# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

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

data_CKJ-SH-3-258
_database_code_depnum_ccdc_archive 'CCDC 1829735'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(1-cyclohexyl-1H-tetrazol-5-yl)-2-(9H-fluoren-9-yl)-1,2,3,4-tetrahydroisoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 N5'
_chemical_formula_weight         447.57

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7181(5)
_cell_length_b                   11.6016(7)
_cell_length_c                   12.0845(7)
_cell_angle_alpha                69.980(4)
_cell_angle_beta                 78.308(4)
_cell_angle_gamma                71.223(4)
_cell_volume                     1205.45(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3167
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17100
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4265
_reflns_number_gt                2854
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4265
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8624(2) 0.5040(2) 0.1977(2) 0.0572(6) Uani 1 1 d . . .
H1 H 0.9427 0.5436 0.1796 0.069 Uiso 1 1 calc R . .
C8 C 0.8538(3) 0.3822(3) 0.0756(2) 0.0637(7) Uani 1 1 d . . .
C9 C 0.8228(2) 0.5056(3) 0.0817(2) 0.0604(6) Uani 1 1 d . . .
C2 C 0.9227(3) 0.3616(2) 0.2565(2) 0.0617(6) Uani 1 1 d . . .
C7 C 0.9176(3) 0.2927(3) 0.1834(2) 0.0643(7) Uani 1 1 d . . .
C3 C 0.9860(3) 0.2982(3) 0.3614(3) 0.0760(8) Uani 1 1 d . . .
H3 H 0.9915 0.3433 0.4100 0.091 Uiso 1 1 calc R . .
C13 C 0.8252(3) 0.3627(3) -0.0236(3) 0.0839(9) Uani 1 1 d . . .
H13 H 0.8483 0.2806 -0.0295 0.101 Uiso 1 1 calc R . .
C10 C 0.7619(3) 0.6091(3) -0.0085(2) 0.0773(8) Uani 1 1 d . . .
H10 H 0.7408 0.6915 -0.0039 0.093 Uiso 1 1 calc R . .
C6 C 0.9737(3) 0.1613(3) 0.2162(3) 0.0816(8) Uani 1 1 d . . .
H6 H 0.9703 0.1153 0.1675 0.098 Uiso 1 1 calc R . .
C12 C 0.7623(3) 0.4668(4) -0.1131(3) 0.0967(11) Uani 1 1 d . . .
H12 H 0.7397 0.4542 -0.1786 0.116 Uiso 1 1 calc R . .
C11 C 0.7325(3) 0.5880(4) -0.1073(3) 0.0937(10) Uani 1 1 d . . .
H11 H 0.6923 0.6570 -0.1696 0.112 Uiso 1 1 calc R . .
C4 C 1.0407(3) 0.1671(3) 0.3930(3) 0.0925(10) Uani 1 1 d . . .
H4 H 1.0825 0.1240 0.4639 0.111 Uiso 1 1 calc R . .
C5 C 1.0345(4) 0.0995(3) 0.3217(3) 0.0963(10) Uani 1 1 d . . .
H5 H 1.0717 0.0112 0.3447 0.116 Uiso 1 1 calc R . .
C18 C 0.7728(2) 0.5967(2) 0.3634(2) 0.0593(6) Uani 1 1 d . . .
H18 H 0.8112 0.5129 0.4193 0.071 Uiso 1 1 calc R . .
C17 C 0.6370(3) 0.6710(2) 0.4241(2) 0.0617(6) Uani 1 1 d . . .
C16 C 0.4986(3) 0.6936(2) 0.3943(2) 0.0618(6) Uani 1 1 d . . .
C14 C 0.6092(3) 0.5300(3) 0.2895(2) 0.0657(7) Uani 1 1 d . . .
H14A H 0.6204 0.4583 0.3613 0.079 Uiso 1 1 calc R . .
H14B H 0.5984 0.5009 0.2262 0.079 Uiso 1 1 calc R . .
C15 C 0.4766(3) 0.6355(3) 0.3079(2) 0.0711(7) Uani 1 1 d . . .
H15A H 0.4572 0.7008 0.2327 0.085 Uiso 1 1 calc R . .
H15B H 0.3924 0.6018 0.3374 0.085 Uiso 1 1 calc R . .
C22 C 0.3795(3) 0.7689(3) 0.4474(3) 0.0781(8) Uani 1 1 d . . .
H22 H 0.2865 0.7867 0.4260 0.094 Uiso 1 1 calc R . .
C19 C 0.6538(3) 0.7174(3) 0.5107(3) 0.0881(9) Uani 1 1 d . . .
H19 H 0.7461 0.6988 0.5338 0.106 Uiso 1 1 calc R . .
C21 C 0.3978(4) 0.8169(3) 0.5305(3) 0.0938(10) Uani 1 1 d . . .
H21 H 0.3175 0.8673 0.5650 0.113 Uiso 1 1 calc R . .
C20 C 0.5341(4) 0.7910(4) 0.5629(3) 0.1044(11) Uani 1 1 d . . .
H20 H 0.5463 0.8229 0.6201 0.125 Uiso 1 1 calc R . .
C23 C 0.8791(2) 0.7855(2) 0.2523(2) 0.0464(5) Uani 1 1 d . . .
C24 C 0.7621(3) 0.8732(2) 0.1857(2) 0.0643(7) Uani 1 1 d . . .
H24 H 0.6932 0.8265 0.1878 0.077 Uiso 1 1 calc R . .
C25 C 0.8203(3) 0.9243(3) 0.0574(3) 0.0889(9) Uani 1 1 d . . .
H25A H 0.8927 0.9672 0.0533 0.107 Uiso 1 1 calc R . .
H25B H 0.8673 0.8539 0.0245 0.107 Uiso 1 1 calc R . .
C29 C 0.6804(4) 0.9811(3) 0.2380(3) 0.0947(10) Uani 1 1 d . . .
H29A H 0.7467 1.0281 0.2383 0.114 Uiso 1 1 calc R . .
H29B H 0.6420 0.9465 0.3192 0.114 Uiso 1 1 calc R . .
C26 C 0.6978(4) 1.0164(4) -0.0145(3) 0.1062(12) Uani 1 1 d . . .
H26A H 0.7386 1.0531 -0.0943 0.127 Uiso 1 1 calc R . .
H26B H 0.6332 0.9701 -0.0195 0.127 Uiso 1 1 calc R . .
C27 C 0.6105(5) 1.1223(4) 0.0374(4) 0.1295(15) Uani 1 1 d . . .
H27A H 0.5279 1.1737 -0.0075 0.155 Uiso 1 1 calc R . .
H27B H 0.6710 1.1768 0.0313 0.155 Uiso 1 1 calc R . .
C28 C 0.5558(5) 1.0702(4) 0.1659(4) 0.1195(13) Uani 1 1 d . . .
H28A H 0.4857 1.0246 0.1711 0.143 Uiso 1 1 calc R . .
H28B H 0.5064 1.1405 0.1985 0.143 Uiso 1 1 calc R . .
N5 N 0.73758(19) 0.57901(18) 0.25889(16) 0.0551(5) Uani 1 1 d . . .
N1 N 0.8897(2) 0.6696(3) 0.3259(2) 0.0972(9) Uani 1 1 d . . .
N2 N 1.0179(2) 0.6194(3) 0.3712(2) 0.0834(7) Uani 1 1 d . . .
N4 N 1.0036(3) 0.8125(3) 0.2504(2) 0.0860(8) Uani 1 1 d . . .
N3 N 1.0856(3) 0.7140(3) 0.3210(3) 0.0953(9) 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
C1 N5 1.474(3) . ?
C1 C9 1.520(3) . ?
C1 C2 1.523(3) . ?
C8 C13 1.388(4) . ?
C8 C9 1.389(4) . ?
C8 C7 1.465(4) . ?
C9 C10 1.374(4) . ?
C2 C3 1.382(4) . ?
C2 C7 1.396(3) . ?
C7 C6 1.384(4) . ?
C3 C4 1.381(4) . ?
C13 C12 1.379(5) . ?
C10 C11 1.397(4) . ?
C6 C5 1.377(4) . ?
C12 C11 1.365(5) . ?
C4 C5 1.370(5) . ?
C18 N5 1.467(3) . ?
C18 C17 1.526(3) . ?
C18 N1 1.536(4) . ?
C17 C16 1.383(3) . ?
C17 C19 1.387(4) . ?
C16 C22 1.395(3) . ?
C16 C15 1.503(4) . ?
C14 N5 1.464(3) . ?
C14 C15 1.504(3) . ?
C22 C21 1.367(4) . ?
C19 C20 1.383(4) . ?
C21 C20 1.368(4) . ?
C23 N1 1.319(4) . ?
C23 N4 1.338(3) . ?
C23 C24 1.428(3) . ?
C24 C29 1.515(4) . ?
C24 C25 1.519(4) . ?
C25 C26 1.510(4) . ?
C29 C28 1.516(4) . ?
C26 C27 1.504(5) . ?
C27 C28 1.513(5) . ?
N1 N2 1.335(3) . ?
N2 N3 1.361(4) . ?
N4 N3 1.301(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 C1 C9 110.79(18) . . ?
N5 C1 C2 119.6(2) . . ?
C9 C1 C2 101.7(2) . . ?
C13 C8 C9 119.8(3) . . ?
C13 C8 C7 131.5(3) . . ?
C9 C8 C7 108.6(2) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 C1 128.3(2) . . ?
C8 C9 C1 110.7(2) . . ?
C3 C2 C7 119.7(2) . . ?
C3 C2 C1 130.0(2) . . ?
C7 C2 C1 110.2(2) . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 C8 130.8(3) . . ?
C2 C7 C8 108.8(2) . . ?
C4 C3 C2 119.2(3) . . ?
C12 C13 C8 119.0(3) . . ?
C9 C10 C11 118.6(3) . . ?
C5 C6 C7 119.2(3) . . ?
C11 C12 C13 121.1(3) . . ?
C12 C11 C10 120.5(3) . . ?
C5 C4 C3 121.0(3) . . ?
C4 C5 C6 120.5(3) . . ?
N5 C18 C17 110.85(18) . . ?
N5 C18 N1 109.47(19) . . ?
C17 C18 N1 109.4(2) . . ?
C16 C17 C19 119.5(2) . . ?
C16 C17 C18 121.7(2) . . ?
C19 C17 C18 118.8(2) . . ?
C17 C16 C22 119.1(2) . . ?
C17 C16 C15 120.4(2) . . ?
C22 C16 C15 120.5(2) . . ?
N5 C14 C15 108.5(2) . . ?
C16 C15 C14 111.1(2) . . ?
C21 C22 C16 120.9(3) . . ?
C20 C19 C17 120.4(3) . . ?
C22 C21 C20 120.0(3) . . ?
C21 C20 C19 120.0(3) . . ?
N1 C23 N4 106.7(2) . . ?
N1 C23 C24 130.2(2) . . ?
N4 C23 C24 123.0(2) . . ?
C23 C24 C29 112.0(2) . . ?
C23 C24 C25 109.9(2) . . ?
C29 C24 C25 111.0(3) . . ?
C26 C25 C24 110.6(2) . . ?
C24 C29 C28 110.1(3) . . ?
C27 C26 C25 112.7(3) . . ?
C26 C27 C28 111.3(3) . . ?
C27 C28 C29 111.3(3) . . ?
C14 N5 C18 110.01(19) . . ?
C14 N5 C1 113.27(18) . . ?
C18 N5 C1 114.08(17) . . ?
C23 N1 N2 111.5(3) . . ?
C23 N1 C18 127.2(2) . . ?
N2 N1 C18 121.2(3) . . ?
N1 N2 N3 103.1(3) . . ?
N3 N4 C23 107.6(3) . . ?
N4 N3 N2 111.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl aeetate and 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_mono_p_a
_database_code_depnum_ccdc_archive 'CCDC 1829737'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-(1-(9H-fluoren-9-yl)pyrrolidin-2-yl)-1-tert-butyl-1H-tetrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N5'
_chemical_formula_sum            'C22 H25 N5'
_chemical_formula_weight         359.47

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1540(14)
_cell_length_b                   14.767(2)
_cell_length_c                   16.628(3)
_cell_angle_alpha                90.056(11)
_cell_angle_beta                 100.409(11)
_cell_angle_gamma                90.188(11)
_cell_volume                     1969.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24877
_cell_measurement_theta_min      1.25
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26548
_diffrn_reflns_av_R_equivalents  0.4404
_diffrn_reflns_av_sigmaI/netI    0.2430
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6938
_reflns_number_gt                3049
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Brucker SHELXTL'
_computing_publication_material  'Brucker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0050P)²+6.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6797
_refine_ls_number_parameters     493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1677
_refine_ls_R_factor_gt           0.1109
_refine_ls_wR_factor_ref         0.3007
_refine_ls_wR_factor_gt          0.2542
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.9740(8) 0.6506(5) 0.4573(3) 0.0568(17) Uani 1 1 d . . .
C19 C 0.7343(7) 0.8412(4) 0.2403(3) 0.0522(15) Uani 1 1 d . . .
C18 C 0.8478(7) 0.6772(4) 0.2551(3) 0.0500(15) Uani 1 1 d . . .
C13 C 1.1377(7) 0.6520(5) 0.4223(3) 0.0590(17) Uani 1 1 d . . .
H13 H 1.2143 0.6084 0.4536 0.071 Uiso 1 1 calc R . .
C6 C 1.1015(8) 0.7907(5) 0.4921(3) 0.0582(16) Uani 1 1 d . . .
C17 C 1.0333(7) 0.6907(5) 0.2758(3) 0.0586(17) Uani 1 1 d . . .
H17 H 1.0579 0.7517 0.2981 0.070 Uiso 1 1 calc R . .
C7 C 0.9591(8) 0.7308(5) 0.4974(3) 0.0610(18) Uani 1 1 d . . .
C1 C 1.2023(8) 0.7424(5) 0.4445(3) 0.0636(18) Uani 1 1 d . . .
C11 C 0.8547(8) 0.5846(5) 0.4501(4) 0.0650(18) Uani 1 1 d . . .
H11 H 0.8660 0.5313 0.4218 0.078 Uiso 1 1 calc R . .
C16 C 1.1229(8) 0.6761(5) 0.2022(3) 0.0694(19) Uani 1 1 d . . .
H16A H 1.0456 0.6810 0.1508 0.083 Uiso 1 1 calc R . .
H16B H 1.2127 0.7196 0.2029 0.083 Uiso 1 1 calc R . .
C20 C 0.7979(9) 0.8739(5) 0.3291(4) 0.076(2) Uani 1 1 d . . .
H20A H 0.7470 0.8383 0.3662 0.114 Uiso 1 1 calc R . .
H20B H 0.7692 0.9365 0.3339 0.114 Uiso 1 1 calc R . .
H20C H 0.9168 0.8674 0.3421 0.114 Uiso 1 1 calc R . .
C15 C 1.1910(9) 0.5790(6) 0.2159(4) 0.082(2) Uani 1 1 d . . .
H15A H 1.1045 0.5343 0.1981 0.099 Uiso 1 1 calc R . .
H15B H 1.2832 0.5688 0.1875 0.099 Uiso 1 1 calc R . .
C2 C 1.3425(9) 0.7881(6) 0.4262(4) 0.084(2) Uani 1 1 d . . .
H2 H 1.4125 0.7591 0.3960 0.101 Uiso 1 1 calc R . .
C22 C 0.5602(8) 0.8810(5) 0.2110(4) 0.076(2) Uani 1 1 d . . .
H22A H 0.5224 0.8654 0.1546 0.114 Uiso 1 1 calc R . .
H22B H 0.5650 0.9457 0.2167 0.114 Uiso 1 1 calc R . .
H22C H 0.4841 0.8568 0.2433 0.114 Uiso 1 1 calc R . .
C8 C 0.8179(9) 0.7454(6) 0.5341(3) 0.072(2) Uani 1 1 d . . .
H8 H 0.8067 0.7989 0.5622 0.086 Uiso 1 1 calc R . .
C21 C 0.8415(8) 0.8709(5) 0.1808(4) 0.075(2) Uani 1 1 d . . .
H21A H 0.9489 0.8428 0.1944 0.113 Uiso 1 1 calc R . .
H21B H 0.8546 0.9355 0.1833 0.113 Uiso 1 1 calc R . .
H21C H 0.7897 0.8534 0.1265 0.113 Uiso 1 1 calc R . .
C10 C 0.7131(9) 0.5993(6) 0.4869(4) 0.083(2) Uani 1 1 d . . .
H10 H 0.6300 0.5554 0.4840 0.099 Uiso 1 1 calc R . .
C14 C 1.2477(7) 0.5766(5) 0.3076(4) 0.0692(19) Uani 1 1 d . . .
H14A H 1.2600 0.5149 0.3277 0.083 Uiso 1 1 calc R . .
H14B H 1.3522 0.6089 0.3241 0.083 Uiso 1 1 calc R . .
C9 C 0.7013(9) 0.6813(6) 0.5278(4) 0.077(2) Uani 1 1 d . . .
H9 H 0.6080 0.6913 0.5515 0.092 Uiso 1 1 calc R . .
C5 C 1.1364(11) 0.8736(6) 0.5193(4) 0.087(2) Uani 1 1 d . . .
H5 H 1.0694 0.9022 0.5513 0.104 Uiso 1 1 calc R . .
C3 C 1.3751(11) 0.8724(7) 0.4520(5) 0.105(3) Uani 1 1 d . . .
H3 H 1.4666 0.9025 0.4382 0.126 Uiso 1 1 calc R . .
C4 C 1.2742(13) 0.9177(8) 0.4998(5) 0.110(3) Uani 1 1 d . . .
H4 H 1.3001 0.9765 0.5180 0.133 Uiso 1 1 calc R . .
N5 N 0.7300(6) 0.7435(3) 0.2407(3) 0.0532(13) Uani 1 1 d . . .
N4 N 0.5798(6) 0.6983(4) 0.2232(3) 0.0642(14) Uani 1 1 d . . .
N1 N 1.1086(6) 0.6233(4) 0.3364(3) 0.0599(15) Uani 1 1 d . . .
N2 N 0.7750(6) 0.5976(4) 0.2467(3) 0.0634(15) Uani 1 1 d . . .
N3 N 0.6100(6) 0.6142(4) 0.2264(3) 0.0677(15) Uani 1 1 d . . .
C39 C 0.4629(6) 0.1886(4) 0.2231(3) 0.0535(16) Uani 1 1 d . . .
H39 H 0.4357 0.2497 0.2019 0.064 Uiso 1 1 calc R . .
C40 C 0.6550(7) 0.1786(4) 0.2451(3) 0.0511(15) Uani 1 1 d . . .
C29 C 0.3947(8) 0.2883(5) 0.0097(3) 0.0644(19) Uani 1 1 d . . .
C23 C 0.5239(7) 0.1512(5) 0.0425(3) 0.0563(16) Uani 1 1 d . . .
C28 C 0.5422(7) 0.2311(5) 0.0018(3) 0.0581(17) Uani 1 1 d . . .
C38 C 0.3847(7) 0.1735(5) 0.2986(4) 0.0649(18) Uani 1 1 d . . .
H38A H 0.2990 0.2180 0.3020 0.078 Uiso 1 1 calc R . .
H38B H 0.4681 0.1760 0.3482 0.078 Uiso 1 1 calc R . .
C41 C 0.7648(8) 0.3425(4) 0.2590(3) 0.0602(17) Uani 1 1 d . . .
C34 C 0.2982(8) 0.2450(5) 0.0556(3) 0.0657(19) Uani 1 1 d . . .
C35 C 0.3667(8) 0.1504(5) 0.0779(3) 0.0622(18) Uani 1 1 d . . .
H35 H 0.2898 0.1063 0.0470 0.075 Uiso 1 1 calc R . .
C24 C 0.6462(8) 0.0829(5) 0.0496(4) 0.0663(19) Uani 1 1 d . . .
H24 H 0.6357 0.0289 0.0770 0.080 Uiso 1 1 calc R . .
C33 C 0.1555(8) 0.2858(5) 0.0757(4) 0.077(2) Uani 1 1 d . . .
H33 H 0.0864 0.2554 0.1056 0.093 Uiso 1 1 calc R . .
C37 C 0.3105(8) 0.0787(6) 0.2842(4) 0.077(2) Uani 1 1 d . . .
H37A H 0.3932 0.0327 0.3030 0.093 Uiso 1 1 calc R . .
H37B H 0.2164 0.0707 0.3118 0.093 Uiso 1 1 calc R . .
C25 C 0.7840(9) 0.1011(6) 0.0129(4) 0.081(2) Uani 1 1 d . . .
H25 H 0.8689 0.0585 0.0174 0.098 Uiso 1 1 calc R . .
C43 C 0.6499(9) 0.3728(5) 0.3194(4) 0.074(2) Uani 1 1 d . . .
H43A H 0.5382 0.3518 0.2999 0.111 Uiso 1 1 calc R . .
H43B H 0.6505 0.4376 0.3232 0.111 Uiso 1 1 calc R . .
H43C H 0.6902 0.3475 0.3725 0.111 Uiso 1 1 calc R . .
C36 C 0.2558(8) 0.0748(5) 0.1919(4) 0.0696(18) Uani 1 1 d . . .
H36A H 0.2479 0.0129 0.1720 0.084 Uiso 1 1 calc R . .
H36B H 0.1496 0.1048 0.1746 0.084 Uiso 1 1 calc R . .
C42 C 0.6903(10) 0.3741(5) 0.1712(4) 0.080(2) Uani 1 1 d . . .
H42A H 0.6938 0.3252 0.1335 0.120 Uiso 1 1 calc R . .
H42B H 0.7542 0.4243 0.1566 0.120 Uiso 1 1 calc R . .
H42C H 0.5768 0.3926 0.1691 0.120 Uiso 1 1 calc R . .
C27 C 0.6798(9) 0.2486(6) -0.0346(4) 0.076(2) Uani 1 1 d . . .
H27 H 0.6926 0.3029 -0.0610 0.092 Uiso 1 1 calc R . .
C30 C 0.3614(10) 0.3766(6) -0.0190(4) 0.085(2) Uani 1 1 d . . .
H30 H 0.4292 0.4064 -0.0500 0.102 Uiso 1 1 calc R . .
C44 C 0.9379(8) 0.3795(5) 0.2882(4) 0.077(2) Uani 1 1 d . . .
H44A H 0.9766 0.3612 0.3437 0.115 Uiso 1 1 calc R . .
H44B H 0.9355 0.4444 0.2852 0.115 Uiso 1 1 calc R . .
H44C H 1.0117 0.3565 0.2542 0.115 Uiso 1 1 calc R . .
C26 C 0.7984(8) 0.1787(6) -0.0289(4) 0.080(2) Uani 1 1 d . . .
H26 H 0.8897 0.1860 -0.0547 0.096 Uiso 1 1 calc R . .
C31 C 0.2181(12) 0.4179(6) 0.0018(5) 0.100(3) Uani 1 1 d . . .
H31 H 0.1889 0.4760 -0.0170 0.120 Uiso 1 1 calc R . .
C32 C 0.1233(12) 0.3748(7) 0.0484(5) 0.105(3) Uani 1 1 d . . .
H32 H 0.0332 0.4052 0.0628 0.126 Uiso 1 1 calc R . .
N10 N 0.7709(5) 0.2423(3) 0.2589(3) 0.0501(12) Uani 1 1 d . . .
N9 N 0.9211(6) 0.1995(4) 0.2766(3) 0.0623(14) Uani 1 1 d . . .
N6 N 0.3933(6) 0.1246(4) 0.1642(3) 0.0589(14) Uani 1 1 d . . .
N7 N 0.7246(6) 0.0977(3) 0.2537(3) 0.0620(15) Uani 1 1 d . . .
N8 N 0.8901(7) 0.1147(4) 0.2747(3) 0.0721(17) 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
C12 C11 1.365(10) . ?
C12 C7 1.375(8) . ?
C12 C13 1.550(9) . ?
C19 N5 1.443(8) . ?
C19 C21 1.500(9) . ?
C19 C22 1.534(7) . ?
C19 C20 1.550(7) . ?
C18 N2 1.311(8) . ?
C18 N5 1.365(6) . ?
C18 C17 1.502(8) . ?
C13 C1 1.456(10) . ?
C13 N1 1.466(7) . ?
C6 C5 1.317(11) . ?
C6 C1 1.432(8) . ?
C6 C7 1.472(10) . ?
C17 N1 1.472(7) . ?
C17 C16 1.549(8) . ?
C7 C8 1.415(9) . ?
C1 C2 1.406(11) . ?
C11 C10 1.418(9) . ?
C16 C15 1.542(9) . ?
C15 C14 1.511(8) . ?
C2 C3 1.327(12) . ?
C8 C9 1.330(11) . ?
C10 C9 1.400(11) . ?
C14 N1 1.480(6) . ?
C5 C4 1.385(14) . ?
C3 C4 1.413(12) . ?
N5 N4 1.378(7) . ?
N4 N3 1.266(7) . ?
N2 N3 1.349(6) . ?
C39 N6 1.404(7) . ?
C39 C38 1.522(8) . ?
C39 C40 1.550(7) . ?
C40 N7 1.321(7) . ?
C40 N10 1.322(8) . ?
C29 C34 1.352(11) . ?
C29 C30 1.399(10) . ?
C29 C28 1.497(8) . ?
C23 C28 1.382(9) . ?
C23 C24 1.410(7) . ?
C23 C35 1.504(8) . ?
C28 C27 1.391(10) . ?
C38 C37 1.525(10) . ?
C41 N10 1.480(8) . ?
C41 C44 1.507(9) . ?
C41 C42 1.549(8) . ?
C41 C43 1.559(8) . ?
C34 C33 1.405(8) . ?
C34 C35 1.527(9) . ?
C35 N6 1.463(7) . ?
C24 C25 1.398(10) . ?
C33 C32 1.402(12) . ?
C37 C36 1.520(9) . ?
C25 C26 1.357(11) . ?
C36 N6 1.481(9) . ?
C27 C26 1.408(9) . ?
C30 C31 1.418(11) . ?
C31 C32 1.348(13) . ?
N10 N9 1.364(5) . ?
N9 N8 1.276(8) . ?
N7 N8 1.354(7) . ?

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
C11 C12 C7 122.1(6) . . ?
C11 C12 C13 128.5(6) . . ?
C7 C12 C13 109.3(6) . . ?
N5 C19 C21 108.1(5) . . ?
N5 C19 C22 111.5(5) . . ?
C21 C19 C22 107.1(5) . . ?
N5 C19 C20 108.1(5) . . ?
C21 C19 C20 113.8(6) . . ?
C22 C19 C20 108.3(5) . . ?
N2 C18 N5 109.6(5) . . ?
N2 C18 C17 123.9(5) . . ?
N5 C18 C17 126.5(6) . . ?
C1 C13 N1 119.9(6) . . ?
C1 C13 C12 102.1(5) . . ?
N1 C13 C12 111.3(5) . . ?
C5 C6 C1 123.0(8) . . ?
C5 C6 C7 131.2(7) . . ?
C1 C6 C7 105.7(6) . . ?
N1 C17 C18 110.3(6) . . ?
N1 C17 C16 104.4(4) . . ?
C18 C17 C16 113.6(4) . . ?
C12 C7 C8 119.5(7) . . ?
C12 C7 C6 110.3(6) . . ?
C8 C7 C6 130.2(7) . . ?
C2 C1 C6 116.8(7) . . ?
C2 C1 C13 130.8(6) . . ?
C6 C1 C13 112.4(7) . . ?
C12 C11 C10 118.4(7) . . ?
C15 C16 C17 102.8(5) . . ?
C14 C15 C16 102.1(5) . . ?
C3 C2 C1 120.1(8) . . ?
C9 C8 C7 118.8(7) . . ?
C9 C10 C11 118.4(8) . . ?
N1 C14 C15 101.6(4) . . ?
C8 C9 C10 122.8(7) . . ?
C6 C5 C4 119.2(8) . . ?
C2 C3 C4 121.5(10) . . ?
C5 C4 C3 119.4(10) . . ?
C18 N5 N4 105.1(5) . . ?
C18 N5 C19 134.8(5) . . ?
N4 N5 C19 120.1(4) . . ?
N3 N4 N5 107.8(4) . . ?
C13 N1 C17 116.5(4) . . ?
C13 N1 C14 116.8(4) . . ?
C17 N1 C14 110.2(5) . . ?
C18 N2 N3 105.8(5) . . ?
N4 N3 N2 111.7(5) . . ?
N6 C39 C38 107.5(6) . . ?
N6 C39 C40 111.2(4) . . ?
C38 C39 C40 110.3(4) . . ?
N7 C40 N10 110.1(5) . . ?
N7 C40 C39 120.8(6) . . ?
N10 C40 C39 129.1(5) . . ?
C34 C29 C30 122.4(6) . . ?
C34 C29 C28 109.9(6) . . ?
C30 C29 C28 127.5(8) . . ?
C28 C23 C24 121.1(6) . . ?
C28 C23 C35 111.8(5) . . ?
C24 C23 C35 127.1(6) . . ?
C23 C28 C27 122.4(6) . . ?
C23 C28 C29 106.4(6) . . ?
C27 C28 C29 131.2(7) . . ?
C39 C38 C37 102.6(5) . . ?
N10 C41 C44 109.3(4) . . ?
N10 C41 C42 108.1(5) . . ?
C44 C41 C42 112.3(6) . . ?
N10 C41 C43 108.2(6) . . ?
C44 C41 C43 109.0(5) . . ?
C42 C41 C43 109.9(5) . . ?
C29 C34 C33 121.5(7) . . ?
C29 C34 C35 110.2(5) . . ?
C33 C34 C35 128.3(7) . . ?
N6 C35 C23 113.5(4) . . ?
N6 C35 C34 117.4(5) . . ?
C23 C35 C34 101.5(6) . . ?
C25 C24 C23 116.1(7) . . ?
C32 C33 C34 116.2(8) . . ?
C36 C37 C38 103.1(6) . . ?
C26 C25 C24 122.3(6) . . ?
N6 C36 C37 101.3(5) . . ?
C28 C27 C26 115.8(8) . . ?
C29 C30 C31 116.0(9) . . ?
C25 C26 C27 122.2(7) . . ?
C32 C31 C30 121.3(8) . . ?
C31 C32 C33 122.4(7) . . ?
C40 N10 N9 107.0(5) . . ?
C40 N10 C41 133.3(4) . . ?
N9 N10 C41 119.7(5) . . ?
N8 N9 N10 106.6(5) . . ?
C39 N6 C35 118.6(6) . . ?
C39 N6 C36 110.3(5) . . ?
C35 N6 C36 116.6(5) . . ?
C40 N7 N8 104.6(5) . . ?
N9 N8 N7 111.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.094
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and 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_CKJ-SH-04-291D
_database_code_depnum_ccdc_archive 'CCDC 1829745'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
((2S,5R)-5-(1-(4-chlorobenzyl)-1H-tetrazol-5-yl)-1-(9H-fluoren-9-yl)pyrrolidin-2-yl)methanol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 Cl N5 O'
_chemical_formula_weight         457.95

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_chemical_absolute_configuration syn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5211(10)
_cell_length_b                   11.9295(7)
_cell_length_c                   20.9205(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.110(8)
_cell_angle_gamma                90.00
_cell_volume                     2339.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    892
_cell_measurement_theta_min      3.4080
_cell_measurement_theta_max      17.6780

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9851
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.1605
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6254
_reflns_number_gt                2769
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0050P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(13)
_refine_ls_number_reflns         6254
_refine_ls_number_parameters     597
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1806
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl31 Cl 1.1326(4) 0.5501(3) 0.22306(13) 0.0989(11) Uani 1 1 d . . .
Cl Cl 0.4433(4) 0.7583(3) 1.22152(15) 0.1134(12) Uani 1 1 d . . .
N23 N 0.6496(8) 0.4400(6) 0.4128(3) 0.0490(19) Uani 1 1 d . . .
C56 C 0.9078(8) 0.6558(6) 1.0202(4) 0.030(2) Uani 1 1 d . . .
N20 N 0.6044(8) 0.2734(6) 0.4453(4) 0.057(2) Uani 1 1 d . . .
N21 N 0.5421(9) 0.2871(7) 0.3823(4) 0.072(3) Uani 1 1 d . . .
O33 O 0.5820(7) 0.1123(6) 0.5485(3) 0.071(2) Uani 1 1 d . . .
H33 H 0.6115 0.1416 0.5180 0.107 Uiso 1 1 calc R . .
N22 N 0.5698(9) 0.3866(7) 0.3625(4) 0.063(2) Uani 1 1 d . . .
N14 N 0.8025(8) 0.2939(6) 0.5642(3) 0.051(2) Uani 1 1 d . . .
N47 N 0.6780(8) 0.6256(6) 0.8572(3) 0.0475(19) Uani 1 1 d . . .
N55 N 0.9848(8) 0.5676(7) 1.0467(3) 0.065(2) Uani 1 1 d . . .
N54 N 0.9725(9) 0.4880(6) 1.0045(5) 0.071(3) Uani 1 1 d . . .
C2 C 1.1497(9) 0.4126(7) 0.5878(4) 0.043(2) Uani 1 1 d . . .
C19 C 0.6699(9) 0.3690(8) 0.4628(4) 0.046(2) Uani 1 1 d . . .
C9 C 1.0336(9) 0.2715(8) 0.5263(4) 0.050(2) Uani 1 1 d . . .
N53 N 0.8879(8) 0.5180(6) 0.9477(4) 0.062(2) Uani 1 1 d . . .
C1 C 1.1456(9) 0.3454(7) 0.5297(4) 0.043(2) Uani 1 1 d . . .
C8 C 0.9553(10) 0.2811(7) 0.5835(4) 0.049(2) Uani 1 1 d . . .
H8 H 0.9739 0.2133 0.6100 0.059 Uiso 1 1 calc R . .
C25 C 0.8128(10) 0.5481(8) 0.3587(4) 0.046(2) Uani 1 1 d . . .
C29 C 1.0167(10) 0.4665(8) 0.3216(4) 0.061(3) Uani 1 1 d . . .
H29 H 1.0880 0.4124 0.3252 0.073 Uiso 1 1 calc R . .
C18 C 0.7478(9) 0.3968(7) 0.5300(4) 0.048(2) Uani 1 1 d . . .
H18 H 0.8264 0.4488 0.5276 0.057 Uiso 1 1 calc R . .
C12 C 1.2054(10) 0.2671(9) 0.4330(5) 0.064(3) Uani 1 1 d . . .
H12 H 1.2645 0.2638 0.4021 0.076 Uiso 1 1 calc R . .
C42 C 0.4287(11) 0.7150(7) 0.8434(4) 0.053(3) Uani 1 1 d . . .
O66 O 0.8575(10) 0.4704(6) 0.8019(4) 0.100(3) Uani 1 1 d . . .
H66 H 0.8304 0.4577 0.8363 0.150 Uiso 1 1 calc R . .
C24 C 0.7062(9) 0.5514(7) 0.4044(4) 0.050(2) Uani 1 1 d . . .
H24A H 0.7520 0.5803 0.4462 0.060 Uiso 1 1 calc R . .
H24B H 0.6285 0.6015 0.3871 0.060 Uiso 1 1 calc R . .
C58 C 0.7832(10) 0.7527(7) 1.0971(4) 0.048(2) Uani 1 1 d . . .
N52 N 0.8491(10) 0.6245(7) 0.9606(5) 0.086(3) Uani 1 1 d . . .
C30 C 0.9187(11) 0.4658(8) 0.3636(4) 0.058(3) Uani 1 1 d . . .
H30 H 0.9236 0.4103 0.3951 0.070 Uiso 1 1 calc R . .
C34 C 0.3385(10) 0.7121(8) 0.8900(4) 0.053(2) Uani 1 1 d . . .
C16 C 0.5877(10) 0.3443(7) 0.6007(4) 0.058(3) Uani 1 1 d . . .
H16A H 0.5101 0.3121 0.5699 0.069 Uiso 1 1 calc R . .
H16B H 0.5536 0.3622 0.6405 0.069 Uiso 1 1 calc R . .
C63 C 0.6769(11) 0.6706(7) 1.0906(4) 0.059(3) Uani 1 1 d . . .
H63 H 0.6762 0.6144 1.0598 0.071 Uiso 1 1 calc R . .
C15 C 0.7145(9) 0.2644(8) 0.6136(4) 0.057(3) Uani 1 1 d . . .
H15 H 0.7691 0.2779 0.6572 0.068 Uiso 1 1 calc R . .
C7 C 1.0400(10) 0.3788(7) 0.6198(4) 0.047(2) Uani 1 1 d . . .
C28 C 1.0068(11) 0.5483(9) 0.2744(4) 0.059(3) Uani 1 1 d . . .
C51 C 0.7494(9) 0.6963(6) 0.9102(4) 0.045(2) Uani 1 1 d . . .
H51 H 0.6780 0.7337 0.9312 0.053 Uiso 1 1 calc R . .
C17 C 0.6467(10) 0.4465(7) 0.5729(4) 0.058(3) Uani 1 1 d . . .
H17A H 0.6984 0.4934 0.6070 0.070 Uiso 1 1 calc R . .
H17B H 0.5714 0.4902 0.5472 0.070 Uiso 1 1 calc R . .
C11 C 1.0915(12) 0.1940(8) 0.4285(5) 0.068(3) Uani 1 1 d . . .
H11 H 1.0742 0.1432 0.3943 0.081 Uiso 1 1 calc R . .
C10 C 1.0022(11) 0.1954(7) 0.4748(5) 0.064(3) Uani 1 1 d . . .
H10 H 0.9242 0.1475 0.4715 0.077 Uiso 1 1 calc R . .
C50 C 0.8312(10) 0.7841(7) 0.8774(4) 0.064(3) Uani 1 1 d . . .
H50A H 0.9170 0.8083 0.9061 0.077 Uiso 1 1 calc R . .
H50B H 0.7721 0.8489 0.8636 0.077 Uiso 1 1 calc R . .
C26 C 0.8050(10) 0.6280(8) 0.3106(4) 0.057(3) Uani 1 1 d . . .
H26 H 0.7331 0.6816 0.3063 0.069 Uiso 1 1 calc R . .
C41 C 0.5251(10) 0.6111(7) 0.8509(4) 0.052(2) Uani 1 1 d . . .
H41 H 0.4935 0.5620 0.8136 0.062 Uiso 1 1 calc R . .
C40 C 0.4832(10) 0.5565(7) 0.9103(4) 0.051(2) Uani 1 1 d . . .
C5 C 1.1186(11) 0.5167(8) 0.7027(4) 0.063(3) Uani 1 1 d . . .
H5 H 1.1085 0.5516 0.7414 0.076 Uiso 1 1 calc R . .
C27 C 0.9038(11) 0.6297(8) 0.2682(4) 0.060(3) Uani 1 1 d . . .
H27 H 0.8995 0.6849 0.2366 0.072 Uiso 1 1 calc R . .
C62 C 0.5721(11) 0.6711(8) 1.1292(4) 0.065(3) Uani 1 1 d . . .
H62 H 0.5019 0.6161 1.1250 0.078 Uiso 1 1 calc R . .
C61 C 0.5759(12) 0.7561(10) 1.1740(4) 0.068(3) Uani 1 1 d . . .
C6 C 1.0266(10) 0.4317(7) 0.6782(4) 0.054(3) Uani 1 1 d . . .
H6 H 0.9551 0.4094 0.7005 0.064 Uiso 1 1 calc R . .
C60 C 0.6794(12) 0.8362(8) 1.1823(4) 0.067(3) Uani 1 1 d . . .
H60 H 0.6811 0.8910 1.2140 0.080 Uiso 1 1 calc R . .
C3 C 1.2442(11) 0.4971(7) 0.6126(5) 0.064(3) Uani 1 1 d . . .
H3 H 1.3182 0.5178 0.5913 0.077 Uiso 1 1 calc R . .
C35 C 0.3758(11) 0.6151(8) 0.9318(5) 0.062(3) Uani 1 1 d . . .
C13 C 1.2330(10) 0.3445(8) 0.4821(4) 0.058(3) Uani 1 1 d . . .
H13 H 1.3078 0.3952 0.4838 0.070 Uiso 1 1 calc R . .
C57 C 0.8973(10) 0.7554(7) 1.0543(4) 0.057(3) Uani 1 1 d . . .
H57A H 0.8764 0.8163 1.0235 0.069 Uiso 1 1 calc R . .
H57B H 0.9889 0.7709 1.0813 0.069 Uiso 1 1 calc R . .
C4 C 1.2260(11) 0.5504(8) 0.6699(5) 0.064(3) Uani 1 1 d . . .
H4 H 1.2864 0.6088 0.6863 0.077 Uiso 1 1 calc R . .
C43 C 0.2392(10) 0.7976(9) 0.8915(5) 0.071(3) Uani 1 1 d . . .
H43 H 0.1796 0.7973 0.9222 0.086 Uiso 1 1 calc R . .
C38 C 0.4814(14) 0.4228(9) 0.9953(6) 0.085(4) Uani 1 1 d . . .
H38 H 0.5169 0.3578 1.0168 0.103 Uiso 1 1 calc R . .
C46 C 0.4202(12) 0.8030(8) 0.7996(5) 0.068(3) Uani 1 1 d . . .
H46 H 0.4816 0.8063 0.7696 0.082 Uiso 1 1 calc R . .
C39 C 0.5399(11) 0.4620(8) 0.9422(5) 0.072(3) Uani 1 1 d . . .
H39 H 0.6156 0.4245 0.9290 0.087 Uiso 1 1 calc R . .
C45 C 0.3209(14) 0.8845(9) 0.8012(6) 0.085(4) Uani 1 1 d . . .
H45 H 0.3135 0.9425 0.7710 0.102 Uiso 1 1 calc R . .
C48 C 0.7329(11) 0.6500(8) 0.7969(4) 0.065(3) Uani 1 1 d . . .
H48 H 0.6630 0.6953 0.7680 0.078 Uiso 1 1 calc R . .
C59 C 0.7806(11) 0.8353(7) 1.1435(4) 0.058(3) Uani 1 1 d . . .
H59 H 0.8494 0.8915 1.1484 0.070 Uiso 1 1 calc R . .
C44 C 0.2313(13) 0.8835(10) 0.8459(6) 0.087(4) Uani 1 1 d . . .
H44 H 0.1648 0.9407 0.8458 0.104 Uiso 1 1 calc R . .
C32 C 0.6723(11) 0.1393(8) 0.6062(5) 0.075(3) Uani 1 1 d . . .
H32A H 0.7586 0.0949 0.6093 0.089 Uiso 1 1 calc R . .
H32B H 0.6261 0.1182 0.6423 0.089 Uiso 1 1 calc R . .
C49 C 0.8673(12) 0.7186(7) 0.8183(4) 0.071(3) Uani 1 1 d . . .
H49A H 0.8850 0.7690 0.7843 0.086 Uiso 1 1 calc R . .
H49B H 0.9498 0.6706 0.8310 0.086 Uiso 1 1 calc R . .
C65 C 0.7580(12) 0.5405(9) 0.7630(5) 0.090(4) Uani 1 1 d . . .
H65A H 0.6680 0.5009 0.7517 0.107 Uiso 1 1 calc R . .
H65B H 0.7922 0.5573 0.7231 0.107 Uiso 1 1 calc R . .
C36 C 0.3168(11) 0.5784(9) 0.9838(5) 0.077(3) Uani 1 1 d . . .
H36 H 0.2428 0.6177 0.9973 0.092 Uiso 1 1 calc R . .
C37 C 0.3710(14) 0.4809(10) 1.0155(5) 0.088(4) Uani 1 1 d . . .
H37 H 0.3327 0.4545 1.0506 0.105 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
Cl31 C28 1.745(9) . ?
Cl C61 1.738(10) . ?
N23 C19 1.334(9) . ?
N23 N22 1.345(9) . ?
N23 C24 1.456(10) . ?
C56 N52 1.327(10) . ?
C56 N55 1.345(10) . ?
C56 C57 1.398(10) . ?
N20 C19 1.320(10) . ?
N20 N21 1.356(9) . ?
N21 N22 1.300(9) . ?
O33 C32 1.391(10) . ?
O33 H33 0.8200 . ?
N14 C8 1.447(10) . ?
N14 C18 1.470(10) . ?
N14 C15 1.483(9) . ?
N47 C41 1.449(10) . ?
N47 C51 1.462(9) . ?
N47 C48 1.477(10) . ?
N55 N54 1.287(9) . ?
N54 N53 1.361(9) . ?
C2 C3 1.389(11) . ?
C2 C7 1.395(11) . ?
C2 C1 1.451(10) . ?
C19 C18 1.508(10) . ?
C9 C1 1.376(11) . ?
C9 C10 1.401(11) . ?
C9 C8 1.520(11) . ?
N53 N52 1.363(9) . ?
C1 C13 1.406(11) . ?
C8 C7 1.540(11) . ?
C8 H8 0.9800 . ?
C25 C26 1.377(11) . ?
C25 C30 1.398(11) . ?
C25 C24 1.513(10) . ?
C29 C28 1.379(11) . ?
C29 C30 1.389(11) . ?
C29 H29 0.9300 . ?
C18 C17 1.544(10) . ?
C18 H18 0.9800 . ?
C12 C13 1.372(11) . ?
C12 C11 1.382(12) . ?
C12 H12 0.9300 . ?
C42 C46 1.386(11) . ?
C42 C34 1.409(12) . ?
C42 C41 1.534(11) . ?
O66 C65 1.410(11) . ?
O66 H66 0.8200 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C58 C59 1.388(10) . ?
C58 C63 1.398(11) . ?
C58 C57 1.523(11) . ?
N52 C51 1.548(11) . ?
C30 H30 0.9300 . ?
C34 C43 1.395(11) . ?
C34 C35 1.457(12) . ?
C16 C17 1.501(10) . ?
C16 C15 1.524(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C63 C62 1.390(11) . ?
C63 H63 0.9300 . ?
C15 C32 1.547(12) . ?
C15 H15 0.9800 . ?
C7 C6 1.400(10) . ?
C28 C27 1.370(12) . ?
C51 C50 1.537(10) . ?
C51 H51 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C11 C10 1.396(12) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C50 C49 1.550(10) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C26 C27 1.402(11) . ?
C26 H26 0.9300 . ?
C41 C40 1.517(10) . ?
C41 H41 0.9800 . ?
C40 C39 1.372(12) . ?
C40 C35 1.378(12) . ?
C5 C6 1.379(11) . ?
C5 C4 1.387(12) . ?
C5 H5 0.9300 . ?
C27 H27 0.9300 . ?
C62 C61 1.376(12) . ?
C62 H62 0.9300 . ?
C61 C60 1.363(13) . ?
C6 H6 0.9300 . ?
C60 C59 1.363(12) . ?
C60 H60 0.9300 . ?
C3 C4 1.395(11) . ?
C3 H3 0.9300 . ?
C35 C36 1.381(11) . ?
C13 H13 0.9300 . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C4 H4 0.9300 . ?
C43 C44 1.392(13) . ?
C43 H43 0.9300 . ?
C38 C37 1.387(14) . ?
C38 C39 1.406(13) . ?
C38 H38 0.9300 . ?
C46 C45 1.360(13) . ?
C46 H46 0.9300 . ?
C39 H39 0.9300 . ?
C45 C44 1.374(14) . ?
C45 H45 0.9300 . ?
C48 C49 1.519(12) . ?
C48 C65 1.524(12) . ?
C48 H48 0.9800 . ?
C59 H59 0.9300 . ?
C44 H44 0.9300 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C36 C37 1.392(13) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N23 N22 107.3(7) . . ?
C19 N23 C24 132.0(8) . . ?
N22 N23 C24 120.5(7) . . ?
N52 C56 N55 106.0(7) . . ?
N52 C56 C57 131.5(9) . . ?
N55 C56 C57 122.5(8) . . ?
C19 N20 N21 105.6(7) . . ?
N22 N21 N20 110.0(8) . . ?
C32 O33 H33 109.5 . . ?
N21 N22 N23 107.5(7) . . ?
C8 N14 C18 118.4(7) . . ?
C8 N14 C15 116.4(7) . . ?
C18 N14 C15 110.0(7) . . ?
C41 N47 C51 117.7(7) . . ?
C41 N47 C48 116.5(7) . . ?
C51 N47 C48 110.3(7) . . ?
N54 N55 C56 108.5(7) . . ?
N55 N54 N53 111.9(7) . . ?
C3 C2 C7 121.4(8) . . ?
C3 C2 C1 129.3(9) . . ?
C7 C2 C1 109.3(7) . . ?
N20 C19 N23 109.6(8) . . ?
N20 C19 C18 125.4(8) . . ?
N23 C19 C18 124.9(8) . . ?
C1 C9 C10 120.9(8) . . ?
C1 C9 C8 113.2(8) . . ?
C10 C9 C8 125.9(9) . . ?
N54 N53 N52 102.2(8) . . ?
C9 C1 C13 120.6(8) . . ?
C9 C1 C2 107.7(8) . . ?
C13 C1 C2 131.7(9) . . ?
N14 C8 C9 113.4(7) . . ?
N14 C8 C7 118.1(8) . . ?
C9 C8 C7 99.1(7) . . ?
N14 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C26 C25 C30 119.0(8) . . ?
C26 C25 C24 119.2(9) . . ?
C30 C25 C24 121.8(8) . . ?
C28 C29 C30 119.1(9) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
N14 C18 C19 110.2(7) . . ?
N14 C18 C17 104.0(7) . . ?
C19 C18 C17 111.8(7) . . ?
N14 C18 H18 110.2 . . ?
C19 C18 H18 110.2 . . ?
C17 C18 H18 110.2 . . ?
C13 C12 C11 121.4(9) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C46 C42 C34 120.3(9) . . ?
C46 C42 C41 130.1(9) . . ?
C34 C42 C41 109.6(8) . . ?
C65 O66 H66 109.5 . . ?
N23 C24 C25 110.9(7) . . ?
N23 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
N23 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C59 C58 C63 117.6(9) . . ?
C59 C58 C57 119.9(9) . . ?
C63 C58 C57 122.5(8) . . ?
C56 N52 N53 111.4(8) . . ?
C56 N52 C51 126.2(8) . . ?
N53 N52 C51 122.4(9) . . ?
C29 C30 C25 120.4(8) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C43 C34 C42 119.7(9) . . ?
C43 C34 C35 131.5(10) . . ?
C42 C34 C35 108.7(9) . . ?
C17 C16 C15 103.8(7) . . ?
C17 C16 H16A 111.0 . . ?
C15 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C62 C63 C58 121.5(9) . . ?
C62 C63 H63 119.2 . . ?
C58 C63 H63 119.2 . . ?
N14 C15 C16 104.8(7) . . ?
N14 C15 C32 109.1(7) . . ?
C16 C15 C32 113.7(8) . . ?
N14 C15 H15 109.7 . . ?
C16 C15 H15 109.7 . . ?
C32 C15 H15 109.7 . . ?
C2 C7 C6 118.6(8) . . ?
C2 C7 C8 110.7(7) . . ?
C6 C7 C8 130.7(8) . . ?
C27 C28 C29 121.9(9) . . ?
C27 C28 Cl31 119.4(8) . . ?
C29 C28 Cl31 118.7(9) . . ?
N47 C51 C50 105.0(6) . . ?
N47 C51 N52 110.2(7) . . ?
C50 C51 N52 112.5(7) . . ?
N47 C51 H51 109.7 . . ?
C50 C51 H51 109.7 . . ?
N52 C51 H51 109.7 . . ?
C16 C17 C18 103.1(6) . . ?
C16 C17 H17A 111.1 . . ?
C18 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C18 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C12 C11 C10 120.8(9) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C10 C9 117.9(9) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C51 C50 C49 102.3(6) . . ?
C51 C50 H50A 111.3 . . ?
C49 C50 H50A 111.3 . . ?
C51 C50 H50B 111.3 . . ?
C49 C50 H50B 111.3 . . ?
H50A C50 H50B 109.2 . . ?
C25 C26 C27 121.1(9) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
N47 C41 C40 112.4(7) . . ?
N47 C41 C42 119.1(7) . . ?
C40 C41 C42 101.1(7) . . ?
N47 C41 H41 107.9 . . ?
C40 C41 H41 107.9 . . ?
C42 C41 H41 107.9 . . ?
C39 C40 C35 120.6(9) . . ?
C39 C40 C41 127.9(9) . . ?
C35 C40 C41 111.5(8) . . ?
C6 C5 C4 120.3(9) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C28 C27 C26 118.6(9) . . ?
C28 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C61 C62 C63 117.6(10) . . ?
C61 C62 H62 121.2 . . ?
C63 C62 H62 121.2 . . ?
C60 C61 C62 122.3(10) . . ?
C60 C61 Cl 119.9(9) . . ?
C62 C61 Cl 117.7(10) . . ?
C5 C6 C7 120.5(9) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C61 C60 C59 119.4(9) . . ?
C61 C60 H60 120.3 . . ?
C59 C60 H60 120.3 . . ?
C2 C3 C4 118.8(9) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C40 C35 C36 121.7(10) . . ?
C40 C35 C34 108.9(9) . . ?
C36 C35 C34 129.4(11) . . ?
C12 C13 C1 118.4(9) . . ?
C12 C13 H13 120.8 . . ?
C1 C13 H13 120.8 . . ?
C56 C57 C58 113.8(7) . . ?
C56 C57 H57A 108.8 . . ?
C58 C57 H57A 108.8 . . ?
C56 C57 H57B 108.8 . . ?
C58 C57 H57B 108.8 . . ?
H57A C57 H57B 107.7 . . ?
C5 C4 C3 120.5(9) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C44 C43 C34 118.6(10) . . ?
C44 C43 H43 120.7 . . ?
C34 C43 H43 120.7 . . ?
C37 C38 C39 120.1(11) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C45 C46 C42 119.0(10) . . ?
C45 C46 H46 120.5 . . ?
C42 C46 H46 120.5 . . ?
C40 C39 C38 118.7(10) . . ?
C40 C39 H39 120.6 . . ?
C38 C39 H39 120.6 . . ?
C46 C45 C44 121.9(11) . . ?
C46 C45 H45 119.1 . . ?
C44 C45 H45 119.1 . . ?
N47 C48 C49 105.0(8) . . ?
N47 C48 C65 109.6(8) . . ?
C49 C48 C65 114.0(9) . . ?
N47 C48 H48 109.3 . . ?
C49 C48 H48 109.3 . . ?
C65 C48 H48 109.3 . . ?
C60 C59 C58 121.6(10) . . ?
C60 C59 H59 119.2 . . ?
C58 C59 H59 119.2 . . ?
C45 C44 C43 120.5(11) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
O33 C32 C15 114.8(8) . . ?
O33 C32 H32A 108.6 . . ?
C15 C32 H32A 108.6 . . ?
O33 C32 H32B 108.6 . . ?
C15 C32 H32B 108.6 . . ?
H32A C32 H32B 107.5 . . ?
C48 C49 C50 102.4(8) . . ?
C48 C49 H49A 111.3 . . ?
C50 C49 H49A 111.3 . . ?
C48 C49 H49B 111.3 . . ?
C50 C49 H49B 111.3 . . ?
H49A C49 H49B 109.2 . . ?
O66 C65 C48 112.6(8) . . ?
O66 C65 H65A 109.1 . . ?
C48 C65 H65A 109.1 . . ?
O66 C65 H65B 109.1 . . ?
C48 C65 H65B 109.1 . . ?
H65A C65 H65B 107.8 . . ?
C35 C36 C37 118.2(11) . . ?
C35 C36 H36 120.9 . . ?
C37 C36 H36 120.9 . . ?
C38 C37 C36 120.7(11) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and 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_SH4-271_0m
_database_code_depnum_ccdc_archive 'CCDC 1829739'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-(1-(9H-fluoren-9-yl)pyrrolidin-2-yl)-1-(2,6-dimethylphenyl)-1H-tetrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N5'
_chemical_formula_weight         407.51

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   10.7702(4)
_cell_length_b                   13.9788(4)
_cell_length_c                   15.8020(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.391(4)
_cell_angle_gamma                90.00
_cell_volume                     2244.11(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2782
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      20.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11780
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3809
_reflns_number_gt                2643
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_number_reflns         3809
_refine_ls_number_parameters     282
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1626
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.0649(3) 0.3832(3) 0.2569(2) 0.0646(9) Uani 1 1 d . . .
C4 C 0.1214(3) 0.2227(3) 0.2546(2) 0.0663(9) Uani 1 1 d . . .
C1 C 0.1857(3) 0.3663(2) 0.3394(2) 0.0588(8) Uani 1 1 d . . .
H1 H 0.2591 0.4048 0.3345 0.071 Uiso 1 1 calc R . .
C3 C 0.0281(3) 0.2964(3) 0.2092(2) 0.0692(9) Uani 1 1 d . . .
C5 C 0.2135(3) 0.2623(2) 0.3296(2) 0.0625(8) Uani 1 1 d . . .
C13 C -0.0090(4) 0.4641(3) 0.2270(3) 0.0827(11) Uani 1 1 d . . .
H13 H 0.0143 0.5219 0.2574 0.099 Uiso 1 1 calc R . .
C6 C 0.3152(4) 0.2069(3) 0.3846(3) 0.0829(11) Uani 1 1 d . . .
H6 H 0.3791 0.2334 0.4341 0.099 Uiso 1 1 calc R . .
C11 C -0.1538(5) 0.3739(5) 0.1047(3) 0.1050(16) Uani 1 1 d . . .
H11 H -0.2286 0.3715 0.0539 0.126 Uiso 1 1 calc R . .
C10 C -0.0808(4) 0.2938(4) 0.1322(3) 0.0917(13) Uani 1 1 d . . .
H10 H -0.1037 0.2375 0.0994 0.110 Uiso 1 1 calc R . .
C7 C 0.3189(6) 0.1122(4) 0.3640(4) 0.1057(15) Uani 1 1 d . . .
H7 H 0.3856 0.0741 0.4011 0.127 Uiso 1 1 calc R . .
C12 C -0.1197(4) 0.4578(4) 0.1501(3) 0.1033(17) Uani 1 1 d . . .
H12 H -0.1711 0.5119 0.1295 0.124 Uiso 1 1 calc R . .
C8 C 0.2284(6) 0.0718(3) 0.2912(4) 0.1010(14) Uani 1 1 d . . .
H8 H 0.2341 0.0071 0.2793 0.121 Uiso 1 1 calc R . .
C9 C 0.1291(5) 0.1258(3) 0.2354(3) 0.0899(12) Uani 1 1 d . . .
H9 H 0.0675 0.0984 0.1853 0.108 Uiso 1 1 calc R . .
C14 C 0.1854(3) 0.4797(2) 0.4622(2) 0.0600(8) Uani 1 1 d . . .
H14 H 0.1263 0.5224 0.4175 0.072 Uiso 1 1 calc R . .
C15 C 0.1391(4) 0.4714(3) 0.5430(3) 0.0805(10) Uani 1 1 d . . .
H15A H 0.2137 0.4641 0.5977 0.097 Uiso 1 1 calc R . .
H15B H 0.0903 0.5280 0.5484 0.097 Uiso 1 1 calc R . .
C17 C 0.0539(3) 0.3440(3) 0.4396(2) 0.0687(9) Uani 1 1 d . . .
H17A H 0.0576 0.2747 0.4421 0.082 Uiso 1 1 calc R . .
H17B H -0.0240 0.3633 0.3909 0.082 Uiso 1 1 calc R . .
C16 C 0.0529(4) 0.3850(3) 0.5272(3) 0.0931(13) Uani 1 1 d . . .
H16A H -0.0358 0.4025 0.5236 0.112 Uiso 1 1 calc R . .
H16B H 0.0870 0.3390 0.5753 0.112 Uiso 1 1 calc R . .
C18 C 0.3243(3) 0.5136(2) 0.4842(2) 0.0632(8) Uani 1 1 d . . .
C19 C 0.2832(3) 0.6849(3) 0.4421(3) 0.0795(11) Uani 1 1 d . . .
C22 C 0.2490(5) 0.7044(4) 0.3541(5) 0.118(2) Uani 1 1 d . . .
C23 C 0.2967(7) 0.6455(6) 0.2942(4) 0.154(3) Uani 1 1 d . . .
H23A H 0.3882 0.6312 0.3232 0.231 Uiso 1 1 calc R . .
H23B H 0.2856 0.6799 0.2396 0.231 Uiso 1 1 calc R . .
H23C H 0.2473 0.5870 0.2808 0.231 Uiso 1 1 calc R . .
C20 C 0.2499(5) 0.7408(4) 0.5102(6) 0.134(3) Uani 1 1 d . . .
C21 C 0.3044(9) 0.7158(5) 0.6084(5) 0.167(3) Uani 1 1 d . . .
H21A H 0.2668 0.7575 0.6417 0.251 Uiso 1 1 calc R . .
H21B H 0.3983 0.7235 0.6292 0.251 Uiso 1 1 calc R . .
H21C H 0.2829 0.6507 0.6168 0.251 Uiso 1 1 calc R . .
N1 N 0.3598(2) 0.60300(19) 0.47629(17) 0.0624(7) Uani 1 1 d . . .
N2 N 0.4921(3) 0.6077(3) 0.5076(3) 0.0883(10) Uani 1 1 d . . .
N3 N 0.5319(3) 0.5243(3) 0.5328(3) 0.1184(15) Uani 1 1 d . . .
N4 N 0.1712(2) 0.38288(18) 0.42773(17) 0.0590(7) Uani 1 1 d . . .
N5 N 0.4296(3) 0.4622(2) 0.5195(3) 0.1040(13) Uani 1 1 d . . .
C25 C 0.1351(8) 0.8355(8) 0.3885(11) 0.189(6) Uani 1 1 d . . .
H25 H 0.0735 0.8840 0.3675 0.227 Uiso 1 1 calc R . .
C24 C 0.1721(9) 0.7870(7) 0.3207(9) 0.201(5) Uani 1 1 d . . .
H24 H 0.1483 0.8074 0.2615 0.242 Uiso 1 1 calc R . .
C26 C 0.1767(8) 0.8214(6) 0.4805(11) 0.189(5) Uani 1 1 d . . .
H26 H 0.1562 0.8639 0.5193 0.227 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
C2 C13 1.374(5) . ?
C2 C3 1.414(5) . ?
C2 C1 1.524(5) . ?
C4 C5 1.384(4) . ?
C4 C9 1.397(5) . ?
C4 C3 1.452(5) . ?
C1 N4 1.475(4) . ?
C1 C5 1.501(5) . ?
C3 C10 1.382(5) . ?
C5 C6 1.387(5) . ?
C13 C12 1.394(6) . ?
C6 C7 1.367(6) . ?
C11 C10 1.354(7) . ?
C11 C12 1.360(7) . ?
C7 C8 1.360(8) . ?
C8 C9 1.364(6) . ?
C14 N4 1.448(4) . ?
C14 C18 1.496(4) . ?
C14 C15 1.522(6) . ?
C15 C16 1.492(5) . ?
C17 N4 1.443(4) . ?
C17 C16 1.502(5) . ?
C18 N5 1.301(4) . ?
C18 N1 1.325(4) . ?
C19 C22 1.342(8) . ?
C19 N1 1.410(5) . ?
C19 C20 1.468(9) . ?
C22 C24 1.417(11) . ?
C22 C23 1.469(10) . ?
C20 C26 1.366(11) . ?
C20 C21 1.506(10) . ?
N1 N2 1.347(4) . ?
N2 N3 1.261(5) . ?
N3 N5 1.363(5) . ?
C25 C26 1.386(16) . ?
C25 C24 1.431(16) . ?

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
C13 C2 C3 119.7(3) . . ?
C13 C2 C1 130.9(3) . . ?
C3 C2 C1 109.4(3) . . ?
C5 C4 C9 119.8(4) . . ?
C5 C4 C3 108.7(3) . . ?
C9 C4 C3 131.5(3) . . ?
N4 C1 C5 109.7(2) . . ?
N4 C1 C2 117.1(3) . . ?
C5 C1 C2 101.8(2) . . ?
C10 C3 C2 119.8(4) . . ?
C10 C3 C4 131.5(4) . . ?
C2 C3 C4 108.7(3) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 C1 111.4(3) . . ?
C6 C5 C1 128.3(3) . . ?
C2 C13 C12 118.5(4) . . ?
C7 C6 C5 118.1(4) . . ?
C10 C11 C12 121.1(4) . . ?
C11 C10 C3 119.6(5) . . ?
C8 C7 C6 122.3(5) . . ?
C11 C12 C13 121.2(4) . . ?
C7 C8 C9 120.3(4) . . ?
C8 C9 C4 119.1(4) . . ?
N4 C14 C18 110.8(3) . . ?
N4 C14 C15 102.7(3) . . ?
C18 C14 C15 114.2(3) . . ?
C16 C15 C14 106.3(3) . . ?
N4 C17 C16 104.5(3) . . ?
C15 C16 C17 105.6(3) . . ?
N5 C18 N1 108.9(3) . . ?
N5 C18 C14 126.0(3) . . ?
N1 C18 C14 125.0(3) . . ?
C22 C19 N1 119.1(5) . . ?
C22 C19 C20 127.0(5) . . ?
N1 C19 C20 113.9(5) . . ?
C19 C22 C24 118.5(9) . . ?
C19 C22 C23 121.3(5) . . ?
C24 C22 C23 120.2(9) . . ?
C26 C20 C19 116.2(9) . . ?
C26 C20 C21 121.9(9) . . ?
C19 C20 C21 121.7(5) . . ?
C18 N1 N2 108.4(3) . . ?
C18 N1 C19 130.7(3) . . ?
N2 N1 C19 120.9(3) . . ?
N3 N2 N1 106.1(3) . . ?
N2 N3 N5 111.6(3) . . ?
C17 N4 C14 107.0(3) . . ?
C17 N4 C1 115.9(2) . . ?
C14 N4 C1 118.2(2) . . ?
C18 N5 N3 105.0(3) . . ?
C26 C25 C24 130.1(10) . . ?
C22 C24 C25 112.4(10) . . ?
C20 C26 C25 115.2(10) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.030
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and 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_exp_CKJ-SH-04-100C
_database_code_depnum_ccdc_archive 'CCDC 1829746'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-((R)-1-(9H-fluoren-9-yl)pyrrolidin-2-yl)-1-((R)-1-phenylethyl)-1H-tetrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N5'
_chemical_formula_weight         407.51

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   13.8953(7)
_cell_length_b                   9.4127(5)
_cell_length_c                   16.8510(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.186(4)
_cell_angle_gamma                90.00
_cell_volume                     2186.67(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2806
_cell_measurement_theta_min      3.6580
_cell_measurement_theta_max      26.1670

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   faceinstalled

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8225
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3836
_reflns_number_gt                2827
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0742P)²+5.8496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3836
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.2368
_refine_ls_wR_factor_gt          0.2200
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.2708(2) 0.3395(3) 0.50635(18) 0.0423(8) Uani 1 1 d . . .
N19 N 0.1981(2) 0.5709(4) 0.6130(2) 0.0499(9) Uani 1 1 d . . .
N18 N 0.1872(3) 0.7117(4) 0.6259(3) 0.0668(11) Uani 1 1 d . . .
N16 N 0.1498(3) 0.6656(5) 0.4988(2) 0.0670(11) Uani 1 1 d . . .
C1 C 0.3487(3) 0.4118(4) 0.4695(2) 0.0393(8) Uani 1 1 d . . .
H1 H 0.3571 0.5079 0.4916 0.047 Uiso 1 1 calc R . .
C9 C 0.4427(3) 0.3310(4) 0.4889(2) 0.0417(9) Uani 1 1 d . . .
C8 C 0.4802(3) 0.2907(4) 0.4192(2) 0.0454(9) Uani 1 1 d . . .
N17 N 0.1574(3) 0.7664(5) 0.5562(3) 0.0736(12) Uani 1 1 d . . .
C2 C 0.3398(3) 0.4204(4) 0.3783(2) 0.0449(9) Uani 1 1 d . . .
C7 C 0.4161(3) 0.3473(4) 0.3505(2) 0.0449(9) Uani 1 1 d . . .
C20 C 0.2319(3) 0.4748(5) 0.6818(2) 0.0490(10) Uani 1 1 d . . .
H20 H 0.2364 0.3785 0.6606 0.059 Uiso 1 1 calc R . .
C26 C 0.1589(3) 0.4720(5) 0.7410(2) 0.0493(10) Uani 1 1 d . . .
C15 C 0.1743(3) 0.5448(5) 0.5348(3) 0.0494(10) Uani 1 1 d . . .
C14 C 0.2533(3) 0.1902(5) 0.4837(3) 0.0557(11) Uani 1 1 d . . .
H14A H 0.3083 0.1308 0.5032 0.067 Uiso 1 1 calc R . .
H14B H 0.2391 0.1794 0.4262 0.067 Uiso 1 1 calc R . .
C11 C 0.1758(3) 0.4068(5) 0.4929(2) 0.0500(10) Uani 1 1 d . . .
H11 H 0.1597 0.4238 0.4353 0.060 Uiso 1 1 calc R . .
C22 C 0.4899(3) 0.2937(5) 0.5631(3) 0.0561(11) Uani 1 1 d . . .
H22 H 0.4648 0.3200 0.6096 0.067 Uiso 1 1 calc R . .
C27 C 0.1498(4) 0.5827(5) 0.7933(3) 0.0588(12) Uani 1 1 d . . .
H27 H 0.1904 0.6612 0.7933 0.071 Uiso 1 1 calc R . .
C3 C 0.2735(3) 0.4931(5) 0.3254(3) 0.0571(11) Uani 1 1 d . . .
H3 H 0.2233 0.5438 0.3437 0.069 Uiso 1 1 calc R . .
C25 C 0.5656(3) 0.2137(5) 0.4232(3) 0.0599(12) Uani 1 1 d . . .
H25 H 0.5906 0.1868 0.3768 0.072 Uiso 1 1 calc R . .
C6 C 0.4249(4) 0.3424(5) 0.2695(3) 0.0602(12) Uani 1 1 d . . .
H6 H 0.4755 0.2929 0.2509 0.072 Uiso 1 1 calc R . .
C21 C 0.3329(3) 0.5197(6) 0.7175(3) 0.0678(13) Uani 1 1 d . . .
H21A H 0.3759 0.5149 0.6772 0.102 Uiso 1 1 calc R . .
H21B H 0.3558 0.4573 0.7608 0.102 Uiso 1 1 calc R . .
H21C H 0.3310 0.6153 0.7371 0.102 Uiso 1 1 calc R . .
C23 C 0.5754(3) 0.2163(6) 0.5669(3) 0.0687(14) Uani 1 1 d . . .
H23 H 0.6078 0.1903 0.6164 0.082 Uiso 1 1 calc R . .
C24 C 0.6130(4) 0.1773(5) 0.4977(4) 0.0710(14) Uani 1 1 d . . .
H24 H 0.6707 0.1262 0.5013 0.085 Uiso 1 1 calc R . .
C12 C 0.1059(3) 0.2912(6) 0.5184(3) 0.0688(14) Uani 1 1 d . . .
H12A H 0.0841 0.3153 0.5692 0.083 Uiso 1 1 calc R . .
H12B H 0.0497 0.2809 0.4784 0.083 Uiso 1 1 calc R . .
C13 C 0.1652(4) 0.1557(6) 0.5255(3) 0.0681(14) Uani 1 1 d . . .
H13A H 0.1287 0.0772 0.4993 0.082 Uiso 1 1 calc R . .
H13B H 0.1845 0.1313 0.5811 0.082 Uiso 1 1 calc R . .
C28 C 0.0808(4) 0.5781(6) 0.8457(3) 0.0682(14) Uani 1 1 d . . .
H28 H 0.0753 0.6536 0.8805 0.082 Uiso 1 1 calc R . .
C4 C 0.2828(4) 0.4891(6) 0.2438(3) 0.0732(15) Uani 1 1 d . . .
H4 H 0.2391 0.5384 0.2075 0.088 Uiso 1 1 calc R . .
C5 C 0.3567(4) 0.4126(6) 0.2171(3) 0.0739(15) Uani 1 1 d . . .
H5 H 0.3607 0.4080 0.1625 0.089 Uiso 1 1 calc R . .
C31 C 0.1014(4) 0.3541(6) 0.7457(3) 0.0791(17) Uani 1 1 d . . .
H31 H 0.1095 0.2756 0.7136 0.095 Uiso 1 1 calc R . .
C29 C 0.0209(4) 0.4637(7) 0.8467(3) 0.0784(16) Uani 1 1 d . . .
H29 H -0.0269 0.4628 0.8807 0.094 Uiso 1 1 calc R . .
C30 C 0.0309(5) 0.3509(8) 0.7980(3) 0.093(2) Uani 1 1 d . . .
H30 H -0.0090 0.2718 0.7995 0.112 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
N10 C11 1.457(5) . ?
N10 C14 1.469(5) . ?
N10 C1 1.478(5) . ?
N19 C15 1.341(5) . ?
N19 N18 1.355(5) . ?
N19 C20 1.498(5) . ?
N18 N17 1.302(6) . ?
N16 C15 1.314(6) . ?
N16 N17 1.349(6) . ?
C1 C9 1.511(5) . ?
C1 C2 1.529(5) . ?
C1 H1 0.9800 . ?
C9 C22 1.383(6) . ?
C9 C8 1.396(5) . ?
C8 C25 1.385(6) . ?
C8 C7 1.468(6) . ?
C2 C3 1.381(6) . ?
C2 C7 1.394(6) . ?
C7 C6 1.386(6) . ?
C20 C26 1.509(6) . ?
C20 C21 1.517(6) . ?
C20 H20 0.9800 . ?
C26 C31 1.376(7) . ?
C26 C27 1.380(6) . ?
C15 C11 1.480(6) . ?
C14 C13 1.521(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C11 C12 1.555(6) . ?
C11 H11 0.9800 . ?
C22 C23 1.389(6) . ?
C22 H22 0.9300 . ?
C27 C28 1.382(7) . ?
C27 H27 0.9300 . ?
C3 C4 1.397(7) . ?
C3 H3 0.9300 . ?
C25 C24 1.386(7) . ?
C25 H25 0.9300 . ?
C6 C5 1.381(7) . ?
C6 H6 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 C24 1.386(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C12 C13 1.515(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C28 C29 1.363(8) . ?
C28 H28 0.9300 . ?
C4 C5 1.374(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C31 C30 1.398(7) . ?
C31 H31 0.9300 . ?
C29 C30 1.360(8) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N10 C14 105.0(3) . . ?
C11 N10 C1 115.5(3) . . ?
C14 N10 C1 115.9(3) . . ?
C15 N19 N18 108.5(4) . . ?
C15 N19 C20 131.7(4) . . ?
N18 N19 C20 119.8(4) . . ?
N17 N18 N19 105.8(4) . . ?
C15 N16 N17 106.6(4) . . ?
N10 C1 C9 109.6(3) . . ?
N10 C1 C2 118.4(3) . . ?
C9 C1 C2 101.7(3) . . ?
N10 C1 H1 108.9 . . ?
C9 C1 H1 108.9 . . ?
C2 C1 H1 108.9 . . ?
C22 C9 C8 120.5(4) . . ?
C22 C9 C1 128.5(4) . . ?
C8 C9 C1 111.0(3) . . ?
C25 C8 C9 120.5(4) . . ?
C25 C8 C7 131.3(4) . . ?
C9 C8 C7 108.2(3) . . ?
N18 N17 N16 110.9(4) . . ?
C3 C2 C7 120.2(4) . . ?
C3 C2 C1 129.7(4) . . ?
C7 C2 C1 110.0(3) . . ?
C6 C7 C2 120.7(4) . . ?
C6 C7 C8 130.1(4) . . ?
C2 C7 C8 109.0(3) . . ?
N19 C20 C26 110.6(3) . . ?
N19 C20 C21 108.9(4) . . ?
C26 C20 C21 114.1(3) . . ?
N19 C20 H20 107.7 . . ?
C26 C20 H20 107.7 . . ?
C21 C20 H20 107.7 . . ?
C31 C26 C27 118.2(4) . . ?
C31 C26 C20 119.6(4) . . ?
C27 C26 C20 122.1(4) . . ?
N16 C15 N19 108.2(4) . . ?
N16 C15 C11 123.9(4) . . ?
N19 C15 C11 127.9(4) . . ?
N10 C14 C13 101.6(4) . . ?
N10 C14 H14A 111.5 . . ?
C13 C14 H14A 111.5 . . ?
N10 C14 H14B 111.5 . . ?
C13 C14 H14B 111.5 . . ?
H14A C14 H14B 109.3 . . ?
N10 C11 C15 112.0(3) . . ?
N10 C11 C12 103.8(4) . . ?
C15 C11 C12 115.8(4) . . ?
N10 C11 H11 108.3 . . ?
C15 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C9 C22 C23 118.7(4) . . ?
C9 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C26 C27 C28 120.7(5) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C2 C3 C4 119.0(5) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C8 C25 C24 118.8(4) . . ?
C8 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C5 C6 C7 118.4(5) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C24 C23 C22 120.8(5) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C13 C12 C11 105.0(4) . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
C12 C13 C14 104.2(4) . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C29 C28 C27 120.4(5) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.5(5) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C26 C31 C30 120.7(5) . . ?
C26 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C30 C29 C28 120.1(5) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 119.8(5) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.053
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1829738'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
1-(1-tert-butyl-1H-tetrazol-5-yl)-2-(9H-fluoren-9-yl)-1,2,3,4-tetrahydroisoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 N5'
_chemical_formula_sum            'C1.61 H1.61 N0.30'
_chemical_formula_weight         25.17

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.3769(3)
_cell_length_b                   17.6453(5)
_cell_length_c                   11.4216(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.532(2)
_cell_angle_gamma                90
_cell_volume                     2277.99(11)
_cell_formula_units_Z            67
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    34219
_cell_measurement_theta_min      2.134
_cell_measurement_theta_max      25.247

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31002
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.134
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4096
_reflns_number_gt                3244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Brucker SHELXTL'
_computing_publication_material  'Brucker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0863P)²+0.0007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4096
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1581
_refine_ls_goodness_of_fit_ref   1.442
_refine_ls_restrained_S_all      1.442
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.64092(14) 0.01983(9) 0.85587(14) 0.0453(4) Uani 1 1 d . . . . .
H13 H 0.6098 0.0691 0.8773 0.054 Uiso 1 1 calc R U . . .
C16 C 0.80974(15) 0.02704(9) 0.53846(15) 0.0481(4) Uani 1 1 d . . . . .
C20 C 0.82938(14) 0.08616(9) 0.61878(14) 0.0438(4) Uani 1 1 d . . . . .
C12 C 0.54202(15) -0.03807(9) 0.85102(15) 0.0480(4) Uani 1 1 d . . . . .
C7 C 0.56776(17) -0.09326(10) 0.93720(16) 0.0535(5) Uani 1 1 d . . . . .
C5 C 0.72615(15) -0.00927(10) 0.95954(14) 0.0497(4) Uani 1 1 d . . . . .
C6 C 0.68212(17) -0.07537(10) 1.00367(16) 0.0542(5) Uani 1 1 d . . . . .
C15 C 0.73517(18) -0.03909(10) 0.56608(16) 0.0561(5) Uani 1 1 d . . . . .
H15A H 0.7688 -0.0854 0.5383 0.067 Uiso 1 1 calc R U . . .
H15B H 0.6561 -0.0333 0.5253 0.067 Uiso 1 1 calc R U . . .
C17 C 0.86302(18) 0.03001(11) 0.43523(17) 0.0596(5) Uani 1 1 d . . . . .
H17 H 0.8487 -0.0087 0.3801 0.071 Uiso 1 1 calc R U . . .
C19 C 0.90468(17) 0.14475(10) 0.59547(17) 0.0559(5) Uani 1 1 d . . . . .
H19 H 0.9194 0.1839 0.6497 0.067 Uiso 1 1 calc R U . . .
C14 C 0.72821(17) -0.04499(9) 0.69695(16) 0.0515(5) Uani 1 1 d . . . . .
H14A H 0.6753 -0.0859 0.7129 0.062 Uiso 1 1 calc R U . . .
H14B H 0.8059 -0.0558 0.7377 0.062 Uiso 1 1 calc R U . . .
C4 C 0.82997(17) 0.02195(12) 1.01374(16) 0.0613(5) Uani 1 1 d . . . . .
H4 H 0.8582 0.0675 0.9870 0.074 Uiso 1 1 calc R U . . .
C18 C 0.93590(18) 0.08818(12) 0.41244(18) 0.0670(6) Uani 1 1 d . . . . .
H18 H 0.9706 0.0890 0.3425 0.080 Uiso 1 1 calc R U . . .
C11 C 0.43951(17) -0.04281(11) 0.77429(18) 0.0598(5) Uani 1 1 d . . . . .
H11 H 0.4221 -0.0065 0.7158 0.072 Uiso 1 1 calc R U . . .
C21 C 0.95784(19) 0.14560(12) 0.4933(2) 0.0685(6) Uani 1 1 d . . . . .
H21 H 1.0086 0.1850 0.4789 0.082 Uiso 1 1 calc R U . . .
C3 C 0.8911(2) -0.01555(15) 1.10824(18) 0.0756(7) Uani 1 1 d . . . . .
H3 H 0.9615 0.0048 1.1443 0.091 Uiso 1 1 calc R U . . .
C8 C 0.4901(2) -0.15224(11) 0.94874(19) 0.0694(6) Uani 1 1 d . . . . .
H8 H 0.5067 -0.1886 1.0073 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3879(2) -0.15637(12) 0.8725(2) 0.0767(7) Uani 1 1 d . . . . .
H9 H 0.3351 -0.1959 0.8793 0.092 Uiso 1 1 calc R U . . .
C1 C 0.7442(2) -0.11234(13) 1.09992(19) 0.0721(6) Uani 1 1 d . . . . .
H1 H 0.7146 -0.1566 1.1298 0.087 Uiso 1 1 calc R U . . .
C2 C 0.8497(2) -0.08221(16) 1.14959(19) 0.0813(7) Uani 1 1 d . . . . .
H2 H 0.8933 -0.1073 1.2117 0.098 Uiso 1 1 calc R U . . .
C10 C 0.36302(19) -0.10281(12) 0.7862(2) 0.0727(6) Uani 1 1 d . . . . .
H10 H 0.2937 -0.1068 0.7348 0.087 Uiso 1 1 calc R U . . .
C22 C 0.55462(15) 0.21249(10) 0.62917(16) 0.0494(4) Uani 1 1 d . . . . .
C25 C 0.5472(4) 0.29085(16) 0.5820(3) 0.1409(16) Uani 1 1 d . . . . .
H25A H 0.5347 0.3255 0.6442 0.211 Uiso 1 1 calc R U . . .
H25B H 0.4824 0.2944 0.5206 0.211 Uiso 1 1 calc R U . . .
H25C H 0.6196 0.3034 0.5508 0.211 Uiso 1 1 calc R U . . .
C24 C 0.5745(3) 0.15470(18) 0.5375(2) 0.1068(10) Uani 1 1 d . . . . .
H24A H 0.6446 0.1674 0.5022 0.160 Uiso 1 1 calc R U . . .
H24B H 0.5077 0.1541 0.4779 0.160 Uiso 1 1 calc R U . . .
H24C H 0.5839 0.1056 0.5735 0.160 Uiso 1 1 calc R U . . .
C23 C 0.4400(2) 0.1927(2) 0.6793(3) 0.1188(11) Uani 1 1 d . . . . .
H23A H 0.4467 0.1431 0.7141 0.178 Uiso 1 1 calc R U . . .
H23B H 0.3756 0.1932 0.6172 0.178 Uiso 1 1 calc R U . . .
H23C H 0.4254 0.2292 0.7383 0.178 Uiso 1 1 calc R U . . .
N1 N 0.68432(12) 0.02683(7) 0.73890(11) 0.0424(4) Uani 1 1 d . . . . .
N2 N 0.65096(12) 0.21055(7) 0.73058(12) 0.0438(4) Uani 1 1 d . . . . .
N5 N 0.79489(14) 0.19281(8) 0.86810(13) 0.0570(4) Uani 1 1 d . . . . .
N4 N 0.74323(17) 0.26021(9) 0.88404(15) 0.0666(5) Uani 1 1 d . . . . .
N3 N 0.65734(16) 0.27146(8) 0.80280(15) 0.0604(4) Uani 1 1 d . . . . .
C27 C 0.77663(14) 0.08501(8) 0.73577(14) 0.0418(4) Uani 1 1 d . . . . .
H27 H 0.8412 0.0696 0.7951 0.050 Uiso 1 1 calc R U . . .
C26 C 0.73776(14) 0.16212(8) 0.77412(14) 0.0417(4) 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
C13 N1 1.4811(19) . ?
C13 C12 1.516(2) . ?
C13 C5 1.531(2) . ?
C16 C17 1.387(2) . ?
C16 C20 1.390(2) . ?
C16 C15 1.497(2) . ?
C20 C19 1.388(2) . ?
C20 C27 1.526(2) . ?
C12 C11 1.379(3) . ?
C12 C7 1.392(2) . ?
C7 C8 1.382(3) . ?
C7 C6 1.464(3) . ?
C5 C4 1.384(3) . ?
C5 C6 1.387(3) . ?
C6 C1 1.399(3) . ?
C15 C14 1.509(3) . ?
C17 C18 1.363(3) . ?
C19 C21 1.374(3) . ?
C14 N1 1.463(2) . ?
C4 C3 1.384(3) . ?
C18 C21 1.375(3) . ?
C11 C10 1.387(3) . ?
C3 C2 1.371(3) . ?
C8 C9 1.373(3) . ?
C9 C10 1.371(3) . ?
C1 C2 1.375(3) . ?
C22 C25 1.483(3) . ?
C22 C24 1.497(3) . ?
C22 N2 1.502(2) . ?
C22 C23 1.524(3) . ?
N1 C27 1.472(2) . ?
N2 N3 1.3518(19) . ?
N2 C26 1.357(2) . ?
N5 C26 1.307(2) . ?
N5 N4 1.348(2) . ?
N4 N3 1.284(2) . ?
C27 C26 1.511(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
N1 C13 C12 110.21(13) . . ?
N1 C13 C5 118.60(12) . . ?
C12 C13 C5 101.78(13) . . ?
C17 C16 C20 118.66(16) . . ?
C17 C16 C15 121.44(16) . . ?
C20 C16 C15 119.88(14) . . ?
C19 C20 C16 119.27(15) . . ?
C19 C20 C27 119.39(14) . . ?
C16 C20 C27 121.20(14) . . ?
C11 C12 C7 120.11(17) . . ?
C11 C12 C13 129.37(15) . . ?
C7 C12 C13 110.49(16) . . ?
C8 C7 C12 120.6(2) . . ?
C8 C7 C6 130.81(18) . . ?
C12 C7 C6 108.60(16) . . ?
C4 C5 C6 119.83(18) . . ?
C4 C5 C13 130.21(17) . . ?
C6 C5 C13 109.88(16) . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 C7 109.23(16) . . ?
C1 C6 C7 130.26(19) . . ?
C16 C15 C14 110.92(15) . . ?
C18 C17 C16 121.67(17) . . ?
C21 C19 C20 120.79(17) . . ?
N1 C14 C15 108.84(14) . . ?
C3 C4 C5 119.1(2) . . ?
C17 C18 C21 119.65(17) . . ?
C12 C11 C10 118.60(18) . . ?
C18 C21 C19 119.91(18) . . ?
C2 C3 C4 121.1(2) . . ?
C9 C8 C7 118.96(19) . . ?
C8 C9 C10 120.7(2) . . ?
C2 C1 C6 118.9(2) . . ?
C3 C2 C1 120.5(2) . . ?
C9 C10 C11 121.0(2) . . ?
C25 C22 C24 112.8(3) . . ?
C25 C22 N2 107.92(17) . . ?
C24 C22 N2 111.65(15) . . ?
C25 C22 C23 109.6(3) . . ?
C24 C22 C23 108.1(2) . . ?
N2 C22 C23 106.60(17) . . ?
C14 N1 C27 108.97(12) . . ?
C14 N1 C13 112.61(12) . . ?
C27 N1 C13 113.08(12) . . ?
N3 N2 C26 106.91(14) . . ?
N3 N2 C22 115.86(13) . . ?
C26 N2 C22 137.22(13) . . ?
C26 N5 N4 107.02(15) . . ?
N3 N4 N5 110.27(14) . . ?
N4 N3 N2 107.55(14) . . ?
N1 C27 C26 112.82(12) . . ?
N1 C27 C20 112.54(12) . . ?
C26 C27 C20 113.52(12) . . ?
N5 C26 N2 108.25(14) . . ?
N5 C26 C27 118.45(15) . . ?
N2 C26 C27 133.29(15) . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and 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_CKJ-SH-04-268
_database_code_depnum_ccdc_archive 'CCDC 1829751'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(S)-2-(9H-fluoren-9-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-(1-((R)-1-phenylethyl)-1H-tetrazol-5-yl)isoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H31 N5 O2'
_chemical_formula_weight         529.63

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_chemical_absolute_configuration syn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.5012(10)
_cell_length_b                   15.8064(15)
_cell_length_c                   18.7456(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2815.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5586
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      21.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29404
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4964
_reflns_number_gt                3377
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.7(14)
_refine_ls_number_reflns         4964
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7 C 0.4367(2) 0.91541(13) -0.04062(11) 0.0531(6) Uani 1 1 d . . .
H7 H 0.5241 0.9167 -0.0129 0.064 Uiso 1 1 calc R . .
C8 C 0.3914(3) 0.82446(14) -0.04898(12) 0.0591(6) Uani 1 1 d . . .
C6 C 0.4701(2) 0.94087(14) -0.11715(11) 0.0535(6) Uani 1 1 d . . .
C5 C 0.4414(2) 0.87311(15) -0.16281(11) 0.0557(6) Uani 1 1 d . . .
C13 C 0.3948(2) 0.80116(14) -0.12024(13) 0.0593(6) Uani 1 1 d . . .
C3 C 0.5184(3) 0.9557(2) -0.26140(15) 0.0852(9) Uani 1 1 d . . .
H3 H 0.5334 0.9618 -0.3102 0.102 Uiso 1 1 calc R . .
C1 C 0.5291(3) 1.01379(17) -0.14391(13) 0.0708(7) Uani 1 1 d . . .
H1 H 0.5536 1.0579 -0.1136 0.085 Uiso 1 1 calc R . .
C2 C 0.5513(3) 1.0204(2) -0.21692(14) 0.0833(9) Uani 1 1 d . . .
H2 H 0.5892 1.0699 -0.2356 0.100 Uiso 1 1 calc R . .
C4 C 0.4634(3) 0.8811(2) -0.23575(13) 0.0737(8) Uani 1 1 d . . .
H4 H 0.4414 0.8370 -0.2666 0.088 Uiso 1 1 calc R . .
C9 C 0.3534(3) 0.76720(16) 0.00254(15) 0.0810(8) Uani 1 1 d . . .
H9 H 0.3485 0.7832 0.0502 0.097 Uiso 1 1 calc R . .
C12 C 0.3647(3) 0.71880(18) -0.13959(17) 0.0815(8) Uani 1 1 d . . .
H12 H 0.3675 0.7026 -0.1873 0.098 Uiso 1 1 calc R . .
C10 C 0.3228(4) 0.68550(19) -0.0177(2) 0.1024(10) Uani 1 1 d . . .
H10 H 0.2964 0.6462 0.0167 0.123 Uiso 1 1 calc R . .
C11 C 0.3305(3) 0.66123(19) -0.0876(2) 0.0996(11) Uani 1 1 d . . .
H11 H 0.3124 0.6053 -0.1000 0.120 Uiso 1 1 calc R . .
C16 C 0.1257(3) 1.08704(13) 0.03980(10) 0.0501(5) Uani 1 1 d . . .
C17 C 0.2661(2) 1.10760(13) 0.04551(10) 0.0464(5) Uani 1 1 d . . .
C15 C 0.0831(2) 1.00455(14) 0.00662(12) 0.0588(6) Uani 1 1 d . . .
H15A H -0.0028 1.0124 -0.0205 0.071 Uiso 1 1 calc R . .
H15B H 0.0646 0.9634 0.0438 0.071 Uiso 1 1 calc R . .
C14 C 0.1968(2) 0.97189(14) -0.04166(12) 0.0579(6) Uani 1 1 d . . .
H14A H 0.1709 0.9165 -0.0597 0.070 Uiso 1 1 calc R . .
H14B H 0.2081 1.0097 -0.0820 0.070 Uiso 1 1 calc R . .
C18 C 0.3813(2) 1.05075(12) 0.01700(10) 0.0490(5) Uani 1 1 d . . .
H18 H 0.4184 1.0771 -0.0264 0.059 Uiso 1 1 calc R . .
C19 C 0.3049(3) 1.18494(14) 0.07610(11) 0.0533(6) Uani 1 1 d . . .
H19 H 0.3997 1.1989 0.0799 0.064 Uiso 1 1 calc R . .
C22 C 0.0247(3) 1.14437(14) 0.06427(11) 0.0544(6) Uani 1 1 d . . .
H22 H -0.0702 1.1307 0.0603 0.065 Uiso 1 1 calc R . .
C20 C 0.2049(3) 1.24023(15) 0.10053(11) 0.0569(6) Uani 1 1 d . . .
C21 C 0.0624(3) 1.22014(15) 0.09394(11) 0.0558(6) Uani 1 1 d . . .
C23 C -0.1749(3) 1.26128(17) 0.11771(15) 0.0791(8) Uani 1 1 d . . .
H23A H -0.2029 1.2509 0.0693 0.119 Uiso 1 1 calc R . .
H23B H -0.2268 1.3085 0.1363 0.119 Uiso 1 1 calc R . .
H23C H -0.1938 1.2120 0.1461 0.119 Uiso 1 1 calc R . .
C24 C 0.3699(4) 1.3470(2) 0.12935(19) 0.1194(12) Uani 1 1 d . . .
H24A H 0.4309 1.3120 0.1576 0.179 Uiso 1 1 calc R . .
H24B H 0.3723 1.4039 0.1472 0.179 Uiso 1 1 calc R . .
H24C H 0.4008 1.3464 0.0806 0.179 Uiso 1 1 calc R . .
C25 C 0.4999(3) 1.04304(13) 0.06847(11) 0.0511(6) Uani 1 1 d . . .
C28 C 0.3800(3) 0.88375(16) 0.18074(11) 0.0601(6) Uani 1 1 d . . .
C26 C 0.3743(2) 0.97833(15) 0.17597(11) 0.0598(6) Uani 1 1 d . . .
H26 H 0.2876 0.9935 0.1507 0.072 Uiso 1 1 calc R . .
C27 C 0.3694(3) 1.0204(2) 0.24936(13) 0.0867(9) Uani 1 1 d . . .
H27A H 0.4558 1.0095 0.2743 0.130 Uiso 1 1 calc R . .
H27B H 0.2919 0.9978 0.2762 0.130 Uiso 1 1 calc R . .
H27C H 0.3573 1.0803 0.2437 0.130 Uiso 1 1 calc R . .
C33 C 0.5006(3) 0.8379(2) 0.1819(2) 0.1071(11) Uani 1 1 d . . .
H33 H 0.5865 0.8655 0.1770 0.129 Uiso 1 1 calc R . .
C29 C 0.2565(3) 0.8393(2) 0.18470(16) 0.0908(9) Uani 1 1 d . . .
H29 H 0.1715 0.8683 0.1817 0.109 Uiso 1 1 calc R . .
C31 C 0.3762(5) 0.7096(2) 0.19657(18) 0.1079(11) Uani 1 1 d . . .
H31 H 0.3748 0.6513 0.2034 0.129 Uiso 1 1 calc R . .
C32 C 0.4988(4) 0.7514(2) 0.1900(2) 0.1312(15) Uani 1 1 d . . .
H32 H 0.5832 0.7216 0.1911 0.157 Uiso 1 1 calc R . .
C30 C 0.2553(4) 0.7540(3) 0.19294(18) 0.1043(11) Uani 1 1 d . . .
H30 H 0.1696 0.7258 0.1961 0.125 Uiso 1 1 calc R . .
O1 O -0.02889(19) 1.27960(10) 0.11984(9) 0.0743(5) Uani 1 1 d . . .
O2 O 0.2330(2) 1.31601(10) 0.13327(9) 0.0781(5) Uani 1 1 d . . .
N1 N 0.32937(18) 0.96600(10) -0.00237(8) 0.0500(5) Uani 1 1 d . . .
N2 N 0.49340(19) 1.01332(11) 0.13528(10) 0.0532(5) Uani 1 1 d . . .
N3 N 0.6222(2) 1.02073(13) 0.16525(11) 0.0681(6) Uani 1 1 d . . .
N5 N 0.6292(2) 1.06902(12) 0.05622(11) 0.0666(5) Uani 1 1 d . . .
N4 N 0.7019(2) 1.05375(14) 0.11729(14) 0.0756(6) 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
C7 N1 1.481(3) . ?
C7 C8 1.509(3) . ?
C7 C6 1.524(3) . ?
C8 C9 1.372(3) . ?
C8 C13 1.386(3) . ?
C6 C1 1.376(3) . ?
C6 C5 1.398(3) . ?
C5 C4 1.389(3) . ?
C5 C13 1.458(3) . ?
C13 C12 1.381(3) . ?
C3 C2 1.357(4) . ?
C3 C4 1.376(4) . ?
C1 C2 1.389(3) . ?
C9 C10 1.377(4) . ?
C12 C11 1.372(4) . ?
C10 C11 1.367(4) . ?
C16 C17 1.377(3) . ?
C16 C22 1.397(3) . ?
C16 C15 1.500(3) . ?
C17 C19 1.400(3) . ?
C17 C18 1.514(3) . ?
C15 C14 1.501(3) . ?
C14 N1 1.462(3) . ?
C18 N1 1.473(2) . ?
C18 C25 1.489(3) . ?
C19 C20 1.369(3) . ?
C22 C21 1.368(3) . ?
C20 O2 1.372(3) . ?
C20 C21 1.396(3) . ?
C21 O1 1.368(3) . ?
C23 O1 1.418(3) . ?
C24 O2 1.392(3) . ?
C25 N5 1.315(3) . ?
C25 N2 1.339(3) . ?
C28 C33 1.356(4) . ?
C28 C29 1.369(4) . ?
C28 C26 1.499(3) . ?
C26 N2 1.473(3) . ?
C26 C27 1.529(3) . ?
C33 C32 1.376(4) . ?
C29 C30 1.357(4) . ?
C31 C30 1.348(4) . ?
C31 C32 1.346(4) . ?
N2 N3 1.352(2) . ?
N3 N4 1.286(3) . ?
N5 N4 1.359(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C7 C8 111.64(18) . . ?
N1 C7 C6 117.20(18) . . ?
C8 C7 C6 102.32(17) . . ?
C9 C8 C13 120.6(2) . . ?
C9 C8 C7 129.1(2) . . ?
C13 C8 C7 110.3(2) . . ?
C1 C6 C5 119.9(2) . . ?
C1 C6 C7 130.5(2) . . ?
C5 C6 C7 109.47(19) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C13 131.0(2) . . ?
C6 C5 C13 108.78(18) . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 C5 130.9(2) . . ?
C8 C13 C5 109.10(19) . . ?
C2 C3 C4 121.2(3) . . ?
C6 C1 C2 119.0(2) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C4 C5 118.7(2) . . ?
C8 C9 C10 118.7(3) . . ?
C11 C12 C13 119.2(3) . . ?
C11 C10 C9 121.1(3) . . ?
C10 C11 C12 120.5(3) . . ?
C17 C16 C22 119.1(2) . . ?
C17 C16 C15 119.93(19) . . ?
C22 C16 C15 120.9(2) . . ?
C16 C17 C19 119.5(2) . . ?
C16 C17 C18 122.21(19) . . ?
C19 C17 C18 118.2(2) . . ?
C16 C15 C14 110.76(19) . . ?
N1 C14 C15 109.77(17) . . ?
N1 C18 C25 109.83(16) . . ?
N1 C18 C17 112.60(18) . . ?
C25 C18 C17 111.55(16) . . ?
C20 C19 C17 120.8(2) . . ?
C21 C22 C16 121.4(2) . . ?
C19 C20 O2 124.9(2) . . ?
C19 C20 C21 119.9(2) . . ?
O2 C20 C21 115.2(2) . . ?
O1 C21 C22 125.4(2) . . ?
O1 C21 C20 115.3(2) . . ?
C22 C21 C20 119.3(2) . . ?
N5 C25 N2 108.4(2) . . ?
N5 C25 C18 124.6(2) . . ?
N2 C25 C18 126.9(2) . . ?
C33 C28 C29 116.7(2) . . ?
C33 C28 C26 124.4(2) . . ?
C29 C28 C26 119.0(3) . . ?
N2 C26 C28 112.19(19) . . ?
N2 C26 C27 109.0(2) . . ?
C28 C26 C27 112.4(2) . . ?
C28 C33 C32 121.5(3) . . ?
C28 C29 C30 121.6(3) . . ?
C30 C31 C32 118.5(3) . . ?
C31 C32 C33 120.6(4) . . ?
C31 C30 C29 121.1(3) . . ?
C21 O1 C23 118.0(2) . . ?
C20 O2 C24 117.7(2) . . ?
C14 N1 C18 110.80(16) . . ?
C14 N1 C7 112.55(16) . . ?
C18 N1 C7 112.31(17) . . ?
C25 N2 N3 108.45(19) . . ?
C25 N2 C26 130.68(19) . . ?
N3 N2 C26 120.87(19) . . ?
N4 N3 N2 106.11(19) . . ?
C25 N5 N4 105.79(19) . . ?
N3 N4 N5 111.22(19) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
