# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_apcjmo
_database_code_depnum_ccdc_archive 'CCDC 1456778'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-03-22 downloaded from the CCDC.
;
_nottingham_internal_coll_name   APCJMO
_nottingham_internal_coll_number 11441
_nottingham_internal_coll_client AP/CJM
_nottingham_internal_coll_type   sphere
_nottingham_internal_coll_frame_method \w
_nottingham_internal_coll_frame_time 30
_nottingham_internal_coll_frame_width 0.3
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   1/5/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 02/05/2012
_nottingham_internal_process_user WL
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user wl
_nottingham_internal_refinement_date ?
_nottingham_internal_refinement_user wl
_nottingham_internal_validation_date ?
_nottingham_internal_validation_user wl
_nottingham_internal_archive_date ?
_refine_special_details          
;
The molecule is shows some rotational disorder, with the central ring being well-
located, and the pendant rings being disordered. The occupancies of each disordered 
ring were refined competitiveley. The ring-C and C-F distances of the CF3 groups were 
restrained to approximately equal. Each of the rings was also restrained to 
approximately planar geometry. Rigid bond and simialrity restraints were applied to 
disordered rings.
;
_audit_creation_date             2016-02-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H25 F6 N3 O3, 0.5(C7 H8)'
_chemical_formula_sum            'C36.50 H29 F6 N3 O3'
_chemical_formula_weight         671.63
_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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9280(18)
_cell_length_b                   11.7780(19)
_cell_length_c                   13.075(2)
_cell_angle_alpha                87.909(3)
_cell_angle_beta                 87.569(3)
_cell_angle_gamma                77.316(2)
_cell_volume                     1639.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5651
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2007/2 (Bruker,2007) was used for absorption correction.
wR2(int) was 0.0607 before and 0.0336 after correction.
The Ratio of minimum to maximum transmission is 0.9432.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14312
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.338
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5578
_reflns_number_total             7237
_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       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     802
_refine_ls_number_reflns         7237
_refine_ls_number_restraints     812
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.156
_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)+(0.0929P)²+0.6475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1798
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C22-C18 \\sim C22A-C18A \\sim C20A-C26A \\sim C20-C26
 with sigma of 0.02
 F23A-C22A \\sim F23-C22 \\sim F25A-C22A \\sim F25-C22 \\sim F24-C22 \\sim
F24A-C22A \\sim F29-C26 ~
 F27-C26 \\sim F28-C26 \\sim F29A-C26A \\sim F28A-C26A \\sim F27A-C26A
 with sigma of 0.02
 F25-F24 \\sim F24-F23 \\sim F23-F25 \\sim F27A-F29A \\sim F29A-F28A \\sim
F28A-F27A \\sim F24A-F25A ~
 F25A-F23A \\sim F23A-F24A \\sim F28-F27 \\sim F27-F29 \\sim F29-F28
 with sigma of 0.02
3. Restrained planarity
 C30, C31A, C32A, C33A, C34A, C35A, O36A
 with sigma of 0.1
 C35, C31, C32, C34, O36, C33, C30
 with sigma of 0.1
 C6A, C7A, C12A, C8A, C9A, C11A, C10A, C13A
 with sigma of 0.1
 C6, C7, C12, C8, C9, C11, C10, C13
 with sigma of 0.1
 C5, C43, C38, C39, C42, C40, C41, O44
 with sigma of 0.1
 C5, C38A, C39A, C43A, C42A, C40A, C41A, O44A
 with sigma of 0.1
 C16, C21, C17, C18, C22, C19, C20, C26, C2
 with sigma of 0.1
 C2, C17A, C16A, C18A, C22A, C19A, C20A, C21A, C26A
 with sigma of 0.1
 C10, C13, N15, O14
 with sigma of 0.1
 C10A, C13A, N15A, O14A
 with sigma of 0.1
4. Rigid bond restraints
 O14, N15, C7, C11, C10, C31, C39, C38, C8, C17, C6, C13, C32, C12, C16, C9,
 C35, O36, C18, C40, C43, C33, O44, C34, C41, C21, C42, C45, C20, C19, C37, C22,
  C26, F23, F24, F25, F29, F27, F28
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O36A, C33A, C37A, C34A, C32A, C31A, C35A, C46, C6A, C7A, C12A, C8A, C11A,
 C10A, C13A, C9A, N15A, O14A, C38A, C43A, C42A, C39A, C41A, C40A, O44A, C45A,
 C17A, C18A, C19A, C20A, C21A, C16A, C26A, C22A, F27A, F25A, F23A, F24A, F29A,
 F28A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Uiso/Uaniso restraints and constraints
O14 \\sim N15 \\sim C7 \\sim C11 \\sim C10 \\sim C31 \\sim C39 \\sim C38 \\sim
C8 \\sim C17 \\sim C6 \\sim C13 \\sim C32 \\sim C12 \\sim C16 \\sim C9 \\sim
C35 \\sim O36 \\sim C18 \\sim C40 \\sim C43 \\sim C33 \\sim O44 \\sim C34 \\sim
C41 \\sim C21 \\sim C42 \\sim C45 \\sim C20 \\sim C19 \\sim C37 \\sim C22 \\sim
C26 \\sim F23 \\sim F24 \\sim F25 \\sim F29 \\sim F27 \\sim F28: within 1.7A
with sigma of 0.008 and sigma for terminal atoms of 0.016
O36A \\sim C33A \\sim C37A \\sim C34A \\sim C32A \\sim C31A \\sim C35A \\sim
C46 \\sim C6A \\sim C7A \\sim C12A \\sim C8A \\sim C11A \\sim C10A \\sim C13A
\\sim C9A \\sim N15A \\sim O14A \\sim C38A \\sim C43A \\sim C42A \\sim C39A
\\sim C41A \\sim C40A \\sim O44A \\sim C45A \\sim C17A \\sim C18A \\sim C19A
\\sim C20A \\sim C21A \\sim C16A \\sim C26A \\sim C22A \\sim F27A \\sim F25A
\\sim F23A \\sim F24A \\sim F29A \\sim F28A: within 1.7A with sigma of 0.008
and sigma for terminal atoms of 0.016
6. Others
 Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(C34A)=Sof(H34A)=
 Sof(C35A)=Sof(H35A)=Sof(O36A)=Sof(C37A)=Sof(H37d)=Sof(H37e)=Sof(H37f)=1-FVAR(1)
 Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(C34)=Sof(H34)=Sof(C35)=
 Sof(H35)=Sof(O36)=Sof(C37)=Sof(H37a)=Sof(H37b)=Sof(H37c)=FVAR(1)
 Sof(C6A)=Sof(H6Aa)=Sof(H6Ab)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(O14A)=
 Sof(N15A)=Sof(H15c)=Sof(H15d)=1-FVAR(2)
 Sof(C6)=Sof(H6a)=Sof(H6b)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(O14)=Sof(N15)=Sof(H15a)=
 Sof(H15b)=FVAR(2)
 Sof(C38A)=Sof(C39A)=Sof(H39A)=Sof(C40A)=Sof(H40A)=Sof(C41A)=Sof(C42A)=
 Sof(H42A)=Sof(C43A)=Sof(H43A)=Sof(O44A)=Sof(C45A)=Sof(H45d)=Sof(H45e)=
 Sof(H45f)=1-FVAR(3)
 Sof(C38)=Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40)=Sof(C41)=Sof(C42)=Sof(H42)=
 Sof(C43)=Sof(H43)=Sof(O44)=Sof(C45)=Sof(H45a)=Sof(H45b)=Sof(H45c)=FVAR(3)
 Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(F23A)=Sof(F24A)=Sof(F25A)=Sof(C26A)=
 Sof(F27A)=Sof(F28A)=Sof(F29A)=1-FVAR(4)
 Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(C21)=
 Sof(H21)=Sof(C22)=Sof(F23)=Sof(F24)=Sof(F25)=Sof(C26)=Sof(F27)=Sof(F28)=
 Sof(F29)=FVAR(4)
 Fixed Sof: C46(0.5) H46a(0.5) H46b(0.5) H46c(0.5) H47(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C6A(H6Aa,H6Ab)
7.b Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C8(H8), C9(H9), C9A(H9A), C11(H11), C11A(H11A), C12A(H12A),
 C12(H12), C17A(H17A), C17(H17), C19A(H19A), C19(H19), C21A(H21A), C21(H21),
 C31A(H31A), C31(H31), C32(H32), C32A(H32A), C34(H34), C34A(H34A), C35A(H35A),
 C35(H35), C39A(H39A), C39(H39), C40(H40), C40A(H40A), C42A(H42A), C42(H42),
 C43(H43), C43A(H43A), C47(H47), C48(H48), C49(H49)
7.c X=CH2 refined with riding coordinates:
 N15(H15a,H15b), N15A(H15c,H15d)
7.d Idealised Me refined as rotating group:
 C37(H37a,H37b,H37c), C37A(H37d,H37e,H37f), C45(H45a,H45b,H45c), C45A(H45d,
 H45e,H45f), C46(H46a,H46b,H46c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.12928(12) 0.73432(11) 0.99986(12) 0.0374(3) Uani 1 1 d . . . . .
C2 C 0.01737(15) 0.75999(13) 1.05370(14) 0.0358(4) Uani 1 1 d . . . . .
N3 N -0.06789(12) 0.83558(11) 1.00283(12) 0.0348(3) Uani 1 1 d . . . . .
C4 C -0.00878(14) 0.86081(13) 0.91221(14) 0.0341(4) Uani 1 1 d . . . . .
C5 C 0.11387(15) 0.79972(13) 0.90891(15) 0.0369(4) Uani 1 1 d . . . . .
C6 C 0.2577(9) 0.6787(8) 1.0273(7) 0.0305(14) Uani 0.531(16) 1 d . U P A 1
H6A H 0.2675 0.6926 1.1004 0.037 Uiso 0.531(16) 1 calc R . P A 1
H6B H 0.3165 0.7172 0.9868 0.037 Uiso 0.531(16) 1 calc R . P A 1
C6A C 0.2401(10) 0.6728(9) 1.0579(8) 0.0297(15) Uani 0.469(16) 1 d . U P A 2
H6AA H 0.2203 0.6846 1.1318 0.036 Uiso 0.469(16) 1 calc R . P A 2
H6AB H 0.3113 0.7098 1.0391 0.036 Uiso 0.469(16) 1 calc R . P A 2
C7 C 0.2957(7) 0.5499(7) 1.0108(6) 0.0270(11) Uani 0.531(16) 1 d . U P A 1
C7A C 0.2824(8) 0.5414(8) 1.0407(7) 0.0256(12) Uani 0.469(16) 1 d . U P A 2
C8A C 0.3771(7) 0.4807(6) 1.1018(7) 0.0292(13) Uani 0.469(16) 1 d . U P A 2
H8A H 0.4100 0.5208 1.1521 0.035 Uiso 0.469(16) 1 calc R . P A 2
C8 C 0.3937(6) 0.4862(6) 1.0665(6) 0.0293(12) Uani 0.531(16) 1 d . U P A 1
H8 H 0.4316 0.5239 1.1155 0.035 Uiso 0.531(16) 1 calc R . P A 1
C9 C 0.4374(6) 0.3667(5) 1.0515(7) 0.0302(11) Uani 0.531(16) 1 d . U P A 1
H9 H 0.5072 0.3243 1.0878 0.036 Uiso 0.531(16) 1 calc R . P A 1
C9A C 0.4240(6) 0.3636(6) 1.0909(8) 0.0293(13) Uani 0.469(16) 1 d . U P A 2
H9A H 0.4893 0.3237 1.1332 0.035 Uiso 0.469(16) 1 calc R . P A 2
C10 C 0.3786(7) 0.3108(6) 0.9835(6) 0.0262(11) Uani 0.531(16) 1 d . U P A 1
C10A C 0.3768(8) 0.3031(7) 1.0183(7) 0.0284(13) Uani 0.469(16) 1 d . U P A 2
C11 C 0.2798(8) 0.3740(7) 0.9291(7) 0.0292(13) Uani 0.531(16) 1 d . U P A 1
H11 H 0.2393 0.3356 0.8824 0.035 Uiso 0.531(16) 1 calc R . P A 1
C11A C 0.2785(9) 0.3612(8) 0.9588(7) 0.0284(14) Uani 0.469(16) 1 d . U P A 2
H11A H 0.2437 0.3199 0.9105 0.034 Uiso 0.469(16) 1 calc R . P A 2
C12A C 0.2304(10) 0.4823(9) 0.9707(8) 0.0293(15) Uani 0.469(16) 1 d . U P A 2
H12A H 0.1629 0.5224 0.9307 0.035 Uiso 0.469(16) 1 calc R . P A 2
C12 C 0.2393(9) 0.4920(8) 0.9415(7) 0.0293(13) Uani 0.531(16) 1 d . U P A 1
H12 H 0.1721 0.5345 0.9025 0.035 Uiso 0.531(16) 1 calc R . P A 1
C13A C 0.4323(6) 0.1750(5) 1.0097(8) 0.0282(12) Uani 0.469(16) 1 d . U P A 2
C13 C 0.4322(5) 0.1826(5) 0.9691(7) 0.0277(11) Uani 0.531(16) 1 d . U P A 1
O14 O 0.5471(3) 0.1448(3) 0.9691(7) 0.0328(12) Uani 0.531(16) 1 d . U P A 1
O14A O 0.5444(3) 0.1383(3) 1.0222(9) 0.0362(15) Uani 0.469(16) 1 d . U P A 2
N15 N 0.3512(9) 0.1166(7) 0.9555(7) 0.0343(15) Uani 0.531(16) 1 d . U P A 1
H15A H 0.3783 0.0416 0.9459 0.041 Uiso 0.531(16) 1 calc R . P A 1
H15B H 0.2702 0.1477 0.9561 0.041 Uiso 0.531(16) 1 calc R . P A 1
N15A N 0.3547(10) 0.1058(9) 0.9898(7) 0.0327(14) Uani 0.469(16) 1 d . U P A 2
H15C H 0.3839 0.0303 0.9851 0.039 Uiso 0.469(16) 1 calc R . P A 2
H15D H 0.2746 0.1358 0.9813 0.039 Uiso 0.469(16) 1 calc R . P A 2
C16A C 0.0106(8) 0.7056(15) 1.1537(13) 0.0376(17) Uani 0.391(3) 1 d . U P B 2
C16 C -0.0152(6) 0.7149(9) 1.1569(9) 0.0433(13) Uani 0.609(3) 1 d . U P B 1
C17A C 0.0452(14) 0.5863(15) 1.1712(12) 0.0350(18) Uani 0.391(3) 1 d . U P B 2
H17A H 0.0750 0.5361 1.1161 0.042 Uiso 0.391(3) 1 calc R . P B 2
C17 C 0.0265(9) 0.5963(10) 1.1846(8) 0.0407(15) Uani 0.609(3) 1 d . U P B 1
H17 H 0.0788 0.5454 1.1381 0.049 Uiso 0.609(3) 1 calc R . P B 1
C18 C -0.0078(4) 0.5536(4) 1.2789(5) 0.0451(10) Uani 0.609(3) 1 d D U P B 1
C18A C 0.0360(7) 0.5410(7) 1.2699(7) 0.0433(15) Uani 0.391(3) 1 d D U P B 2
C19A C -0.0111(5) 0.6102(5) 1.3516(4) 0.0433(11) Uani 0.391(3) 1 d . U P B 2
H19A H -0.0198 0.5767 1.4179 0.052 Uiso 0.391(3) 1 calc R . P B 2
C19 C -0.0841(5) 0.6265(3) 1.3479(3) 0.0594(10) Uani 0.609(3) 1 d . U P B 1
H19 H -0.1064 0.5976 1.4133 0.071 Uiso 0.609(3) 1 calc R . P B 1
C20A C -0.0455(5) 0.7303(4) 1.3347(4) 0.0428(10) Uani 0.391(3) 1 d D U P B 2
C20 C -0.1278(5) 0.7440(3) 1.3191(3) 0.0635(10) Uani 0.609(3) 1 d D U P B 1
C21A C -0.0300(5) 0.7781(4) 1.2390(5) 0.0400(10) Uani 0.391(3) 1 d . U P B 2
H21A H -0.0465 0.8604 1.2295 0.048 Uiso 0.391(3) 1 calc R . P B 2
C21 C -0.0926(4) 0.7871(3) 1.2252(3) 0.0520(9) Uani 0.609(3) 1 d . U P B 1
H21 H -0.1219 0.8671 1.2075 0.062 Uiso 0.609(3) 1 calc R . P B 1
C22 C 0.0418(5) 0.4269(5) 1.3045(5) 0.0528(12) Uani 0.609(3) 1 d D U P B 1
C22A C 0.0708(9) 0.4111(8) 1.2895(8) 0.0617(19) Uani 0.391(3) 1 d D U P B 2
F23 F 0.0482(4) 0.3599(2) 1.2243(2) 0.0719(9) Uani 0.609(3) 1 d D U P B 1
F23A F 0.1568(9) 0.3598(5) 1.2287(6) 0.152(3) Uani 0.391(3) 1 d D U P B 2
F24 F 0.1566(3) 0.4069(3) 1.3385(4) 0.1107(17) Uani 0.609(3) 1 d D U P B 1
F24A F 0.1070(8) 0.3819(5) 1.3820(4) 0.111(2) Uani 0.391(3) 1 d D U P B 2
F25A F -0.0246(7) 0.3618(4) 1.2802(9) 0.137(3) Uani 0.391(3) 1 d D U P B 2
F25 F -0.0294(3) 0.3879(2) 1.3749(3) 0.0849(9) Uani 0.609(3) 1 d D U P B 1
C26 C -0.2160(6) 0.8216(4) 1.3948(4) 0.0841(13) Uani 0.609(3) 1 d D U P B 1
C26A C -0.0928(6) 0.8051(4) 1.4262(5) 0.0558(12) Uani 0.391(3) 1 d D U P B 2
F27 F -0.1734(9) 0.8024(5) 1.4859(4) 0.196(3) Uani 0.609(3) 1 d D U P B 1
F27A F -0.0044(4) 0.7998(3) 1.4933(2) 0.0708(12) Uani 0.391(3) 1 d D U P B 2
F28A F -0.1904(7) 0.7675(6) 1.4757(6) 0.105(2) Uani 0.391(3) 1 d D U P B 2
F28 F -0.3266(4) 0.8137(4) 1.3910(4) 0.172(2) Uani 0.609(3) 1 d D U P B 1
F29 F -0.2095(5) 0.9324(3) 1.3799(4) 0.1221(16) Uani 0.609(3) 1 d D U P B 1
F29A F -0.1301(5) 0.9156(3) 1.3995(3) 0.0730(13) Uani 0.391(3) 1 d D U P B 2
C30 C -0.07642(17) 0.94194(13) 0.83486(15) 0.0399(4) Uani 1 1 d . . . . .
C31A C -0.1915(12) 1.0294(11) 0.8747(9) 0.0323(18) Uani 0.464(5) 1 d . U P C 2
H31A H -0.2092 1.0370 0.9462 0.039 Uiso 0.464(5) 1 calc R . P C 2
C31 C -0.1730(11) 1.0245(10) 0.8543(7) 0.0327(17) Uani 0.536(5) 1 d . U P C 1
H31 H -0.2062 1.0307 0.9227 0.039 Uiso 0.536(5) 1 calc R . P C 1
C32 C -0.2314(5) 1.1050(5) 0.7815(4) 0.0327(10) Uani 0.536(5) 1 d . U P C 1
H32 H -0.3039 1.1622 0.8002 0.039 Uiso 0.536(5) 1 calc R . P C 1
C32A C -0.2692(6) 1.0971(5) 0.8051(5) 0.0351(12) Uani 0.464(5) 1 d . U P C 2
H32A H -0.3416 1.1510 0.8293 0.042 Uiso 0.464(5) 1 calc R . P C 2
C33 C -0.1840(5) 1.1014(3) 0.6829(3) 0.0370(8) Uani 0.536(5) 1 d . U P C 1
C33A C -0.2443(5) 1.0882(3) 0.7010(4) 0.0395(10) Uani 0.464(5) 1 d . U P C 2
C34 C -0.0782(5) 1.0165(3) 0.6560(3) 0.0445(10) Uani 0.536(5) 1 d . U P C 1
H34 H -0.0447 1.0142 0.5876 0.053 Uiso 0.536(5) 1 calc R . P C 1
C34A C -0.1388(5) 1.0086(4) 0.6646(4) 0.0400(10) Uani 0.464(5) 1 d . U P C 2
H34A H -0.1175 1.0036 0.5935 0.048 Uiso 0.464(5) 1 calc R . P C 2
C35A C -0.0645(6) 0.9353(7) 0.7377(8) 0.0389(14) Uani 0.464(5) 1 d . U P C 2
H35A H 0.0007 0.8752 0.7116 0.047 Uiso 0.464(5) 1 calc R . P C 2
C35 C -0.0225(5) 0.9366(6) 0.7277(6) 0.0396(13) Uani 0.536(5) 1 d . U P C 1
H35 H 0.0495 0.8784 0.7098 0.048 Uiso 0.536(5) 1 calc R . P C 1
O36 O -0.2469(4) 1.1855(2) 0.6172(2) 0.0498(9) Uani 0.536(5) 1 d . U P C 1
O36A O -0.3272(4) 1.1607(3) 0.6384(3) 0.0519(12) Uani 0.464(5) 1 d . U P C 2
C37 C -0.1945(6) 1.1914(4) 0.5157(3) 0.0684(16) Uani 0.536(5) 1 d . U P C 1
H37A H -0.2446 1.2576 0.4779 0.103 Uiso 0.536(5) 1 calc GR . P C 1
H37B H -0.1949 1.1192 0.4808 0.103 Uiso 0.536(5) 1 calc GR . P C 1
H37C H -0.1080 1.2013 0.5189 0.103 Uiso 0.536(5) 1 calc GR . P C 1
C37A C -0.3083(6) 1.1502(5) 0.5302(4) 0.0703(19) Uani 0.464(5) 1 d . U P C 2
H37D H -0.3773 1.2028 0.4956 0.105 Uiso 0.464(5) 1 calc GR . P C 2
H37E H -0.3059 1.0698 0.5118 0.105 Uiso 0.464(5) 1 calc GR . P C 2
H37F H -0.2287 1.1707 0.5088 0.105 Uiso 0.464(5) 1 calc GR . P C 2
C38 C 0.2203(9) 0.8181(9) 0.8254(7) 0.0364(15) Uani 0.454(7) 1 d . U P D 1
C38A C 0.2189(8) 0.7950(7) 0.8455(6) 0.0352(13) Uani 0.546(7) 1 d . U P D 2
C39A C 0.2723(7) 0.7026(6) 0.7813(6) 0.0339(12) Uani 0.546(7) 1 d . U P D 2
H39A H 0.2353 0.6368 0.7809 0.041 Uiso 0.546(7) 1 calc R . P D 2
C39 C 0.2828(9) 0.7287(7) 0.7624(8) 0.0366(14) Uani 0.454(7) 1 d . U P D 1
H39 H 0.2591 0.6557 0.7656 0.044 Uiso 0.454(7) 1 calc R . P D 1
C40 C 0.3775(6) 0.7457(6) 0.6966(5) 0.0384(12) Uani 0.454(7) 1 d . U P D 1
H40 H 0.4212 0.6842 0.6551 0.046 Uiso 0.454(7) 1 calc R . P D 1
C40A C 0.3769(5) 0.7044(5) 0.7188(4) 0.0409(11) Uani 0.546(7) 1 d . U P D 2
H40A H 0.4092 0.6413 0.6752 0.049 Uiso 0.546(7) 1 calc R . P D 2
C41 C 0.4095(5) 0.8530(6) 0.6906(4) 0.0452(11) Uani 0.454(7) 1 d . U P D 1
C41A C 0.4352(4) 0.7980(5) 0.7192(3) 0.0422(10) Uani 0.546(7) 1 d . U P D 2
C42A C 0.3867(4) 0.8920(4) 0.7819(3) 0.0408(9) Uani 0.546(7) 1 d . U P D 2
H42A H 0.4249 0.9571 0.7820 0.049 Uiso 0.546(7) 1 calc R . P D 2
C42 C 0.3429(5) 0.9443(5) 0.7474(4) 0.0462(12) Uani 0.454(7) 1 d . U P D 1
H42 H 0.3632 1.0187 0.7408 0.055 Uiso 0.454(7) 1 calc R . P D 1
C43 C 0.2465(6) 0.9269(5) 0.8142(4) 0.0396(11) Uani 0.454(7) 1 d . U P D 1
H43 H 0.1987 0.9899 0.8520 0.048 Uiso 0.454(7) 1 calc R . P D 1
C43A C 0.2809(4) 0.8882(4) 0.8443(4) 0.0352(9) Uani 0.546(7) 1 d . U P D 2
H43A H 0.2492 0.9514 0.8880 0.042 Uiso 0.546(7) 1 calc R . P D 2
O44 O 0.5075(5) 0.8607(5) 0.6235(4) 0.0608(13) Uani 0.454(7) 1 d . U P D 1
O44A O 0.5396(3) 0.7911(5) 0.6572(3) 0.0545(11) Uani 0.546(7) 1 d . U P D 2
C45 C 0.5524(9) 0.9657(8) 0.6241(6) 0.093(3) Uani 0.454(7) 1 d . U P D 1
H45A H 0.6295 0.9572 0.5814 0.139 Uiso 0.454(7) 1 calc GR . P D 1
H45B H 0.5698 0.9817 0.6944 0.139 Uiso 0.454(7) 1 calc GR . P D 1
H45C H 0.4886 1.0304 0.5969 0.139 Uiso 0.454(7) 1 calc GR . P D 1
C45A C 0.6106(4) 0.8798(6) 0.6668(3) 0.0623(15) Uani 0.546(7) 1 d . U P D 2
H45D H 0.6860 0.8628 0.6217 0.093 Uiso 0.546(7) 1 calc GR . P D 2
H45E H 0.6352 0.8810 0.7379 0.093 Uiso 0.546(7) 1 calc GR . P D 2
H45F H 0.5589 0.9559 0.6473 0.093 Uiso 0.546(7) 1 calc GR . P D 2
C46 C 0.5591(8) 0.6743(7) 0.3420(7) 0.120(3) Uani 0.5 1 d . U P E 1
H46A H 0.6482 0.6751 0.3459 0.180 Uiso 0.5 1 calc GR . P E 1
H46B H 0.5083 0.7525 0.3546 0.180 Uiso 0.5 1 calc GR . P E 1
H46C H 0.5427 0.6504 0.2738 0.180 Uiso 0.5 1 calc GR . P E 1
C47 C 0.5225(3) 0.5833(2) 0.4277(3) 0.0841(9) Uani 1 1 d . . . . .
H47 H 0.5379 0.6401 0.3783 0.101 Uiso 0.5 1 calc R . P E 2
C48 C 0.6062(3) 0.5428(2) 0.5026(3) 0.0866(9) Uani 1 1 d . . . . .
H48 H 0.6802 0.5723 0.5050 0.104 Uiso 1 1 calc R . . . .
C49 C 0.5853(3) 0.4603(2) 0.5745(3) 0.0857(9) Uani 1 1 d . . . . .
H49 H 0.6448 0.4331 0.6257 0.103 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.365(2) . ?
N1 C5 1.389(2) . ?
N1 C6 1.466(10) . ?
N1 C6A 1.489(11) . ?
C2 N3 1.322(2) . ?
C2 C16A 1.44(2) . ?
C2 C16 1.490(12) . ?
N3 C4 1.380(2) . ?
C4 C5 1.375(2) . ?
C4 C30 1.471(2) . ?
C5 C38 1.605(11) . ?
C5 C38A 1.379(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.503(11) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.537(13) . ?
C7 C8 1.383(9) . ?
C7 C12 1.394(10) . ?
C7A C8A 1.387(10) . ?
C7A C12A 1.382(12) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.372(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.402(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(7) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.388(8) . ?
C10 C11 1.378(8) . ?
C10 C13 1.510(8) . ?
C10A C11A 1.391(9) . ?
C10A C13A 1.504(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(11) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.419(13) . ?
C12A H12A 0.9500 . ?
C12 H12 0.9500 . ?
C13A O14A 1.222(7) . ?
C13A N15A 1.338(13) . ?
C13 O14 1.238(6) . ?
C13 N15 1.320(11) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
N15A H15C 0.8800 . ?
N15A H15D 0.8800 . ?
C16A C17A 1.39(2) . ?
C16A C21A 1.425(14) . ?
C16 C17 1.409(14) . ?
C16 C21 1.383(10) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.386(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(12) . ?
C18 C19 1.388(6) . ?
C18 C22 1.502(6) . ?
C18A C19A 1.379(10) . ?
C18A C22A 1.509(10) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.394(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.405(5) . ?
C20A C21A 1.372(8) . ?
C20A C26A 1.516(7) . ?
C20 C21 1.382(6) . ?
C20 C26 1.530(6) . ?
C21A H21A 0.9500 . ?
C21 H21 0.9500 . ?
C22 F23 1.325(6) . ?
C22 F24 1.318(6) . ?
C22 F25 1.316(6) . ?
C22A F23A 1.265(9) . ?
C22A F24A 1.299(10) . ?
C22A F25A 1.312(10) . ?
C26 F27 1.291(7) . ?
C26 F28 1.236(6) . ?
C26 F29 1.329(6) . ?
C26A F27A 1.323(7) . ?
C26A F28A 1.371(8) . ?
C26A F29A 1.314(6) . ?
C30 C31A 1.526(13) . ?
C30 C31 1.292(13) . ?
C30 C35A 1.275(10) . ?
C30 C35 1.494(8) . ?
C31A H31A 0.9500 . ?
C31A C32A 1.379(14) . ?
C31 H31 0.9500 . ?
C31 C32 1.390(13) . ?
C32 H32 0.9500 . ?
C32 C33 1.368(6) . ?
C32A H32A 0.9500 . ?
C32A C33A 1.380(7) . ?
C33 C34 1.394(5) . ?
C33 O36 1.371(4) . ?
C33A C34A 1.395(6) . ?
C33A O36A 1.375(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.367(9) . ?
C34A H34A 0.9500 . ?
C34A C35A 1.420(10) . ?
C35A H35A 0.9500 . ?
C35 H35 0.9500 . ?
O36 C37 1.429(5) . ?
O36A C37A 1.428(6) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C37A H37D 0.9800 . ?
C37A H37E 0.9800 . ?
C37A H37F 0.9800 . ?
C38 C39 1.398(14) . ?
C38 C43 1.375(9) . ?
C38A C39A 1.406(11) . ?
C38A C43A 1.411(7) . ?
C39A H39A 0.9500 . ?
C39A C40A 1.380(8) . ?
C39 H39 0.9500 . ?
C39 C40 1.361(10) . ?
C40 H40 0.9500 . ?
C40 C41 1.383(7) . ?
C40A H40A 0.9500 . ?
C40A C41A 1.389(6) . ?
C41 C42 1.381(7) . ?
C41 O44 1.372(6) . ?
C41A C42A 1.397(5) . ?
C41A O44A 1.361(5) . ?
C42A H42A 0.9500 . ?
C42A C43A 1.393(5) . ?
C42 H42 0.9500 . ?
C42 C43 1.385(7) . ?
C43 H43 0.9500 . ?
C43A H43A 0.9500 . ?
O44 C45 1.427(7) . ?
O44A C45A 1.443(6) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C45A H45D 0.9800 . ?
C45A H45E 0.9800 . ?
C45A H45F 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C46 C47 1.621(8) . ?
C47 H47 0.9500 . ?
C47 C48 1.368(5) . ?
C47 C49 1.386(5) 2_666 ?
C48 H48 0.9500 . ?
C48 C49 1.376(4) . ?
C49 C47 1.386(5) 2_666 ?
C49 H49 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 106.96(13) . . ?
C2 N1 C6 133.7(4) . . ?
C2 N1 C6A 116.4(4) . . ?
C5 N1 C6 117.5(4) . . ?
C5 N1 C6A 134.4(4) . . ?
N1 C2 C16A 117.6(4) . . ?
N1 C2 C16 128.5(3) . . ?
N3 C2 N1 111.51(16) . . ?
N3 C2 C16A 130.8(4) . . ?
N3 C2 C16 120.0(3) . . ?
C2 N3 C4 105.88(14) . . ?
N3 C4 C30 121.13(14) . . ?
C5 C4 N3 110.06(15) . . ?
C5 C4 C30 128.81(17) . . ?
N1 C5 C38 127.8(3) . . ?
C4 C5 N1 105.57(15) . . ?
C4 C5 C38 125.9(3) . . ?
C4 C5 C38A 137.1(3) . . ?
C38A C5 N1 117.1(3) . . ?
N1 C6 H6A 108.4 . . ?
N1 C6 H6B 108.4 . . ?
N1 C6 C7 115.6(6) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
N1 C6A H6AA 108.4 . . ?
N1 C6A H6AB 108.4 . . ?
N1 C6A C7A 115.7(7) . . ?
H6AA C6A H6AB 107.4 . . ?
C7A C6A H6AA 108.4 . . ?
C7A C6A H6AB 108.4 . . ?
C8 C7 C6 117.8(6) . . ?
C8 C7 C12 118.5(7) . . ?
C12 C7 C6 123.7(6) . . ?
C8A C7A C6A 116.4(7) . . ?
C12A C7A C6A 124.0(7) . . ?
C12A C7A C8A 119.6(8) . . ?
C7A C8A H8A 119.4 . . ?
C9A C8A C7A 121.1(6) . . ?
C9A C8A H8A 119.4 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.7(5) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.7(5) . . ?
C10 C9 H9 120.2 . . ?
C8A C9A H9A 119.8 . . ?
C8A C9A C10A 120.4(6) . . ?
C10A C9A H9A 119.8 . . ?
C9 C10 C13 117.1(5) . . ?
C11 C10 C9 119.6(6) . . ?
C11 C10 C13 123.3(6) . . ?
C9A C10A C11A 119.6(7) . . ?
C9A C10A C13A 117.9(5) . . ?
C11A C10A C13A 122.5(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(7) . . ?
C12 C11 H11 119.7 . . ?
C10A C11A H11A 120.2 . . ?
C10A C11A C12A 119.7(7) . . ?
C12A C11A H11A 120.2 . . ?
C7A C12A C11A 119.6(8) . . ?
C7A C12A H12A 120.2 . . ?
C11A C12A H12A 120.2 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.8(7) . . ?
C11 C12 H12 119.6 . . ?
O14A C13A C10A 119.5(6) . . ?
O14A C13A N15A 122.9(7) . . ?
N15A C13A C10A 117.6(7) . . ?
O14 C13 C10 119.8(5) . . ?
O14 C13 N15 123.4(6) . . ?
N15 C13 C10 116.9(6) . . ?
C13 N15 H15A 120.0 . . ?
C13 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
C13A N15A H15C 120.0 . . ?
C13A N15A H15D 120.0 . . ?
H15C N15A H15D 120.0 . . ?
C17A C16A C2 123.0(10) . . ?
C17A C16A C21A 118.5(14) . . ?
C21A C16A C2 118.5(12) . . ?
C17 C16 C2 120.6(7) . . ?
C21 C16 C2 120.6(8) . . ?
C21 C16 C17 118.7(9) . . ?
C16A C17A H17A 120.3 . . ?
C16A C17A C18A 119.4(12) . . ?
C18A C17A H17A 120.3 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(7) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 120.7(5) . . ?
C17 C18 C22 117.9(6) . . ?
C19 C18 C22 121.4(5) . . ?
C17A C18A C22A 119.9(9) . . ?
C19A C18A C17A 122.3(9) . . ?
C19A C18A C22A 117.7(8) . . ?
C18A C19A H19A 120.7 . . ?
C18A C19A C20A 118.6(6) . . ?
C20A C19A H19A 120.7 . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.5(4) . . ?
C20 C19 H19 120.7 . . ?
C19A C20A C26A 117.7(5) . . ?
C21A C20A C19A 120.3(5) . . ?
C21A C20A C26A 121.9(4) . . ?
C19 C20 C26 117.6(4) . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 C26 121.6(4) . . ?
C16A C21A H21A 119.7 . . ?
C20A C21A C16A 120.7(9) . . ?
C20A C21A H21A 119.7 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.7(6) . . ?
C20 C21 H21 119.7 . . ?
F23 C22 C18 112.8(5) . . ?
F24 C22 C18 112.1(4) . . ?
F24 C22 F23 105.7(5) . . ?
F25 C22 C18 111.6(4) . . ?
F25 C22 F23 106.7(4) . . ?
F25 C22 F24 107.7(5) . . ?
F23A C22A C18A 113.1(8) . . ?
F23A C22A F24A 107.2(8) . . ?
F23A C22A F25A 106.2(9) . . ?
F24A C22A C18A 113.4(8) . . ?
F24A C22A F25A 104.0(8) . . ?
F25A C22A C18A 112.3(7) . . ?
F27 C26 C20 109.7(5) . . ?
F27 C26 F29 100.3(5) . . ?
F28 C26 C20 113.6(4) . . ?
F28 C26 F27 112.6(7) . . ?
F28 C26 F29 109.1(5) . . ?
F29 C26 C20 110.8(4) . . ?
F27A C26A C20A 111.8(5) . . ?
F27A C26A F28A 107.4(6) . . ?
F28A C26A C20A 110.1(5) . . ?
F29A C26A C20A 111.9(5) . . ?
F29A C26A F27A 106.2(4) . . ?
F29A C26A F28A 109.2(5) . . ?
C4 C30 C31A 115.7(5) . . ?
C4 C30 C35 117.8(3) . . ?
C31 C30 C4 124.7(5) . . ?
C31 C30 C35 117.1(5) . . ?
C35A C30 C4 127.7(4) . . ?
C35A C30 C31A 115.4(6) . . ?
C30 C31A H31A 120.6 . . ?
C32A C31A C30 118.8(8) . . ?
C32A C31A H31A 120.6 . . ?
C30 C31 H31 117.9 . . ?
C30 C31 C32 124.2(7) . . ?
C32 C31 H31 117.9 . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.7(5) . . ?
C33 C32 H32 120.2 . . ?
C31A C32A H32A 119.2 . . ?
C31A C32A C33A 121.5(6) . . ?
C33A C32A H32A 119.2 . . ?
C32 C33 C34 119.8(4) . . ?
C32 C33 O36 115.3(4) . . ?
O36 C33 C34 124.9(4) . . ?
C32A C33A C34A 119.7(4) . . ?
O36A C33A C32A 116.7(4) . . ?
O36A C33A C34A 123.6(4) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.1(4) . . ?
C35 C34 H34 119.9 . . ?
C33A C34A H34A 121.2 . . ?
C33A C34A C35A 117.6(5) . . ?
C35A C34A H34A 121.2 . . ?
C30 C35A C34A 126.7(6) . . ?
C30 C35A H35A 116.7 . . ?
C34A C35A H35A 116.7 . . ?
C30 C35 H35 120.5 . . ?
C34 C35 C30 119.1(4) . . ?
C34 C35 H35 120.5 . . ?
C33 O36 C37 117.2(3) . . ?
C33A O36A C37A 118.4(4) . . ?
O36 C37 H37A 109.5 . . ?
O36 C37 H37B 109.5 . . ?
O36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O36A C37A H37D 109.5 . . ?
O36A C37A H37E 109.5 . . ?
O36A C37A H37F 109.5 . . ?
H37D C37A H37E 109.5 . . ?
H37D C37A H37F 109.5 . . ?
H37E C37A H37F 109.5 . . ?
C39 C38 C5 122.1(6) . . ?
C43 C38 C5 118.1(9) . . ?
C43 C38 C39 119.8(8) . . ?
C5 C38A C39A 125.2(5) . . ?
C5 C38A C43A 118.9(7) . . ?
C39A C38A C43A 115.8(6) . . ?
C38A C39A H39A 119.0 . . ?
C40A C39A C38A 122.1(5) . . ?
C40A C39A H39A 119.0 . . ?
C38 C39 H39 119.8 . . ?
C40 C39 C38 120.4(6) . . ?
C40 C39 H39 119.8 . . ?
C39 C40 H40 120.2 . . ?
C39 C40 C41 119.5(6) . . ?
C41 C40 H40 120.2 . . ?
C39A C40A H40A 119.7 . . ?
C39A C40A C41A 120.5(4) . . ?
C41A C40A H40A 119.7 . . ?
C42 C41 C40 120.6(5) . . ?
O44 C41 C40 115.1(5) . . ?
O44 C41 C42 124.3(4) . . ?
C40A C41A C42A 119.9(4) . . ?
O44A C41A C40A 116.6(4) . . ?
O44A C41A C42A 123.5(4) . . ?
C41A C42A H42A 120.7 . . ?
C43A C42A C41A 118.5(3) . . ?
C43A C42A H42A 120.7 . . ?
C41 C42 H42 120.1 . . ?
C41 C42 C43 119.7(4) . . ?
C43 C42 H42 120.1 . . ?
C38 C43 C42 119.7(6) . . ?
C38 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C38A C43A H43A 118.5 . . ?
C42A C43A C38A 123.1(5) . . ?
C42A C43A H43A 118.5 . . ?
C41 O44 C45 116.5(4) . . ?
C41A O44A C45A 117.1(3) . . ?
O44 C45 H45A 109.5 . . ?
O44 C45 H45B 109.5 . . ?
O44 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O44A C45A H45D 109.5 . . ?
O44A C45A H45E 109.5 . . ?
O44A C45A H45F 109.5 . . ?
H45D C45A H45E 109.5 . . ?
H45D C45A H45F 109.5 . . ?
H45E C45A H45F 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C47 C46 H46A 109.5 . . ?
C47 C46 H46B 109.5 . . ?
C47 C46 H46C 109.5 . . ?
C48 C47 C46 117.9(4) . . ?
C48 C47 H47 120.7 . . ?
C48 C47 C49 118.6(3) . 2_666 ?
C49 C47 C46 123.3(4) 2_666 . ?
C49 C47 H47 120.7 2_666 . ?
C47 C48 H48 119.3 . . ?
C47 C48 C49 121.4(3) . . ?
C49 C48 H48 119.3 . . ?
C47 C49 H49 120.0 2_666 . ?
C48 C49 C47 120.0(3) . 2_666 ?
C48 C49 H49 120.0 . . ?

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
N15 H15A O14 0.88 2.41 3.171(11) 144.2 2_657
N15 H15B N3 0.88 2.22 3.052(9) 157.4 2_567
N15A H15C O14A 0.88 1.97 2.852(11) 177.5 2_657
N15A H15D N3 0.88 2.21 3.056(11) 160.9 2_567

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
N1 C2 N3 C4 -0.38(17) . . . . ?
N1 C2 C16A C17A -53.5(7) . . . . ?
N1 C2 C16A C21A 124.6(5) . . . . ?
N1 C2 C16 C17 -41.8(6) . . . . ?
N1 C2 C16 C21 141.7(4) . . . . ?
N1 C5 C38 C39 70.6(7) . . . . ?
N1 C5 C38 C43 -111.6(5) . . . . ?
N1 C5 C38A C39A 77.3(6) . . . . ?
N1 C5 C38A C43A -101.8(5) . . . . ?
N1 C6 C7 C8 -157.4(5) . . . . ?
N1 C6 C7 C12 23.7(7) . . . . ?
N1 C6A C7A C8A -173.6(6) . . . . ?
N1 C6A C7A C12A 5.0(8) . . . . ?
C2 N1 C5 C4 -0.90(16) . . . . ?
C2 N1 C5 C38 169.8(5) . . . . ?
C2 N1 C5 C38A 174.7(4) . . . . ?
C2 N1 C6 C7 93.8(5) . . . . ?
C2 N1 C6A C7A 102.2(4) . . . . ?
C2 N3 C4 C5 -0.22(17) . . . . ?
C2 N3 C4 C30 179.25(14) . . . . ?
C2 C16A C17A C18A 179.9(10) . . . . ?
C2 C16A C21A C20A 175.9(5) . . . . ?
C2 C16 C17 C18 -177.5(7) . . . . ?
C2 C16 C21 C20 176.9(5) . . . . ?
N3 C2 C16A C17A 128.2(8) . . . . ?
N3 C2 C16A C21A -53.7(9) . . . . ?
N3 C2 C16 C17 138.6(5) . . . . ?
N3 C2 C16 C21 -37.9(7) . . . . ?
N3 C4 C5 N1 0.70(17) . . . . ?
N3 C4 C5 C38 -170.3(5) . . . . ?
N3 C4 C5 C38A -173.6(5) . . . . ?
N3 C4 C30 C31A 23.2(5) . . . . ?
N3 C4 C30 C31 25.8(5) . . . . ?
N3 C4 C30 C35A -143.3(4) . . . . ?
N3 C4 C30 C35 -160.7(3) . . . . ?
C4 C5 C38 C39 -120.4(7) . . . . ?
C4 C5 C38 C43 57.4(6) . . . . ?
C4 C5 C38A C39A -108.9(6) . . . . ?
C4 C5 C38A C43A 72.0(6) . . . . ?
C4 C30 C31A C32A -171.1(5) . . . . ?
C4 C30 C31 C32 175.9(4) . . . . ?
C4 C30 C35A C34A 173.7(4) . . . . ?
C4 C30 C35 C34 -175.2(4) . . . . ?
C5 N1 C2 N3 0.82(17) . . . . ?
C5 N1 C2 C16A -177.8(6) . . . . ?
C5 N1 C2 C16 -178.8(5) . . . . ?
C5 N1 C6 C7 -103.8(4) . . . . ?
C5 N1 C6A C7A -97.6(6) . . . . ?
C5 C4 C30 C31A -157.5(4) . . . . ?
C5 C4 C30 C31 -154.9(5) . . . . ?
C5 C4 C30 C35A 36.0(5) . . . . ?
C5 C4 C30 C35 18.6(4) . . . . ?
C5 C38 C39 C40 -176.2(7) . . . . ?
C5 C38 C43 C42 176.1(5) . . . . ?
C5 C38A C39A C40A 179.2(6) . . . . ?
C5 C38A C43A C42A -179.1(4) . . . . ?
C6 N1 C2 N3 164.5(5) . . . . ?
C6 N1 C2 C16 -15.2(7) . . . . ?
C6 N1 C5 C4 -167.6(4) . . . . ?
C6 N1 C5 C38 3.1(6) . . . . ?
C6 C7 C8 C9 -177.2(4) . . . . ?
C6 C7 C12 C11 179.1(6) . . . . ?
C6A N1 C2 N3 166.1(5) . . . . ?
C6A N1 C2 C16A -12.5(7) . . . . ?
C6A N1 C5 C4 -162.4(6) . . . . ?
C6A N1 C5 C38A 13.2(7) . . . . ?
C6A C7A C8A C9A -178.3(5) . . . . ?
C6A C7A C12A C11A 178.4(6) . . . . ?
C7 C8 C9 C10 -2.8(7) . . . . ?
C7A C8A C9A C10A -0.4(8) . . . . ?
C8A C7A C12A C11A -3.0(9) . . . . ?
C8A C9A C10A C11A -2.1(9) . . . . ?
C8A C9A C10A C13A 179.8(5) . . . . ?
C8 C7 C12 C11 0.2(8) . . . . ?
C8 C9 C10 C11 1.9(8) . . . . ?
C8 C9 C10 C13 178.7(5) . . . . ?
C9 C10 C11 C12 0.1(9) . . . . ?
C9 C10 C13 O14 -37.3(6) . . . . ?
C9 C10 C13 N15 143.6(5) . . . . ?
C9A C10A C11A C12A 2.0(10) . . . . ?
C9A C10A C13A O14A -35.9(8) . . . . ?
C9A C10A C13A N15A 143.2(6) . . . . ?
C10 C11 C12 C7 -1.2(10) . . . . ?
C10A C11A C12A C7A 0.5(11) . . . . ?
C11 C10 C13 O14 139.4(6) . . . . ?
C11 C10 C13 N15 -39.8(7) . . . . ?
C11A C10A C13A O14A 146.0(7) . . . . ?
C11A C10A C13A N15A -34.9(9) . . . . ?
C12A C7A C8A C9A 3.0(8) . . . . ?
C12 C7 C8 C9 1.8(7) . . . . ?
C13A C10A C11A C12A -179.9(7) . . . . ?
C13 C10 C11 C12 -176.5(6) . . . . ?
C16A C2 N3 C4 178.0(7) . . . . ?
C16A C17A C18A C19A 2.5(15) . . . . ?
C16A C17A C18A C22A 178.7(8) . . . . ?
C16 C2 N3 C4 179.3(4) . . . . ?
C16 C17 C18 C19 0.0(10) . . . . ?
C16 C17 C18 C22 -178.9(5) . . . . ?
C17A C16A C21A C20A -5.9(9) . . . . ?
C17A C18A C19A C20A -2.8(12) . . . . ?
C17A C18A C22A F23A 31.4(14) . . . . ?
C17A C18A C22A F24A 153.8(10) . . . . ?
C17A C18A C22A F25A -88.7(12) . . . . ?
C17 C16 C21 C20 0.3(7) . . . . ?
C17 C18 C19 C20 1.3(9) . . . . ?
C17 C18 C22 F23 -37.0(8) . . . . ?
C17 C18 C22 F24 82.1(8) . . . . ?
C17 C18 C22 F25 -157.1(6) . . . . ?
C18 C19 C20 C21 -1.9(7) . . . . ?
C18 C19 C20 C26 177.6(5) . . . . ?
C18A C19A C20A C21A -1.4(8) . . . . ?
C18A C19A C20A C26A -177.9(6) . . . . ?
C19A C18A C22A F23A -152.2(9) . . . . ?
C19A C18A C22A F24A -29.8(11) . . . . ?
C19A C18A C22A F25A 87.7(11) . . . . ?
C19A C20A C21A C16A 5.7(9) . . . . ?
C19A C20A C26A F27A 65.2(6) . . . . ?
C19A C20A C26A F28A -54.1(8) . . . . ?
C19A C20A C26A F29A -175.7(5) . . . . ?
C19 C18 C22 F23 144.1(5) . . . . ?
C19 C18 C22 F24 -96.8(6) . . . . ?
C19 C18 C22 F25 24.0(7) . . . . ?
C19 C20 C21 C16 1.1(8) . . . . ?
C19 C20 C26 F27 44.9(8) . . . . ?
C19 C20 C26 F28 -82.1(6) . . . . ?
C19 C20 C26 F29 154.7(5) . . . . ?
C21A C16A C17A C18A 1.8(12) . . . . ?
C21A C20A C26A F27A -111.3(6) . . . . ?
C21A C20A C26A F28A 129.4(6) . . . . ?
C21A C20A C26A F29A 7.8(8) . . . . ?
C21 C16 C17 C18 -0.9(9) . . . . ?
C21 C20 C26 F27 -135.6(7) . . . . ?
C21 C20 C26 F28 97.4(6) . . . . ?
C21 C20 C26 F29 -25.8(7) . . . . ?
C22 C18 C19 C20 -179.8(5) . . . . ?
C22A C18A C19A C20A -179.1(6) . . . . ?
C26 C20 C21 C16 -178.4(5) . . . . ?
C26A C20A C21A C16A -177.9(6) . . . . ?
C30 C4 C5 N1 -178.71(15) . . . . ?
C30 C4 C5 C38 10.3(5) . . . . ?
C30 C4 C5 C38A 7.0(5) . . . . ?
C30 C31A C32A C33A -0.8(9) . . . . ?
C30 C31 C32 C33 -2.1(8) . . . . ?
C31A C30 C35A C34A 7.2(9) . . . . ?
C31A C32A C33A C34A 0.5(8) . . . . ?
C31A C32A C33A O36A -179.3(5) . . . . ?
C31 C30 C35 C34 -1.2(8) . . . . ?
C31 C32 C33 C34 0.5(7) . . . . ?
C31 C32 C33 O36 -179.0(4) . . . . ?
C32 C33 C34 C35 0.5(7) . . . . ?
C32 C33 O36 C37 174.7(4) . . . . ?
C32A C33A C34A C35A 3.1(8) . . . . ?
C32A C33A O36A C37A -176.9(5) . . . . ?
C33 C34 C35 C30 -0.2(8) . . . . ?
C33A C34A C35A C30 -7.6(9) . . . . ?
C34 C33 O36 C37 -4.7(6) . . . . ?
C34A C33A O36A C37A 3.3(7) . . . . ?
C35A C30 C31A C32A -2.9(9) . . . . ?
C35 C30 C31 C32 2.3(9) . . . . ?
O36 C33 C34 C35 179.9(5) . . . . ?
O36A C33A C34A C35A -177.1(5) . . . . ?
C38 C39 C40 C41 -1.5(12) . . . . ?
C38A C39A C40A C41A 1.5(9) . . . . ?
C39A C38A C43A C42A 1.7(7) . . . . ?
C39A C40A C41A C42A -1.1(8) . . . . ?
C39A C40A C41A O44A 178.3(5) . . . . ?
C39 C38 C43 C42 -6.1(9) . . . . ?
C39 C40 C41 C42 -2.8(10) . . . . ?
C39 C40 C41 O44 178.8(7) . . . . ?
C40 C41 C42 C43 2.7(8) . . . . ?
C40 C41 O44 C45 -173.0(6) . . . . ?
C40A C41A C42A C43A 1.0(7) . . . . ?
C40A C41A O44A C45A -172.0(4) . . . . ?
C41 C42 C43 C38 1.8(8) . . . . ?
C41A C42A C43A C38A -1.4(7) . . . . ?
C42A C41A O44A C45A 7.5(6) . . . . ?
C42 C41 O44 C45 8.7(9) . . . . ?
C43 C38 C39 C40 6.0(11) . . . . ?
C43A C38A C39A C40A -1.7(9) . . . . ?
O44 C41 C42 C43 -179.1(5) . . . . ?
O44A C41A C42A C43A -178.4(4) . . . . ?
C46 C47 C48 C49 -176.1(5) . . . . ?
C47 C48 C49 C47 -0.2(5) . . . 2_666 ?
C49 C47 C48 C49 0.2(5) 2_666 . . . ?

_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_apcjmj
_database_code_depnum_ccdc_archive 'CCDC 1456779'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-03-22 downloaded from the CCDC.
;
_nottingham_internal_coll_name   APCJMJ
_nottingham_internal_coll_number 11350
_nottingham_internal_coll_client AP/CJM
_nottingham_internal_coll_type   hemi
_nottingham_internal_coll_frame_method '\f and \w scans'
_nottingham_internal_coll_frame_time ?
_nottingham_internal_coll_frame_width 0.3
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   ?
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument ?
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date ?
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date ?
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 29/2/2016
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 3/5/2013
_refine_special_details          ?
_audit_creation_date             2016-02-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37
_chemical_absolute_configuration .
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   7.3173(2)
_cell_length_b                   15.5645(4)
_cell_length_c                   13.0802(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1489.71(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10907
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2007/2 (Bruker,2007) was used for absorption correction.
wR2(int) was 0.0760 before and 0.0319 after correction.
The Ratio of minimum to maximum transmission is 0.9267.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15358
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.389
_diffrn_reflns_theta_min         2.617
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      90(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                3111
_reflns_number_total             3166
_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       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1352 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(6)
_refine_ls_extinction_coef       0.0092(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.057
_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)+(0.0522P)²+0.2317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0795
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.48529(18) 0.32045(8) 0.47612(11) 0.0153(3) Uani 1 1 d . . . . .
C2 C 0.5312(2) 0.27445(10) 0.38991(13) 0.0163(3) Uani 1 1 d . . . . .
N3 N 0.52706(19) 0.19019(8) 0.40512(12) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.4736(2) 0.18138(10) 0.50511(13) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.4490(2) 0.26049(10) 0.55173(12) 0.0153(3) Uani 1 1 d . . . . .
C6 C 0.4388(2) 0.41187(9) 0.47967(14) 0.0186(3) Uani 1 1 d . . . . .
H6A H 0.5372 0.4436 0.5136 0.028 Uiso 1 1 calc GR . . . .
H6B H 0.3247 0.4196 0.5179 0.028 Uiso 1 1 calc GR . . . .
H6C H 0.4232 0.4336 0.4099 0.028 Uiso 1 1 calc GR . . . .
C7 C 0.5728(2) 0.31342(9) 0.28995(13) 0.0164(3) Uani 1 1 d . . . . .
C8 C 0.6714(2) 0.39001(10) 0.27962(13) 0.0177(3) Uani 1 1 d . . . . .
H8 H 0.7127 0.4195 0.3389 0.021 Uiso 1 1 calc R . . . .
C9 C 0.7095(2) 0.42315(9) 0.18309(14) 0.0197(3) Uani 1 1 d . . . . .
H9 H 0.7761 0.4753 0.1767 0.024 Uiso 1 1 calc R . . . .
C10 C 0.6501(2) 0.38015(11) 0.09597(14) 0.0211(3) Uani 1 1 d . . . . .
H10 H 0.6750 0.4031 0.0301 0.025 Uiso 1 1 calc R . . . .
C11 C 0.5540(2) 0.30324(10) 0.10566(14) 0.0203(3) Uani 1 1 d . . . . .
H11 H 0.5144 0.2735 0.0462 0.024 Uiso 1 1 calc R . . . .
C12 C 0.5157(2) 0.26980(10) 0.20198(13) 0.0179(3) Uani 1 1 d . . . . .
H12 H 0.4507 0.2172 0.2080 0.022 Uiso 1 1 calc R . . . .
C13 C 0.4316(2) 0.10255(9) 0.55748(13) 0.0157(3) Uani 1 1 d . . . . .
C14 C 0.3680(2) 0.10834(10) 0.65938(13) 0.0173(3) Uani 1 1 d . . . . .
C15 C 0.3134(2) 0.03103(10) 0.70802(14) 0.0211(4) Uani 1 1 d . . . . .
H15 H 0.2705 0.0330 0.7765 0.025 Uiso 1 1 calc R . . . .
C16 C 0.3212(2) -0.04696(11) 0.65794(15) 0.0231(4) Uani 1 1 d . . . . .
H16 H 0.2818 -0.0977 0.6918 0.028 Uiso 1 1 calc R . . . .
C17 C 0.3869(2) -0.05191(10) 0.55758(14) 0.0221(4) Uani 1 1 d . . . . .
H17 H 0.3936 -0.1059 0.5239 0.027 Uiso 1 1 calc R . . . .
C18 C 0.4420(2) 0.02215(10) 0.50763(13) 0.0189(3) Uani 1 1 d . . . . .
H18 H 0.4869 0.0189 0.4396 0.023 Uiso 1 1 calc R . . . .
C19 C 0.3963(2) 0.26959(10) 0.65677(12) 0.0164(3) Uani 1 1 d . . . . .
C20 C 0.3566(2) 0.19214(10) 0.71059(13) 0.0171(3) Uani 1 1 d . . . . .
C21 C 0.3048(2) 0.19877(11) 0.81405(14) 0.0204(3) Uani 1 1 d . . . . .
H21 H 0.2788 0.1479 0.8514 0.024 Uiso 1 1 calc R . . . .
C22 C 0.2910(2) 0.27711(11) 0.86253(14) 0.0219(4) Uani 1 1 d . . . . .
H22 H 0.2527 0.2797 0.9319 0.026 Uiso 1 1 calc R . . . .
C23 C 0.3331(2) 0.35277(10) 0.80991(14) 0.0213(3) Uani 1 1 d . . . . .
H23 H 0.3251 0.4067 0.8437 0.026 Uiso 1 1 calc R . . . .
C24 C 0.3862(2) 0.34909(10) 0.70916(13) 0.0188(3) Uani 1 1 d . . . . .
H24 H 0.4167 0.4006 0.6742 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.377(2) . ?
N1 C5 1.386(2) . ?
N1 C6 1.4638(19) . ?
C2 N3 1.327(2) . ?
C2 C7 1.473(2) . ?
N3 C4 1.372(2) . ?
C4 C5 1.386(2) . ?
C4 C13 1.438(2) . ?
C5 C19 1.434(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.400(2) . ?
C7 C12 1.400(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.415(2) . ?
C13 C18 1.413(2) . ?
C14 C15 1.418(2) . ?
C14 C20 1.468(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.400(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.426(2) . ?
C19 C24 1.416(2) . ?
C20 C21 1.409(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.398(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.375(2) . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 106.32(13) . . ?
C2 N1 C6 126.01(14) . . ?
C5 N1 C6 125.98(14) . . ?
N1 C2 C7 124.27(14) . . ?
N3 C2 N1 112.68(15) . . ?
N3 C2 C7 123.00(15) . . ?
C2 N3 C4 104.37(13) . . ?
N3 C4 C5 111.58(13) . . ?
N3 C4 C13 126.88(14) . . ?
C5 C4 C13 121.37(15) . . ?
N1 C5 C4 105.04(14) . . ?
N1 C5 C19 131.98(14) . . ?
C4 C5 C19 122.98(14) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C2 122.86(15) . . ?
C12 C7 C2 117.93(14) . . ?
C12 C7 C8 119.17(15) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.40(15) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.15(15) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.74(16) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.33(16) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.18(14) . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C4 117.69(14) . . ?
C18 C13 C4 121.61(15) . . ?
C18 C13 C14 120.58(14) . . ?
C13 C14 C15 117.46(15) . . ?
C13 C14 C20 120.33(13) . . ?
C15 C14 C20 122.20(15) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.42(16) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.50(15) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.77(15) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.25(16) . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C5 116.37(14) . . ?
C24 C19 C5 124.32(14) . . ?
C24 C19 C20 119.29(15) . . ?
C19 C20 C14 120.94(14) . . ?
C21 C20 C14 121.22(14) . . ?
C21 C20 C19 117.83(15) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 C20 121.78(16) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.16(16) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.93(15) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.5 . . ?
C23 C24 C19 120.98(15) . . ?
C23 C24 H24 119.5 . . ?

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
N1 C2 N3 C4 0.88(18) . . . . ?
N1 C2 C7 C8 38.5(2) . . . . ?
N1 C2 C7 C12 -143.73(16) . . . . ?
N1 C5 C19 C20 175.37(15) . . . . ?
N1 C5 C19 C24 -6.2(3) . . . . ?
C2 N1 C5 C4 -0.70(16) . . . . ?
C2 N1 C5 C19 179.47(16) . . . . ?
C2 N3 C4 C5 -1.35(17) . . . . ?
C2 N3 C4 C13 173.86(15) . . . . ?
C2 C7 C8 C9 178.89(15) . . . . ?
C2 C7 C12 C11 -179.05(15) . . . . ?
N3 C2 C7 C8 -144.31(16) . . . . ?
N3 C2 C7 C12 33.5(2) . . . . ?
N3 C4 C5 N1 1.29(17) . . . . ?
N3 C4 C5 C19 -178.86(14) . . . . ?
N3 C4 C13 C14 -176.19(14) . . . . ?
N3 C4 C13 C18 -0.1(2) . . . . ?
C4 C5 C19 C20 -4.4(2) . . . . ?
C4 C5 C19 C24 173.95(15) . . . . ?
C4 C13 C14 C15 175.25(14) . . . . ?
C4 C13 C14 C20 -3.6(2) . . . . ?
C4 C13 C18 C17 -174.87(14) . . . . ?
C5 N1 C2 N3 -0.12(18) . . . . ?
C5 N1 C2 C7 177.33(14) . . . . ?
C5 C4 C13 C14 -1.4(2) . . . . ?
C5 C4 C13 C18 174.67(14) . . . . ?
C5 C19 C20 C14 -0.7(2) . . . . ?
C5 C19 C20 C21 179.84(13) . . . . ?
C5 C19 C24 C23 179.50(15) . . . . ?
C6 N1 C2 N3 -165.97(14) . . . . ?
C6 N1 C2 C7 11.5(2) . . . . ?
C6 N1 C5 C4 165.16(14) . . . . ?
C6 N1 C5 C19 -14.7(3) . . . . ?
C7 C2 N3 C4 -176.61(14) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C7 C12 C11 -1.2(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C7 0.3(2) . . . . ?
C12 C7 C8 C9 1.1(2) . . . . ?
C13 C4 C5 N1 -174.22(14) . . . . ?
C13 C4 C5 C19 5.6(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C13 C14 C20 C19 4.6(2) . . . . ?
C13 C14 C20 C21 -175.88(14) . . . . ?
C14 C13 C18 C17 1.1(2) . . . . ?
C14 C15 C16 C17 1.1(2) . . . . ?
C14 C20 C21 C22 -179.00(15) . . . . ?
C15 C14 C20 C19 -174.11(14) . . . . ?
C15 C14 C20 C21 5.4(2) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 C13 -0.2(2) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?
C18 C13 C14 C20 -179.67(14) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C20 C14 C15 C16 178.55(15) . . . . ?
C20 C19 C24 C23 -2.2(2) . . . . ?
C20 C21 C22 C23 -1.6(3) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C22 C23 C24 C19 1.0(2) . . . . ?
C24 C19 C20 C14 -179.13(14) . . . . ?
C24 C19 C20 C21 1.4(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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_apcjmk
_database_code_depnum_ccdc_archive 'CCDC 1456780'
_audit_update_record             
;
2016-03-01 deposited with the CCDC.
2016-03-22 downloaded from the CCDC.
;
_nottingham_internal_coll_name   APCJMK
_nottingham_internal_coll_number 11427
_nottingham_internal_coll_client AP/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '100.0000 and 400.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   25/5/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 30/05/2012
_nottingham_internal_process_user WL
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user WL
_nottingham_internal_refinement_date ?
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_date ?
_nottingham_internal_validation_user WL
_nottingham_internal_archive_date ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_audit_creation_date             2016-02-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O2'
_chemical_formula_sum            'C23 H20 N2 O2'
_chemical_formula_weight         356.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H20 N2 O2'
_chemical_oxdiff_usercomment     
'APCJMK #11427 IN FOMBLIN FIML ON MICROMOUNT FOR AP/CJM'
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/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                   12.5059(10)
_cell_length_b                   32.640(2)
_cell_length_c                   9.2776(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.765(7)
_cell_angle_gamma                90
_cell_volume                     3778.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3368
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.30
_cell_measurement_theta_min      3.54
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.113
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.2866
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1119
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6629
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.542
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -65.00   26.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   38.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   27.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   38.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   24.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   57.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00   75.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   38.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega   42.00   71.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega   80.00  147.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   77.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   71.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   36.00   68.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   33.00   67.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   68.00  133.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -77.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
 11 omega  103.00  151.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega   34.00   61.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00   64.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -77.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   35.00   68.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 15 omega   28.00  135.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -15.0000 -150.0000 107
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0365261000
_diffrn_orient_matrix_UB_12      -0.0395033000
_diffrn_orient_matrix_UB_13      -0.0795372000
_diffrn_orient_matrix_UB_21      -0.1173986000
_diffrn_orient_matrix_UB_22      0.0099017000
_diffrn_orient_matrix_UB_23      0.0279277000
_diffrn_orient_matrix_UB_31      -0.0120656000
_diffrn_orient_matrix_UB_32      0.0238593000
_diffrn_orient_matrix_UB_33      -0.1433602000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4342
_reflns_number_total             6629
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_reflns_special_details          
;
 _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.

 The crystal was determined to be a pseudo-merohedral twin,
 and the data was deconvoluted to produce an HKLF5 style file
 using the TWINROTMATR routine in PLATON. This reflection file 
 was used for the final refinement, with the ratio of twin 
 components being 0.51:0.49.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         6629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0919
_refine_ls_restrained_S_all      1.135
_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)+8.4171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1916
_refine_ls_wR_factor_ref         0.2091
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.503(3) 0.497(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C21(H21), C22(H22), C24(H24), C25(H25), N30(H30), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38), C40(H40), C41(H41), C43(H43),
 C44(H44), C48(H48), C49(H49), C51(H51), C52(H52)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C27(H27A,H27B,H27C), C46(H46A,H46B,H46C), C54(H54A,H54B,
 H54C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.3337(3) 0.56898(12) 0.5974(5) 0.0169(9) Uani 1 1 d . . . . .
C2 C 0.2596(4) 0.56008(14) 0.6892(5) 0.0160(10) Uani 1 1 d . . . . .
N3 N 0.2707(3) 0.58413(12) 0.8092(5) 0.0182(9) Uani 1 1 d . . . . .
H3 H 0.2292 0.5838 0.8822 0.022 Uiso 1 1 calc R . . . .
C4 C 0.3590(4) 0.60920(14) 0.7955(5) 0.0156(10) Uani 1 1 d . . . . .
C5 C 0.3962(4) 0.59932(14) 0.6632(6) 0.0177(10) Uani 1 1 d . . . . .
C6 C 0.1813(4) 0.52693(14) 0.6679(5) 0.0176(10) Uani 1 1 d . . . . .
C7 C 0.1961(4) 0.49760(15) 0.5616(6) 0.0216(11) Uani 1 1 d . . . . .
H7 H 0.2548 0.4999 0.5021 0.026 Uiso 1 1 calc R . . . .
C8 C 0.1251(4) 0.46498(16) 0.5427(7) 0.0300(13) Uani 1 1 d . . . . .
H8 H 0.1355 0.4449 0.4707 0.036 Uiso 1 1 calc R . . . .
C9 C 0.0397(4) 0.46176(16) 0.6282(7) 0.0298(13) Uani 1 1 d . . . . .
H9 H -0.0089 0.4395 0.6144 0.036 Uiso 1 1 calc R . . . .
C10 C 0.0241(5) 0.49036(17) 0.7330(7) 0.0313(13) Uani 1 1 d . . . . .
H10 H -0.0346 0.4875 0.7923 0.038 Uiso 1 1 calc R . . . .
C11 C 0.0938(4) 0.52358(16) 0.7532(6) 0.0243(12) Uani 1 1 d . . . . .
H11 H 0.0818 0.5437 0.8244 0.029 Uiso 1 1 calc R . . . .
C12 C 0.4880(4) 0.61491(14) 0.5879(5) 0.0172(10) Uani 1 1 d . . . . .
C13 C 0.5456(4) 0.58754(15) 0.5094(6) 0.0222(11) Uani 1 1 d . . . . .
H13 H 0.5285 0.5592 0.5128 0.027 Uiso 1 1 calc R . . . .
C14 C 0.6277(4) 0.60018(16) 0.4257(6) 0.0242(12) Uani 1 1 d . . . . .
H14 H 0.6650 0.5808 0.3712 0.029 Uiso 1 1 calc R . . . .
C15 C 0.6545(4) 0.64146(16) 0.4229(6) 0.0226(11) Uani 1 1 d . . . . .
C16 C 0.6009(4) 0.66929(16) 0.5053(6) 0.0243(12) Uani 1 1 d . . . . .
H16 H 0.6211 0.6974 0.5071 0.029 Uiso 1 1 calc R . . . .
C17 C 0.5176(4) 0.65593(15) 0.5849(6) 0.0236(12) Uani 1 1 d . . . . .
H17 H 0.4798 0.6753 0.6387 0.028 Uiso 1 1 calc R . . . .
O18 O 0.7323(3) 0.65730(12) 0.3417(4) 0.0305(9) Uani 1 1 d . . . . .
C19 C 0.7694(4) 0.63114(17) 0.2320(6) 0.0280(12) Uani 1 1 d . . . . .
H19A H 0.7086 0.6225 0.1671 0.042 Uiso 1 1 calc GR . . . .
H19B H 0.8040 0.6070 0.2769 0.042 Uiso 1 1 calc GR . . . .
H19C H 0.8212 0.6460 0.1767 0.042 Uiso 1 1 calc GR . . . .
C20 C 0.3970(4) 0.63777(14) 0.9104(6) 0.0183(11) Uani 1 1 d . . . . .
C21 C 0.5066(4) 0.64747(15) 0.9337(6) 0.0215(11) Uani 1 1 d . . . . .
H21 H 0.5573 0.6349 0.8757 0.026 Uiso 1 1 calc R . . . .
C22 C 0.5412(4) 0.67502(15) 1.0399(6) 0.0208(11) Uani 1 1 d . . . . .
H22 H 0.6152 0.6814 1.0538 0.025 Uiso 1 1 calc R . . . .
C23 C 0.4685(4) 0.69337(14) 1.1262(6) 0.0209(11) Uani 1 1 d . . . . .
C24 C 0.3609(4) 0.68327(15) 1.1089(6) 0.0232(11) Uani 1 1 d . . . . .
H24 H 0.3112 0.6949 1.1704 0.028 Uiso 1 1 calc R . . . .
C25 C 0.3263(4) 0.65588(15) 1.0004(6) 0.0210(11) Uani 1 1 d . . . . .
H25 H 0.2522 0.6494 0.9877 0.025 Uiso 1 1 calc R . . . .
O26 O 0.5115(3) 0.72130(11) 1.2232(4) 0.0279(9) Uani 1 1 d . . . . .
C27 C 0.4397(5) 0.74038(17) 1.3162(7) 0.0389(16) Uani 1 1 d . . . . .
H27A H 0.3870 0.7567 1.2584 0.058 Uiso 1 1 calc GR . . . .
H27B H 0.4802 0.7582 1.3850 0.058 Uiso 1 1 calc GR . . . .
H27C H 0.4025 0.7193 1.3691 0.058 Uiso 1 1 calc GR . . . .
N28 N 0.1569(3) 0.57788(12) 0.0822(5) 0.0174(9) Uani 1 1 d . . . . .
C29 C 0.2304(4) 0.56400(14) 0.1795(5) 0.0174(10) Uani 1 1 d . . . . .
N30 N 0.2300(3) 0.58574(12) 0.3041(5) 0.0188(9) Uani 1 1 d . . . . .
H30 H 0.2723 0.5816 0.3824 0.023 Uiso 1 1 calc R . . . .
C31 C 0.1509(4) 0.61565(14) 0.2864(5) 0.0165(10) Uani 1 1 d . . . . .
C32 C 0.1067(4) 0.61048(14) 0.1471(6) 0.0183(10) Uani 1 1 d . . . . .
C33 C 0.3015(4) 0.52940(15) 0.1578(6) 0.0209(11) Uani 1 1 d . . . . .
C34 C 0.2699(5) 0.49860(16) 0.0609(6) 0.0310(13) Uani 1 1 d . . . . .
H34 H 0.2011 0.4997 0.0110 0.037 Uiso 1 1 calc R . . . .
C35 C 0.3380(6) 0.46637(18) 0.0369(8) 0.0434(17) Uani 1 1 d . . . . .
H35 H 0.3162 0.4455 -0.0301 0.052 Uiso 1 1 calc R . . . .
C36 C 0.4386(6) 0.46429(19) 0.1105(7) 0.0423(17) Uani 1 1 d . . . . .
H36 H 0.4859 0.4424 0.0927 0.051 Uiso 1 1 calc R . . . .
C37 C 0.4689(5) 0.49427(19) 0.2094(7) 0.0394(16) Uani 1 1 d . . . . .
H37 H 0.5364 0.4925 0.2622 0.047 Uiso 1 1 calc R . . . .
C38 C 0.4011(4) 0.52703(17) 0.2323(7) 0.0300(13) Uani 1 1 d . . . . .
H38 H 0.4231 0.5479 0.2994 0.036 Uiso 1 1 calc R . . . .
C39 C 0.0232(4) 0.63433(15) 0.0662(6) 0.0189(11) Uani 1 1 d . . . . .
C40 C -0.0463(4) 0.61510(15) -0.0385(6) 0.0234(12) Uani 1 1 d . . . . .
H40 H -0.0400 0.5865 -0.0545 0.028 Uiso 1 1 calc R . . . .
C41 C -0.1242(4) 0.63746(17) -0.1189(6) 0.0272(12) Uani 1 1 d . . . . .
H41 H -0.1705 0.6241 -0.1893 0.033 Uiso 1 1 calc R . . . .
C42 C -0.1339(4) 0.67926(17) -0.0958(6) 0.0257(12) Uani 1 1 d . . . . .
C43 C -0.0665(4) 0.69869(16) 0.0079(6) 0.0242(12) Uani 1 1 d . . . . .
H43 H -0.0740 0.7272 0.0255 0.029 Uiso 1 1 calc R . . . .
C44 C 0.0116(4) 0.67625(15) 0.0853(6) 0.0207(11) Uani 1 1 d . . . . .
H44 H 0.0587 0.6900 0.1538 0.025 Uiso 1 1 calc R . . . .
O45 O -0.2128(3) 0.69839(12) -0.1819(5) 0.0356(10) Uani 1 1 d . . . . .
C46 C -0.2242(5) 0.74167(18) -0.1648(8) 0.0409(16) Uani 1 1 d . . . . .
H46A H -0.2834 0.7516 -0.2301 0.061 Uiso 1 1 calc GR . . . .
H46B H -0.1576 0.7553 -0.1880 0.061 Uiso 1 1 calc GR . . . .
H46C H -0.2392 0.7478 -0.0648 0.061 Uiso 1 1 calc GR . . . .
C47 C 0.1273(4) 0.64305(14) 0.4059(5) 0.0172(10) Uani 1 1 d . . . . .
C48 C 0.0214(4) 0.65273(15) 0.4341(6) 0.0197(11) Uani 1 1 d . . . . .
H48 H -0.0358 0.6409 0.3757 0.024 Uiso 1 1 calc R . . . .
C49 C -0.0018(4) 0.67885(15) 0.5440(6) 0.0209(11) Uani 1 1 d . . . . .
H49 H -0.0742 0.6852 0.5604 0.025 Uiso 1 1 calc R . . . .
C50 C 0.0816(4) 0.69589(14) 0.6313(5) 0.0192(11) Uani 1 1 d . . . . .
C51 C 0.1877(4) 0.68562(15) 0.6096(6) 0.0208(11) Uani 1 1 d . . . . .
H51 H 0.2448 0.6962 0.6712 0.025 Uiso 1 1 calc R . . . .
C52 C 0.2082(4) 0.65959(14) 0.4964(6) 0.0193(11) Uani 1 1 d . . . . .
H52 H 0.2805 0.6529 0.4805 0.023 Uiso 1 1 calc R . . . .
O53 O 0.0517(3) 0.72326(11) 0.7333(4) 0.0247(8) Uani 1 1 d . . . . .
C54 C 0.1342(4) 0.74079(16) 0.8271(6) 0.0282(13) Uani 1 1 d . . . . .
H54A H 0.1846 0.7557 0.7697 0.042 Uiso 1 1 calc GR . . . .
H54B H 0.1724 0.7190 0.8818 0.042 Uiso 1 1 calc GR . . . .
H54C H 0.1024 0.7597 0.8941 0.042 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
N1 C2 1.331(6) . ?
N1 C5 1.379(6) . ?
C2 N3 1.362(6) . ?
C2 C6 1.464(7) . ?
N3 H3 0.8800 . ?
N3 C4 1.387(6) . ?
C4 C5 1.379(7) . ?
C4 C20 1.472(7) . ?
C5 C12 1.473(7) . ?
C6 C7 1.395(7) . ?
C6 C11 1.396(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.372(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(7) . ?
C12 C17 1.390(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(7) . ?
C15 C16 1.388(8) . ?
C15 O18 1.369(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(8) . ?
C17 H17 0.9500 . ?
O18 C19 1.430(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.410(7) . ?
C20 C25 1.387(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(7) . ?
C23 C24 1.384(7) . ?
C23 O26 1.366(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.394(7) . ?
C25 H25 0.9500 . ?
O26 C27 1.429(7) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N28 C29 1.325(7) . ?
N28 C32 1.392(6) . ?
C29 N30 1.357(6) . ?
C29 C33 1.460(7) . ?
N30 H30 0.8800 . ?
N30 C31 1.392(6) . ?
C31 C32 1.382(7) . ?
C31 C47 1.470(7) . ?
C32 C39 1.469(7) . ?
C33 C34 1.389(8) . ?
C33 C38 1.386(8) . ?
C34 H34 0.9500 . ?
C34 C35 1.381(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.393(10) . ?
C36 H36 0.9500 . ?
C36 C37 1.377(10) . ?
C37 H37 0.9500 . ?
C37 C38 1.390(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.408(7) . ?
C39 C44 1.388(7) . ?
C40 H40 0.9500 . ?
C40 C41 1.393(8) . ?
C41 H41 0.9500 . ?
C41 C42 1.387(8) . ?
C42 C43 1.390(8) . ?
C42 O45 1.378(7) . ?
C43 H43 0.9500 . ?
C43 C44 1.383(7) . ?
C44 H44 0.9500 . ?
O45 C46 1.430(7) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C48 1.402(7) . ?
C47 C52 1.382(7) . ?
C48 H48 0.9500 . ?
C48 C49 1.375(7) . ?
C49 H49 0.9500 . ?
C49 C50 1.394(8) . ?
C50 C51 1.396(7) . ?
C50 O53 1.371(6) . ?
C51 H51 0.9500 . ?
C51 C52 1.388(7) . ?
C52 H52 0.9500 . ?
O53 C54 1.425(7) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 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
C2 N1 C5 105.8(4) . . ?
N1 C2 N3 111.1(4) . . ?
N1 C2 C6 124.2(4) . . ?
N3 C2 C6 124.6(4) . . ?
C2 N3 H3 126.1 . . ?
C2 N3 C4 107.7(4) . . ?
C4 N3 H3 126.1 . . ?
N3 C4 C20 121.9(4) . . ?
C5 C4 N3 105.1(4) . . ?
C5 C4 C20 132.9(4) . . ?
N1 C5 C4 110.3(4) . . ?
N1 C5 C12 118.4(5) . . ?
C4 C5 C12 131.3(5) . . ?
C7 C6 C2 118.9(5) . . ?
C7 C6 C11 119.5(5) . . ?
C11 C6 C2 121.6(5) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(5) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.9(5) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(5) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(6) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 120.3 . . ?
C10 C11 C6 119.3(5) . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C5 118.4(4) . . ?
C13 C12 C17 117.6(5) . . ?
C17 C12 C5 124.0(5) . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.1(5) . . ?
C14 C13 H13 118.9 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.1(5) . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 119.9(5) . . ?
O18 C15 C14 123.9(5) . . ?
O18 C15 C16 116.2(5) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.6(5) . . ?
C16 C17 H17 119.2 . . ?
C15 O18 C19 116.2(4) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C4 121.2(5) . . ?
C25 C20 C4 121.2(4) . . ?
C25 C20 C21 117.6(5) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.5(5) . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 119.9(5) . . ?
O26 C23 C22 115.1(4) . . ?
O26 C23 C24 124.9(5) . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.3(5) . . ?
C25 C24 H24 120.3 . . ?
C20 C25 C24 121.9(5) . . ?
C20 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C23 O26 C27 117.0(4) . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 N28 C32 106.2(4) . . ?
N28 C29 N30 111.1(4) . . ?
N28 C29 C33 124.9(5) . . ?
N30 C29 C33 124.0(5) . . ?
C29 N30 H30 126.0 . . ?
C29 N30 C31 108.0(4) . . ?
C31 N30 H30 126.0 . . ?
N30 C31 C47 120.9(4) . . ?
C32 C31 N30 105.2(4) . . ?
C32 C31 C47 133.8(5) . . ?
N28 C32 C39 120.6(5) . . ?
C31 C32 N28 109.5(4) . . ?
C31 C32 C39 129.8(5) . . ?
C34 C33 C29 119.9(5) . . ?
C38 C33 C29 120.6(5) . . ?
C38 C33 C34 119.4(5) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.2(6) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 119.8 . . ?
C34 C35 C36 120.3(6) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 120.3 . . ?
C37 C36 C35 119.5(5) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.3(6) . . ?
C38 C37 H37 119.8 . . ?
C33 C38 C37 120.2(6) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C40 C39 C32 120.1(4) . . ?
C44 C39 C32 122.3(5) . . ?
C44 C39 C40 117.5(5) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 C39 120.9(5) . . ?
C41 C40 H40 119.5 . . ?
C40 C41 H41 120.1 . . ?
C42 C41 C40 119.9(5) . . ?
C42 C41 H41 120.1 . . ?
C41 C42 C43 120.0(5) . . ?
O45 C42 C41 115.0(5) . . ?
O45 C42 C43 125.0(5) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 C42 119.6(5) . . ?
C44 C43 H43 120.2 . . ?
C39 C44 H44 118.9 . . ?
C43 C44 C39 122.2(5) . . ?
C43 C44 H44 118.9 . . ?
C42 O45 C46 117.1(5) . . ?
O45 C46 H46A 109.5 . . ?
O45 C46 H46B 109.5 . . ?
O45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C48 C47 C31 121.1(4) . . ?
C52 C47 C31 121.3(5) . . ?
C52 C47 C48 117.5(5) . . ?
C47 C48 H48 119.1 . . ?
C49 C48 C47 121.8(5) . . ?
C49 C48 H48 119.1 . . ?
C48 C49 H49 120.3 . . ?
C48 C49 C50 119.5(5) . . ?
C50 C49 H49 120.3 . . ?
C49 C50 C51 120.2(4) . . ?
O53 C50 C49 115.7(4) . . ?
O53 C50 C51 124.1(5) . . ?
C50 C51 H51 120.6 . . ?
C52 C51 C50 118.8(5) . . ?
C52 C51 H51 120.6 . . ?
C47 C52 C51 122.3(5) . . ?
C47 C52 H52 118.9 . . ?
C51 C52 H52 118.9 . . ?
C50 O53 C54 117.6(4) . . ?
O53 C54 H54A 109.5 . . ?
O53 C54 H54B 109.5 . . ?
O53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?

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
N3 H3 N28 0.88 2.13 2.993(6) 168.3 1_556
N30 H30 N1 0.88 2.13 2.986(6) 164.2 .

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
N1 C2 N3 C4 -1.7(5) . . . . ?
N1 C2 C6 C7 13.1(7) . . . . ?
N1 C2 C6 C11 -168.3(5) . . . . ?
N1 C5 C12 C13 -36.5(7) . . . . ?
N1 C5 C12 C17 140.3(5) . . . . ?
C2 N1 C5 C4 -0.6(5) . . . . ?
C2 N1 C5 C12 178.5(4) . . . . ?
C2 N3 C4 C5 1.2(5) . . . . ?
C2 N3 C4 C20 -176.9(4) . . . . ?
C2 C6 C7 C8 177.7(5) . . . . ?
C2 C6 C11 C10 -177.1(5) . . . . ?
N3 C2 C6 C7 -162.6(5) . . . . ?
N3 C2 C6 C11 16.0(8) . . . . ?
N3 C4 C5 N1 -0.4(5) . . . . ?
N3 C4 C5 C12 -179.3(5) . . . . ?
N3 C4 C20 C21 148.2(5) . . . . ?
N3 C4 C20 C25 -31.3(7) . . . . ?
C4 C5 C12 C13 142.4(5) . . . . ?
C4 C5 C12 C17 -40.9(9) . . . . ?
C4 C20 C21 C22 178.6(5) . . . . ?
C4 C20 C25 C24 -179.5(5) . . . . ?
C5 N1 C2 N3 1.5(5) . . . . ?
C5 N1 C2 C6 -174.7(4) . . . . ?
C5 C4 C20 C21 -29.4(8) . . . . ?
C5 C4 C20 C25 151.1(5) . . . . ?
C5 C12 C13 C14 174.7(5) . . . . ?
C5 C12 C17 C16 -176.2(5) . . . . ?
C6 C2 N3 C4 174.4(4) . . . . ?
C6 C7 C8 C9 0.4(8) . . . . ?
C7 C6 C11 C10 1.5(8) . . . . ?
C7 C8 C9 C10 -0.4(9) . . . . ?
C8 C9 C10 C11 1.0(9) . . . . ?
C9 C10 C11 C6 -1.5(8) . . . . ?
C11 C6 C7 C8 -1.0(8) . . . . ?
C12 C13 C14 C15 1.4(8) . . . . ?
C13 C12 C17 C16 0.6(8) . . . . ?
C13 C14 C15 C16 1.3(8) . . . . ?
C13 C14 C15 O18 -178.5(5) . . . . ?
C14 C15 C16 C17 -2.9(8) . . . . ?
C14 C15 O18 C19 14.2(8) . . . . ?
C15 C16 C17 C12 1.9(9) . . . . ?
C16 C15 O18 C19 -165.5(5) . . . . ?
C17 C12 C13 C14 -2.3(8) . . . . ?
O18 C15 C16 C17 176.9(5) . . . . ?
C20 C4 C5 N1 177.5(5) . . . . ?
C20 C4 C5 C12 -1.5(9) . . . . ?
C20 C21 C22 C23 0.5(8) . . . . ?
C21 C20 C25 C24 1.0(7) . . . . ?
C21 C22 C23 C24 1.8(8) . . . . ?
C21 C22 C23 O26 -177.4(4) . . . . ?
C22 C23 C24 C25 -2.6(8) . . . . ?
C22 C23 O26 C27 -178.9(5) . . . . ?
C23 C24 C25 C20 1.2(8) . . . . ?
C24 C23 O26 C27 2.1(7) . . . . ?
C25 C20 C21 C22 -1.9(7) . . . . ?
O26 C23 C24 C25 176.4(5) . . . . ?
N28 C29 N30 C31 0.1(6) . . . . ?
N28 C29 C33 C34 -26.8(8) . . . . ?
N28 C29 C33 C38 152.8(5) . . . . ?
N28 C32 C39 C40 33.6(7) . . . . ?
N28 C32 C39 C44 -144.2(5) . . . . ?
C29 N28 C32 C31 -0.6(5) . . . . ?
C29 N28 C32 C39 177.3(4) . . . . ?
C29 N30 C31 C32 -0.4(5) . . . . ?
C29 N30 C31 C47 177.0(4) . . . . ?
C29 C33 C34 C35 178.2(6) . . . . ?
C29 C33 C38 C37 -179.1(5) . . . . ?
N30 C29 C33 C34 151.9(5) . . . . ?
N30 C29 C33 C38 -28.4(8) . . . . ?
N30 C31 C32 N28 0.6(5) . . . . ?
N30 C31 C32 C39 -177.0(5) . . . . ?
N30 C31 C47 C48 -137.6(5) . . . . ?
N30 C31 C47 C52 41.1(7) . . . . ?
C31 C32 C39 C40 -148.9(5) . . . . ?
C31 C32 C39 C44 33.2(8) . . . . ?
C31 C47 C48 C49 -178.9(5) . . . . ?
C31 C47 C52 C51 179.8(5) . . . . ?
C32 N28 C29 N30 0.3(6) . . . . ?
C32 N28 C29 C33 179.2(5) . . . . ?
C32 C31 C47 C48 39.0(8) . . . . ?
C32 C31 C47 C52 -142.3(6) . . . . ?
C32 C39 C40 C41 -178.3(5) . . . . ?
C32 C39 C44 C43 179.3(5) . . . . ?
C33 C29 N30 C31 -178.9(5) . . . . ?
C33 C34 C35 C36 0.6(10) . . . . ?
C34 C33 C38 C37 0.5(9) . . . . ?
C34 C35 C36 C37 1.1(11) . . . . ?
C35 C36 C37 C38 -2.0(11) . . . . ?
C36 C37 C38 C33 1.2(10) . . . . ?
C38 C33 C34 C35 -1.4(9) . . . . ?
C39 C40 C41 C42 -0.1(9) . . . . ?
C40 C39 C44 C43 1.5(8) . . . . ?
C40 C41 C42 C43 -0.4(9) . . . . ?
C40 C41 C42 O45 179.5(5) . . . . ?
C41 C42 C43 C44 1.4(8) . . . . ?
C41 C42 O45 C46 -178.4(5) . . . . ?
C42 C43 C44 C39 -2.0(8) . . . . ?
C43 C42 O45 C46 1.5(8) . . . . ?
C44 C39 C40 C41 -0.4(8) . . . . ?
O45 C42 C43 C44 -178.5(5) . . . . ?
C47 C31 C32 N28 -176.3(5) . . . . ?
C47 C31 C32 C39 6.0(9) . . . . ?
C47 C48 C49 C50 -0.8(8) . . . . ?
C48 C47 C52 C51 -1.4(7) . . . . ?
C48 C49 C50 C51 -1.7(7) . . . . ?
C48 C49 C50 O53 176.7(4) . . . . ?
C49 C50 C51 C52 2.6(7) . . . . ?
C49 C50 O53 C54 178.7(4) . . . . ?
C50 C51 C52 C47 -1.0(8) . . . . ?
C51 C50 O53 C54 -3.0(7) . . . . ?
C52 C47 C48 C49 2.3(7) . . . . ?
O53 C50 C51 C52 -175.6(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
-3 20 0 0.0323 -2.9999 19.9994 -0.0002 -0.6805 0.5502 0.5134
1 0 -6 0.1423 1.0000 -0.0026 -6.0000 0.4408 -0.2850 0.8480
-1 0 6 0.1423 -1.0000 0.0026 6.0000 -0.4408 0.2850 -0.8480
8 1 0 0.0230 7.9997 0.9989 -0.0000 -0.3317 -0.9293 -0.0727
-8 -1 0 0.0010 -7.9997 -0.9989 0.0000 0.3317 0.9293 0.0727
4 18 0 0.0323 3.9999 17.9986 -0.0002 -0.8571 -0.2914 0.3812
0 -21 0 0.0132 -0.0000 -20.9990 0.0002 0.8295 -0.2079 -0.5011

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.503(3)
2 0.497(3)
