# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_6269
_database_code_depnum_ccdc_archive 'CCDC 1487050'
_audit_update_record             
;
2016-06-21 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_audit_creation_date             2016-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H18 O2'
_chemical_formula_sum            'C25 H18 O2'
_chemical_formula_weight         350.42
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C20 H20 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n 21 a'
_space_group_name_Hall           ' P 2c -2n (-x,z,y)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,y,-z+1/2

_symmetry_Int_Tables_number      33
_cell_length_a                   14.3717(6)
_cell_length_b                   5.9170(2)
_cell_length_c                   21.4597(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1824.88(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    300
_cell_measurement_theta_max      70.9993
_cell_measurement_theta_min      3.0733
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81730
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             738.2524
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5075
_diffrn_reflns_theta_full        71.0934
_diffrn_reflns_theta_max         71.09
_diffrn_reflns_theta_min         3.70
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -64.00  -35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -66.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   20.0000   39.0000 77

#__ type_ start__ end____ width___ exp.time_
  3 omega   41.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -113.0000  130.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega   70.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega   77.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega  113.00  149.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  164.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -180.0000 125

#__ type_ start__ end____ width___ exp.time_
 10 omega -101.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 11 omega -103.00   -5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -120.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0029318000
_diffrn_orient_matrix_UB_12      0.0510137000
_diffrn_orient_matrix_UB_13      -0.0703606000
_diffrn_orient_matrix_UB_21      -0.1052512000
_diffrn_orient_matrix_UB_22      -0.0470783000
_diffrn_orient_matrix_UB_23      -0.0045827000
_diffrn_orient_matrix_UB_31      -0.0203739000
_diffrn_orient_matrix_UB_32      0.2508397000
_diffrn_orient_matrix_UB_33      0.0134677000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.325
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              7
_reflns_limit_k_min              -4
_reflns_limit_l_max              25
_reflns_limit_l_min              -23
_reflns_number_gt                1444
_reflns_number_total             2374
_reflns_odcompleteness_completeness 97.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.2273
_refine_diff_density_min         -0.3235
_refine_diff_density_rms         0.0629
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.8(4)
_refine_ls_d_res_high            0.8149
_refine_ls_d_res_low             11.9412
_refine_ls_goodness_of_fit_ref   1.0503
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.0503
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0910P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1967
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C6(H6),
 C5(H5), C4(H4), C3(H3), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O -0.2377(2) -0.1232(7) -0.41637(16) 0.0620(11) Uani 1.000000 .
O2 O -0.0726(3) -0.2626(9) -0.07001(18) 0.0897(15) Uani 1.000000 .
C2 C -0.1682(4) -0.4090(11) -0.4849(3) 0.0599(15) Uani 1.000000 .
C13 C -0.2941(4) 0.0977(11) -0.3314(3) 0.0591(15) Uani 1.000000 .
C18 C -0.3241(4) 0.2725(11) -0.3713(3) 0.0681(17) Uani 1.000000 .
C19 C -0.1451(4) -0.2305(10) -0.2576(2) 0.0551(14) Uani 1.000000 .
C12 C -0.2329(4) -0.0812(11) -0.3522(2) 0.0600(15) Uani 1.000000 .
C3 C -0.2099(4) -0.3350(12) -0.5403(2) 0.074(2) Uani 1.000000 .
C21 C -0.0712(4) -0.0579(10) -0.1684(3) 0.0636(16) Uani 1.000000 .
C24 C -0.1661(4) -0.4188(10) -0.2204(3) 0.0621(15) Uani 1.000000 .
C20 C -0.0976(4) -0.0559(11) -0.2306(3) 0.0651(16) Uani 1.000000 .
C22 C -0.0947(4) -0.2398(12) -0.1323(3) 0.0648(16) Uani 1.000000 .
C11 C -0.1734(4) -0.2290(10) -0.3244(2) 0.0560(14) Uani 1.000000 .
C1 C -0.1798(4) -0.3076(11) -0.4266(3) 0.0601(15) Uani 1.000000 .
C17 C -0.3803(4) 0.4396(12) -0.3498(3) 0.0763(19) Uani 1.000000 .
C10 C -0.1401(4) -0.3770(10) -0.3718(3) 0.0558(15) Uani 1.000000 .
C15 C -0.3822(4) 0.2764(11) -0.2490(3) 0.074(2) Uani 1.000000 .
C7 C -0.1123(4) -0.6058(12) -0.4841(3) 0.0655(17) Uani 1.000000 .
C16 C -0.4098(5) 0.4460(13) -0.2886(3) 0.082(2) Uani 1.000000 .
C14 C -0.3262(4) 0.1026(11) -0.2698(3) 0.0677(17) Uani 1.000000 .
C23 C -0.1406(4) -0.4248(11) -0.1581(3) 0.0681(17) Uani 1.000000 .
C9 C -0.0829(4) -0.5672(11) -0.3729(3) 0.0651(16) Uani 1.000000 .
C8 C -0.0700(4) -0.6814(11) -0.4277(3) 0.0701(18) Uani 1.000000 .
C6 C -0.0983(5) -0.7231(13) -0.5413(3) 0.085(2) Uani 1.000000 .
C25 C -0.0340(6) -0.0716(13) -0.0396(3) 0.112(3) Uani 1.000000 .
C5 C -0.1392(5) -0.6476(15) -0.5946(4) 0.098(3) Uani 1.000000 .
C4 C -0.1948(5) -0.4551(14) -0.5942(3) 0.087(2) Uani 1.000000 .
H9 H -0.0538(4) -0.6162(11) -0.3367(3) 0.0782(19) Uiso 1.000000 R
H8 H -0.0330(4) -0.8103(11) -0.4282(3) 0.084(2) Uiso 1.000000 R
H14 H -0.3095(4) -0.0125(11) -0.2425(3) 0.081(2) Uiso 1.000000 R
H15 H -0.4016(4) 0.2787(11) -0.2077(3) 0.089(2) Uiso 1.000000 R
H16 H -0.4476(5) 0.5629(13) -0.2745(3) 0.098(2) Uiso 1.000000 R
H17 H -0.3995(4) 0.5527(12) -0.3770(3) 0.092(2) Uiso 1.000000 R
H18 H -0.3051(4) 0.2733(11) -0.4128(3) 0.082(2) Uiso 1.000000 R
H6 H -0.0612(5) -0.8517(13) -0.5422(3) 0.102(3) Uiso 1.000000 R
H5 H -0.1299(5) -0.7257(15) -0.6317(4) 0.118(3) Uiso 1.000000 R
H4 H -0.2222(5) -0.4067(14) -0.6311(3) 0.105(3) Uiso 1.000000 R
H3 H -0.2472(4) -0.2066(12) -0.5406(2) 0.088(2) Uiso 1.000000 R
H20 H -0.0824(4) 0.0690(11) -0.2548(3) 0.0781(19) Uiso 1.000000 R
H21 H -0.0381(4) 0.0624(10) -0.1515(3) 0.0763(19) Uiso 1.000000 R
H23 H -0.1540(4) -0.5509(11) -0.1338(3) 0.082(2) Uiso 1.000000 R
H24 H -0.1975(4) -0.5410(10) -0.2377(3) 0.0745(18) Uiso 1.000000 R
H25a H 0.0273(14) -0.044(5) -0.0555(17) 0.168(4) Uiso 1.000000 GR
H25b H -0.0726(19) 0.058(2) -0.0470(19) 0.168(4) Uiso 1.000000 GR
H25c H -0.031(3) -0.100(4) 0.0044(4) 0.168(4) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.402(6) . ?
O1 C1 1.390(7) . ?
O2 C22 1.380(6) . ?
O2 C25 1.418(8) . ?
C2 C3 1.401(7) . ?
C2 C1 1.399(7) . ?
C2 C7 1.415(9) . ?
C13 C18 1.410(8) . ?
C13 C12 1.446(8) . ?
C13 C14 1.402(7) . ?
C18 C17 1.358(8) . ?
C19 C24 1.404(7) . ?
C19 C20 1.367(7) . ?
C19 C11 1.491(7) . ?
C12 C11 1.360(7) . ?
C3 C4 1.375(8) . ?
C21 C20 1.387(7) . ?
C21 C22 1.368(8) . ?
C24 C23 1.387(7) . ?
C22 C23 1.393(8) . ?
C11 C10 1.425(7) . ?
C1 C10 1.369(7) . ?
C17 C16 1.380(8) . ?
C10 C9 1.394(8) . ?
C15 C16 1.373(8) . ?
C15 C14 1.380(7) . ?
C7 C8 1.426(8) . ?
C7 C6 1.425(8) . ?
C9 C8 1.368(7) . ?
C6 C5 1.362(9) . ?
C5 C4 1.391(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C12 105.4(4) . . ?
C25 O2 C22 117.3(5) . . ?
C1 C2 C3 125.1(6) . . ?
C7 C2 C3 120.8(6) . . ?
C7 C2 C1 114.1(5) . . ?
C12 C13 C18 122.4(5) . . ?
C14 C13 C18 117.2(6) . . ?
C14 C13 C12 120.4(6) . . ?
C17 C18 C13 120.7(6) . . ?
C20 C19 C24 117.8(5) . . ?
C11 C19 C24 119.5(5) . . ?
C11 C19 C20 122.7(5) . . ?
C13 C12 O1 113.7(5) . . ?
C11 C12 O1 110.3(5) . . ?
C11 C12 C13 135.9(5) . . ?
C4 C3 C2 119.0(7) . . ?
C22 C21 C20 119.0(6) . . ?
C23 C24 C19 120.8(6) . . ?
C21 C20 C19 122.5(6) . . ?
C21 C22 O2 124.7(6) . . ?
C23 C22 O2 114.7(6) . . ?
C23 C22 C21 120.6(5) . . ?
C12 C11 C19 126.6(5) . . ?
C10 C11 C19 126.3(5) . . ?
C10 C11 C12 107.1(5) . . ?
C2 C1 O1 123.3(5) . . ?
C10 C1 O1 110.5(5) . . ?
C10 C1 C2 126.2(6) . . ?
C16 C17 C18 121.7(7) . . ?
C1 C10 C11 106.8(5) . . ?
C9 C10 C11 134.9(5) . . ?
C9 C10 C1 118.3(5) . . ?
C14 C15 C16 120.9(6) . . ?
C8 C7 C2 120.8(5) . . ?
C6 C7 C2 118.0(6) . . ?
C6 C7 C8 121.2(7) . . ?
C15 C16 C17 118.7(7) . . ?
C15 C14 C13 120.8(6) . . ?
C22 C23 C24 119.2(6) . . ?
C8 C9 C10 119.5(6) . . ?
C9 C8 C7 121.0(6) . . ?
C5 C6 C7 120.3(7) . . ?
C4 C5 C6 120.7(7) . . ?
C5 C4 C3 121.3(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_6157
_database_code_depnum_ccdc_archive 'CCDC 1479244'
_audit_update_record             
;
2016-05-11 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_audit_creation_date             2016-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r5103)
;
_chemical_name_systematic        2,3-diphenylbenzofuran
_chemical_formula_moiety         'C20 H14 O'
_chemical_formula_sum            'C20 H14 O'
_chemical_formula_weight         270.33
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C22 H15 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.9447(3)
_cell_length_b                   10.3826(4)
_cell_length_c                   17.0108(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1403.16(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    300
_cell_measurement_theta_max      71.2827
_cell_measurement_theta_min      4.2547
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2796
_exptl_crystal_description       block
_exptl_crystal_F_000             569.6775
_exptl_crystal_preparation       synthesized
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3193
_diffrn_reflns_theta_full        71.4234
_diffrn_reflns_theta_max         71.42
_diffrn_reflns_theta_min         4.99
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9614
_diffrn_measured_fraction_theta_max 0.8614
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  120.0000  -61.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00  -41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -19.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega   82.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1393  154.0000  -83.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  137.00  166.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786   63.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  9 omega   68.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   54.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 13 omega   43.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -50.0000    0.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0431598000
_diffrn_orient_matrix_UB_12      0.1068620000
_diffrn_orient_matrix_UB_13      -0.0595256000
_diffrn_orient_matrix_UB_21      -0.1878291000
_diffrn_orient_matrix_UB_22      -0.0124635000
_diffrn_orient_matrix_UB_23      0.0213047000
_diffrn_orient_matrix_UB_31      0.0221751000
_diffrn_orient_matrix_UB_32      0.1021360000
_diffrn_orient_matrix_UB_33      0.0648159000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.694
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                2022
_reflns_number_total             2350
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.1550
_refine_diff_density_min         -0.2508
_refine_diff_density_rms         0.0566
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_d_res_high            0.8133
_refine_ls_d_res_low             8.8623
_refine_ls_goodness_of_fit_ref   1.0451
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.0451
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1338
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C4(H4), C14(H14), C13(H13), C12(H12), C11(H11),
 C10(H10), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O -0.7085(2) -0.43085(18) -0.85285(9) 0.0460(4) Uani 1.000000 .
C1 C -0.7203(3) -0.4292(3) -0.77056(13) 0.0416(5) Uani 1.000000 .
C9 C -0.8807(3) -0.4786(2) -0.74146(14) 0.0412(5) Uani 1.000000 .
C2 C -0.5779(3) -0.3815(2) -0.73786(13) 0.0404(5) Uani 1.000000 .
C4 C -0.3009(3) -0.3046(3) -0.80933(15) 0.0484(6) Uani 1.000000 .
C3 C -0.4652(3) -0.3500(2) -0.80268(14) 0.0411(5) Uani 1.000000 .
C5 C -0.2327(4) -0.2918(3) -0.88342(18) 0.0571(7) Uani 1.000000 .
C15 C -0.5342(3) -0.3651(2) -0.65381(13) 0.0415(6) Uani 1.000000 .
C8 C -0.5516(3) -0.3821(3) -0.87053(14) 0.0440(6) Uani 1.000000 .
C20 C -0.5568(3) -0.4641(3) -0.59960(14) 0.0464(6) Uani 1.000000 .
C16 C -0.4602(4) -0.2507(3) -0.62864(15) 0.0527(7) Uani 1.000000 .
C17 C -0.4076(4) -0.2369(3) -0.55187(16) 0.0650(8) Uani 1.000000 .
C10 C -0.9739(3) -0.5639(3) -0.78687(15) 0.0503(6) Uani 1.000000 .
C14 C -0.9440(3) -0.4416(3) -0.66823(15) 0.0483(6) Uani 1.000000 .
C13 C -1.0966(3) -0.4909(3) -0.64160(17) 0.0549(7) Uani 1.000000 .
C11 C -1.1252(4) -0.6124(3) -0.75945(18) 0.0581(7) Uani 1.000000 .
C7 C -0.4869(4) -0.3695(3) -0.94554(15) 0.0534(7) Uani 1.000000 .
C19 C -0.5034(4) -0.4493(3) -0.52266(15) 0.0584(8) Uani 1.000000 .
C6 C -0.3249(4) -0.3218(3) -0.95033(16) 0.0578(8) Uani 1.000000 .
C12 C -1.1858(4) -0.5768(3) -0.68708(18) 0.0585(7) Uani 1.000000 .
C18 C -0.4280(4) -0.3357(3) -0.49882(17) 0.0667(9) Uani 1.000000 .
H7 H -0.5486(4) -0.3918(3) -0.98998(15) 0.0641(8) Uiso 1.000000 R
H6 H -0.2764(4) -0.3094(3) -0.99953(16) 0.0694(9) Uiso 1.000000 R
H5 H -0.1227(4) -0.2624(3) -0.88871(18) 0.0685(9) Uiso 1.000000 R
H4 H -0.2386(3) -0.2834(3) -0.76486(15) 0.0581(7) Uiso 1.000000 R
H14 H -0.8840(3) -0.3838(3) -0.63722(15) 0.0580(7) Uiso 1.000000 R
H13 H -1.1385(3) -0.4658(3) -0.59291(17) 0.0658(8) Uiso 1.000000 R
H12 H -1.2869(4) -0.6106(3) -0.66881(18) 0.0702(9) Uiso 1.000000 R
H11 H -1.1864(4) -0.6696(3) -0.79035(18) 0.0697(9) Uiso 1.000000 R
H10 H -0.9344(3) -0.5885(3) -0.83608(15) 0.0603(8) Uiso 1.000000 R
H16 H -0.4462(4) -0.1831(3) -0.66390(15) 0.0632(8) Uiso 1.000000 R
H17 H -0.3580(4) -0.1602(3) -0.53583(16) 0.0779(10) Uiso 1.000000 R
H18 H -0.3913(4) -0.3261(3) -0.44723(17) 0.0801(10) Uiso 1.000000 R
H19 H -0.5183(4) -0.5160(3) -0.48683(15) 0.0701(9) Uiso 1.000000 R
H20 H -0.6080(3) -0.5405(3) -0.61515(14) 0.0557(7) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.403(3) . ?
O1 C8 1.379(3) . ?
C1 C9 1.460(3) . ?
C1 C2 1.354(3) . ?
C9 C10 1.389(3) . ?
C9 C14 1.397(3) . ?
C2 C3 1.458(3) . ?
C2 C15 1.481(3) . ?
C4 C3 1.392(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C3 C8 1.383(3) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C15 C20 1.392(3) . ?
C15 C16 1.392(3) . ?
C8 C7 1.382(3) . ?
C20 C19 1.385(4) . ?
C20 H20 0.9300 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9300 . ?
C14 C13 1.392(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.377(4) . ?
C13 H13 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C7 C6 1.382(4) . ?
C7 H7 0.9300 . ?
C19 C18 1.384(4) . ?
C19 H19 0.9300 . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C18 H18 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
C8 O1 C1 105.87(19) . . ?
C9 C1 O1 113.1(2) . . ?
C2 C1 O1 111.0(2) . . ?
C2 C1 C9 135.9(2) . . ?
C10 C9 C1 120.1(2) . . ?
C14 C9 C1 121.3(2) . . ?
C14 C9 C10 118.7(2) . . ?
C3 C2 C1 106.5(2) . . ?
C15 C2 C1 129.4(2) . . ?
C15 C2 C3 124.1(2) . . ?
C5 C4 C3 118.4(3) . . ?
H4 C4 C3 120.81(16) . . ?
H4 C4 C5 120.81(17) . . ?
C4 C3 C2 135.5(2) . . ?
C8 C3 C2 105.8(2) . . ?
C8 C3 C4 118.6(2) . . ?
C6 C5 C4 121.4(3) . . ?
H5 C5 C4 119.32(17) . . ?
H5 C5 C6 119.32(17) . . ?
C20 C15 C2 121.6(2) . . ?
C16 C15 C2 119.6(2) . . ?
C16 C15 C20 118.7(2) . . ?
C3 C8 O1 110.8(2) . . ?
C7 C8 O1 124.9(2) . . ?
C7 C8 C3 124.3(3) . . ?
C19 C20 C15 120.3(3) . . ?
H20 C20 C15 119.85(15) . . ?
H20 C20 C19 119.85(17) . . ?
C17 C16 C15 120.5(3) . . ?
H16 C16 C15 119.74(15) . . ?
H16 C16 C17 119.74(19) . . ?
C18 C17 C16 120.6(3) . . ?
H17 C17 C16 119.72(19) . . ?
H17 C17 C18 119.72(18) . . ?
C11 C10 C9 120.5(3) . . ?
H10 C10 C9 119.75(15) . . ?
H10 C10 C11 119.75(18) . . ?
C13 C14 C9 120.1(3) . . ?
H14 C14 C9 119.93(15) . . ?
H14 C14 C13 119.93(17) . . ?
C12 C13 C14 120.2(3) . . ?
H13 C13 C14 119.88(17) . . ?
H13 C13 C12 119.88(17) . . ?
C12 C11 C10 120.6(3) . . ?
H11 C11 C10 119.71(18) . . ?
H11 C11 C12 119.71(17) . . ?
C6 C7 C8 115.7(3) . . ?
H7 C7 C8 122.13(17) . . ?
H7 C7 C6 122.13(17) . . ?
C18 C19 C20 120.3(3) . . ?
H19 C19 C20 119.85(17) . . ?
H19 C19 C18 119.85(18) . . ?
C7 C6 C5 121.6(3) . . ?
H6 C6 C5 119.22(17) . . ?
H6 C6 C7 119.22(17) . . ?
C11 C12 C13 119.8(3) . . ?
H12 C12 C13 120.08(17) . . ?
H12 C12 C11 120.08(17) . . ?
C19 C18 C17 119.6(3) . . ?
H18 C18 C17 120.20(18) . . ?
H18 C18 C19 120.20(18) . . ?

_olex2_exptl_crystal_mounting_method recrystalized
_olex2_submission_original_sample_id 'C B SRINIVAS'
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method 
'mixture of dichloromethane and hexane'
_chemical_compound_source        'Synthesized compound'
