# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_zhengz10cult
_database_code_depnum_ccdc_archive 'CCDC 1921645'
loop_
_audit_author_name
_audit_author_address
'Zheng ZHENG'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2019-06-07 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2017-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C39 H34 N3 O, F6 P'
_chemical_formula_sum            'C39 H34 F6 N3 O P'
_chemical_formula_weight         705.66
_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 0.0181 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'
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'
P P 0.2955 0.4335 '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                   9.3923(3)
_cell_length_b                   29.4208(8)
_cell_length_c                   11.9664(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.511(3)
_cell_angle_gamma                90
_cell_volume                     3228.14(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4012
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.6850
_cell_measurement_theta_min      4.0400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.390
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red

_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10260
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         76.186
_diffrn_reflns_theta_min         4.072
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     85.00 176.00   1.00    3.00    --  110.76  45.00-180.00   91
  2  ω    -62.00  33.00   1.00    2.00    --  -41.51  37.00  60.00   95
  3  ω   -115.00 -13.00   1.00    2.00    --  -41.51 -57.00 -90.00  102
  4  ω    106.00 178.00   1.00    3.00    --  110.76 125.00  30.00   72
  5  ω     83.00 178.00   1.00    3.00    --  110.76  30.00  90.00   95
  6  ω     32.00 109.00   1.00    3.00    --  110.76 -94.00 -30.00   77
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1038510000
_diffrn_orient_matrix_UB_12      0.0110673000
_diffrn_orient_matrix_UB_13      -0.0798496000
_diffrn_orient_matrix_UB_21      0.1098073000
_diffrn_orient_matrix_UB_22      0.0208242000
_diffrn_orient_matrix_UB_23      0.1015337000
_diffrn_orient_matrix_UB_31      0.0734229000
_diffrn_orient_matrix_UB_32      -0.0467514000
_diffrn_orient_matrix_UB_33      0.0265425000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5333
_reflns_number_total             6341
_reflns_odcompleteness_completeness 98.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.026
_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)+(0.0980P)²+3.9500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1803
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C39(H39A,H39B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.2080(2) -0.02735(7) 0.01009(18) 0.0339(5) Uani 1 1 d . . . . .
H1 H -0.2714 -0.0090 0.0224 0.051 Uiso 1 1 calc GR . . . .
N1 N 0.0242(2) -0.06047(7) 0.20488(19) 0.0255(5) Uani 1 1 d . . . . .
N2 N 0.7615(2) 0.16668(8) 0.58710(18) 0.0244(4) Uani 1 1 d . . . . .
N3 N 1.1041(2) 0.25536(8) 0.87844(19) 0.0270(5) Uani 1 1 d . . . . .
C1 C -0.2177(3) -0.06819(10) 0.0696(2) 0.0295(6) Uani 1 1 d . . . . .
H1A H -0.2794 -0.0904 0.0188 0.035 Uiso 1 1 calc R . . . .
H1B H -0.2618 -0.0624 0.1363 0.035 Uiso 1 1 calc R . . . .
C2 C -0.0641(3) -0.08685(10) 0.1095(2) 0.0290(6) Uani 1 1 d . . . . .
H2A H -0.0699 -0.1188 0.1342 0.035 Uiso 1 1 calc R . . . .
H2B H -0.0147 -0.0867 0.0443 0.035 Uiso 1 1 calc R . . . .
C4 C 0.1142(3) -0.02906(9) 0.1807(2) 0.0289(6) Uani 1 1 d . . . . .
H4 H 0.1177 -0.0240 0.1029 0.035 Uiso 1 1 calc R . . . .
C5 C 0.2037(3) -0.00327(9) 0.2650(2) 0.0276(5) Uani 1 1 d . . . . .
H5 H 0.2663 0.0190 0.2439 0.033 Uiso 1 1 calc R . . . .
C6 C 0.2023(3) -0.00974(9) 0.3796(2) 0.0252(5) Uani 1 1 d . . . . .
C7 C 0.1027(3) -0.04308(8) 0.4063(2) 0.0235(5) Uani 1 1 d . . . . .
C8 C 0.0885(3) -0.05207(9) 0.5201(2) 0.0265(5) Uani 1 1 d . . . . .
H8 H 0.1482 -0.0359 0.5816 0.032 Uiso 1 1 calc R . . . .
C9 C -0.0084(3) -0.08315(9) 0.5432(2) 0.0293(6) Uani 1 1 d . . . . .
H9 H -0.0154 -0.0886 0.6201 0.035 Uiso 1 1 calc R . . . .
C10 C -0.0982(3) -0.10732(9) 0.4532(3) 0.0301(6) Uani 1 1 d . . . . .
H10 H -0.1668 -0.1287 0.4696 0.036 Uiso 1 1 calc R . . . .
C11 C -0.0876(3) -0.10027(9) 0.3426(2) 0.0282(5) Uani 1 1 d . . . . .
H11 H -0.1477 -0.1171 0.2826 0.034 Uiso 1 1 calc R . . . .
C12 C 0.0120(3) -0.06828(9) 0.3168(2) 0.0239(5) Uani 1 1 d . . . . .
C13 C 0.2961(3) 0.01587(9) 0.4705(2) 0.0276(5) Uani 1 1 d . . . . .
H13 H 0.2967 0.0072 0.5471 0.033 Uiso 1 1 calc R . . . .
C14 C 0.3818(3) 0.05067(9) 0.4553(2) 0.0261(5) Uani 1 1 d . . . . .
H14 H 0.3827 0.0588 0.3786 0.031 Uiso 1 1 calc R . . . .
C15 C 0.6580(3) 0.13462(9) 0.5985(2) 0.0232(5) Uani 1 1 d . . . . .
C16 C 0.5672(3) 0.10938(9) 0.5134(2) 0.0246(5) Uani 1 1 d . . . . .
H16 H 0.5684 0.1139 0.4350 0.030 Uiso 1 1 calc R . . . .
C17 C 0.4740(3) 0.07730(9) 0.5460(2) 0.0246(5) Uani 1 1 d . . . . .
C18 C 0.4732(3) 0.07160(9) 0.6632(2) 0.0265(5) Uani 1 1 d . . . . .
H18 H 0.4094 0.0498 0.6846 0.032 Uiso 1 1 calc R . . . .
C19 C 0.5629(3) 0.09689(9) 0.7475(2) 0.0254(5) Uani 1 1 d . . . . .
H19 H 0.5607 0.0926 0.8258 0.031 Uiso 1 1 calc R . . . .
C20 C 0.6572(3) 0.12899(9) 0.7158(2) 0.0237(5) Uani 1 1 d . . . . .
C21 C 0.7661(3) 0.15968(9) 0.7777(2) 0.0237(5) Uani 1 1 d . . . . .
C22 C 0.8211(3) 0.16887(9) 0.8938(2) 0.0247(5) Uani 1 1 d . . . . .
H22 H 0.7821 0.1539 0.9509 0.030 Uiso 1 1 calc R . . . .
C23 C 0.9332(3) 0.20018(9) 0.9246(2) 0.0260(5) Uani 1 1 d . . . . .
H23 H 0.9718 0.2063 1.0032 0.031 Uiso 1 1 calc R . . . .
C24 C 0.9906(3) 0.22292(9) 0.8408(2) 0.0245(5) Uani 1 1 d . . . . .
C25 C 0.9397(3) 0.21389(9) 0.7248(2) 0.0240(5) Uani 1 1 d . . . . .
H25 H 0.9804 0.2286 0.6684 0.029 Uiso 1 1 calc R . . . .
C26 C 0.8268(3) 0.18241(9) 0.6944(2) 0.0233(5) Uani 1 1 d . . . . .
C27 C 1.2327(3) 0.23928(9) 0.9557(2) 0.0275(5) Uani 1 1 d . . . . .
C28 C 1.2934(3) 0.26418(10) 1.0532(3) 0.0350(6) Uani 1 1 d . . . . .
H28 H 1.2469 0.2911 1.0707 0.042 Uiso 1 1 calc R . . . .
C29 C 1.4227(4) 0.24964(12) 1.1253(3) 0.0418(7) Uani 1 1 d . . . . .
H29 H 1.4650 0.2670 1.1910 0.050 Uiso 1 1 calc R . . . .
C30 C 1.4893(3) 0.20994(12) 1.1011(3) 0.0414(7) Uani 1 1 d . . . . .
H30 H 1.5767 0.1999 1.1508 0.050 Uiso 1 1 calc R . . . .
C31 C 1.4290(3) 0.18502(11) 1.0052(3) 0.0398(7) Uani 1 1 d . . . . .
H31 H 1.4744 0.1576 0.9892 0.048 Uiso 1 1 calc R . . . .
C32 C 1.3017(3) 0.19981(10) 0.9316(3) 0.0331(6) Uani 1 1 d . . . . .
H32 H 1.2618 0.1828 0.8646 0.040 Uiso 1 1 calc R . . . .
C33 C 1.1148(3) 0.29495(9) 0.8140(2) 0.0236(5) Uani 1 1 d . . . . .
C34 C 0.9894(3) 0.31778(9) 0.7565(2) 0.0264(5) Uani 1 1 d . . . . .
H34 H 0.8957 0.3061 0.7587 0.032 Uiso 1 1 calc R . . . .
C35 C 1.0017(3) 0.35732(10) 0.6964(2) 0.0299(6) Uani 1 1 d . . . . .
H35 H 0.9160 0.3725 0.6575 0.036 Uiso 1 1 calc R . . . .
C36 C 1.1377(4) 0.37512(10) 0.6923(2) 0.0341(6) Uani 1 1 d . . . . .
H36 H 1.1455 0.4024 0.6514 0.041 Uiso 1 1 calc R . . . .
C37 C 1.2609(3) 0.35248(11) 0.7485(3) 0.0357(6) Uani 1 1 d . . . . .
H37 H 1.3544 0.3643 0.7464 0.043 Uiso 1 1 calc R . . . .
C38 C 1.2505(3) 0.31276(10) 0.8078(2) 0.0312(6) Uani 1 1 d . . . . .
H38 H 1.3368 0.2974 0.8449 0.037 Uiso 1 1 calc R . . . .
C39 C 0.7885(3) 0.18281(9) 0.4783(2) 0.0240(5) Uani 1 1 d . . . . .
H39A H 0.7883 0.1565 0.4265 0.029 Uiso 1 1 calc R . . . .
H39B H 0.8864 0.1970 0.4917 0.029 Uiso 1 1 calc R . . . .
C40 C 0.6757(3) 0.21699(11) 0.4207(3) 0.0350(6) Uani 1 1 d . . . . .
H40A H 0.7002 0.2276 0.3495 0.053 Uiso 1 1 calc GR . . . .
H40B H 0.6746 0.2429 0.4720 0.053 Uiso 1 1 calc GR . . . .
H40C H 0.5793 0.2026 0.4034 0.053 Uiso 1 1 calc GR . . . .
P1 P 0.63078(8) 0.06342(3) 0.17172(6) 0.0310(2) Uani 1 1 d . . . . .
F1 F 0.6566(3) 0.08518(11) 0.05690(19) 0.0758(8) Uani 1 1 d . . . . .
F2 F 0.6029(2) 0.04202(8) 0.28945(17) 0.0508(5) Uani 1 1 d . . . . .
F3 F 0.5777(2) 0.01679(8) 0.1076(2) 0.0568(6) Uani 1 1 d . . . . .
F4 F 0.4668(2) 0.08042(8) 0.14496(18) 0.0544(6) Uani 1 1 d . . . . .
F5 F 0.6819(2) 0.10893(7) 0.24040(18) 0.0526(5) Uani 1 1 d . . . . .
F6 F 0.7942(2) 0.04573(7) 0.20237(19) 0.0513(5) Uani 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 C1 1.410(3) . ?
N1 C2 1.477(3) . ?
N1 C4 1.326(4) . ?
N1 C12 1.388(3) . ?
N2 C15 1.383(3) . ?
N2 C26 1.377(3) . ?
N2 C39 1.459(3) . ?
N3 C24 1.429(3) . ?
N3 C27 1.433(3) . ?
N3 C33 1.413(3) . ?
C1 C2 1.520(4) . ?
C4 C5 1.390(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.439(4) . ?
C6 C13 1.453(3) . ?
C7 C8 1.421(4) . ?
C7 C12 1.424(3) . ?
C8 C9 1.360(4) . ?
C9 C10 1.408(4) . ?
C10 C11 1.365(4) . ?
C11 C12 1.407(4) . ?
C13 C14 1.339(4) . ?
C14 C17 1.461(3) . ?
C15 C16 1.393(3) . ?
C15 C20 1.414(4) . ?
C16 C17 1.399(4) . ?
C17 C18 1.414(4) . ?
C18 C19 1.383(4) . ?
C19 C20 1.402(4) . ?
C20 C21 1.443(3) . ?
C21 C22 1.401(3) . ?
C21 C26 1.418(4) . ?
C22 C23 1.387(4) . ?
C23 C24 1.405(4) . ?
C24 C25 1.392(4) . ?
C25 C26 1.396(3) . ?
C27 C28 1.391(4) . ?
C27 C32 1.390(4) . ?
C28 C29 1.395(4) . ?
C29 C30 1.385(5) . ?
C30 C31 1.376(5) . ?
C31 C32 1.393(4) . ?
C33 C34 1.400(4) . ?
C33 C38 1.395(4) . ?
C34 C35 1.385(4) . ?
C35 C36 1.392(4) . ?
C36 C37 1.377(4) . ?
C37 C38 1.382(4) . ?
C39 C40 1.514(4) . ?
P1 F1 1.581(2) . ?
P1 F2 1.616(2) . ?
P1 F3 1.598(2) . ?
P1 F4 1.5843(19) . ?
P1 F5 1.590(2) . ?
P1 F6 1.5866(19) . ?

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
C4 N1 C2 118.4(2) . . ?
C4 N1 C12 121.1(2) . . ?
C12 N1 C2 120.6(2) . . ?
C15 N2 C39 124.9(2) . . ?
C26 N2 C15 108.5(2) . . ?
C26 N2 C39 126.5(2) . . ?
C24 N3 C27 116.7(2) . . ?
C33 N3 C24 121.0(2) . . ?
C33 N3 C27 118.3(2) . . ?
O1 C1 C2 107.8(2) . . ?
N1 C2 C1 112.8(2) . . ?
N1 C4 C5 122.4(3) . . ?
C6 C5 C4 120.6(2) . . ?
C5 C6 C7 117.3(2) . . ?
C5 C6 C13 122.3(2) . . ?
C7 C6 C13 120.4(2) . . ?
C8 C7 C6 122.7(2) . . ?
C8 C7 C12 117.3(2) . . ?
C12 C7 C6 120.0(2) . . ?
C9 C8 C7 121.7(2) . . ?
C8 C9 C10 120.0(3) . . ?
C11 C10 C9 120.5(2) . . ?
C10 C11 C12 120.4(2) . . ?
N1 C12 C7 118.6(2) . . ?
N1 C12 C11 121.3(2) . . ?
C11 C12 C7 120.1(2) . . ?
C14 C13 C6 125.4(3) . . ?
C13 C14 C17 125.8(3) . . ?
N2 C15 C16 128.6(2) . . ?
N2 C15 C20 109.4(2) . . ?
C16 C15 C20 122.0(2) . . ?
C15 C16 C17 118.4(2) . . ?
C16 C17 C14 117.4(2) . . ?
C16 C17 C18 119.7(2) . . ?
C18 C17 C14 123.0(2) . . ?
C19 C18 C17 121.8(2) . . ?
C18 C19 C20 119.1(2) . . ?
C15 C20 C21 106.3(2) . . ?
C19 C20 C15 119.1(2) . . ?
C19 C20 C21 134.6(2) . . ?
C22 C21 C20 134.3(2) . . ?
C22 C21 C26 119.3(2) . . ?
C26 C21 C20 106.4(2) . . ?
C23 C22 C21 119.1(2) . . ?
C22 C23 C24 120.9(2) . . ?
C23 C24 N3 117.9(2) . . ?
C25 C24 N3 120.8(2) . . ?
C25 C24 C23 121.2(2) . . ?
C24 C25 C26 117.6(2) . . ?
N2 C26 C21 109.4(2) . . ?
N2 C26 C25 128.7(2) . . ?
C25 C26 C21 121.9(2) . . ?
C28 C27 N3 120.1(3) . . ?
C32 C27 N3 120.5(2) . . ?
C32 C27 C28 119.3(3) . . ?
C27 C28 C29 120.1(3) . . ?
C30 C29 C28 120.1(3) . . ?
C31 C30 C29 120.1(3) . . ?
C30 C31 C32 120.2(3) . . ?
C27 C32 C31 120.3(3) . . ?
C34 C33 N3 120.8(2) . . ?
C38 C33 N3 120.8(2) . . ?
C38 C33 C34 118.3(2) . . ?
C35 C34 C33 120.2(3) . . ?
C34 C35 C36 121.0(3) . . ?
C37 C36 C35 118.8(3) . . ?
C36 C37 C38 121.0(3) . . ?
C37 C38 C33 120.8(3) . . ?
N2 C39 C40 112.5(2) . . ?
F1 P1 F2 178.95(15) . . ?
F1 P1 F3 91.22(15) . . ?
F1 P1 F4 91.24(14) . . ?
F1 P1 F5 91.27(14) . . ?
F1 P1 F6 90.64(14) . . ?
F3 P1 F2 89.49(13) . . ?
F4 P1 F2 87.99(12) . . ?
F4 P1 F3 89.16(11) . . ?
F4 P1 F5 90.59(12) . . ?
F4 P1 F6 178.12(14) . . ?
F5 P1 F2 88.02(12) . . ?
F5 P1 F3 177.50(14) . . ?
F6 P1 F2 90.13(12) . . ?
F6 P1 F3 90.86(11) . . ?
F6 P1 F5 89.31(11) . . ?

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
O1 H1 F3 0.84 2.06 2.849(3) 155.9 1_455

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 C1 C2 N1 72.6(3) . . . . ?
N1 C4 C5 C6 0.3(4) . . . . ?
N2 C15 C16 C17 177.5(2) . . . . ?
N2 C15 C20 C19 -178.1(2) . . . . ?
N2 C15 C20 C21 0.3(3) . . . . ?
N3 C24 C25 C26 -178.8(2) . . . . ?
N3 C27 C28 C29 -176.8(3) . . . . ?
N3 C27 C32 C31 178.1(3) . . . . ?
N3 C33 C34 C35 178.1(2) . . . . ?
N3 C33 C38 C37 -177.4(3) . . . . ?
C2 N1 C4 C5 -178.6(2) . . . . ?
C2 N1 C12 C7 178.0(2) . . . . ?
C2 N1 C12 C11 -2.1(4) . . . . ?
C4 N1 C2 C1 -97.2(3) . . . . ?
C4 N1 C12 C7 -2.5(4) . . . . ?
C4 N1 C12 C11 177.4(2) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
C4 C5 C6 C13 178.8(2) . . . . ?
C5 C6 C7 C8 -178.4(2) . . . . ?
C5 C6 C7 C12 0.8(4) . . . . ?
C5 C6 C13 C14 6.8(4) . . . . ?
C6 C7 C8 C9 178.8(2) . . . . ?
C6 C7 C12 N1 1.2(4) . . . . ?
C6 C7 C12 C11 -178.8(2) . . . . ?
C6 C13 C14 C17 178.5(2) . . . . ?
C7 C6 C13 C14 -172.9(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C7 C12 N1 -179.5(2) . . . . ?
C8 C7 C12 C11 0.5(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 N1 -179.8(2) . . . . ?
C10 C11 C12 C7 0.2(4) . . . . ?
C12 N1 C2 C1 82.3(3) . . . . ?
C12 N1 C4 C5 1.8(4) . . . . ?
C12 C7 C8 C9 -0.5(4) . . . . ?
C13 C6 C7 C8 1.2(4) . . . . ?
C13 C6 C7 C12 -179.5(2) . . . . ?
C13 C14 C17 C16 173.6(3) . . . . ?
C13 C14 C17 C18 -5.8(4) . . . . ?
C14 C17 C18 C19 179.2(2) . . . . ?
C15 N2 C26 C21 0.9(3) . . . . ?
C15 N2 C26 C25 178.0(3) . . . . ?
C15 N2 C39 C40 77.9(3) . . . . ?
C15 C16 C17 C14 -178.9(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C15 C20 C21 C22 -177.1(3) . . . . ?
C15 C20 C21 C26 0.2(3) . . . . ?
C16 C15 C20 C19 0.4(4) . . . . ?
C16 C15 C20 C21 178.8(2) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C15 0.0(4) . . . . ?
C18 C19 C20 C21 -177.9(3) . . . . ?
C19 C20 C21 C22 1.0(5) . . . . ?
C19 C20 C21 C26 178.3(3) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
C20 C21 C22 C23 177.3(3) . . . . ?
C20 C21 C26 N2 -0.7(3) . . . . ?
C20 C21 C26 C25 -178.0(2) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C21 C26 N2 177.1(2) . . . . ?
C22 C21 C26 C25 -0.2(4) . . . . ?
C22 C23 C24 N3 178.8(2) . . . . ?
C22 C23 C24 C25 -1.8(4) . . . . ?
C23 C24 C25 C26 1.9(4) . . . . ?
C24 N3 C27 C28 -133.6(3) . . . . ?
C24 N3 C27 C32 49.3(4) . . . . ?
C24 N3 C33 C34 36.8(4) . . . . ?
C24 N3 C33 C38 -144.4(3) . . . . ?
C24 C25 C26 N2 -177.6(3) . . . . ?
C24 C25 C26 C21 -0.9(4) . . . . ?
C26 N2 C15 C16 -179.1(3) . . . . ?
C26 N2 C15 C20 -0.7(3) . . . . ?
C26 N2 C39 C40 -97.7(3) . . . . ?
C26 C21 C22 C23 0.3(4) . . . . ?
C27 N3 C24 C23 57.1(3) . . . . ?
C27 N3 C24 C25 -122.2(3) . . . . ?
C27 N3 C33 C34 -166.1(2) . . . . ?
C27 N3 C33 C38 12.6(4) . . . . ?
C27 C28 C29 C30 -1.2(5) . . . . ?
C28 C27 C32 C31 0.9(4) . . . . ?
C28 C29 C30 C31 0.7(5) . . . . ?
C29 C30 C31 C32 0.6(5) . . . . ?
C30 C31 C32 C27 -1.4(5) . . . . ?
C32 C27 C28 C29 0.4(5) . . . . ?
C33 N3 C24 C23 -145.5(2) . . . . ?
C33 N3 C24 C25 35.2(4) . . . . ?
C33 N3 C27 C28 68.5(4) . . . . ?
C33 N3 C27 C32 -108.7(3) . . . . ?
C33 C34 C35 C36 -0.2(4) . . . . ?
C34 C33 C38 C37 1.4(4) . . . . ?
C34 C35 C36 C37 0.5(4) . . . . ?
C35 C36 C37 C38 0.2(4) . . . . ?
C36 C37 C38 C33 -1.1(4) . . . . ?
C38 C33 C34 C35 -0.7(4) . . . . ?
C39 N2 C15 C16 4.6(4) . . . . ?
C39 N2 C15 C20 -177.1(2) . . . . ?
C39 N2 C26 C21 177.1(2) . . . . ?
C39 N2 C26 C25 -5.8(4) . . . . ?

_olex2_date_sample_data_collection 2017-06-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.800
####################################################################### 
# 
# 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_zhengz1a
_database_code_depnum_ccdc_archive 'CCDC 1921647'
loop_
_audit_author_name
_audit_author_address
'Zheng ZHENG'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2019-06-07 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2017-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H22 N2 O'
_chemical_formula_sum            'C27 H22 N2 O'
_chemical_formula_weight         390.46
_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 0.0181 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                   9.53897(10)
_cell_length_b                   23.1410(2)
_cell_length_c                   9.57210(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.3297(12)
_cell_angle_gamma                90
_cell_volume                     2017.04(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8335
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.5480
_cell_measurement_theta_min      3.8140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10527
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.485
_diffrn_reflns_theta_min         3.820
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 111.00   1.00    3.00    --  110.57 -45.00   0.00   75
  2  ω     39.00  96.00   1.00    2.00    --   40.57-125.00-120.00   57
  3  ω     85.00 177.00   1.00    3.00    --  110.57  45.00 -90.00   92
  4  ω     47.00 115.00   1.00    3.00    --  110.57-111.00  30.00   68
  5  ω     37.00 140.00   1.00    3.00    --  110.57 -30.00-120.00  103
  6  ω     35.00 160.00   1.00    3.00    --  110.57 -15.00  90.00  125
  7  ω     39.00 108.00   1.00    3.00    --  110.57 -94.00 150.00   69
  8  ω     32.00 127.00   1.00    3.00    --  110.57 -77.00-150.00   95
  9  ω    -70.00  33.00   1.00    2.00    --  -40.57  57.00-180.00  103
 10  ω   -111.00 -11.00   1.00    2.00    --  -40.57 -57.00   0.00  100
 11  ω   -117.00 -14.00   1.00    2.00    --  -40.57 -37.00-120.00  103
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1413772000
_diffrn_orient_matrix_UB_12      0.0075053000
_diffrn_orient_matrix_UB_13      0.0445646000
_diffrn_orient_matrix_UB_21      -0.0324694000
_diffrn_orient_matrix_UB_22      0.0570746000
_diffrn_orient_matrix_UB_23      -0.0865634000
_diffrn_orient_matrix_UB_31      -0.0872369000
_diffrn_orient_matrix_UB_32      -0.0334825000
_diffrn_orient_matrix_UB_33      -0.1374925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3471
_reflns_number_total             3583
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.6120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O1(0.5) O1A(0.5) H20A(0.5) H20(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C20(H20A), C20(H20),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C32(H32), C33(H33), C34(H34),
  C35(H35), C36(H36)
3.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C)
;
_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 0.6434(2) 0.47456(9) -0.41896(19) 0.0366(4) Uani 0.5 1 d . . P A 1
O1A O 0.7112(2) 0.43039(8) -0.2902(2) 0.0353(4) Uani 0.5 1 d . . P A 2
N1 N 0.71329(10) 0.53702(4) 0.20564(10) 0.0195(2) Uani 1 1 d . . . . .
N2 N 0.70755(10) 0.68076(4) 0.57996(10) 0.0194(2) Uani 1 1 d . . . . .
C1 C 0.66548(11) 0.53963(5) 0.05465(12) 0.0189(2) Uani 1 1 d . . . . .
C2 C 0.68696(12) 0.49998(5) -0.04588(13) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.7389 0.4659 -0.0153 0.027 Uiso 1 1 calc R . . . .
C3 C 0.62832(13) 0.51282(5) -0.19370(13) 0.0251(3) Uani 1 1 d . . . . .
C4 C 0.54939(13) 0.56424(5) -0.24025(12) 0.0246(3) Uani 1 1 d . . . . .
H4 H 0.5108 0.5718 -0.3398 0.030 Uiso 1 1 calc R . . . .
C5 C 0.52853(12) 0.60371(5) -0.13950(12) 0.0211(2) Uani 1 1 d . . . . .
H5 H 0.4758 0.6375 -0.1707 0.025 Uiso 1 1 calc R . . . .
C6 C 0.58800(11) 0.59198(5) 0.01015(12) 0.0176(2) Uani 1 1 d . . . . .
C7 C 0.59404(11) 0.62277(5) 0.14277(11) 0.0166(2) Uani 1 1 d . . . . .
C8 C 0.54793(11) 0.67743(5) 0.17450(11) 0.0169(2) Uani 1 1 d . . . . .
H8 H 0.4927 0.7010 0.0995 0.020 Uiso 1 1 calc R . . . .
C9 C 0.58500(11) 0.69604(5) 0.31775(12) 0.0172(2) Uani 1 1 d . . . . .
H9 H 0.5573 0.7328 0.3383 0.021 Uiso 1 1 calc R . . . .
C10 C 0.66445(11) 0.66015(5) 0.43391(11) 0.0169(2) Uani 1 1 d . . . . .
C11 C 0.70656(11) 0.60495(5) 0.40585(12) 0.0177(2) Uani 1 1 d . . . . .
H11 H 0.7550 0.5804 0.4818 0.021 Uiso 1 1 calc R . . . .
C12 C 0.67382(11) 0.58760(4) 0.26022(12) 0.0167(2) Uani 1 1 d . . . . .
C20 C 0.65387(17) 0.47167(7) -0.30061(16) 0.0391(3) Uani 1 1 d . . . . .
H20A H 0.6125 0.4832 -0.3972 0.047 Uiso 0.5 1 calc R . P A 2
H20 H 0.6854 0.4356 -0.2606 0.047 Uiso 0.5 1 calc R . P A 1
C21 C 0.85084(11) 0.66730(4) 0.67348(11) 0.0170(2) Uani 1 1 d . . . . .
C22 C 0.97209(12) 0.66925(4) 0.62003(12) 0.0187(2) Uani 1 1 d . . . . .
H22 H 0.9593 0.6787 0.5226 0.022 Uiso 1 1 calc R . . . .
C23 C 1.11132(12) 0.65710(5) 0.71181(13) 0.0212(2) Uani 1 1 d . . . . .
H23 H 1.1912 0.6578 0.6750 0.025 Uiso 1 1 calc R . . . .
C24 C 1.13289(12) 0.64384(5) 0.85799(13) 0.0223(2) Uani 1 1 d . . . . .
H24 H 1.2269 0.6367 0.9198 0.027 Uiso 1 1 calc R . . . .
C25 C 1.01292(13) 0.64137(5) 0.91081(12) 0.0226(2) Uani 1 1 d . . . . .
H25 H 1.0264 0.6320 1.0084 0.027 Uiso 1 1 calc R . . . .
C26 C 0.87233(12) 0.65269(5) 0.81937(12) 0.0207(2) Uani 1 1 d . . . . .
H26 H 0.7924 0.6505 0.8559 0.025 Uiso 1 1 calc R . . . .
C31 C 0.61717(12) 0.71948(5) 0.62874(11) 0.0180(2) Uani 1 1 d . . . . .
C32 C 0.46416(12) 0.71400(5) 0.57920(11) 0.0197(2) Uani 1 1 d . . . . .
H32 H 0.4214 0.6840 0.5161 0.024 Uiso 1 1 calc R . . . .
C33 C 0.37619(12) 0.75318(5) 0.62404(12) 0.0225(2) Uani 1 1 d . . . . .
H33 H 0.2746 0.7500 0.5880 0.027 Uiso 1 1 calc R . . . .
C34 C 0.43776(13) 0.79696(5) 0.72173(12) 0.0242(3) Uani 1 1 d . . . . .
H34 H 0.3781 0.8226 0.7526 0.029 Uiso 1 1 calc R . . . .
C35 C 0.58978(13) 0.80204(5) 0.77309(12) 0.0240(3) Uani 1 1 d . . . . .
H35 H 0.6320 0.8311 0.8394 0.029 Uiso 1 1 calc R . . . .
C36 C 0.67895(12) 0.76404(5) 0.72591(12) 0.0214(2) Uani 1 1 d . . . . .
H36 H 0.7805 0.7683 0.7593 0.026 Uiso 1 1 calc R . . . .
C41 C 0.80928(13) 0.49253(5) 0.29006(13) 0.0230(3) Uani 1 1 d . . . . .
H41A H 0.7799 0.4553 0.2441 0.028 Uiso 1 1 calc R . . . .
H41B H 0.7983 0.4911 0.3875 0.028 Uiso 1 1 calc R . . . .
C42 C 0.96961(14) 0.50336(6) 0.30188(15) 0.0337(3) Uani 1 1 d . . . . .
H42A H 0.9804 0.5064 0.2056 0.051 Uiso 1 1 calc GR . . . .
H42B H 1.0283 0.4719 0.3531 0.051 Uiso 1 1 calc GR . . . .
H42C H 1.0014 0.5387 0.3544 0.051 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
O1 C20 1.109(2) . ?
O1A C20 1.091(2) . ?
N1 C1 1.3812(14) . ?
N1 C12 1.3790(14) . ?
N1 C41 1.4528(14) . ?
N2 C10 1.4172(14) . ?
N2 C21 1.4275(14) . ?
N2 C31 1.4157(14) . ?
C1 C2 1.3882(16) . ?
C1 C6 1.4170(15) . ?
C2 C3 1.3899(17) . ?
C3 C4 1.4077(18) . ?
C3 C20 1.4704(17) . ?
C4 C5 1.3849(17) . ?
C5 C6 1.4012(15) . ?
C6 C7 1.4418(15) . ?
C7 C8 1.4018(15) . ?
C7 C12 1.4127(15) . ?
C8 C9 1.3791(15) . ?
C9 C10 1.4137(15) . ?
C10 C11 1.3889(15) . ?
C11 C12 1.3939(15) . ?
C21 C22 1.3978(16) . ?
C21 C26 1.3914(15) . ?
C22 C23 1.3855(16) . ?
C23 C24 1.3867(17) . ?
C24 C25 1.3831(17) . ?
C25 C26 1.3906(16) . ?
C31 C32 1.3996(15) . ?
C31 C36 1.3961(16) . ?
C32 C33 1.3874(16) . ?
C33 C34 1.3851(17) . ?
C34 C35 1.3906(17) . ?
C35 C36 1.3892(16) . ?
C41 C42 1.5203(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C41 124.74(9) . . ?
C12 N1 C1 108.49(9) . . ?
C12 N1 C41 126.07(9) . . ?
C10 N2 C21 119.17(9) . . ?
C31 N2 C10 120.81(9) . . ?
C31 N2 C21 119.65(9) . . ?
N1 C1 C2 128.72(10) . . ?
N1 C1 C6 109.39(9) . . ?
C2 C1 C6 121.88(10) . . ?
C1 C2 C3 117.82(11) . . ?
C2 C3 C4 121.20(11) . . ?
C2 C3 C20 118.05(12) . . ?
C4 C3 C20 120.73(12) . . ?
C5 C4 C3 120.75(11) . . ?
C4 C5 C6 119.07(11) . . ?
C1 C6 C7 106.10(9) . . ?
C5 C6 C1 119.27(10) . . ?
C5 C6 C7 134.61(10) . . ?
C8 C7 C6 134.73(10) . . ?
C8 C7 C12 118.48(9) . . ?
C12 C7 C6 106.66(9) . . ?
C9 C8 C7 119.55(10) . . ?
C8 C9 C10 121.14(10) . . ?
C9 C10 N2 120.54(9) . . ?
C11 C10 N2 118.98(10) . . ?
C11 C10 C9 120.42(10) . . ?
C10 C11 C12 117.83(10) . . ?
N1 C12 C7 109.31(9) . . ?
N1 C12 C11 128.19(10) . . ?
C11 C12 C7 122.48(10) . . ?
O1 C20 C3 133.52(19) . . ?
O1A C20 C3 133.34(18) . . ?
C22 C21 N2 120.37(10) . . ?
C26 C21 N2 120.64(10) . . ?
C26 C21 C22 118.99(10) . . ?
C23 C22 C21 120.18(10) . . ?
C22 C23 C24 120.72(10) . . ?
C25 C24 C23 119.19(10) . . ?
C24 C25 C26 120.66(10) . . ?
C25 C26 C21 120.24(10) . . ?
C32 C31 N2 120.46(10) . . ?
C36 C31 N2 120.63(10) . . ?
C36 C31 C32 118.91(10) . . ?
C33 C32 C31 120.11(10) . . ?
C34 C33 C32 120.86(10) . . ?
C33 C34 C35 119.23(10) . . ?
C36 C35 C34 120.43(11) . . ?
C35 C36 C31 120.42(10) . . ?
N1 C41 C42 112.22(10) . . ?

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 C1 C2 C3 -179.44(10) . . . . ?
N1 C1 C6 C5 -179.66(9) . . . . ?
N1 C1 C6 C7 1.65(12) . . . . ?
N2 C10 C11 C12 -174.54(9) . . . . ?
N2 C21 C22 C23 178.91(9) . . . . ?
N2 C21 C26 C25 -178.03(10) . . . . ?
N2 C31 C32 C33 -178.05(10) . . . . ?
N2 C31 C36 C35 179.79(10) . . . . ?
C1 N1 C12 C7 2.27(12) . . . . ?
C1 N1 C12 C11 -176.13(10) . . . . ?
C1 N1 C41 C42 79.90(13) . . . . ?
C1 C2 C3 C4 -0.15(17) . . . . ?
C1 C2 C3 C20 178.51(11) . . . . ?
C1 C6 C7 C8 175.39(11) . . . . ?
C1 C6 C7 C12 -0.26(11) . . . . ?
C2 C1 C6 C5 1.36(16) . . . . ?
C2 C1 C6 C7 -177.33(10) . . . . ?
C2 C3 C4 C5 0.29(17) . . . . ?
C2 C3 C20 O1 -164.0(2) . . . . ?
C2 C3 C20 O1A 0.7(3) . . . . ?
C3 C4 C5 C6 0.39(17) . . . . ?
C4 C3 C20 O1 14.7(3) . . . . ?
C4 C3 C20 O1A 179.4(2) . . . . ?
C4 C5 C6 C1 -1.18(15) . . . . ?
C4 C5 C6 C7 177.04(11) . . . . ?
C5 C6 C7 C8 -3.0(2) . . . . ?
C5 C6 C7 C12 -178.65(11) . . . . ?
C6 C1 C2 C3 -0.67(16) . . . . ?
C6 C7 C8 C9 -173.33(11) . . . . ?
C6 C7 C12 N1 -1.22(11) . . . . ?
C6 C7 C12 C11 177.29(9) . . . . ?
C7 C8 C9 C10 -2.23(15) . . . . ?
C8 C7 C12 N1 -177.70(9) . . . . ?
C8 C7 C12 C11 0.81(15) . . . . ?
C8 C9 C10 N2 177.15(9) . . . . ?
C8 C9 C10 C11 -0.23(15) . . . . ?
C9 C10 C11 C12 2.88(15) . . . . ?
C10 N2 C21 C22 41.06(14) . . . . ?
C10 N2 C21 C26 -139.67(10) . . . . ?
C10 N2 C31 C32 37.01(15) . . . . ?
C10 N2 C31 C36 -142.41(10) . . . . ?
C10 C11 C12 N1 175.02(10) . . . . ?
C10 C11 C12 C7 -3.19(15) . . . . ?
C12 N1 C1 C2 176.44(11) . . . . ?
C12 N1 C1 C6 -2.44(12) . . . . ?
C12 N1 C41 C42 -89.35(13) . . . . ?
C12 C7 C8 C9 1.93(15) . . . . ?
C20 C3 C4 C5 -178.34(11) . . . . ?
C21 N2 C10 C9 -138.42(10) . . . . ?
C21 N2 C10 C11 38.99(14) . . . . ?
C21 N2 C31 C32 -150.04(10) . . . . ?
C21 N2 C31 C36 30.54(15) . . . . ?
C21 C22 C23 C24 -1.10(16) . . . . ?
C22 C21 C26 C25 1.25(16) . . . . ?
C22 C23 C24 C25 1.67(16) . . . . ?
C23 C24 C25 C26 -0.78(17) . . . . ?
C24 C25 C26 C21 -0.68(17) . . . . ?
C26 C21 C22 C23 -0.37(15) . . . . ?
C31 N2 C10 C9 34.56(15) . . . . ?
C31 N2 C10 C11 -148.03(10) . . . . ?
C31 N2 C21 C22 -132.00(11) . . . . ?
C31 N2 C21 C26 47.27(14) . . . . ?
C31 C32 C33 C34 -2.15(16) . . . . ?
C32 C31 C36 C35 0.36(16) . . . . ?
C32 C33 C34 C35 1.13(17) . . . . ?
C33 C34 C35 C36 0.64(17) . . . . ?
C34 C35 C36 C31 -1.38(17) . . . . ?
C36 C31 C32 C33 1.39(16) . . . . ?
C41 N1 C1 C2 5.60(18) . . . . ?
C41 N1 C1 C6 -173.29(10) . . . . ?
C41 N1 C12 C7 172.97(10) . . . . ?
C41 N1 C12 C11 -5.43(18) . . . . ?

_olex2_date_sample_data_collection 2017-05-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.715
