# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lzy-tm-dpid
_database_code_depnum_ccdc_archive 'CCDC 1487656'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_audit_creation_date             2015-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
2-(2,6-dihydroxy-4-(indolin-1-yl)phenyl)-4-(diphenylamino)cyclobuta-1,3-diene-1,3-bis(olate)
_chemical_formula_moiety         'C30 H22 N2 O4, C0.5 Cl'
_chemical_formula_sum            'C30.50 H23 Cl N2 O4'
_chemical_formula_weight         516.96
_chemical_melting_point          523-524
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   11.8232(8)
_cell_length_b                   14.4169(9)
_cell_length_c                   14.7764(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.264(7)
_cell_angle_gamma                90
_cell_volume                     2441.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4925
_cell_measurement_temperature    175(70)
_cell_measurement_theta_max      29.0020
_cell_measurement_theta_min      3.9700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic greenish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14787
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.765
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      175(70)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -56.00   45.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -       15.7256  -19.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   32.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -       15.7256  -57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   88.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -       15.7256  178.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega  -29.00   49.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      -16.8194   19.0000  120.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0152627000
_diffrn_orient_matrix_UB_12      -0.0225323000
_diffrn_orient_matrix_UB_13      -0.0380566000
_diffrn_orient_matrix_UB_21      -0.0459843000
_diffrn_orient_matrix_UB_22      -0.0322310000
_diffrn_orient_matrix_UB_23      -0.0025639000
_diffrn_orient_matrix_UB_31      -0.0383983000
_diffrn_orient_matrix_UB_32      0.0294949000
_diffrn_orient_matrix_UB_33      -0.0317634000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3886
_reflns_number_total             4979
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.807
_refine_diff_density_min         -1.234
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4979
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.090
_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)+(0.0750P)²+2.0210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1758
_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 O(H) groups
2. Others
 Fixed Sof: C1(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00L(H00C,H00D)
3.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00I(H00I), C00K(H00K), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Z(H00Z), C010(H010), C011(H011)
3.c Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003)
;
_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
O002 O 0.29951(16) 0.28574(12) -0.60475(12) 0.0333(4) Uani 1 1 d . . . . .
H002 H 0.3178 0.2989 -0.5491 0.050 Uiso 1 1 calc GR . . . .
O003 O 0.29438(17) 0.62120(12) -0.64842(11) 0.0333(4) Uani 1 1 d . . . . .
H003 H 0.3231 0.6221 -0.5919 0.050 Uiso 1 1 calc GR . . . .
O004 O 0.38919(18) 0.63203(12) -0.47145(12) 0.0392(5) Uani 1 1 d . . . . .
N005 N 0.18171(17) 0.41592(14) -0.90465(13) 0.0259(4) Uani 1 1 d . . . . .
O006 O 0.3537(2) 0.32384(13) -0.42442(13) 0.0481(6) Uani 1 1 d . . . . .
N007 N 0.41384(18) 0.50858(14) -0.28328(13) 0.0271(5) Uani 1 1 d . . . . .
C008 C 0.1762(2) 0.48066(16) -0.97829(16) 0.0244(5) Uani 1 1 d . . . . .
C009 C 0.0983(2) 0.44771(17) -1.05901(16) 0.0265(5) Uani 1 1 d . . . . .
C00A C 0.28045(19) 0.36406(16) -0.65569(16) 0.0250(5) Uani 1 1 d . . . . .
C00B C 0.0504(2) 0.35464(17) -1.04044(16) 0.0288(5) Uani 1 1 d . . . . .
H00A H 0.0571 0.3098 -1.0878 0.035 Uiso 1 1 calc R . . . .
H00B H -0.0308 0.3594 -1.0384 0.035 Uiso 1 1 calc R . . . .
C00C C 0.21892(19) 0.43016(16) -0.81055(16) 0.0239(5) Uani 1 1 d . . . . .
C00D C 0.3048(2) 0.45475(16) -0.61455(16) 0.0251(5) Uani 1 1 d . . . . .
C00E C 0.4993(2) 0.35752(17) -0.22837(17) 0.0280(5) Uani 1 1 d . . . . .
H00E H 0.5240 0.3506 -0.2831 0.034 Uiso 1 1 calc R . . . .
C00F C 0.2398(2) 0.52002(17) -0.77254(16) 0.0256(5) Uani 1 1 d . . . . .
H00F H 0.2256 0.5714 -0.8118 0.031 Uiso 1 1 calc R . . . .
C00G C 0.2808(2) 0.53219(16) -0.67832(16) 0.0251(5) Uani 1 1 d . . . . .
C00H C 0.4093(2) 0.60402(17) -0.25535(15) 0.0257(5) Uani 1 1 d . . . . .
C00I C 0.2379(2) 0.35302(17) -0.75019(16) 0.0263(5) Uani 1 1 d . . . . .
H00I H 0.2213 0.2938 -0.7747 0.032 Uiso 1 1 calc R . . . .
C00J C 0.4392(2) 0.43707(17) -0.21362(16) 0.0257(5) Uani 1 1 d . . . . .
C00K C 0.4045(2) 0.44860(18) -0.13120(17) 0.0309(6) Uani 1 1 d . . . . .
H00K H 0.3644 0.5017 -0.1216 0.037 Uiso 1 1 calc R . . . .
C00L C 0.1277(2) 0.32787(17) -0.94502(17) 0.0297(5) Uani 1 1 d . . . . .
H00C H 0.0815 0.3008 -0.9059 0.036 Uiso 1 1 calc R . . . .
H00D H 0.1869 0.2836 -0.9517 0.036 Uiso 1 1 calc R . . . .
C00M C 0.3444(2) 0.46801(16) -0.51758(16) 0.0274(5) Uani 1 1 d . . . . .
C00N C 0.2389(2) 0.56173(17) -0.97913(16) 0.0274(5) Uani 1 1 d . . . . .
H00N H 0.2951 0.5808 -0.9266 0.033 Uiso 1 1 calc R . . . .
C00O C 0.5219(2) 0.28881(18) -0.16046(18) 0.0323(6) Uani 1 1 d . . . . .
H00O H 0.5601 0.2348 -0.1704 0.039 Uiso 1 1 calc R . . . .
C00P C 0.2153(2) 0.61379(17) -1.06118(17) 0.0296(5) Uani 1 1 d . . . . .
H00P H 0.2557 0.6688 -1.0631 0.036 Uiso 1 1 calc R . . . .
C00Q C 0.0749(2) 0.50049(19) -1.13935(17) 0.0309(6) Uani 1 1 d . . . . .
H00Q H 0.0213 0.4800 -1.1927 0.037 Uiso 1 1 calc R . . . .
C00R C 0.3779(2) 0.54831(17) -0.45719(16) 0.0289(5) Uani 1 1 d . . . . .
C00S C 0.3914(2) 0.48956(17) -0.37476(17) 0.0284(5) Uani 1 1 d . . . . .
C00T C 0.5053(2) 0.64281(19) -0.19436(17) 0.0324(6) Uani 1 1 d . . . . .
H00T H 0.5711 0.6070 -0.1696 0.039 Uiso 1 1 calc R . . . .
C00U C 0.4302(2) 0.38034(19) -0.06359(17) 0.0348(6) Uani 1 1 d . . . . .
H00U H 0.4085 0.3883 -0.0077 0.042 Uiso 1 1 calc R . . . .
C00V C 0.3099(2) 0.65637(19) -0.29055(18) 0.0345(6) Uani 1 1 d . . . . .
H00V H 0.2452 0.6297 -0.3310 0.041 Uiso 1 1 calc R . . . .
C00W C 0.1324(2) 0.58499(19) -1.13988(17) 0.0327(6) Uani 1 1 d . . . . .
H00W H 0.1152 0.6220 -1.1931 0.039 Uiso 1 1 calc R . . . .
C00X C 0.4878(2) 0.30013(19) -0.07804(18) 0.0358(6) Uani 1 1 d . . . . .
H00X H 0.5036 0.2541 -0.0325 0.043 Uiso 1 1 calc R . . . .
C00Y C 0.3625(2) 0.40782(18) -0.43524(17) 0.0324(6) Uani 1 1 d . . . . .
C00Z C 0.5027(3) 0.7357(2) -0.17049(19) 0.0407(7) Uani 1 1 d . . . . .
H00Z H 0.5676 0.7628 -0.1307 0.049 Uiso 1 1 calc R . . . .
C010 C 0.3074(3) 0.7487(2) -0.2652(2) 0.0423(7) Uani 1 1 d . . . . .
H010 H 0.2408 0.7842 -0.2883 0.051 Uiso 1 1 calc R . . . .
C011 C 0.4038(3) 0.78796(19) -0.2057(2) 0.0422(7) Uani 1 1 d . . . . .
H011 H 0.4022 0.8501 -0.1892 0.051 Uiso 1 1 calc R . . . .
Cl1 Cl 0.49518(16) -0.03329(10) 0.09301(10) 0.1098(5) Uani 1 1 d . . . . .
C1 C 0.4349(8) 0.0150(13) -0.0021(7) 0.146(6) Uani 0.5 1 d . . P . .


_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
O002 H002 0.8200 . ?
O002 C00A 1.345(3) . ?
O003 H003 0.8200 . ?
O003 C00G 1.354(3) . ?
O004 C00R 1.238(3) . ?
N005 C008 1.423(3) . ?
N005 C00C 1.367(3) . ?
N005 C00L 1.479(3) . ?
O006 C00Y 1.229(3) . ?
N007 C00H 1.441(3) . ?
N007 C00J 1.435(3) . ?
N007 C00S 1.340(3) . ?
C008 C009 1.398(3) . ?
C008 C00N 1.386(3) . ?
C009 C00B 1.507(3) . ?
C009 C00Q 1.380(3) . ?
C00A C00D 1.441(3) . ?
C00A C00I 1.372(3) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00B C00L 1.529(3) . ?
C00C C00F 1.409(3) . ?
C00C C00I 1.409(3) . ?
C00D C00G 1.443(3) . ?
C00D C00M 1.407(3) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.394(3) . ?
C00E C00O 1.388(3) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.368(3) . ?
C00H C00T 1.382(3) . ?
C00H C00V 1.385(3) . ?
C00I H00I 0.9300 . ?
C00J C00K 1.388(4) . ?
C00K H00K 0.9300 . ?
C00K C00U 1.382(4) . ?
C00L H00C 0.9700 . ?
C00L H00D 0.9700 . ?
C00M C00R 1.456(3) . ?
C00M C00Y 1.467(3) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.394(3) . ?
C00O H00O 0.9300 . ?
C00O C00X 1.383(4) . ?
C00P H00P 0.9300 . ?
C00P C00W 1.387(4) . ?
C00Q H00Q 0.9300 . ?
C00Q C00W 1.396(4) . ?
C00R C00S 1.460(3) . ?
C00S C00Y 1.468(3) . ?
C00T H00T 0.9300 . ?
C00T C00Z 1.387(4) . ?
C00U H00U 0.9300 . ?
C00U C00X 1.385(4) . ?
C00V H00V 0.9300 . ?
C00V C010 1.386(4) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00Z H00Z 0.9300 . ?
C00Z C011 1.381(4) . ?
C010 H010 0.9300 . ?
C010 C011 1.377(4) . ?
C011 H011 0.9300 . ?
Cl1 C1 1.573(9) . ?
Cl1 C1 1.762(11) 3_655 ?
C1 Cl1 1.762(11) 3_655 ?
C1 C1 1.59(2) 3_655 ?

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
C00A O002 H002 109.5 . . ?
C00G O003 H003 109.5 . . ?
C008 N005 C00L 108.69(18) . . ?
C00C N005 C008 128.5(2) . . ?
C00C N005 C00L 122.6(2) . . ?
C00J N007 C00H 119.75(19) . . ?
C00S N007 C00H 118.2(2) . . ?
C00S N007 C00J 122.1(2) . . ?
C009 C008 N005 109.0(2) . . ?
C00N C008 N005 129.5(2) . . ?
C00N C008 C009 121.4(2) . . ?
C008 C009 C00B 110.2(2) . . ?
C00Q C009 C008 119.8(2) . . ?
C00Q C009 C00B 130.0(2) . . ?
O002 C00A C00D 122.5(2) . . ?
O002 C00A C00I 116.2(2) . . ?
C00I C00A C00D 121.3(2) . . ?
C009 C00B H00A 111.1 . . ?
C009 C00B H00B 111.1 . . ?
C009 C00B C00L 103.10(19) . . ?
H00A C00B H00B 109.1 . . ?
C00L C00B H00A 111.1 . . ?
C00L C00B H00B 111.1 . . ?
N005 C00C C00F 121.6(2) . . ?
N005 C00C C00I 119.1(2) . . ?
C00I C00C C00F 119.2(2) . . ?
C00A C00D C00G 116.1(2) . . ?
C00M C00D C00A 122.3(2) . . ?
C00M C00D C00G 121.5(2) . . ?
C00J C00E H00E 120.4 . . ?
C00O C00E H00E 120.4 . . ?
C00O C00E C00J 119.2(2) . . ?
C00C C00F H00F 119.8 . . ?
C00G C00F C00C 120.4(2) . . ?
C00G C00F H00F 119.8 . . ?
O003 C00G C00D 122.1(2) . . ?
O003 C00G C00F 115.9(2) . . ?
C00F C00G C00D 121.9(2) . . ?
C00T C00H N007 119.3(2) . . ?
C00T C00H C00V 120.6(2) . . ?
C00V C00H N007 120.1(2) . . ?
C00A C00I C00C 120.9(2) . . ?
C00A C00I H00I 119.5 . . ?
C00C C00I H00I 119.5 . . ?
C00E C00J N007 120.2(2) . . ?
C00K C00J N007 119.3(2) . . ?
C00K C00J C00E 120.5(2) . . ?
C00J C00K H00K 120.3 . . ?
C00U C00K C00J 119.3(2) . . ?
C00U C00K H00K 120.3 . . ?
N005 C00L C00B 104.83(19) . . ?
N005 C00L H00C 110.8 . . ?
N005 C00L H00D 110.8 . . ?
C00B C00L H00C 110.8 . . ?
C00B C00L H00D 110.8 . . ?
H00C C00L H00D 108.9 . . ?
C00D C00M C00R 134.8(2) . . ?
C00D C00M C00Y 135.1(2) . . ?
C00R C00M C00Y 89.99(19) . . ?
C008 C00N H00N 121.0 . . ?
C008 C00N C00P 117.9(2) . . ?
C00P C00N H00N 121.0 . . ?
C00E C00O H00O 119.8 . . ?
C00X C00O C00E 120.4(2) . . ?
C00X C00O H00O 119.8 . . ?
C00N C00P H00P 119.4 . . ?
C00W C00P C00N 121.1(2) . . ?
C00W C00P H00P 119.4 . . ?
C009 C00Q H00Q 120.3 . . ?
C009 C00Q C00W 119.5(2) . . ?
C00W C00Q H00Q 120.3 . . ?
O004 C00R C00M 134.1(2) . . ?
O004 C00R C00S 135.5(2) . . ?
C00M C00R C00S 90.43(19) . . ?
N007 C00S C00R 132.6(2) . . ?
N007 C00S C00Y 137.5(2) . . ?
C00R C00S C00Y 89.80(19) . . ?
C00H C00T H00T 120.3 . . ?
C00H C00T C00Z 119.3(2) . . ?
C00Z C00T H00T 120.3 . . ?
C00K C00U H00U 119.6 . . ?
C00K C00U C00X 120.8(2) . . ?
C00X C00U H00U 119.6 . . ?
C00H C00V H00V 120.2 . . ?
C00H C00V C010 119.6(2) . . ?
C010 C00V H00V 120.2 . . ?
C00P C00W C00Q 120.1(2) . . ?
C00P C00W H00W 120.0 . . ?
C00Q C00W H00W 120.0 . . ?
C00O C00X C00U 119.7(2) . . ?
C00O C00X H00X 120.2 . . ?
C00U C00X H00X 120.2 . . ?
O006 C00Y C00M 133.7(2) . . ?
O006 C00Y C00S 136.6(2) . . ?
C00M C00Y C00S 89.69(19) . . ?
C00T C00Z H00Z 120.0 . . ?
C011 C00Z C00T 120.1(3) . . ?
C011 C00Z H00Z 120.0 . . ?
C00V C010 H010 120.1 . . ?
C011 C010 C00V 119.9(3) . . ?
C011 C010 H010 120.1 . . ?
C00Z C011 H011 119.8 . . ?
C010 C011 C00Z 120.5(3) . . ?
C010 C011 H011 119.8 . . ?
C1 Cl1 C1 56.4(7) . 3_655 ?
Cl1 C1 Cl1 123.6(7) . 3_655 ?
Cl1 C1 C1 67.8(6) . 3_655 ?
C1 C1 Cl1 55.7(6) 3_655 3_655 ?

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
O002 C00A C00D C00G 179.5(2) . . . . ?
O002 C00A C00D C00M -3.4(4) . . . . ?
O002 C00A C00I C00C -177.6(2) . . . . ?
O004 C00R C00S N007 5.6(5) . . . . ?
O004 C00R C00S C00Y -178.1(3) . . . . ?
N005 C008 C009 C00B -1.5(3) . . . . ?
N005 C008 C009 C00Q 177.7(2) . . . . ?
N005 C008 C00N C00P -179.2(2) . . . . ?
N005 C00C C00F C00G -177.8(2) . . . . ?
N005 C00C C00I C00A 176.9(2) . . . . ?
N007 C00H C00T C00Z 177.4(2) . . . . ?
N007 C00H C00V C010 -178.3(2) . . . . ?
N007 C00J C00K C00U -179.2(2) . . . . ?
N007 C00S C00Y O006 -4.8(6) . . . . ?
N007 C00S C00Y C00M 173.8(3) . . . . ?
C008 N005 C00C C00F 11.2(4) . . . . ?
C008 N005 C00C C00I -168.2(2) . . . . ?
C008 N005 C00L C00B -20.5(3) . . . . ?
C008 C009 C00B C00L -10.9(3) . . . . ?
C008 C009 C00Q C00W 2.1(4) . . . . ?
C008 C00N C00P C00W -0.7(4) . . . . ?
C009 C008 C00N C00P 5.1(4) . . . . ?
C009 C00B C00L N005 18.5(3) . . . . ?
C009 C00Q C00W C00P 2.3(4) . . . . ?
C00A C00D C00G O003 176.8(2) . . . . ?
C00A C00D C00G C00F -1.4(3) . . . . ?
C00A C00D C00M C00R 178.4(3) . . . . ?
C00A C00D C00M C00Y -6.0(4) . . . . ?
C00B C009 C00Q C00W -178.9(2) . . . . ?
C00C N005 C008 C009 -160.0(2) . . . . ?
C00C N005 C008 C00N 23.9(4) . . . . ?
C00C N005 C00L C00B 154.0(2) . . . . ?
C00C C00F C00G O003 -177.9(2) . . . . ?
C00C C00F C00G C00D 0.4(4) . . . . ?
C00D C00A C00I C00C 1.4(4) . . . . ?
C00D C00M C00R O004 -5.1(5) . . . . ?
C00D C00M C00R C00S 174.7(3) . . . . ?
C00D C00M C00Y O006 4.0(6) . . . . ?
C00D C00M C00Y C00S -174.7(3) . . . . ?
C00E C00J C00K C00U 0.0(4) . . . . ?
C00E C00O C00X C00U 0.4(4) . . . . ?
C00F C00C C00I C00A -2.5(3) . . . . ?
C00G C00D C00M C00R -4.6(4) . . . . ?
C00G C00D C00M C00Y 170.9(3) . . . . ?
C00H N007 C00J C00E -148.1(2) . . . . ?
C00H N007 C00J C00K 31.1(3) . . . . ?
C00H N007 C00S C00R 10.3(4) . . . . ?
C00H N007 C00S C00Y -164.3(3) . . . . ?
C00H C00T C00Z C011 1.6(4) . . . . ?
C00H C00V C010 C011 0.4(4) . . . . ?
C00I C00A C00D C00G 0.5(3) . . . . ?
C00I C00A C00D C00M 177.6(2) . . . . ?
C00I C00C C00F C00G 1.6(4) . . . . ?
C00J N007 C00H C00T 56.9(3) . . . . ?
C00J N007 C00H C00V -124.0(2) . . . . ?
C00J N007 C00S C00R -171.2(2) . . . . ?
C00J N007 C00S C00Y 14.2(5) . . . . ?
C00J C00E C00O C00X -1.7(4) . . . . ?
C00J C00K C00U C00X -1.3(4) . . . . ?
C00K C00U C00X C00O 1.1(4) . . . . ?
C00L N005 C008 C009 14.1(3) . . . . ?
C00L N005 C008 C00N -162.0(2) . . . . ?
C00L N005 C00C C00F -162.2(2) . . . . ?
C00L N005 C00C C00I 18.4(3) . . . . ?
C00M C00D C00G O003 -0.4(4) . . . . ?
C00M C00D C00G C00F -178.6(2) . . . . ?
C00M C00R C00S N007 -174.1(3) . . . . ?
C00M C00R C00S C00Y 2.2(2) . . . . ?
C00N C008 C009 C00B 174.9(2) . . . . ?
C00N C008 C009 C00Q -5.9(4) . . . . ?
C00N C00P C00W C00Q -3.0(4) . . . . ?
C00O C00E C00J N007 -179.4(2) . . . . ?
C00O C00E C00J C00K 1.5(3) . . . . ?
C00Q C009 C00B C00L 170.0(3) . . . . ?
C00R C00M C00Y O006 -179.1(3) . . . . ?
C00R C00M C00Y C00S 2.2(2) . . . . ?
C00R C00S C00Y O006 179.2(4) . . . . ?
C00R C00S C00Y C00M -2.2(2) . . . . ?
C00S N007 C00H C00T -124.5(3) . . . . ?
C00S N007 C00H C00V 54.6(3) . . . . ?
C00S N007 C00J C00E 33.5(3) . . . . ?
C00S N007 C00J C00K -147.4(2) . . . . ?
C00T C00H C00V C010 0.8(4) . . . . ?
C00T C00Z C011 C010 -0.5(5) . . . . ?
C00V C00H C00T C00Z -1.7(4) . . . . ?
C00V C010 C011 C00Z -0.5(5) . . . . ?
C00Y C00M C00R O004 178.1(3) . . . . ?
C00Y C00M C00R C00S -2.2(2) . . . . ?
C1 Cl1 C1 Cl1 0.000(1) 3_655 . . 3_655 ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-02
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method dichloromethane/hexane
####################################################################### 
# 
# 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_160622_s2_yl_tizsq
_database_code_depnum_ccdc_archive 'CCDC 1487657'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_audit_creation_date             2016-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
2-(2,6-dihydroxy-4-(1,2,3,3a-tetrahydrocyclopenta[b]indol-4(8bH)-yl)phenyl)-4-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)cyclobuta-1,3-diene-1,3-bis(olate)
_chemical_formula_moiety         'C39 H34 N2 O4'
_chemical_formula_sum            'C39 H34 N2 O4'
_chemical_formula_weight         594.68
_chemical_melting_point          507-509
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.8776(8)
_cell_length_b                   12.2628(8)
_cell_length_c                   15.8498(8)
_cell_angle_alpha                103.335(5)
_cell_angle_beta                 105.575(6)
_cell_angle_gamma                108.689(6)
_cell_volume                     1809.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3113
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      26.0100
_cell_measurement_theta_min      3.3370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'green shiny crystal'
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16147
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.428
_diffrn_reflns_theta_min         2.968
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    0.00   84.00   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000   30.0000 105

#__ type_ start__ end____ width___ exp.time_
  2 omega   40.00   67.20   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   77.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   45.00   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   22.20   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega   -8.00   23.20   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00   42.60   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -77.0000  -90.0000 117

#__ type_ start__ end____ width___ exp.time_
  7 omega  -69.00  -34.60   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  178.0000   90.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0697719000
_diffrn_orient_matrix_UB_12      0.0050246000
_diffrn_orient_matrix_UB_13      0.0155276000
_diffrn_orient_matrix_UB_21      0.0063737000
_diffrn_orient_matrix_UB_22      0.0096625000
_diffrn_orient_matrix_UB_23      -0.0413395000
_diffrn_orient_matrix_UB_31      0.0242556000
_diffrn_orient_matrix_UB_32      0.0641901000
_diffrn_orient_matrix_UB_33      0.0224443000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3428
_reflns_number_total             8322
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.278
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8322
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1694
_refine_ls_R_factor_gt           0.0890
_refine_ls_restrained_S_all      0.954
_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)+(0.1593P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2484
_refine_ls_wR_factor_ref         0.3026
_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. Restrained distances
 C31-C32
 1.42 with sigma of 0.02
 C31A-C32A
 1.42 with sigma of 0.02
 C33-C32
 1.42 with sigma of 0.02
 C36A-C37A
 1.52 with sigma of 0.02
 C35A-C34A
 1.52 with sigma of 0.02
3. Restrained planarity
 C29A, C30A, C31A, C32A, C33A, C34A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C33) = Uanis(C33A)
Uanis(C34) = Uanis(C34A)
Uanis(C35) = Uanis(C35A)
Uanis(C39) = Uanis(C39A)
Uanis(N2) = Uanis(N2A)
Uanis(C29) = Uanis(C29A)
Uanis(C31) = Uanis(C31A)
Uanis(C30) = Uanis(C30A)
Uanis(C32) = Uanis(C32A)
Uanis(C37) = Uanis(C36A)
Uanis(C36) = Uanis(C37A)
Uanis(C38) = Uanis(C38A)
5. Others
 Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(C35A)=Sof(H35A)=Sof(C39A)=Sof(H39A)=1-FVAR(1)
 Sof(C33)=Sof(H33)=Sof(C34)=Sof(C35)=Sof(H35)=Sof(C39)=Sof(H39)=FVAR(1)
 Sof(N2A)=1-FVAR(2)
 Sof(N2)=FVAR(2)
 Sof(C29A)=1-FVAR(3)
 Sof(C29)=FVAR(3)
 Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=1-FVAR(4)
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=FVAR(4)
 Sof(C36A)=Sof(H36C)=Sof(H36D)=1-FVAR(5)
 Sof(C37)=Sof(H37A)=Sof(H37B)=FVAR(5)
 Sof(C37A)=Sof(H37C)=Sof(H37D)=Sof(C38A)=Sof(H38C)=Sof(H38D)=1-FVAR(6)
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C38)=Sof(H38A)=Sof(H38B)=FVAR(6)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12), C35(H35), C39(H39), C35A(H35A), C39A(H39A)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C36(H36A,H36B), C37(H37A,H37B),
 C38(H38A,H38B), C36A(H36C,H36D), C37A(H37C,H37D), C38A(H38C,H38D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C14(H14), C16(H16), C17(H17), C25(H25),
 C27(H27), C30(H30), C31(H31), C32(H32), C33(H33), C30A(H30A), C31A(H31A),
 C32A(H32A), C33A(H33A)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_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 0.5999(3) 0.60986(19) 0.18998(18) 0.1046(8) Uani 1 1 d . . . . .
O2 O 0.2914(2) 0.24090(18) -0.02564(16) 0.0844(7) Uani 1 1 d . . . . .
O3 O 0.7675(2) 0.52247(17) 0.26923(16) 0.0963(8) Uani 1 1 d . . . . .
H3 H 0.7100 0.5462 0.2439 0.144 Uiso 1 1 calc GR . . . .
O4 O 0.4380(2) 0.12653(15) 0.03835(14) 0.0770(6) Uani 1 1 d . . . . .
H4 H 0.3988 0.1676 0.0186 0.115 Uiso 1 1 calc GR . . . .
N1 N 0.0680(2) 0.7185(2) -0.06683(17) 0.0718(7) Uani 1 1 d . . . . .
C1 C -0.3207(5) 0.6306(6) -0.2750(3) 0.1172(15) Uani 1 1 d . . . . .
C2 C -0.2214(5) 0.7432(6) -0.2340(3) 0.1375(18) Uani 1 1 d . . . . .
H2 H -0.2398 0.8062 -0.2500 0.165 Uiso 1 1 calc R . . . .
C3 C -0.0919(5) 0.7723(4) -0.1688(3) 0.1303(16) Uani 1 1 d . . . . .
H3A H -0.0236 0.8518 -0.1469 0.156 Uiso 1 1 calc R . . . .
C4 C -0.0626(3) 0.6878(3) -0.1362(2) 0.0744(8) Uani 1 1 d . . . . .
C5 C -0.1674(4) 0.5699(4) -0.1722(3) 0.1119(13) Uani 1 1 d . . . . .
H5 H -0.1517 0.5097 -0.1501 0.134 Uiso 1 1 calc R . . . .
C6 C -0.2945(5) 0.5407(5) -0.2403(3) 0.1349(17) Uani 1 1 d . . . . .
H6 H -0.3634 0.4612 -0.2634 0.162 Uiso 1 1 calc R . . . .
C7 C -0.4594(5) 0.5988(7) -0.3509(3) 0.169(2) Uani 1 1 d . . . . .
H7A H -0.5259 0.6061 -0.3230 0.254 Uiso 1 1 calc GR . . . .
H7B H -0.4936 0.5160 -0.3927 0.254 Uiso 1 1 calc GR . . . .
H7C H -0.4465 0.6540 -0.3851 0.254 Uiso 1 1 calc GR . . . .
C8 C 0.1541(3) 0.8470(3) -0.0026(2) 0.0761(9) Uani 1 1 d . . . . .
H8 H 0.1767 0.9027 -0.0370 0.091 Uiso 1 1 calc R . . . .
C9 C 0.0871(4) 0.8903(4) 0.0632(3) 0.1213(15) Uani 1 1 d . . . . .
H9A H -0.0138 0.8469 0.0353 0.146 Uiso 1 1 calc R . . . .
H9B H 0.1114 0.9777 0.0785 0.146 Uiso 1 1 calc R . . . .
C10 C 0.1458(4) 0.8616(4) 0.1496(3) 0.1134(13) Uani 1 1 d . . . . .
H10A H 0.1379 0.9110 0.2036 0.136 Uiso 1 1 calc R . . . .
H10B H 0.0986 0.7754 0.1401 0.136 Uiso 1 1 calc R . . . .
C11 C 0.2969(4) 0.8950(3) 0.1605(2) 0.0843(9) Uani 1 1 d . . . . .
H11A H 0.3397 0.8574 0.2003 0.101 Uiso 1 1 calc R . . . .
H11B H 0.3501 0.9832 0.1866 0.101 Uiso 1 1 calc R . . . .
C12 C 0.2877(3) 0.8433(2) 0.0607(2) 0.0692(8) Uani 1 1 d . . . . .
H12 H 0.3704 0.8934 0.0518 0.083 Uiso 1 1 calc R . . . .
C13 C 0.2617(3) 0.7101(2) 0.0276(2) 0.0644(7) Uani 1 1 d . . . . .
C14 C 0.3438(3) 0.6542(2) 0.0602(2) 0.0699(8) Uani 1 1 d . . . . .
H14 H 0.4279 0.6993 0.1109 0.084 Uiso 1 1 calc R . . . .
C15 C 0.3001(3) 0.5264(3) 0.0160(2) 0.0727(8) Uani 1 1 d . . . . .
C16 C 0.1769(3) 0.4628(3) -0.0617(2) 0.0752(8) Uani 1 1 d . . . . .
H16 H 0.1502 0.3798 -0.0925 0.090 Uiso 1 1 calc R . . . .
C17 C 0.0938(3) 0.5183(3) -0.0944(2) 0.0766(9) Uani 1 1 d . . . . .
H17 H 0.0117 0.4736 -0.1467 0.092 Uiso 1 1 calc R . . . .
C18 C 0.1329(3) 0.6421(3) -0.0491(2) 0.0685(8) Uani 1 1 d . . . . .
C19 C 0.3849(3) 0.4673(3) 0.0525(2) 0.0741(8) Uani 1 1 d . . . . .
C20 C 0.5147(3) 0.5101(3) 0.1298(2) 0.0773(9) Uani 1 1 d . . . . .
C21 C 0.5076(3) 0.3841(2) 0.1107(2) 0.0658(7) Uani 1 1 d . . . . .
C22 C 0.3749(3) 0.3436(3) 0.0327(2) 0.0681(8) Uani 1 1 d . . . . .
C23 C 0.5910(3) 0.3308(2) 0.15027(18) 0.0565(6) Uani 1 1 d . . . . .
C24 C 0.7192(3) 0.4003(2) 0.22972(19) 0.0663(7) Uani 1 1 d . . . . .
C25 C 0.7997(3) 0.3460(2) 0.2679(2) 0.0727(8) Uani 1 1 d . . . . .
H25 H 0.8836 0.3943 0.3182 0.087 Uiso 1 1 calc R . . . .
C26 C 0.7583(3) 0.2177(2) 0.23247(19) 0.0669(7) Uani 1 1 d . . . . .
C27 C 0.6341(3) 0.1483(2) 0.15383(19) 0.0655(8) Uani 1 1 d . . . . .
H27 H 0.6067 0.0641 0.1285 0.079 Uiso 1 1 calc R . . . .
C28 C 0.5533(3) 0.2002(2) 0.11392(18) 0.0596(7) Uani 1 1 d . . . . .
N2 N 0.8401(10) 0.1600(4) 0.2680(6) 0.068(2) Uani 0.79(3) 1 d . . P A 1
C29 C 0.964(2) 0.2120(9) 0.3481(16) 0.076(4) Uani 0.79(8) 1 d . . P A 1
C30 C 1.0257(11) 0.3165(9) 0.4226(6) 0.086(3) Uani 0.609(10) 1 d . . P A 1
H30 H 0.9881 0.3749 0.4244 0.104 Uiso 0.609(10) 1 calc R . P A 1
C31 C 1.1433(11) 0.3392(9) 0.4966(7) 0.098(3) Uani 0.609(10) 1 d D . P A 1
H31 H 1.1776 0.4091 0.5490 0.118 Uiso 0.609(10) 1 calc R . P A 1
C32 C 1.2142(10) 0.2601(11) 0.4957(9) 0.125(4) Uani 0.609(10) 1 d D . P A 1
H32 H 1.3016 0.2810 0.5399 0.150 Uiso 0.609(10) 1 calc R . P A 1
C33 C 1.1389(6) 0.1456(6) 0.4207(4) 0.1091(17) Uani 0.708(3) 1 d D . P A 1
H33 H 1.1731 0.0852 0.4215 0.131 Uiso 0.708(3) 1 calc R . P A 1
C34 C 1.0176(5) 0.1176(5) 0.3462(3) 0.0845(12) Uani 0.708(3) 1 d . . P A 1
C35 C 0.9289(6) 0.0035(5) 0.2665(4) 0.0933(14) Uani 0.708(3) 1 d . . P A 1
H35 H 0.9756 -0.0094 0.2226 0.112 Uiso 0.708(3) 1 calc R . P A 1
C36 C 0.8746(8) -0.1091(6) 0.2906(7) 0.122(3) Uani 0.739(6) 1 d . . P A 1
H36A H 0.9446 -0.1093 0.3434 0.147 Uiso 0.739(6) 1 calc R . P A 1
H36B H 0.8438 -0.1832 0.2378 0.147 Uiso 0.739(6) 1 calc R . P A 1
C37 C 0.7508(8) -0.0966(6) 0.3150(5) 0.103(2) Uani 0.651(10) 1 d . . P A 1
H37A H 0.6874 -0.1747 0.3128 0.124 Uiso 0.651(10) 1 calc R . P A 1
H37B H 0.7832 -0.0365 0.3768 0.124 Uiso 0.651(10) 1 calc R . P A 1
C38 C 0.6794(6) -0.0542(5) 0.2399(4) 0.0917(16) Uani 0.739(6) 1 d . . P A 1
H38A H 0.6147 -0.1235 0.1837 0.110 Uiso 0.739(6) 1 calc R . P A 1
H38B H 0.6291 -0.0088 0.2621 0.110 Uiso 0.739(6) 1 calc R . P A 1
C39 C 0.7986(5) 0.0268(4) 0.2219(3) 0.0760(12) Uani 0.708(3) 1 d . . P A 1
H39 H 0.7761 0.0071 0.1546 0.091 Uiso 0.708(3) 1 calc R . P A 1
N2A N 0.803(3) 0.161(2) 0.290(2) 0.068(2) Uani 0.21(3) 1 d . . P A 2
C29A C 0.937(6) 0.203(5) 0.364(3) 0.076(4) Uani 0.21(8) 1 d . . P A 2
C30A C 1.0587(18) 0.3305(15) 0.3919(11) 0.086(3) Uani 0.391(10) 1 d . . P A 2
H30A H 1.0526 0.3844 0.3598 0.104 Uiso 0.391(10) 1 calc R . P A 2
C31A C 1.176(2) 0.3576(17) 0.4674(10) 0.098(3) Uani 0.391(10) 1 d D . P A 2
H31A H 1.2540 0.4319 0.4931 0.118 Uiso 0.391(10) 1 calc R . P A 2
C32A C 1.1636(14) 0.260(2) 0.5011(16) 0.125(4) Uani 0.391(10) 1 d D . P A 2
H32A H 1.2476 0.2725 0.5454 0.150 Uiso 0.391(10) 1 calc R . P A 2
C33A C 1.0668(14) 0.1587(13) 0.4862(10) 0.1091(17) Uani 0.292(3) 1 d . . P A 2
H33A H 1.0739 0.1089 0.5219 0.131 Uiso 0.292(3) 1 calc R . P A 2
C34A C 0.9515(12) 0.1317(10) 0.4118(8) 0.0845(12) Uani 0.292(3) 1 d D . P A 2
C35A C 0.8219(13) 0.0124(11) 0.3656(8) 0.0933(14) Uani 0.292(3) 1 d D . P A 2
H35A H 0.7680 0.0022 0.4059 0.112 Uiso 0.292(3) 1 calc R . P A 2
C36A C 0.844(2) -0.0941(14) 0.3324(12) 0.103(2) Uani 0.349(10) 1 d D . P A 2
H36C H 0.7605 -0.1673 0.3164 0.124 Uiso 0.349(10) 1 calc R . P A 2
H36D H 0.9209 -0.0959 0.3792 0.124 Uiso 0.349(10) 1 calc R . P A 2
C37A C 0.877(3) -0.086(2) 0.2462(15) 0.122(3) Uani 0.261(6) 1 d D . P A 2
H37C H 0.8714 -0.1637 0.2084 0.147 Uiso 0.261(6) 1 calc R . P A 2
H37D H 0.9674 -0.0213 0.2612 0.147 Uiso 0.261(6) 1 calc R . P A 2
C38A C 0.7539(18) -0.0557(15) 0.2011(11) 0.0917(16) Uani 0.261(6) 1 d . . P A 2
H38C H 0.7714 -0.0183 0.1555 0.110 Uiso 0.261(6) 1 calc R . P A 2
H38D H 0.6682 -0.1297 0.1700 0.110 Uiso 0.261(6) 1 calc R . P A 2
C39A C 0.7418(13) 0.0312(10) 0.2780(8) 0.0760(12) Uani 0.292(3) 1 d . . P A 2
H39A H 0.6433 0.0066 0.2706 0.091 Uiso 0.292(3) 1 calc R . P A 2


_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 1.236(4) . ?
O2 C22 1.243(3) . ?
O3 C24 1.342(3) . ?
O4 C28 1.339(3) . ?
N1 C4 1.413(4) . ?
N1 C8 1.484(4) . ?
N1 C18 1.376(3) . ?
C1 C2 1.322(7) . ?
C1 C6 1.413(6) . ?
C1 C7 1.520(5) . ?
C2 C3 1.381(6) . ?
C3 C4 1.345(5) . ?
C4 C5 1.389(5) . ?
C5 C6 1.381(5) . ?
C8 C9 1.516(5) . ?
C8 C12 1.549(4) . ?
C9 C10 1.518(5) . ?
C10 C11 1.510(5) . ?
C11 C12 1.526(4) . ?
C12 C13 1.501(4) . ?
C13 C14 1.357(3) . ?
C13 C18 1.416(4) . ?
C14 C15 1.418(4) . ?
C15 C16 1.386(4) . ?
C15 C19 1.431(4) . ?
C16 C17 1.362(4) . ?
C17 C18 1.386(4) . ?
C19 C20 1.438(4) . ?
C19 C22 1.438(4) . ?
C20 C21 1.476(4) . ?
C21 C22 1.469(4) . ?
C21 C23 1.381(3) . ?
C23 C24 1.434(4) . ?
C23 C28 1.446(3) . ?
C24 C25 1.360(4) . ?
C25 C26 1.413(4) . ?
C26 C27 1.405(4) . ?
C26 N2 1.389(6) . ?
C26 N2A 1.35(2) . ?
C27 C28 1.350(3) . ?
N2 C29 1.411(12) . ?
N2 C39 1.485(7) . ?
C29 C30 1.347(17) . ?
C29 C34 1.452(15) . ?
C30 C31 1.380(14) . ?
C31 C32 1.420(12) . ?
C32 C33 1.423(13) . ?
C33 C34 1.392(7) . ?
C34 C35 1.466(7) . ?
C35 C36 1.498(10) . ?
C35 C39 1.550(6) . ?
C36 C37 1.541(13) . ?
C37 C38 1.530(7) . ?
C38 C39 1.501(8) . ?
N2A C29A 1.44(6) . ?
N2A C39A 1.46(3) . ?
C29A C30A 1.56(6) . ?
C29A C34A 1.30(6) . ?
C30A C31A 1.38(2) . ?
C31A C32A 1.406(17) . ?
C32A C33A 1.26(2) . ?
C33A C34A 1.354(15) . ?
C34A C35A 1.514(13) . ?
C35A C36A 1.41(2) . ?
C35A C39A 1.538(14) . ?
C36A C37A 1.522(18) . ?
C37A C38A 1.54(3) . ?
C38A C39A 1.49(2) . ?

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 C8 120.4(2) . . ?
C18 N1 C4 128.1(2) . . ?
C18 N1 C8 111.6(2) . . ?
C2 C1 C6 116.1(4) . . ?
C2 C1 C7 123.0(5) . . ?
C6 C1 C7 120.8(5) . . ?
C1 C2 C3 123.6(4) . . ?
C4 C3 C2 121.3(4) . . ?
C3 C4 N1 121.4(3) . . ?
C3 C4 C5 117.1(3) . . ?
C5 C4 N1 121.5(3) . . ?
C6 C5 C4 121.0(4) . . ?
C5 C6 C1 120.5(5) . . ?
N1 C8 C9 112.4(3) . . ?
N1 C8 C12 104.8(2) . . ?
C9 C8 C12 105.3(3) . . ?
C8 C9 C10 104.9(2) . . ?
C11 C10 C9 102.5(3) . . ?
C10 C11 C12 103.2(3) . . ?
C11 C12 C8 105.6(2) . . ?
C13 C12 C8 103.6(2) . . ?
C13 C12 C11 115.2(2) . . ?
C14 C13 C12 128.9(3) . . ?
C14 C13 C18 120.8(3) . . ?
C18 C13 C12 110.3(2) . . ?
C13 C14 C15 119.3(3) . . ?
C14 C15 C19 119.0(3) . . ?
C16 C15 C14 118.9(2) . . ?
C16 C15 C19 122.1(3) . . ?
C17 C16 C15 122.0(3) . . ?
C16 C17 C18 119.4(3) . . ?
N1 C18 C13 109.6(2) . . ?
N1 C18 C17 130.8(3) . . ?
C17 C18 C13 119.5(2) . . ?
C15 C19 C20 133.5(3) . . ?
C15 C19 C22 136.2(3) . . ?
C22 C19 C20 90.2(2) . . ?
O1 C20 C19 136.1(3) . . ?
O1 C20 C21 132.9(3) . . ?
C19 C20 C21 91.0(2) . . ?
C22 C21 C20 87.5(2) . . ?
C23 C21 C20 135.3(3) . . ?
C23 C21 C22 137.2(2) . . ?
O2 C22 C19 136.5(3) . . ?
O2 C22 C21 132.2(2) . . ?
C19 C22 C21 91.3(2) . . ?
C21 C23 C24 122.6(2) . . ?
C21 C23 C28 121.6(2) . . ?
C24 C23 C28 115.8(2) . . ?
O3 C24 C23 121.8(2) . . ?
O3 C24 C25 116.5(3) . . ?
C25 C24 C23 121.7(2) . . ?
C24 C25 C26 121.3(3) . . ?
C27 C26 C25 117.8(2) . . ?
N2 C26 C25 122.7(3) . . ?
N2 C26 C27 119.4(3) . . ?
N2A C26 C25 119.5(11) . . ?
N2A C26 C27 118.2(11) . . ?
C28 C27 C26 122.1(2) . . ?
O4 C28 C23 121.1(2) . . ?
O4 C28 C27 117.6(2) . . ?
C27 C28 C23 121.3(2) . . ?
C26 N2 C29 127.9(7) . . ?
C26 N2 C39 120.4(4) . . ?
C29 N2 C39 111.7(6) . . ?
N2 C29 C34 105.4(10) . . ?
C30 C29 N2 134.3(14) . . ?
C30 C29 C34 119.8(9) . . ?
C29 C30 C31 121.7(10) . . ?
C30 C31 C32 122.6(9) . . ?
C31 C32 C33 113.7(7) . . ?
C34 C33 C32 124.6(5) . . ?
C29 C34 C35 113.2(6) . . ?
C33 C34 C29 116.6(6) . . ?
C33 C34 C35 130.1(4) . . ?
C34 C35 C36 115.6(5) . . ?
C34 C35 C39 102.9(4) . . ?
C36 C35 C39 105.4(5) . . ?
C35 C36 C37 101.9(5) . . ?
C38 C37 C36 104.0(6) . . ?
C39 C38 C37 103.6(5) . . ?
N2 C39 C35 104.9(4) . . ?
N2 C39 C38 113.8(7) . . ?
C38 C39 C35 107.6(4) . . ?
C26 N2A C29A 129(3) . . ?
C26 N2A C39A 127.8(18) . . ?
C29A N2A C39A 102(3) . . ?
N2A C29A C30A 124(4) . . ?
C34A C29A N2A 117(5) . . ?
C34A C29A C30A 119(4) . . ?
C31A C30A C29A 115(2) . . ?
C30A C31A C32A 112.0(16) . . ?
C33A C32A C31A 135.8(16) . . ?
C32A C33A C34A 111.7(13) . . ?
C29A C34A C33A 125(3) . . ?
C29A C34A C35A 108(3) . . ?
C33A C34A C35A 127.0(10) . . ?
C34A C35A C39A 101.9(9) . . ?
C36A C35A C34A 115.9(13) . . ?
C36A C35A C39A 105.6(11) . . ?
C35A C36A C37A 105.3(13) . . ?
C36A C37A C38A 95.6(16) . . ?
C39A C38A C37A 106.8(13) . . ?
N2A C39A C35A 108.5(13) . . ?
N2A C39A C38A 116.3(19) . . ?
C38A C39A C35A 102.9(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method dichloromethane/cyclohexane
