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

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

data_test33
_database_code_depnum_ccdc_archive 'CCDC 1485825'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_date             2016-05-19T15:29:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
6-(2-methoxyphenyl)-5a-phenyl-5aH-benzo[4,5]cyclohepta[1,2-b]benzofuran
;
_chemical_name_common            
'methoxyphenyl phenyl benzo cyclohepta benzofuran'
_chemical_formula_moiety         'C30 H22 O2'
_chemical_formula_sum            'C30 H22 O2'
_chemical_formula_weight         414.48
_chemical_melting_point          none
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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                   15.6898(4)
_cell_length_b                   10.3140(2)
_cell_length_c                   13.7275(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2221.45(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.816
_cell_measurement_theta_max      68.135

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.8566
_exptl_absorpt_correction_T_max  0.8974

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_number            41636
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.13
_diffrn_reflns_theta_max         70.24
_diffrn_reflns_theta_full        70.24
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             4204
_reflns_number_gt                4107
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0471P)²+0.1344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4204
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(1)
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.14
_refine_diff_density_rms         0.028

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.32275(5) 0.55189(8) 0.46086(6) 0.04591(19) Uani 1 1 d . . .
O2 O 0.19560(7) 0.72701(10) 0.53335(7) 0.0610(2) Uani 1 1 d . . .
C8 C 0.27759(7) 0.46656(10) 0.61245(9) 0.0405(2) Uani 1 1 d . . .
C9 C 0.23624(7) 0.39510(11) 0.67909(8) 0.0434(2) Uani 1 1 d . . .
H9 H 0.2477 0.4136 0.7441 0.052 Uiso 1 1 calc R . .
C16 C 0.11523(7) 0.39236(12) 0.50665(9) 0.0476(3) Uani 1 1 d . . .
H16 H 0.0612 0.4048 0.4802 0.057 Uiso 1 1 calc R . .
C2 C 0.36565(7) 0.61048(10) 0.53497(10) 0.0453(3) Uani 1 1 d . . .
C15 C 0.12254(7) 0.28616(12) 0.57713(9) 0.0443(3) Uani 1 1 d . . .
C17 C 0.17538(7) 0.47372(12) 0.47515(9) 0.0442(3) Uani 1 1 d . . .
C10 C 0.17525(7) 0.29153(11) 0.66004(9) 0.0432(2) Uani 1 1 d . . .
C18 C 0.14935(8) 0.58439(14) 0.41219(10) 0.0524(3) Uani 1 1 d . . .
C12 C 0.11277(9) 0.09015(13) 0.71739(11) 0.0570(3) Uani 1 1 d . . .
H12 H 0.1095 0.0252 0.7642 0.068 Uiso 1 1 calc R . .
C1 C 0.26829(7) 0.45049(10) 0.50310(8) 0.0402(2) Uani 1 1 d . . .
C11 C 0.16760(9) 0.19286(13) 0.73027(10) 0.0515(3) Uani 1 1 d . . .
H11 H 0.2003 0.1972 0.7867 0.062 Uiso 1 1 calc R . .
C7 C 0.34142(7) 0.56757(11) 0.62673(9) 0.0436(3) Uani 1 1 d . . .
C13 C 0.06253(8) 0.08361(12) 0.63457(12) 0.0565(3) Uani 1 1 d . . .
H13 H 0.0264 0.0133 0.6249 0.068 Uiso 1 1 calc R . .
C30 C 0.29547(10) 0.30268(14) 0.36092(11) 0.0576(3) Uani 1 1 d . . .
H30 H 0.2688 0.3645 0.3221 0.069 Uiso 1 1 calc R . .
C14 C 0.06628(8) 0.18153(12) 0.56664(11) 0.0513(3) Uani 1 1 d . . .
H14 H 0.0307 0.1782 0.5125 0.062 Uiso 1 1 calc R . .
C25 C 0.30151(7) 0.32292(11) 0.46087(9) 0.0428(3) Uani 1 1 d . . .
C26 C 0.34065(8) 0.22943(13) 0.51748(11) 0.0514(3) Uani 1 1 d . . .
H26 H 0.3456 0.2414 0.5844 0.062 Uiso 1 1 calc R . .
C3 C 0.42708(8) 0.70540(13) 0.52157(12) 0.0569(3) Uani 1 1 d . . .
H3 H 0.4428 0.7332 0.4597 0.068 Uiso 1 1 calc R . .
C27 C 0.37268(9) 0.11735(15) 0.47432(14) 0.0628(4) Uani 1 1 d . . .
H27 H 0.3979 0.054 0.5129 0.075 Uiso 1 1 calc R . .
C19 C 0.15863(8) 0.71224(14) 0.44457(11) 0.0548(3) Uani 1 1 d . . .
C6 C 0.37793(8) 0.62256(13) 0.70935(11) 0.0528(3) Uani 1 1 d . . .
H6 H 0.3612 0.5969 0.7714 0.063 Uiso 1 1 calc R . .
C4 C 0.46408(9) 0.75721(13) 0.60519(14) 0.0663(4) Uani 1 1 d . . .
H4 H 0.5059 0.8205 0.599 0.08 Uiso 1 1 calc R . .
C5 C 0.44029(9) 0.71712(14) 0.69656(14) 0.0641(4) Uani 1 1 d . . .
H5 H 0.4663 0.7537 0.7509 0.077 Uiso 1 1 calc R . .
C29 C 0.32847(11) 0.19220(17) 0.31855(13) 0.0700(4) Uani 1 1 d . . .
H29 H 0.3243 0.1805 0.2515 0.084 Uiso 1 1 calc R . .
C23 C 0.10725(10) 0.56293(19) 0.32478(12) 0.0695(4) Uani 1 1 d . . .
H23 H 0.1003 0.4786 0.3021 0.083 Uiso 1 1 calc R . .
C20 C 0.12753(10) 0.81428(18) 0.38921(15) 0.0727(5) Uani 1 1 d . . .
H20 H 0.1346 0.8992 0.4105 0.087 Uiso 1 1 calc R . .
C28 C 0.36742(11) 0.09933(16) 0.37495(15) 0.0706(4) Uani 1 1 d . . .
H28 H 0.39 0.0251 0.3464 0.085 Uiso 1 1 calc R . .
C21 C 0.08643(11) 0.7900(2) 0.30326(16) 0.0834(6) Uani 1 1 d . . .
H21 H 0.0659 0.8591 0.2666 0.1 Uiso 1 1 calc R . .
C24 C 0.22373(15) 0.85239(18) 0.56144(18) 0.0899(6) Uani 1 1 d . . .
H24A H 0.2481 0.8484 0.6255 0.135 Uiso 1 1 calc R . .
H24B H 0.1762 0.911 0.5617 0.135 Uiso 1 1 calc R . .
H24C H 0.2659 0.8826 0.5161 0.135 Uiso 1 1 calc R . .
C22 C 0.07507(11) 0.6669(2) 0.27041(15) 0.0862(6) Uani 1 1 d . . .
H22 H 0.0462 0.6518 0.2123 0.103 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3614(16) . ?
O1 C1 1.4697(13) . ?
O2 C19 1.3583(19) . ?
O2 C24 1.420(2) . ?
C8 C9 1.3419(16) . ?
C8 C7 1.4583(16) . ?
C8 C1 1.5173(16) . ?
C9 C10 1.4578(17) . ?
C16 C17 1.3349(17) . ?
C16 C15 1.4660(16) . ?
C2 C3 1.3862(16) . ?
C2 C7 1.3881(18) . ?
C15 C14 1.4016(17) . ?
C15 C10 1.4079(18) . ?
C17 C18 1.4889(17) . ?
C17 C1 1.5263(15) . ?
C10 C11 1.4069(17) . ?
C18 C23 1.387(2) . ?
C18 C19 1.399(2) . ?
C12 C11 1.376(2) . ?
C12 C13 1.385(2) . ?
C1 C25 1.5294(16) . ?
C7 C6 1.3916(19) . ?
C13 C14 1.3759(19) . ?
C30 C29 1.380(2) . ?
C30 C25 1.3910(19) . ?
C25 C26 1.3823(18) . ?
C26 C27 1.393(2) . ?
C3 C4 1.393(2) . ?
C27 C28 1.379(3) . ?
C19 C20 1.3869(19) . ?
C6 C5 1.393(2) . ?
C4 C5 1.372(3) . ?
C29 C28 1.375(3) . ?
C23 C22 1.400(2) . ?
C20 C21 1.367(3) . ?
C21 C22 1.360(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
C2 O1 C1 107.97(9) . . ?
C19 O2 C24 118.59(13) . . ?
C9 C8 C7 129.25(11) . . ?
C9 C8 C1 124.61(10) . . ?
C7 C8 C1 106.08(10) . . ?
C8 C9 C10 126.69(11) . . ?
C17 C16 C15 128.91(11) . . ?
O1 C2 C3 123.93(12) . . ?
O1 C2 C7 113.65(9) . . ?
C3 C2 C7 122.42(12) . . ?
C14 C15 C10 118.90(11) . . ?
C14 C15 C16 117.27(11) . . ?
C10 C15 C16 123.37(11) . . ?
C16 C17 C18 118.43(11) . . ?
C16 C17 C1 119.68(10) . . ?
C18 C17 C1 121.89(10) . . ?
C11 C10 C15 118.38(11) . . ?
C11 C10 C9 117.59(11) . . ?
C15 C10 C9 124.01(10) . . ?
C23 C18 C19 118.34(13) . . ?
C23 C18 C17 120.68(14) . . ?
C19 C18 C17 120.63(13) . . ?
C11 C12 C13 119.92(12) . . ?
O1 C1 C8 104.87(9) . . ?
O1 C1 C17 110.14(8) . . ?
C8 C1 C17 108.87(9) . . ?
O1 C1 C25 105.34(8) . . ?
C8 C1 C25 115.86(9) . . ?
C17 C1 C25 111.43(9) . . ?
C12 C11 C10 121.48(13) . . ?
C2 C7 C6 119.79(11) . . ?
C2 C7 C8 107.09(11) . . ?
C6 C7 C8 133.11(12) . . ?
C14 C13 C12 119.75(12) . . ?
C29 C30 C25 120.94(15) . . ?
C13 C14 C15 121.49(13) . . ?
C26 C25 C30 118.69(12) . . ?
C26 C25 C1 122.58(11) . . ?
C30 C25 C1 118.67(11) . . ?
C25 C26 C27 120.01(14) . . ?
C2 C3 C4 116.83(14) . . ?
C28 C27 C26 120.73(15) . . ?
O2 C19 C20 123.84(15) . . ?
O2 C19 C18 115.80(11) . . ?
C20 C19 C18 120.29(16) . . ?
C7 C6 C5 118.16(14) . . ?
C5 C4 C3 121.61(12) . . ?
C4 C5 C6 121.16(14) . . ?
C28 C29 C30 120.30(16) . . ?
C18 C23 C22 120.69(18) . . ?
C21 C20 C19 120.00(19) . . ?
C29 C28 C27 119.32(15) . . ?
C22 C21 C20 121.24(15) . . ?
C21 C22 C23 119.41(18) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method CH3OH/Ch2Cl2
####################################################################### 
# 
# 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_test2
_database_code_depnum_ccdc_archive 'CCDC 1485827'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_date             2016-05-23T09:15:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
5a-(4- fluorophenyl)-6- phenyl-5aH-benzo[4,5]cyclohepta[1,2-b]benzofuran
;
_chemical_name_common            
'fluorophenyl phenyl benzo cyclohepta benzofuran'
_chemical_formula_moiety         'C58 H38 F2 O2'
_chemical_formula_sum            'C58 H38 F2 O2'
_chemical_formula_weight         804.88
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.309(2)
_cell_length_b                   12.473(3)
_cell_length_c                   16.361(4)
_cell_angle_alpha                111.827(18)
_cell_angle_beta                 92.561(18)
_cell_angle_gamma                104.099(12)
_cell_volume                     2054.3(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.998
_cell_measurement_theta_max      66.588

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.8883
_exptl_absorpt_correction_T_max  0.9403

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_number            55020
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         72.31
_diffrn_reflns_theta_full        72.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             8088
_reflns_number_gt                4794
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0497P)²+0.4773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0037(2)
_refine_ls_number_reflns         8088
_refine_ls_number_parameters     560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.06949(13) 0.69690(13) 0.29988(10) 0.0551(4) Uani 1 1 d . . .
O2 O 0.81562(13) 1.16273(13) 0.33693(10) 0.0549(4) Uani 1 1 d . . .
F1 F 0.49944(14) 0.61865(15) 0.50131(10) 0.0895(5) Uani 1 1 d . . .
F2 F 0.59821(15) 0.90512(15) 0.57885(10) 0.0900(5) Uani 1 1 d . . .
C24 C 0.21975(18) 0.59793(18) 0.32178(14) 0.0453(5) Uani 1 1 d . . .
C46 C 0.66447(19) 1.0005(2) 0.21897(14) 0.0479(5) Uani 1 1 d . . .
C53 C 0.71230(19) 0.99687(19) 0.37275(14) 0.0460(5) Uani 1 1 d . . .
C17 C 0.14594(19) 0.58588(19) 0.16771(14) 0.0487(5) Uani 1 1 d . . .
C54 C 0.5957(2) 0.92279(19) 0.36432(15) 0.0523(6) Uani 1 1 d . . .
H54 H 0.5422 0.8934 0.3112 0.063 Uiso 1 1 calc R . .
C8 C 0.00052(19) 0.4852(2) 0.24779(14) 0.0493(5) Uani 1 1 d . . .
C37 C 0.8686(2) 0.9810(2) 0.26703(14) 0.0507(5) Uani 1 1 d . . .
C18 C 0.18230(19) 0.70071(19) 0.15423(15) 0.0509(5) Uani 1 1 d . . .
C47 C 0.61808(19) 1.0966(2) 0.20777(15) 0.0506(5) Uani 1 1 d . . .
C30 C 0.76045(19) 1.03116(18) 0.29765(14) 0.0468(5) Uani 1 1 d . . .
C10 C 0.0600(2) 0.3085(2) 0.14217(15) 0.0536(6) Uani 1 1 d . . .
C7 C -0.08155(19) 0.5400(2) 0.30507(15) 0.0524(6) Uani 1 1 d . . .
C16 C 0.1572(2) 0.4857(2) 0.10267(15) 0.0544(6) Uani 1 1 d . . .
H16 H 0.1803 0.4966 0.0518 0.065 Uiso 1 1 calc R . .
C48 C 0.5708(2) 1.17238(19) 0.27551(16) 0.0545(6) Uani 1 1 d . . .
H48 H 0.5756 1.1684 0.3312 0.065 Uiso 1 1 calc R . .
C15 C 0.1401(2) 0.3632(2) 0.09690(14) 0.0528(6) Uani 1 1 d . . .
C1 C 0.11229(19) 0.58883(18) 0.25652(14) 0.0469(5) Uani 1 1 d . . .
C9 C -0.0165(2) 0.3680(2) 0.20110(15) 0.0564(6) Uani 1 1 d . . .
H9 H -0.0877 0.3174 0.2074 0.068 Uiso 1 1 calc R . .
C23 C 0.2622(2) 0.8036(2) 0.21839(16) 0.0559(6) Uani 1 1 d . . .
H23 H 0.2871 0.8038 0.2734 0.067 Uiso 1 1 calc R . .
C2 C -0.0379(2) 0.6624(2) 0.33211(15) 0.0532(6) Uani 1 1 d . . .
C45 C 0.6136(2) 0.8858(2) 0.16181(15) 0.0556(6) Uani 1 1 d . . .
H45 H 0.5531 0.8758 0.1171 0.067 Uiso 1 1 calc R . .
C31 C 0.9419(2) 1.1853(2) 0.34171(16) 0.0565(6) Uani 1 1 d . . .
C39 C 0.7535(3) 0.7643(2) 0.18281(15) 0.0611(6) Uani 1 1 d . . .
C56 C 0.6360(3) 0.9351(2) 0.51042(16) 0.0619(6) Uani 1 1 d . . .
C29 C 0.2131(2) 0.6373(2) 0.41191(15) 0.0581(6) Uani 1 1 d . . .
H29 H 0.1438 0.6598 0.4322 0.07 Uiso 1 1 calc R . .
C36 C 0.9785(2) 1.0829(2) 0.30288(16) 0.0578(6) Uani 1 1 d . . .
C25 C 0.3234(2) 0.5646(2) 0.29377(16) 0.0606(6) Uani 1 1 d . . .
H25 H 0.3302 0.5375 0.2335 0.073 Uiso 1 1 calc R . .
C55 C 0.5569(2) 0.8913(2) 0.43355(16) 0.0591(6) Uani 1 1 d . . .
H55 H 0.4784 0.8412 0.4273 0.071 Uiso 1 1 calc R . .
C38 C 0.8623(2) 0.8659(2) 0.22014(15) 0.0610(6) Uani 1 1 d . . .
H38 H 0.9373 0.8489 0.2103 0.073 Uiso 1 1 calc R . .
C44 C 0.6373(2) 0.7742(2) 0.15806(15) 0.0588(6) Uani 1 1 d . . .
C22 C 0.3053(2) 0.9059(2) 0.20213(18) 0.0644(7) Uani 1 1 d . . .
H22 H 0.3597 0.974 0.2458 0.077 Uiso 1 1 calc R . .
C27 C 0.4067(2) 0.6102(2) 0.44154(17) 0.0605(6) Uani 1 1 d . . .
C58 C 0.7890(2) 1.0394(2) 0.45333(15) 0.0635(7) Uani 1 1 d . . .
H58 H 0.868 1.0893 0.4604 0.076 Uiso 1 1 calc R . .
C28 C 0.3061(2) 0.6440(2) 0.47241(16) 0.0645(7) Uani 1 1 d . . .
H28 H 0.3004 0.6711 0.5329 0.077 Uiso 1 1 calc R . .
C3 C -0.0962(2) 0.7423(2) 0.38490(17) 0.0666(7) Uani 1 1 d . . .
H3 H -0.0656 0.8249 0.4017 0.08 Uiso 1 1 calc R . .
C57 C 0.7517(3) 1.0099(2) 0.52302(16) 0.0699(7) Uani 1 1 d . . .
H57 H 0.8036 1.04 0.577 0.084 Uiso 1 1 calc R . .
C26 C 0.4178(2) 0.5707(2) 0.35386(17) 0.0674(7) Uani 1 1 d . . .
H26 H 0.4875 0.5481 0.3344 0.081 Uiso 1 1 calc R . .
C11 C 0.0488(3) 0.1877(2) 0.12580(17) 0.0678(7) Uani 1 1 d . . .
H11 H -0.0062 0.1493 0.1536 0.081 Uiso 1 1 calc R . .
C6 C -0.1888(2) 0.4919(3) 0.33230(17) 0.0687(7) Uani 1 1 d . . .
H6 H -0.22 0.4091 0.3142 0.082 Uiso 1 1 calc R . .
C49 C 0.5171(2) 1.2530(2) 0.2619(2) 0.0700(7) Uani 1 1 d . . .
H49 H 0.4848 1.302 0.3078 0.084 Uiso 1 1 calc R . .
C32 C 1.0232(2) 1.2987(2) 0.37950(18) 0.0731(8) Uani 1 1 d . . .
H32 H 0.9966 1.3671 0.4052 0.088 Uiso 1 1 calc R . .
C14 C 0.2055(3) 0.2949(2) 0.03856(17) 0.0701(7) Uani 1 1 d . . .
H14 H 0.2573 0.33 0.0073 0.084 Uiso 1 1 calc R . .
C21 C 0.2688(3) 0.9081(2) 0.1223(2) 0.0756(8) Uani 1 1 d . . .
H21 H 0.2991 0.9768 0.1111 0.091 Uiso 1 1 calc R . .
C19 C 0.1437(3) 0.7053(2) 0.07439(17) 0.0749(8) Uani 1 1 d . . .
H19 H 0.088 0.6382 0.0308 0.09 Uiso 1 1 calc R . .
C4 C -0.2032(3) 0.6920(3) 0.41144(19) 0.0785(8) Uani 1 1 d . . .
H4 H -0.2459 0.7422 0.4469 0.094 Uiso 1 1 calc R . .
C52 C 0.6130(3) 1.1080(3) 0.12676(18) 0.0758(8) Uani 1 1 d . . .
H52 H 0.646 1.06 0.0806 0.091 Uiso 1 1 calc R . .
C5 C -0.2480(2) 0.5686(3) 0.3863(2) 0.0800(8) Uani 1 1 d . . .
H5 H -0.3188 0.5377 0.4063 0.096 Uiso 1 1 calc R . .
C43 C 0.5380(3) 0.6694(2) 0.12201(17) 0.0779(8) Uani 1 1 d . . .
H43 H 0.4607 0.6744 0.1048 0.093 Uiso 1 1 calc R . .
C12 C 0.1173(3) 0.1247(2) 0.06965(19) 0.0811(8) Uani 1 1 d . . .
H12 H 0.1104 0.0454 0.0613 0.097 Uiso 1 1 calc R . .
C40 C 0.7664(3) 0.6493(3) 0.16589(17) 0.0830(9) Uani 1 1 d . . .
H40 H 0.8442 0.6412 0.1775 0.1 Uiso 1 1 calc R . .
C35 C 1.1032(2) 1.0916(3) 0.30235(19) 0.0794(8) Uani 1 1 d . . .
H35 H 1.1299 1.0231 0.2774 0.095 Uiso 1 1 calc R . .
C13 C 0.1959(3) 0.1787(3) 0.02586(19) 0.0835(8) Uani 1 1 d . . .
H13 H 0.2424 0.1362 -0.0122 0.1 Uiso 1 1 calc R . .
C50 C 0.5109(3) 1.2616(3) 0.1809(2) 0.0885(9) Uani 1 1 d . . .
H50 H 0.4739 1.3158 0.1715 0.106 Uiso 1 1 calc R . .
C33 C 1.1475(3) 1.3054(3) 0.3772(2) 0.0933(10) Uani 1 1 d . . .
H33 H 1.2058 1.3802 0.4015 0.112 Uiso 1 1 calc R . .
C41 C 0.6681(4) 0.5491(3) 0.1329(2) 0.1019(11) Uani 1 1 d . . .
H41 H 0.6788 0.4743 0.1246 0.122 Uiso 1 1 calc R . .
C20 C 0.1873(3) 0.8087(3) 0.0588(2) 0.0899(9) Uani 1 1 d . . .
H20 H 0.1609 0.8104 0.0048 0.108 Uiso 1 1 calc R . .
C51 C 0.5594(3) 1.1900(3) 0.1141(2) 0.0977(10) Uani 1 1 d . . .
H51 H 0.5562 1.1965 0.0593 0.117 Uiso 1 1 calc R . .
C42 C 0.5536(4) 0.5587(3) 0.1118(2) 0.0961(10) Uani 1 1 d . . .
H42 H 0.4861 0.4906 0.0906 0.115 Uiso 1 1 calc R . .
C34 C 1.1858(3) 1.2035(4) 0.3395(2) 0.0997(11) Uani 1 1 d . . .
H34 H 1.2696 1.2108 0.3394 0.12 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.381(3) . ?
O1 C1 1.481(2) . ?
O2 C31 1.379(3) . ?
O2 C30 1.475(2) . ?
F1 C27 1.358(2) . ?
F2 C56 1.361(2) . ?
C24 C25 1.379(3) . ?
C24 C29 1.382(3) . ?
C24 C1 1.535(3) . ?
C46 C45 1.345(3) . ?
C46 C47 1.485(3) . ?
C46 C30 1.513(3) . ?
C53 C54 1.381(3) . ?
C53 C58 1.388(3) . ?
C53 C30 1.525(3) . ?
C17 C16 1.346(3) . ?
C17 C18 1.492(3) . ?
C17 C1 1.508(3) . ?
C54 C55 1.386(3) . ?
C8 C9 1.333(3) . ?
C8 C7 1.455(3) . ?
C8 C1 1.529(3) . ?
C37 C38 1.335(3) . ?
C37 C36 1.454(3) . ?
C37 C30 1.527(3) . ?
C18 C23 1.383(3) . ?
C18 C19 1.384(3) . ?
C47 C52 1.384(3) . ?
C47 C48 1.388(3) . ?
C10 C11 1.401(3) . ?
C10 C15 1.403(3) . ?
C10 C9 1.444(3) . ?
C7 C2 1.372(3) . ?
C7 C6 1.386(3) . ?
C16 C15 1.459(3) . ?
C48 C49 1.372(3) . ?
C15 C14 1.396(3) . ?
C23 C22 1.378(3) . ?
C2 C3 1.380(3) . ?
C45 C44 1.460(3) . ?
C31 C36 1.373(3) . ?
C31 C32 1.376(3) . ?
C39 C40 1.402(3) . ?
C39 C44 1.405(3) . ?
C39 C38 1.446(3) . ?
C56 C55 1.353(3) . ?
C56 C57 1.365(3) . ?
C29 C28 1.377(3) . ?
C36 C35 1.388(3) . ?
C25 C26 1.387(3) . ?
C44 C43 1.403(3) . ?
C22 C21 1.365(3) . ?
C27 C26 1.355(3) . ?
C27 C28 1.362(3) . ?
C58 C57 1.376(3) . ?
C3 C4 1.388(4) . ?
C11 C12 1.372(4) . ?
C6 C5 1.372(4) . ?
C49 C50 1.368(4) . ?
C32 C33 1.390(4) . ?
C14 C13 1.362(3) . ?
C21 C20 1.366(4) . ?
C19 C20 1.385(3) . ?
C4 C5 1.387(4) . ?
C52 C51 1.381(4) . ?
C43 C42 1.384(4) . ?
C12 C13 1.371(4) . ?
C40 C41 1.362(4) . ?
C35 C34 1.369(4) . ?
C50 C51 1.363(4) . ?
C33 C34 1.376(4) . ?
C41 C42 1.371(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 107.90(16) . . ?
C31 O2 C30 108.08(16) . . ?
C25 C24 C29 117.6(2) . . ?
C25 C24 C1 122.3(2) . . ?
C29 C24 C1 120.02(19) . . ?
C45 C46 C47 118.9(2) . . ?
C45 C46 C30 121.0(2) . . ?
C47 C46 C30 120.01(19) . . ?
C54 C53 C58 117.6(2) . . ?
C54 C53 C30 123.20(19) . . ?
C58 C53 C30 119.22(19) . . ?
C16 C17 C18 117.8(2) . . ?
C16 C17 C1 122.6(2) . . ?
C18 C17 C1 119.17(19) . . ?
C53 C54 C55 121.3(2) . . ?
C9 C8 C7 126.5(2) . . ?
C9 C8 C1 127.5(2) . . ?
C7 C8 C1 105.88(18) . . ?
C38 C37 C36 127.6(2) . . ?
C38 C37 C30 126.3(2) . . ?
C36 C37 C30 106.0(2) . . ?
C23 C18 C19 117.8(2) . . ?
C23 C18 C17 121.3(2) . . ?
C19 C18 C17 120.8(2) . . ?
C52 C47 C48 117.7(2) . . ?
C52 C47 C46 120.6(2) . . ?
C48 C47 C46 121.6(2) . . ?
O2 C30 C46 108.16(17) . . ?
O2 C30 C53 106.41(16) . . ?
C46 C30 C53 115.49(17) . . ?
O2 C30 C37 104.00(16) . . ?
C46 C30 C37 110.77(18) . . ?
C53 C30 C37 111.22(17) . . ?
C11 C10 C15 118.3(2) . . ?
C11 C10 C9 118.1(2) . . ?
C15 C10 C9 123.6(2) . . ?
C2 C7 C6 119.4(2) . . ?
C2 C7 C8 107.9(2) . . ?
C6 C7 C8 132.6(2) . . ?
C17 C16 C15 132.1(2) . . ?
C49 C48 C47 121.2(2) . . ?
C14 C15 C10 118.4(2) . . ?
C14 C15 C16 116.4(2) . . ?
C10 C15 C16 125.1(2) . . ?
O1 C1 C17 108.25(16) . . ?
O1 C1 C8 103.26(16) . . ?
C17 C1 C8 112.90(17) . . ?
O1 C1 C24 106.46(16) . . ?
C17 C1 C24 114.40(17) . . ?
C8 C1 C24 110.72(17) . . ?
C8 C9 C10 129.1(2) . . ?
C22 C23 C18 121.1(2) . . ?
C7 C2 C3 123.4(2) . . ?
C7 C2 O1 112.9(2) . . ?
C3 C2 O1 123.7(2) . . ?
C46 C45 C44 130.9(2) . . ?
C36 C31 C32 123.1(2) . . ?
C36 C31 O2 113.0(2) . . ?
C32 C31 O2 123.8(2) . . ?
C40 C39 C44 118.4(3) . . ?
C40 C39 C38 118.1(3) . . ?
C44 C39 C38 123.4(2) . . ?
C55 C56 F2 118.8(2) . . ?
C55 C56 C57 122.8(2) . . ?
F2 C56 C57 118.3(2) . . ?
C28 C29 C24 121.9(2) . . ?
C31 C36 C35 119.6(3) . . ?
C31 C36 C37 108.0(2) . . ?
C35 C36 C37 132.4(3) . . ?
C24 C25 C26 121.2(2) . . ?
C56 C55 C54 118.5(2) . . ?
C37 C38 C39 128.1(2) . . ?
C43 C44 C39 118.6(2) . . ?
C43 C44 C45 117.0(2) . . ?
C39 C44 C45 124.3(2) . . ?
C21 C22 C23 120.4(2) . . ?
C26 C27 F1 119.4(2) . . ?
C26 C27 C28 122.2(2) . . ?
F1 C27 C28 118.4(2) . . ?
C57 C58 C53 121.9(2) . . ?
C27 C28 C29 118.4(2) . . ?
C2 C3 C4 116.1(3) . . ?
C56 C57 C58 117.9(2) . . ?
C27 C26 C25 118.8(2) . . ?
C12 C11 C10 121.5(3) . . ?
C5 C6 C7 118.8(3) . . ?
C50 C49 C48 120.3(3) . . ?
C31 C32 C33 116.3(3) . . ?
C13 C14 C15 122.2(3) . . ?
C22 C21 C20 119.6(2) . . ?
C18 C19 C20 120.6(2) . . ?
C5 C4 C3 121.6(3) . . ?
C51 C52 C47 120.4(3) . . ?
C6 C5 C4 120.6(3) . . ?
C42 C43 C44 120.9(3) . . ?
C11 C12 C13 120.1(3) . . ?
C41 C40 C39 121.9(3) . . ?
C34 C35 C36 118.4(3) . . ?
C14 C13 C12 119.5(3) . . ?
C51 C50 C49 119.4(3) . . ?
C34 C33 C32 121.3(3) . . ?
C40 C41 C42 119.9(3) . . ?
C21 C20 C19 120.4(3) . . ?
C50 C51 C52 120.9(3) . . ?
C41 C42 C43 120.2(3) . . ?
C35 C34 C33 121.4(3) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method MeOH/CH2Cl2
####################################################################### 
# 
# 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_test33
_database_code_depnum_ccdc_archive 'CCDC 1485830'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_date             2016-05-20T18:41:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
5a-(4-chlorophenyl)-6-phenyl-5aH-benzo[4,5]cyclohepta[1,2-b]benzofuran
;
_chemical_name_common            
'chlorophenyl phenyl benzo cyclohepta benzofuran'
_chemical_formula_moiety         'C29 H19 Cl O'
_chemical_formula_sum            'C29 H19 Cl O'
_chemical_formula_weight         418.89
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
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                   9.5556(17)
_cell_length_b                   18.935(3)
_cell_length_c                   11.627(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.866(8)
_cell_angle_gamma                90
_cell_volume                     2088.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9178
_cell_measurement_theta_min      2.789
_cell_measurement_theta_max      28.555

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_T_max  0.9722

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_number            41453
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.4
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_full        30.04
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             6097
_reflns_number_gt                4134
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0567P)²+1.2258P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         6097
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
Cl Cl 0.72478(7) 0.30000(4) 0.19412(5) 0.0710(2) Uani 1 1 d . . .
O O 0.31170(15) 0.45719(7) 0.53983(11) 0.0402(3) Uani 1 1 d . . .
C19 C 0.40255(19) 0.37826(10) 0.73232(15) 0.0337(4) Uani 1 1 d . . .
C25 C 0.41309(18) 0.35904(10) 0.44148(15) 0.0329(4) Uani 1 1 d . . .
C8 C 0.1529(2) 0.37299(11) 0.44605(15) 0.0369(4) Uani 1 1 d . . .
C20 C 0.3616(2) 0.37923(11) 0.84286(16) 0.0402(4) Uani 1 1 d . . .
H20 H 0.2727 0.3627 0.8546 0.048 Uiso 1 1 calc R . .
C18 C 0.31132(19) 0.34356(10) 0.63426(15) 0.0340(4) Uani 1 1 d . . .
C10 C 0.0867(2) 0.24577(11) 0.47488(16) 0.0395(4) Uani 1 1 d . . .
C1 C 0.29843(19) 0.37999(10) 0.51741(15) 0.0335(4) Uani 1 1 d . . .
C17 C 0.2569(2) 0.27980(10) 0.65282(16) 0.0379(4) Uani 1 1 d . . .
H17 H 0.2784 0.2643 0.7288 0.045 Uiso 1 1 calc R . .
C7 C 0.1157(2) 0.44495(11) 0.40497(16) 0.0392(4) Uani 1 1 d . . .
C16 C 0.1714(2) 0.22961(10) 0.57997(16) 0.0378(4) Uani 1 1 d . . .
C24 C 0.5348(2) 0.40522(11) 0.71746(17) 0.0406(4) Uani 1 1 d . . .
H24 H 0.5635 0.4062 0.6438 0.049 Uiso 1 1 calc R . .
C9 C 0.0724(2) 0.31584(11) 0.42514(17) 0.0424(5) Uani 1 1 d . . .
H9 H -0.0053 0.322 0.3698 0.051 Uiso 1 1 calc R . .
C2 C 0.2091(2) 0.49117(10) 0.46590(16) 0.0385(4) Uani 1 1 d . . .
C28 C 0.6061(2) 0.32262(12) 0.29085(17) 0.0432(5) Uani 1 1 d . . .
C26 C 0.4741(2) 0.29256(11) 0.44565(18) 0.0432(5) Uani 1 1 d . . .
H26 H 0.4497 0.2598 0.4994 0.052 Uiso 1 1 calc R . .
C22 C 0.5834(3) 0.42977(12) 0.92073(19) 0.0518(5) Uani 1 1 d . . .
H22 H 0.6441 0.4461 0.9836 0.062 Uiso 1 1 calc R . .
C21 C 0.4518(2) 0.40454(12) 0.93613(18) 0.0485(5) Uani 1 1 d . . .
H21 H 0.4231 0.4045 1.0098 0.058 Uiso 1 1 calc R . .
C23 C 0.6242(2) 0.43047(12) 0.81073(19) 0.0481(5) Uani 1 1 d . . .
H23 H 0.7123 0.448 0.7993 0.058 Uiso 1 1 calc R . .
C3 C 0.1985(2) 0.56391(11) 0.45430(18) 0.0458(5) Uani 1 1 d . . .
H3 H 0.2609 0.5942 0.4976 0.055 Uiso 1 1 calc R . .
C30 C 0.4533(2) 0.40714(12) 0.36177(18) 0.0466(5) Uani 1 1 d . . .
H30 H 0.4154 0.4524 0.3592 0.056 Uiso 1 1 calc R . .
C15 C 0.1690(3) 0.16013(11) 0.62223(18) 0.0484(5) Uani 1 1 d . . .
H15 H 0.2245 0.1489 0.691 0.058 Uiso 1 1 calc R . .
C29 C 0.5486(2) 0.38929(13) 0.28617(18) 0.0509(5) Uani 1 1 d . . .
H29 H 0.5736 0.422 0.2326 0.061 Uiso 1 1 calc R . .
C27 C 0.5711(2) 0.27392(11) 0.3708(2) 0.0482(5) Uani 1 1 d . . .
H27 H 0.6118 0.2292 0.3747 0.058 Uiso 1 1 calc R . .
C11 C 0.0008(2) 0.19207(13) 0.4210(2) 0.0512(5) Uani 1 1 d . . .
H11 H -0.0584 0.2026 0.3538 0.061 Uiso 1 1 calc R . .
C6 C 0.0050(2) 0.47165(13) 0.32771(18) 0.0503(5) Uani 1 1 d . . .
H6 H -0.0603 0.4415 0.2872 0.06 Uiso 1 1 calc R . .
C14 C 0.0873(3) 0.10830(12) 0.5651(2) 0.0567(6) Uani 1 1 d . . .
H14 H 0.0899 0.0625 0.5941 0.068 Uiso 1 1 calc R . .
C4 C 0.0902(3) 0.58936(13) 0.3749(2) 0.0560(6) Uani 1 1 d . . .
H4 H 0.0813 0.6378 0.3629 0.067 Uiso 1 1 calc R . .
C5 C -0.0049(3) 0.54418(14) 0.3131(2) 0.0586(7) Uani 1 1 d . . .
H5 H -0.0767 0.5628 0.2608 0.07 Uiso 1 1 calc R . .
C13 C 0.0014(3) 0.12469(13) 0.4645(2) 0.0580(6) Uani 1 1 d . . .
H13 H -0.0558 0.0902 0.4264 0.07 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Cl C28 1.744(2) . ?
O C2 1.383(2) . ?
O C1 1.488(2) . ?
C19 C20 1.388(3) . ?
C19 C24 1.393(3) . ?
C19 C18 1.501(2) . ?
C25 C26 1.386(3) . ?
C25 C30 1.386(3) . ?
C25 C1 1.539(3) . ?
C8 C9 1.333(3) . ?
C8 C7 1.473(3) . ?
C8 C1 1.538(3) . ?
C20 C21 1.388(3) . ?
C18 C17 1.342(3) . ?
C18 C1 1.516(2) . ?
C10 C11 1.406(3) . ?
C10 C16 1.416(3) . ?
C10 C9 1.447(3) . ?
C17 C16 1.457(3) . ?
C7 C2 1.383(3) . ?
C7 C6 1.398(3) . ?
C16 C15 1.406(3) . ?
C24 C23 1.383(3) . ?
C2 C3 1.386(3) . ?
C28 C29 1.375(3) . ?
C28 C27 1.379(3) . ?
C26 C27 1.391(3) . ?
C22 C21 1.377(3) . ?
C22 C23 1.381(3) . ?
C3 C4 1.389(3) . ?
C30 C29 1.381(3) . ?
C15 C14 1.374(3) . ?
C11 C13 1.372(3) . ?
C6 C5 1.386(3) . ?
C14 C13 1.382(4) . ?
C4 C5 1.385(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
C2 O C1 108.00(14) . . ?
C20 C19 C24 118.08(17) . . ?
C20 C19 C18 120.44(17) . . ?
C24 C19 C18 121.29(16) . . ?
C26 C25 C30 118.11(18) . . ?
C26 C25 C1 122.64(16) . . ?
C30 C25 C1 119.18(17) . . ?
C9 C8 C7 125.45(18) . . ?
C9 C8 C1 129.29(18) . . ?
C7 C8 C1 105.24(16) . . ?
C19 C20 C21 120.71(19) . . ?
C17 C18 C19 118.21(16) . . ?
C17 C18 C1 124.20(16) . . ?
C19 C18 C1 117.33(16) . . ?
C11 C10 C16 118.10(19) . . ?
C11 C10 C9 117.56(19) . . ?
C16 C10 C9 124.05(18) . . ?
O C1 C18 107.11(14) . . ?
O C1 C8 103.41(14) . . ?
C18 C1 C8 114.57(15) . . ?
O C1 C25 107.59(14) . . ?
C18 C1 C25 114.19(15) . . ?
C8 C1 C25 109.16(14) . . ?
C18 C17 C16 133.98(17) . . ?
C2 C7 C6 119.5(2) . . ?
C2 C7 C8 107.64(16) . . ?
C6 C7 C8 132.7(2) . . ?
C15 C16 C10 118.20(18) . . ?
C15 C16 C17 116.02(17) . . ?
C10 C16 C17 125.71(18) . . ?
C23 C24 C19 120.91(19) . . ?
C8 C9 C10 130.27(18) . . ?
O C2 C7 112.96(17) . . ?
O C2 C3 124.10(19) . . ?
C7 C2 C3 122.93(19) . . ?
C29 C28 C27 120.85(19) . . ?
C29 C28 Cl 119.18(17) . . ?
C27 C28 Cl 119.97(17) . . ?
C25 C26 C27 121.18(19) . . ?
C21 C22 C23 119.14(19) . . ?
C22 C21 C20 120.7(2) . . ?
C22 C23 C24 120.5(2) . . ?
C2 C3 C4 116.7(2) . . ?
C29 C30 C25 121.4(2) . . ?
C14 C15 C16 122.1(2) . . ?
C28 C29 C30 119.3(2) . . ?
C28 C27 C26 119.1(2) . . ?
C13 C11 C10 122.1(2) . . ?
C5 C6 C7 118.2(2) . . ?
C15 C14 C13 119.6(2) . . ?
C5 C4 C3 121.4(2) . . ?
C4 C5 C6 121.2(2) . . ?
C11 C13 C14 119.8(2) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method CH3OH/CH2Cl2
