) . . ?
C32 C31 C30 119.5(6) . . ?
C3 C4 C5 120.4(5) . . ?
C3 C4 C22 116.4(5) . . ?
C22 C4 C5 123.2(5) . . ?
C22 C23 C1 119.7(6) . . ?
O3 C43 C42 111.5(5) . . ?
C44 C43 O3 121.4(5) . . ?
C44 C43 C42 127.1(5) . . ?
O3 C30 C29 121.2(5) . . ?
O3 C30 C31 112.1(6) . . ?
C29 C30 C31 126.7(5) . . ?
C26 C25 C24 120.3(5) . . ?
C41 C42 C43 119.5(6) . . ?
C37 C42 C43 121.3(6) . . ?
C37 C42 C41 119.2(6) . . ?
C8 C13 C12 120.5(6) . . ?
C13 C8 C7 121.5(5) . . ?
C13 C8 C9 120.0(5) . . ?
C9 C8 C7 118.5(6) . . ?
C45 C46 C24 120.4(6) . . ?
C46 C45 C27 121.3(5) . . ?
C40 C41 C42 119.3(7) . . ?
C17 C18 C19 120.9(7) . . ?
C42 C37 C38 120.0(7) . . ?
C19 C14 C15 121.3(6) . . ?
C3 C2 C1 121.3(6) . . ?
C25 C24 C46 118.6(6) . . ?
O4 C24 C25 117.6(6) . . ?
O4 C24 C46 123.8(6) . . ?
C16 C15 C14 119.1(7) . . ?
C10 C9 C8 118.3(6) . . ?
C11 C10 C9 121.5(6) . . ?
C12 C11 C10 120.7(6) . . ?
C23 C22 C4 122.3(6) . . ?
C35 C36 C31 119.4(7) . . ?
C40 C39 C38 120.8(7) . . ?
C39 C40 C41 120.8(8) . . ?
C11 C12 C13 119.1(7) . . ?
C33 C32 C31 119.1(7) . . ?
C34 C33 C32 121.9(7) . . ?
O2 C1 C23 122.4(7) . . ?
O2 C1 C2 118.7(6) . . ?
C2 C1 C23 118.9(6) . . ?
C33 C34 C35 118.9(6) . . ?
C15 C16 C17 120.7(7) . . ?
C39 C38 C37 119.9(8) . . ?
C18 C17 C16 120.0(7) . . ?
C36 C35 C34 121.5(7) . . ?
C50 O6 C50 110.6(10) 2_575 . ?
C47 O5 C47 100.9(10) . 2_675 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C20 C19 C18 167.1(6) . . . . ?
O1 C20 C19 C14 -9.3(9) . . . . ?
O1 C20 C21 C5 0.0(9) . . . . ?
O1 C7 C8 C13 -15.4(8) . . . . ?
O1 C7 C8 C9 165.2(5) . . . . ?
C28 C27 C26 C25 -179.5(5) . . . . ?
C28 C27 C45 C46 -179.8(6) . . . . ?
C28 C44 C43 O3 1.6(9) . . . . ?
C28 C44 C43 C42 -177.2(6) . . . . ?
C28 C29 C30 O3 1.4(9) . . . . ?
C28 C29 C30 C31 178.7(6) . . . . ?
O3 C43 C42 C41 -162.3(6) . . . . ?
O3 C43 C42 C37 15.4(9) . . . . ?
C27 C28 C44 C43 178.3(5) . . . . ?
C27 C28 C29 C30 -179.8(6) . . . . ?
C27 C26 C25 C24 0.1(9) . . . . ?
C44 C28 C27 C26 178.3(5) . . . . ?
C44 C28 C27 C45 -2.2(8) . . . . ?
C44 C28 C29 C30 -0.7(8) . . . . ?
C44 C43 C42 C41 16.6(10) . . . . ?
C44 C43 C42 C37 -165.7(7) . . . . ?
C5 C6 C7 O1 0.3(8) . . . . ?
C5 C6 C7 C8 -174.8(5) . . . . ?
C5 C4 C22 C23 -176.7(6) . . . . ?
C6 C5 C21 C20 0.0(8) . . . . ?
C6 C5 C4 C3 2.9(8) . . . . ?
C6 C5 C4 C22 -177.5(5) . . . . ?
C6 C7 C8 C13 160.1(6) . . . . ?
C6 C7 C8 C9 -19.3(9) . . . . ?
C26 C27 C45 C46 -0.3(9) . . . . ?
C26 C25 C24 O4 177.5(7) . . . . ?
C26 C25 C24 C46 -1.9(10) . . . . ?
C20 O1 C7 C6 -0.3(7) . . . . ?
C20 O1 C7 C8 175.6(5) . . . . ?
C20 C19 C18 C17 -176.7(7) . . . . ?
C20 C19 C14 C15 176.4(8) . . . . ?
C19 C20 C21 C5 177.8(5) . . . . ?
C19 C18 C17 C16 1.3(14) . . . . ?
C19 C14 C15 C16 -0.7(15) . . . . ?
C21 C5 C6 C7 -0.2(7) . . . . ?
C21 C5 C4 C3 -179.6(5) . . . . ?
C21 C5 C4 C22 0.0(8) . . . . ?
C21 C20 C19 C18 -10.8(10) . . . . ?
C21 C20 C19 C14 172.8(7) . . . . ?
C3 C4 C22 C23 2.9(9) . . . . ?
C3 C2 C1 C23 3.0(11) . . . . ?
C3 C2 C1 O2 -176.7(8) . . . . ?
C29 C28 C27 C26 -2.6(8) . . . . ?
C29 C28 C27 C45 176.8(5) . . . . ?
C29 C28 C44 C43 -0.8(8) . . . . ?
C7 O1 C20 C19 -178.0(5) . . . . ?
C7 O1 C20 C21 0.1(8) . . . . ?
C7 C8 C9 C10 -179.4(6) . . . . ?
C31 C36 C35 C34 1.9(12) . . . . ?
C31 C32 C33 C34 -3.9(13) . . . . ?
C4 C5 C6 C7 177.5(5) . . . . ?
C4 C5 C21 C20 -177.7(5) . . . . ?
C4 C3 C2 C1 -1.7(11) . . . . ?
C43 O3 C30 C29 -0.7(9) . . . . ?
C43 O3 C30 C31 -178.3(5) . . . . ?
C43 C42 C41 C40 177.9(7) . . . . ?
C43 C42 C37 C38 -178.0(7) . . . . ?
C30 O3 C43 C44 -0.8(8) . . . . ?
C30 O3 C43 C42 178.1(5) . . . . ?
C30 C31 C36 C35 -179.8(7) . . . . ?
C30 C31 C32 C33 -179.2(7) . . . . ?
C42 C41 C40 C39 0.0(13) . . . . ?
C42 C37 C38 C39 0.2(14) . . . . ?
C13 C8 C9 C10 1.2(10) . . . . ?
C8 C13 C12 C11 1.3(12) . . . . ?
C8 C9 C10 C11 -1.8(11) . . . . ?
C45 C27 C26 C25 1.0(8) . . . . ?
C45 C46 C24 C25 2.5(10) . . . . ?
C45 C46 C24 O4 -176.8(7) . . . . ?
C41 C42 C37 C38 -0.3(12) . . . . ?
C18 C19 C14 C15 -0.1(13) . . . . ?
C37 C42 C41 C40 0.2(11) . . . . ?
C14 C19 C18 C17 -0.2(12) . . . . ?
C14 C15 C16 C17 1.7(15) . . . . ?
C2 C3 C4 C5 178.4(6) . . . . ?
C2 C3 C4 C22 -1.2(9) . . . . ?
C24 C46 C45 C27 -1.5(10) . . . . ?
C15 C16 C17 C18 -2.1(14) . . . . ?
C9 C10 C11 C12 2.3(13) . . . . ?
C10 C11 C12 C13 -2.0(13) . . . . ?
C22 C23 C1 O2 178.4(8) . . . . ?
C22 C23 C1 C2 -1.3(11) . . . . ?
C36 C31 C30 O3 8.1(9) . . . . ?
C36 C31 C30 C29 -169.3(7) . . . . ?
C36 C31 C32 C33 2.2(11) . . . . ?
C40 C39 C38 C37 0.0(16) . . . . ?
C12 C13 C8 C7 179.7(6) . . . . ?
C12 C13 C8 C9 -1.0(10) . . . . ?
C32 C31 C30 O3 -170.4(6) . . . . ?
C32 C31 C30 C29 12.1(10) . . . . ?
C32 C31 C36 C35 -1.3(11) . . . . ?
C32 C33 C34 C35 4.4(14) . . . . ?
C33 C34 C35 C36 -3.4(14) . . . . ?
C1 C23 C22 C4 -1.7(10) . . . . ?
C38 C39 C40 C41 -0.1(16) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.245 0.650 -0.445 103.6 43.5 ?
2 0.255 0.150 -0.463 103.6 43.5 ?
3 0.745 0.850 -0.804 103.6 43.5 ?
4 0.755 0.350 -0.956 103.6 43.5 ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4 12 0 0.0229 4.0136 12.0077 -0.0093 0.1445 0.9635 -0.0324
-4 -12 0 0.0229 -4.0136 -12.0077 0.0093 -0.1445 -0.9635 0.0324
-3 0 5 0.1360 -3.0068 0.0077 5.0009 -0.0114 -0.0019 1.0918
3 0 -5 0.1360 3.0068 -0.0077 -5.0009 0.0114 0.0019 -1.0918
17 -3 0 0.0232 16.9984 -2.9816 -0.0194 0.9776 -0.1527 -0.1425
-17 3 0 0.0116 -16.9984 2.9816 0.0194 -0.9776 0.1527 0.1425
16 5 0 0.0197 16.0071 5.0194 -0.0212 0.8674 0.4717 -0.1334
14 -7 0 0.0197 13.9937 -6.9861 -0.0143 0.8356 -0.4820 -0.1178

_database_code_depnum_ccdc_archive 'CCDC 977075'
