# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1031281'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;
_chemical_name_systematic        
2,10dibromo3(2isopropylphenyl)3(4methoxyphenyl)3Hbenzo[f]chromene
_chemical_name_common            2,10BrNP
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 Br2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         564.30

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9872(17)
_cell_length_b                   9.0894(17)
_cell_length_c                   15.463(3)
_cell_angle_alpha                79.651(2)
_cell_angle_beta                 77.966(2)
_cell_angle_gamma                77.931(2)
_cell_volume                     1195.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4246
_cell_measurement_theta_min      2.3549
_cell_measurement_theta_max      26.3383
_cell_measurement_temperature    90.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.600
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568

_exptl_absorpt_coefficient_mu    3.414
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.17
_exptl_absorpt_correction_T_max  0.23

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6211
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_full        26.34
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             4637
_reflns_number_gt                4197
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1351
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_number_reflns         4637
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0731P)²+4.5419P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.876
_refine_diff_density_min         -0.515
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.56806(5) 0.23235(5) 0.27948(3) 0.01980(14) Uani d . . . 1 . .
Br Br2 0.30071(5) 0.66216(5) 0.08840(3) 0.02180(14) Uani d . . . 1 . .
O O4 0.3073(3) 0.0419(3) 0.16044(18) 0.0149(6) Uani d . . . 1 . .
C C1 0.2998(4) 0.2938(5) 0.0826(2) 0.0112(7) Uani d . . . 1 . .
O O1 0.6661(4) -0.4078(4) 0.4351(2) 0.0242(7) Uani d . . . 1 . .
C C5 -0.0187(5) 0.3661(5) 0.3546(3) 0.0169(8) Uani d . . . 1 . .
H H5 -0.0403 0.4686 0.3656 0.02 Uiso calc U . R 1 . .
C C6 0.2457(5) 0.5685(5) 0.0016(3) 0.0169(8) Uani d . . . 1 . .
C C7 0.2444(4) 0.4099(5) 0.0122(3) 0.0143(8) Uani d . . . 1 . .
C C8 0.1752(5) 0.3611(5) -0.0510(3) 0.0165(8) Uani d . . . 1 . .
C C9 0.4222(4) 0.2161(5) 0.2110(3) 0.0131(8) Uani d . . . 1 . .
C C10 0.4074(5) 0.3130(5) 0.1369(3) 0.0153(8) Uani d . . . 1 . .
H H10 0.4655 0.393 0.1195 0.018 Uiso calc U . R 1 . .
C C11 -0.1305(5) 0.2760(5) 0.3833(3) 0.0158(8) Uani d . . . 1 . .
H H11 -0.2297 0.3163 0.4138 0.019 Uiso calc U . R 1 . .
C C12 0.1254(5) 0.3059(5) 0.3097(3) 0.0134(8) Uani d . . . 1 . .
H H12 0.2022 0.3682 0.2906 0.016 Uiso calc U . R 1 . .
C C13 0.1566(5) 0.2086(5) -0.0413(3) 0.0208(9) Uani d . . . 1 . .
H H13 0.1151 0.1764 -0.0849 0.025 Uiso calc U . R 1 . .
C C14 0.3922(5) -0.0531(5) 0.3874(3) 0.0147(8) Uani d . . . 1 . .
H H14 0.3228 0.0238 0.4171 0.018 Uiso calc U . R 1 . .
C C15 -0.0969(5) 0.1256(5) 0.3672(3) 0.0147(8) Uani d . . . 1 . .
H H15 -0.1736 0.0636 0.3884 0.018 Uiso calc U . R 1 . .
C C16 0.4777(5) -0.1712(5) 0.4371(3) 0.0149(8) Uani d . . . 1 . .
H H16 0.4691 -0.1731 0.4996 0.018 Uiso calc U . R 1 . .
C C17 0.1605(4) 0.1558(4) 0.2918(2) 0.0113(7) Uani d . . . 1 . .
C C18 0.1324(5) 0.6173(5) -0.1318(3) 0.0200(9) Uani d . . . 1 . .
H H18 0.099 0.6865 -0.1807 0.024 Uiso calc U . R 1 . .
C C19 0.5762(5) -0.2864(5) 0.3941(3) 0.0157(8) Uani d . . . 1 . .
C C20 0.5874(5) -0.2821(5) 0.3015(3) 0.0184(9) Uani d . . . 1 . .
H H20 0.6515 -0.3623 0.2723 0.022 Uiso calc U . R 1 . .
C C21 0.1936(5) 0.6676(5) -0.0688(3) 0.0190(9) Uani d . . . 1 . .
H H21 0.1994 0.7722 -0.0745 0.023 Uiso calc U . R 1 . .
C C22 0.3224(5) 0.0937(4) 0.2417(3) 0.0127(8) Uani d . . . 1 . .
C C23 0.0679(5) -0.0999(5) 0.3028(3) 0.0164(8) Uani d . . . 1 . .
H H23 0.1763 -0.1296 0.2712 0.02 Uiso calc U . R 1 . .
C C24 0.4055(5) -0.0449(5) 0.2957(3) 0.0139(8) Uani d . . . 1 . .
C C25 0.1209(5) 0.4674(5) -0.1223(3) 0.0179(8) Uani d . . . 1 . .
H H25 0.0761 0.4335 -0.1639 0.022 Uiso calc U . R 1 . .
C C26 0.5059(5) -0.1622(5) 0.2536(3) 0.0185(8) Uani d . . . 1 . .
H H26 0.5173 -0.1582 0.1908 0.022 Uiso calc U . R 1 . .
C C27 0.1977(5) 0.1051(5) 0.0306(3) 0.0197(9) Uani d . . . 1 . .
H H27 0.1806 0.0035 0.0381 0.024 Uiso calc U . R 1 . .
C C28 0.0431(7) -0.2097(5) 0.3898(3) 0.0291(11) Uani d . . . 1 . .
H H28A 0.1135 -0.2002 0.4283 0.044 Uiso calc U . R 1 . .
H H28B 0.0639 -0.3141 0.3762 0.044 Uiso calc U . R 1 . .
H H28C -0.0641 -0.1852 0.4206 0.044 Uiso calc U . R 1 . .
C C29 0.2652(5) 0.1528(5) 0.0924(3) 0.0177(8) Uani d . . . 1 . .
C C30 -0.0427(6) -0.1107(5) 0.2418(3) 0.0239(9) Uani d . . . 1 . .
H H30A -0.1497 -0.0874 0.273 0.036 Uiso calc U . R 1 . .
H H30B -0.022 -0.2138 0.2263 0.036 Uiso calc U . R 1 . .
H H30C -0.027 -0.0378 0.1872 0.036 Uiso calc U . R 1 . .
C C33 0.6628(6) -0.4133(5) 0.5284(3) 0.0264(10) Uani d . . . 1 . .
H H33A 0.6962 -0.3228 0.5384 0.04 Uiso calc U . R 1 . .
H H33B 0.7326 -0.5045 0.5497 0.04 Uiso calc U . R 1 . .
H H33C 0.5573 -0.4165 0.561 0.04 Uiso calc U . R 1 . .
C C34 0.0467(5) 0.0635(4) 0.3205(2) 0.0127(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.891(4) ?
Br2 C6 . 1.906(4) ?
O4 C29 . 1.376(5) ?
O4 C22 . 1.460(4) ?
C1 C29 . 1.357(6) ?
C1 C10 . 1.460(5) ?
C1 C7 . 1.463(5) ?
O1 C19 . 1.365(5) ?
O1 C33 . 1.429(5) ?
C5 C11 . 1.379(6) ?
C5 C12 . 1.387(6) ?
C5 H5 . 0.95 ?
C6 C21 . 1.378(6) ?
C6 C7 . 1.424(6) ?
C7 C8 . 1.437(6) ?
C8 C13 . 1.408(6) ?
C8 C25 . 1.425(6) ?
C9 C10 . 1.327(6) ?
C9 C22 . 1.522(6) ?
C10 H10 . 0.95 ?
C11 C15 . 1.393(6) ?
C11 H11 . 0.95 ?
C12 C17 . 1.399(6) ?
C12 H12 . 0.95 ?
C13 C27 . 1.381(6) ?
C13 H13 . 0.95 ?
C14 C24 . 1.388(6) ?
C14 C16 . 1.392(5) ?
C14 H14 . 0.95 ?
C15 C34 . 1.399(6) ?
C15 H15 . 0.95 ?
C16 C19 . 1.392(6) ?
C16 H16 . 0.95 ?
C17 C34 . 1.408(5) ?
C17 C22 . 1.543(5) ?
C18 C25 . 1.367(7) ?
C18 C21 . 1.396(6) ?
C18 H18 . 0.95 ?
C19 C20 . 1.408(6) ?
C20 C26 . 1.370(6) ?
C20 H20 . 0.95 ?
C21 H21 . 0.95 ?
C22 C24 . 1.527(5) ?
C23 C34 . 1.524(5) ?
C23 C28 . 1.530(6) ?
C23 C30 . 1.534(6) ?
C23 H23 . 1.0 ?
C24 C26 . 1.406(6) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C27 C29 . 1.403(6) ?
C27 H27 . 0.95 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?
C33 H33A . 0.98 ?
C33 H33B . 0.98 ?
C33 H33C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C29 O4 C22 . . 116.6(3) ?
C29 C1 C10 . . 116.4(4) ?
C29 C1 C7 . . 119.0(4) ?
C10 C1 C7 . . 124.1(4) ?
C19 O1 C33 . . 117.2(3) ?
C11 C5 C12 . . 119.6(4) ?
C11 C5 H5 . . 120.2 ?
C12 C5 H5 . . 120.2 ?
C21 C6 C7 . . 121.9(4) ?
C21 C6 Br2 . . 114.9(3) ?
C7 C6 Br2 . . 122.9(3) ?
C6 C7 C8 . . 116.0(4) ?
C6 C7 C1 . . 126.8(4) ?
C8 C7 C1 . . 117.2(4) ?
C13 C8 C25 . . 119.6(4) ?
C13 C8 C7 . . 120.0(4) ?
C25 C8 C7 . . 120.3(4) ?
C10 C9 C22 . . 120.8(3) ?
C10 C9 Br1 . . 119.3(3) ?
C22 C9 Br1 . . 119.9(3) ?
C9 C10 C1 . . 118.4(4) ?
C9 C10 H10 . . 120.8 ?
C1 C10 H10 . . 120.8 ?
C5 C11 C15 . . 119.6(4) ?
C5 C11 H11 . . 120.2 ?
C15 C11 H11 . . 120.2 ?
C5 C12 C17 . . 121.7(4) ?
C5 C12 H12 . . 119.2 ?
C17 C12 H12 . . 119.2 ?
C27 C13 C8 . . 121.2(4) ?
C27 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
C24 C14 C16 . . 121.8(4) ?
C24 C14 H14 . . 119.1 ?
C16 C14 H14 . . 119.1 ?
C11 C15 C34 . . 121.8(4) ?
C11 C15 H15 . . 119.1 ?
C34 C15 H15 . . 119.1 ?
C19 C16 C14 . . 119.2(4) ?
C19 C16 H16 . . 120.4 ?
C14 C16 H16 . . 120.4 ?
C12 C17 C34 . . 119.1(4) ?
C12 C17 C22 . . 119.9(3) ?
C34 C17 C22 . . 121.1(3) ?
C25 C18 C21 . . 119.3(4) ?
C25 C18 H18 . . 120.3 ?
C21 C18 H18 . . 120.3 ?
O1 C19 C16 . . 124.9(4) ?
O1 C19 C20 . . 115.4(4) ?
C16 C19 C20 . . 119.7(4) ?
C26 C20 C19 . . 120.0(4) ?
C26 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C6 C21 C18 . . 121.3(4) ?
C6 C21 H21 . . 119.4 ?
C18 C21 H21 . . 119.4 ?
O4 C22 C9 . . 105.7(3) ?
O4 C22 C24 . . 105.6(3) ?
C9 C22 C24 . . 111.1(3) ?
O4 C22 C17 . . 109.4(3) ?
C9 C22 C17 . . 112.0(3) ?
C24 C22 C17 . . 112.6(3) ?
C34 C23 C28 . . 111.6(3) ?
C34 C23 C30 . . 109.9(3) ?
C28 C23 C30 . . 110.6(4) ?
C34 C23 H23 . . 108.2 ?
C28 C23 H23 . . 108.2 ?
C30 C23 H23 . . 108.2 ?
C14 C24 C26 . . 118.1(4) ?
C14 C24 C22 . . 120.5(4) ?
C26 C24 C22 . . 121.2(4) ?
C18 C25 C8 . . 121.0(4) ?
C18 C25 H25 . . 119.5 ?
C8 C25 H25 . . 119.5 ?
C20 C26 C24 . . 121.1(4) ?
C20 C26 H26 . . 119.4 ?
C24 C26 H26 . . 119.4 ?
C13 C27 C29 . . 118.7(4) ?
C13 C27 H27 . . 120.6 ?
C29 C27 H27 . . 120.6 ?
C23 C28 H28A . . 109.5 ?
C23 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C23 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C1 C29 O4 . . 121.3(4) ?
C1 C29 C27 . . 123.2(4) ?
O4 C29 C27 . . 115.2(4) ?
C23 C30 H30A . . 109.5 ?
C23 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C23 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
O1 C33 H33A . . 109.5 ?
O1 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
O1 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C15 C34 C17 . . 118.3(4) ?
C15 C34 C23 . . 117.3(4) ?
C17 C34 C23 . . 124.4(4) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichrolomethane/hexane/methanol mixed solvent'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1031282'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;
_chemical_name_systematic        2,3,3,10tetraphenyl3Hbenzo[f]chromene
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H26 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         486.58

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9865(6)
_cell_length_b                   10.5600(7)
_cell_length_c                   13.7281(8)
_cell_angle_alpha                86.2498(7)
_cell_angle_beta                 84.3378(7)
_cell_angle_gamma                64.1270(5)
_cell_volume                     1295.86(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3643
_cell_measurement_theta_min      2.3549
_cell_measurement_theta_max      25.3159
_cell_measurement_temperature    90.0(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512

_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6396
_diffrn_reflns_av_R_equivalents  0.0094
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_full        25.32
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             4641
_reflns_number_gt                4079
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0845
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_number_reflns         4641
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+0.4765P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.57932(9) 0.82987(8) 0.18055(6) 0.01899(19) Uani d . . . 1 . .
C C2 0.68209(12) 0.58188(12) 0.22333(8) 0.0160(2) Uani d . . . 1 . .
C C3 0.46633(13) 0.82123(12) 0.13667(8) 0.0178(2) Uani d . . . 1 . .
C C4 0.29661(13) 0.57458(12) 0.09600(8) 0.0177(2) Uani d . . . 1 . .
C C5 0.24227(13) 0.81419(13) 0.03455(8) 0.0194(3) Uani d . . . 1 . .
C C6 0.45439(13) 0.69560(12) 0.13641(8) 0.0167(2) Uani d . . . 1 . .
C C7 0.33220(13) 0.69261(12) 0.09057(8) 0.0172(2) Uani d . . . 1 . .
C C8 0.58363(12) 0.57195(12) 0.16807(8) 0.0161(2) Uani d . . . 1 . .
H H8 0.5986 0.4816 0.149 0.019 Uiso calc U . R 1 . .
C C9 0.37350(14) 0.94285(13) 0.08505(9) 0.0213(3) Uani d . . . 1 . .
H H9 0.3852 1.0273 0.0862 0.026 Uiso calc U . R 1 . .
C C10 0.36457(12) 0.45349(12) 0.16615(9) 0.0173(2) Uani d . . . 1 . .
C C11 0.80234(13) 0.32894(12) 0.27033(8) 0.0188(3) Uani d . . . 1 . .
H H11 0.7053 0.3323 0.2791 0.023 Uiso calc U . R 1 . .
C C12 0.81782(13) 0.45320(12) 0.24695(8) 0.0166(2) Uani d . . . 1 . .
C C13 1.08545(14) 0.31698(13) 0.25010(9) 0.0241(3) Uani d . . . 1 . .
H H13 1.1827 0.3133 0.2442 0.029 Uiso calc U . R 1 . .
C C14 0.13098(13) 0.81067(13) -0.01983(9) 0.0224(3) Uani d . . . 1 . .
H H14 0.0734 0.8909 -0.0583 0.027 Uiso calc U . R 1 . .
C C15 0.10483(13) 0.69415(13) -0.01803(9) 0.0234(3) Uani d . . . 1 . .
H H15 0.032 0.6921 -0.0566 0.028 Uiso calc U . R 1 . .
C C16 0.26669(13) 0.93727(13) 0.03343(9) 0.0217(3) Uani d . . . 1 . .
H H16 0.2071 1.0175 -0.0042 0.026 Uiso calc U . R 1 . .
C C17 0.18658(13) 0.57688(13) 0.04143(9) 0.0213(3) Uani d . . . 1 . .
H H17 0.1654 0.4972 0.0441 0.026 Uiso calc U . R 1 . .
C C18 0.44219(13) 0.31544(13) 0.13469(9) 0.0201(3) Uani d . . . 1 . .
H H18 0.453 0.2967 0.0669 0.024 Uiso calc U . R 1 . .
C C19 0.96249(13) 0.44483(13) 0.23828(9) 0.0201(3) Uani d . . . 1 . .
H H19 0.9764 0.5278 0.2241 0.024 Uiso calc U . R 1 . .
C C20 0.48601(14) 0.23094(14) 0.30101(10) 0.0255(3) Uani d . . . 1 . .
H H20 0.5288 0.1556 0.3468 0.031 Uiso calc U . R 1 . .
C C21 0.34597(13) 0.47802(13) 0.26636(9) 0.0198(3) Uani d . . . 1 . .
H H21 0.292 0.5714 0.289 0.024 Uiso calc U . R 1 . .
C C22 1.06810(14) 0.19416(13) 0.27055(9) 0.0243(3) Uani d . . . 1 . .
H H22 1.1529 0.1065 0.2773 0.029 Uiso calc U . R 1 . .
C C23 0.50382(14) 0.20500(13) 0.20174(10) 0.0236(3) Uani d . . . 1 . .
H H23 0.5583 0.1115 0.1795 0.028 Uiso calc U . R 1 . .
C C24 0.51370(13) 0.76758(12) 0.34488(8) 0.0179(2) Uani d . . . 1 . .
C C25 0.92592(14) 0.20097(13) 0.28096(9) 0.0221(3) Uani d . . . 1 . .
H H25 0.9129 0.1177 0.2955 0.027 Uiso calc U . R 1 . .
C C26 0.76769(13) 0.75468(12) 0.29133(9) 0.0195(3) Uani d . . . 1 . .
C C27 0.63842(13) 0.72872(12) 0.26143(8) 0.0172(2) Uani d . . . 1 . .
C C28 0.81525(14) 0.71749(14) 0.38516(10) 0.0252(3) Uani d . . . 1 . .
H H28 0.7655 0.6783 0.4313 0.03 Uiso calc U . R 1 . .
C C29 0.47530(13) 0.66869(13) 0.39565(8) 0.0201(3) Uani d . . . 1 . .
H H29 0.5271 0.5722 0.3794 0.024 Uiso calc U . R 1 . .
C C30 0.40529(14) 0.36766(14) 0.33307(9) 0.0235(3) Uani d . . . 1 . .
H H30 0.3907 0.3855 0.4011 0.028 Uiso calc U . R 1 . .
C C31 0.36098(15) 0.71055(14) 0.47033(9) 0.0256(3) Uani d . . . 1 . .
H H31 0.3351 0.6424 0.5048 0.031 Uiso calc U . R 1 . .
C C32 0.43728(15) 0.90773(13) 0.37065(10) 0.0263(3) Uani d . . . 1 . .
H H32 0.4633 0.9762 0.3367 0.032 Uiso calc U . R 1 . .
C C33 0.84226(14) 0.81145(13) 0.22452(10) 0.0239(3) Uani d . . . 1 . .
H H33 0.8111 0.8367 0.16 0.029 Uiso calc U . R 1 . .
C C34 0.28509(14) 0.85031(15) 0.49463(9) 0.0283(3) Uani d . . . 1 . .
H H34 0.2065 0.8786 0.5453 0.034 Uiso calc U . R 1 . .
C C35 0.96181(14) 0.83128(13) 0.25167(11) 0.0300(3) Uani d . . . 1 . .
H H35 1.0123 0.8698 0.2056 0.036 Uiso calc U . R 1 . .
C C36 0.32403(15) 0.94913(15) 0.44483(10) 0.0308(3) Uani d . . . 1 . .
H H36 0.2729 1.0454 0.4617 0.037 Uiso calc U . R 1 . .
C C37 0.93562(15) 0.73743(15) 0.41178(11) 0.0320(3) Uani d . . . 1 . .
H H37 0.9682 0.7111 0.4759 0.038 Uiso calc U . R 1 . .
C C38 1.00785(15) 0.79543(14) 0.34511(11) 0.0329(3) Uani d . . . 1 . .
H H38 1.0888 0.8105 0.3637 0.039 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.3696(14) ?
O1 C27 . 1.4650(14) ?
C2 C8 . 1.3419(16) ?
C2 C12 . 1.4868(16) ?
C2 C27 . 1.5295(16) ?
C3 C6 . 1.3831(17) ?
C3 C9 . 1.4080(17) ?
C4 C17 . 1.3806(17) ?
C4 C7 . 1.4334(17) ?
C4 C10 . 1.4945(16) ?
C5 C14 . 1.4133(17) ?
C5 C16 . 1.4220(18) ?
C5 C7 . 1.4308(16) ?
C6 C7 . 1.4401(16) ?
C6 C8 . 1.4578(16) ?
C8 H8 . 0.95 ?
C9 C16 . 1.3613(18) ?
C9 H9 . 0.95 ?
C10 C18 . 1.3938(17) ?
C10 C21 . 1.3959(17) ?
C11 C25 . 1.3873(17) ?
C11 C12 . 1.4004(16) ?
C11 H11 . 0.95 ?
C12 C19 . 1.4018(16) ?
C13 C19 . 1.3859(17) ?
C13 C22 . 1.3891(18) ?
C13 H13 . 0.95 ?
C14 C15 . 1.3632(18) ?
C14 H14 . 0.95 ?
C15 C17 . 1.4083(18) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C23 . 1.3896(17) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
C20 C30 . 1.3875(19) ?
C20 C23 . 1.3866(19) ?
C20 H20 . 0.95 ?
C21 C30 . 1.3830(17) ?
C21 H21 . 0.95 ?
C22 C25 . 1.3834(18) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?
C24 C32 . 1.3883(17) ?
C24 C29 . 1.3875(17) ?
C24 C27 . 1.5382(16) ?
C25 H25 . 0.95 ?
C26 C33 . 1.3923(17) ?
C26 C28 . 1.3895(18) ?
C26 C27 . 1.5292(16) ?
C28 C37 . 1.3930(19) ?
C28 H28 . 0.95 ?
C29 C31 . 1.3920(17) ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?
C31 C34 . 1.3793(19) ?
C31 H31 . 0.95 ?
C32 C36 . 1.3809(19) ?
C32 H32 . 0.95 ?
C33 C35 . 1.3872(18) ?
C33 H33 . 0.95 ?
C34 C36 . 1.384(2) ?
C34 H34 . 0.95 ?
C35 C38 . 1.379(2) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C37 C38 . 1.384(2) ?
C37 H37 . 0.95 ?
C38 H38 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C27 . . 115.32(8) ?
C8 C2 C12 . . 119.52(10) ?
C8 C2 C27 . . 115.22(10) ?
C12 C2 C27 . . 125.18(10) ?
O1 C3 C6 . . 120.99(10) ?
O1 C3 C9 . . 116.08(10) ?
C6 C3 C9 . . 122.67(11) ?
C17 C4 C7 . . 119.61(11) ?
C17 C4 C10 . . 117.99(11) ?
C7 C4 C10 . . 122.15(10) ?
C14 C5 C16 . . 120.56(11) ?
C14 C5 C7 . . 119.84(11) ?
C16 C5 C7 . . 119.60(11) ?
C3 C6 C7 . . 118.82(11) ?
C3 C6 C8 . . 115.08(10) ?
C7 C6 C8 . . 125.17(10) ?
C5 C7 C4 . . 117.90(11) ?
C5 C7 C6 . . 117.93(11) ?
C4 C7 C6 . . 124.16(11) ?
C2 C8 C6 . . 122.03(11) ?
C2 C8 H8 . . 119.0 ?
C6 C8 H8 . . 119.0 ?
C16 C9 C3 . . 118.82(11) ?
C16 C9 H9 . . 120.6 ?
C3 C9 H9 . . 120.6 ?
C18 C10 C21 . . 118.73(11) ?
C18 C10 C4 . . 121.85(11) ?
C21 C10 C4 . . 119.38(10) ?
C25 C11 C12 . . 121.31(11) ?
C25 C11 H11 . . 119.3 ?
C12 C11 H11 . . 119.3 ?
C19 C12 C11 . . 117.65(11) ?
C19 C12 C2 . . 124.15(10) ?
C11 C12 C2 . . 117.91(10) ?
C19 C13 C22 . . 120.72(11) ?
C19 C13 H13 . . 119.6 ?
C22 C13 H13 . . 119.6 ?
C15 C14 C5 . . 121.10(11) ?
C15 C14 H14 . . 119.5 ?
C5 C14 H14 . . 119.5 ?
C14 C15 C17 . . 119.55(11) ?
C14 C15 H15 . . 120.2 ?
C17 C15 H15 . . 120.2 ?
C9 C16 C5 . . 121.54(11) ?
C9 C16 H16 . . 119.2 ?
C5 C16 H16 . . 119.2 ?
C4 C17 C15 . . 121.75(12) ?
C4 C17 H17 . . 119.1 ?
C15 C17 H17 . . 119.1 ?
C23 C18 C10 . . 120.51(11) ?
C23 C18 H18 . . 119.7 ?
C10 C18 H18 . . 119.7 ?
C13 C19 C12 . . 120.77(11) ?
C13 C19 H19 . . 119.6 ?
C12 C19 H19 . . 119.6 ?
C30 C20 C23 . . 119.62(12) ?
C30 C20 H20 . . 120.2 ?
C23 C20 H20 . . 120.2 ?
C30 C21 C10 . . 120.63(11) ?
C30 C21 H21 . . 119.7 ?
C10 C21 H21 . . 119.7 ?
C25 C22 C13 . . 119.23(11) ?
C25 C22 H22 . . 120.4 ?
C13 C22 H22 . . 120.4 ?
C20 C23 C18 . . 120.18(12) ?
C20 C23 H23 . . 119.9 ?
C18 C23 H23 . . 119.9 ?
C32 C24 C29 . . 118.83(11) ?
C32 C24 C27 . . 118.31(11) ?
C29 C24 C27 . . 122.86(10) ?
C22 C25 C11 . . 120.28(11) ?
C22 C25 H25 . . 119.9 ?
C11 C25 H25 . . 119.9 ?
C33 C26 C28 . . 119.10(11) ?
C33 C26 C27 . . 120.77(11) ?
C28 C26 C27 . . 120.11(11) ?
O1 C27 C2 . . 107.44(9) ?
O1 C27 C26 . . 104.22(9) ?
C2 C27 C26 . . 115.27(9) ?
O1 C27 C24 . . 107.16(9) ?
C2 C27 C24 . . 111.82(9) ?
C26 C27 C24 . . 110.30(9) ?
C26 C28 C37 . . 120.25(13) ?
C26 C28 H28 . . 119.9 ?
C37 C28 H28 . . 119.9 ?
C24 C29 C31 . . 120.14(12) ?
C24 C29 H29 . . 119.9 ?
C31 C29 H29 . . 119.9 ?
C21 C30 C20 . . 120.30(12) ?
C21 C30 H30 . . 119.9 ?
C20 C30 H30 . . 119.9 ?
C34 C31 C29 . . 120.44(12) ?
C34 C31 H31 . . 119.8 ?
C29 C31 H31 . . 119.8 ?
C36 C32 C24 . . 120.98(12) ?
C36 C32 H32 . . 119.5 ?
C24 C32 H32 . . 119.5 ?
C35 C33 C26 . . 120.30(13) ?
C35 C33 H33 . . 119.8 ?
C26 C33 H33 . . 119.8 ?
C31 C34 C36 . . 119.61(12) ?
C31 C34 H34 . . 120.2 ?
C36 C34 H34 . . 120.2 ?
C38 C35 C33 . . 120.44(13) ?
C38 C35 H35 . . 119.8 ?
C33 C35 H35 . . 119.8 ?
C32 C36 C34 . . 119.99(12) ?
C32 C36 H36 . . 120.0 ?
C34 C36 H36 . . 120.0 ?
C38 C37 C28 . . 120.16(13) ?
C38 C37 H37 . . 119.9 ?
C28 C37 H37 . . 119.9 ?
C35 C38 C37 . . 119.75(12) ?
C35 C38 H38 . . 120.1 ?
C37 C38 H38 . . 120.1 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichrolomethane/hexane/methanol mixed solvent'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1031283'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;
_chemical_name_systematic        
2bromo3(2isopropylphenyl)3(4methoxyphenyl)3Hbenzo[f]chromene
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H25 Br O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         485.40

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4379(3)
_cell_length_b                   16.1157(6)
_cell_length_c                   16.8070(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.4400(5)
_cell_angle_gamma                90
_cell_volume                     2240.06(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7268
_cell_measurement_theta_min      2.4728
_cell_measurement_theta_max      26.0262
_cell_measurement_temperature    90.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000

_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.52

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11385
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4403
_reflns_number_gt                4044
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0601
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         4403
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+1.1707P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.95082(2) 0.36305(2) 0.77251(2) 0.02136(6) Uani d . . . 1 . .
O O1 0.63999(12) 0.34568(6) 0.54907(6) 0.0156(2) Uani d . . . 1 . .
O O2 0.32143(13) 0.43541(7) 0.84642(7) 0.0211(2) Uani d . . . 1 . .
C C3 0.87061(18) 0.35397(9) 0.65954(9) 0.0144(3) Uani d . . . 1 . .
C C5 0.74282(18) 0.35390(9) 0.49545(9) 0.0147(3) Uani d . . . 1 . .
C C6 0.86864(18) 0.17994(10) 0.64938(9) 0.0172(3) Uani d . . . 1 . .
H H6 0.9621 0.2134 0.6657 0.021 Uiso calc U . R 1 . .
C C8 0.71836(18) 0.21799(9) 0.62550(8) 0.0142(3) Uani d . . . 1 . .
C C9 0.96167(18) 0.38106(9) 0.60871(9) 0.0155(3) Uani d . . . 1 . .
H H9 1.0639 0.4057 0.6292 0.019 Uiso calc U . R 1 . .
C C10 0.7656(2) 0.36369(9) 0.35577(9) 0.0180(3) Uani d . . . 1 . .
H H10 0.7184 0.3597 0.2997 0.022 Uiso calc U . R 1 . .
C C11 0.7491(2) 0.04529(10) 0.62763(10) 0.0229(3) Uani d . . . 1 . .
H H11 0.7582 -0.0135 0.6299 0.027 Uiso calc U . R 1 . .
C C12 0.40751(18) 0.44196(9) 0.72251(9) 0.0169(3) Uani d . . . 1 . .
H H12 0.3447 0.4909 0.7105 0.02 Uiso calc U . R 1 . .
C C13 0.57983(18) 0.16866(10) 0.59908(9) 0.0167(3) Uani d . . . 1 . .
C C14 0.90388(18) 0.37272(9) 0.52179(9) 0.0145(3) Uani d . . . 1 . .
C C15 0.70607(17) 0.31301(9) 0.63013(8) 0.0137(3) Uani d . . . 1 . .
C C16 0.58883(17) 0.34048(9) 0.68378(9) 0.0138(3) Uani d . . . 1 . .
C C17 0.8849(2) 0.09419(10) 0.64979(9) 0.0205(3) Uani d . . . 1 . .
H H17 0.9887 0.0694 0.6652 0.025 Uiso calc U . R 1 . .
C C18 0.50066(17) 0.41382(9) 0.66871(9) 0.0155(3) Uani d . . . 1 . .
H H18 0.5044 0.4449 0.6211 0.019 Uiso calc U . R 1 . .
C C19 0.40556(17) 0.39865(10) 0.79427(9) 0.0163(3) Uani d . . . 1 . .
C C20 0.57933(18) 0.29580(9) 0.75349(9) 0.0160(3) Uani d . . . 1 . .
H H20 0.6359 0.2447 0.7637 0.019 Uiso calc U . R 1 . .
C C21 1.1884(2) 0.42363(10) 0.34538(10) 0.0224(3) Uani d . . . 1 . .
H H21 1.2514 0.4363 0.306 0.027 Uiso calc U . R 1 . .
C C22 1.2600(2) 0.42449(10) 0.42861(10) 0.0216(3) Uani d . . . 1 . .
H H22 1.3717 0.4371 0.445 0.026 Uiso calc U . R 1 . .
C C23 0.67207(19) 0.34853(9) 0.41221(9) 0.0167(3) Uani d . . . 1 . .
H H23 0.5611 0.3346 0.3955 0.02 Uiso calc U . R 1 . .
C C24 0.93134(19) 0.38524(9) 0.37916(9) 0.0170(3) Uani d . . . 1 . .
C C25 0.41347(18) 0.20445(10) 0.56374(9) 0.0193(3) Uani d . . . 1 . .
H H25 0.4211 0.2662 0.5689 0.023 Uiso calc U . R 1 . .
C C26 1.16984(19) 0.40735(10) 0.48616(10) 0.0190(3) Uani d . . . 1 . .
H H26 1.2199 0.4084 0.542 0.023 Uiso calc U . R 1 . .
C C27 0.48867(18) 0.32440(10) 0.80869(9) 0.0167(3) Uani d . . . 1 . .
H H27 0.4839 0.2931 0.856 0.02 Uiso calc U . R 1 . .
C C28 1.0277(2) 0.40445(9) 0.32135(10) 0.0204(3) Uani d . . . 1 . .
H H28 0.9802 0.404 0.2652 0.024 Uiso calc U . R 1 . .
C C29 0.5989(2) 0.08232(10) 0.60198(10) 0.0216(3) Uani d . . . 1 . .
H H29 0.5065 0.0481 0.5859 0.026 Uiso calc U . R 1 . .
C C30 1.00287(18) 0.38810(9) 0.46336(9) 0.0155(3) Uani d . . . 1 . .
C C31 0.3245(2) 0.39453(13) 0.92210(11) 0.0314(4) Uani d . . . 1 . .
H H31A 0.2808 0.3383 0.9121 0.047 Uiso calc U . R 1 . .
H H31B 0.2586 0.4257 0.9537 0.047 Uiso calc U . R 1 . .
H H31C 0.4361 0.3915 0.9525 0.047 Uiso calc U . R 1 . .
C C32 0.3685(2) 0.18360(12) 0.47296(10) 0.0291(4) Uani d . . . 1 . .
H H32A 0.4556 0.2017 0.4461 0.044 Uiso calc U . R 1 . .
H H32B 0.2681 0.2123 0.4487 0.044 Uiso calc U . R 1 . .
H H32C 0.3531 0.1236 0.4661 0.044 Uiso calc U . R 1 . .
C C33 0.2809(2) 0.17523(13) 0.60796(11) 0.0306(4) Uani d . . . 1 . .
H H33A 0.2736 0.1146 0.6057 0.046 Uiso calc U . R 1 . .
H H33B 0.177 0.1993 0.5817 0.046 Uiso calc U . R 1 . .
H H33C 0.3074 0.1932 0.6648 0.046 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C3 . 1.8906(15) ?
O1 C5 . 1.3757(18) ?
O1 C15 . 1.4638(17) ?
O2 C19 . 1.3674(18) ?
O2 C31 . 1.428(2) ?
C3 C9 . 1.331(2) ?
C3 C15 . 1.528(2) ?
C5 C14 . 1.377(2) ?
C5 C23 . 1.411(2) ?
C6 C17 . 1.389(2) ?
C6 C8 . 1.394(2) ?
C6 H6 . 0.95 ?
C8 C13 . 1.411(2) ?
C8 C15 . 1.538(2) ?
C9 C14 . 1.452(2) ?
C9 H9 . 0.95 ?
C10 C23 . 1.371(2) ?
C10 C24 . 1.418(2) ?
C10 H10 . 0.95 ?
C11 C17 . 1.380(2) ?
C11 C29 . 1.389(2) ?
C11 H11 . 0.95 ?
C12 C18 . 1.387(2) ?
C12 C19 . 1.396(2) ?
C12 H12 . 0.95 ?
C13 C29 . 1.401(2) ?
C13 C25 . 1.525(2) ?
C14 C30 . 1.431(2) ?
C15 C16 . 1.530(2) ?
C16 C20 . 1.391(2) ?
C16 C18 . 1.393(2) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 C27 . 1.384(2) ?
C20 C27 . 1.393(2) ?
C20 H20 . 0.95 ?
C21 C28 . 1.371(2) ?
C21 C22 . 1.409(2) ?
C21 H21 . 0.95 ?
C22 C26 . 1.372(2) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?
C24 C28 . 1.419(2) ?
C24 C30 . 1.425(2) ?
C25 C32 . 1.535(2) ?
C25 C33 . 1.535(2) ?
C25 H25 . 1.0 ?
C26 C30 . 1.419(2) ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?
C28 H28 . 0.95 ?
C29 H29 . 0.95 ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
C33 H33A . 0.98 ?
C33 H33B . 0.98 ?
C33 H33C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C15 . . 118.10(11) ?
C19 O2 C31 . . 116.82(13) ?
C9 C3 C15 . . 122.49(13) ?
C9 C3 Br1 . . 118.81(12) ?
C15 C3 Br1 . . 118.66(10) ?
O1 C5 C14 . . 121.41(13) ?
O1 C5 C23 . . 116.48(13) ?
C14 C5 C23 . . 121.93(14) ?
C17 C6 C8 . . 121.52(15) ?
C17 C6 H6 . . 119.2 ?
C8 C6 H6 . . 119.2 ?
C6 C8 C13 . . 119.50(14) ?
C6 C8 C15 . . 119.34(13) ?
C13 C8 C15 . . 121.14(13) ?
C3 C9 C14 . . 119.61(14) ?
C3 C9 H9 . . 120.2 ?
C14 C9 H9 . . 120.2 ?
C23 C10 C24 . . 121.54(14) ?
C23 C10 H10 . . 119.2 ?
C24 C10 H10 . . 119.2 ?
C17 C11 C29 . . 119.74(15) ?
C17 C11 H11 . . 120.1 ?
C29 C11 H11 . . 120.1 ?
C18 C12 C19 . . 120.34(14) ?
C18 C12 H12 . . 119.8 ?
C19 C12 H12 . . 119.8 ?
C29 C13 C8 . . 117.82(14) ?
C29 C13 C25 . . 118.68(14) ?
C8 C13 C25 . . 123.43(14) ?
C5 C14 C30 . . 119.38(14) ?
C5 C14 C9 . . 117.19(13) ?
C30 C14 C9 . . 123.30(14) ?
O1 C15 C3 . . 107.44(11) ?
O1 C15 C16 . . 105.84(11) ?
C3 C15 C16 . . 109.66(12) ?
O1 C15 C8 . . 109.15(11) ?
C3 C15 C8 . . 112.36(12) ?
C16 C15 C8 . . 112.07(12) ?
C20 C16 C18 . . 118.33(14) ?
C20 C16 C15 . . 119.91(13) ?
C18 C16 C15 . . 121.52(13) ?
C11 C17 C6 . . 119.38(15) ?
C11 C17 H17 . . 120.3 ?
C6 C17 H17 . . 120.3 ?
C12 C18 C16 . . 120.68(14) ?
C12 C18 H18 . . 119.7 ?
C16 C18 H18 . . 119.7 ?
O2 C19 C27 . . 124.88(14) ?
O2 C19 C12 . . 115.70(14) ?
C27 C19 C12 . . 119.41(14) ?
C16 C20 C27 . . 121.38(14) ?
C16 C20 H20 . . 119.3 ?
C27 C20 H20 . . 119.3 ?
C28 C21 C22 . . 119.91(14) ?
C28 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C26 C22 C21 . . 120.62(15) ?
C26 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C10 C23 C5 . . 119.13(14) ?
C10 C23 H23 . . 120.4 ?
C5 C23 H23 . . 120.4 ?
C10 C24 C28 . . 122.05(14) ?
C10 C24 C30 . . 118.90(14) ?
C28 C24 C30 . . 119.04(14) ?
C13 C25 C32 . . 109.36(13) ?
C13 C25 C33 . . 113.49(14) ?
C32 C25 C33 . . 110.73(14) ?
C13 C25 H25 . . 107.7 ?
C32 C25 H25 . . 107.7 ?
C33 C25 H25 . . 107.7 ?
C22 C26 C30 . . 120.88(15) ?
C22 C26 H26 . . 119.6 ?
C30 C26 H26 . . 119.6 ?
C19 C27 C20 . . 119.72(14) ?
C19 C27 H27 . . 120.1 ?
C20 C27 H27 . . 120.1 ?
C21 C28 C24 . . 120.99(15) ?
C21 C28 H28 . . 119.5 ?
C24 C28 H28 . . 119.5 ?
C11 C29 C13 . . 121.94(15) ?
C11 C29 H29 . . 119.0 ?
C13 C29 H29 . . 119.0 ?
C26 C30 C24 . . 118.53(14) ?
C26 C30 C14 . . 122.40(14) ?
C24 C30 C14 . . 119.07(14) ?
O2 C31 H31A . . 109.5 ?
O2 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
O2 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C25 C32 H32A . . 109.5 ?
C25 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C25 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C25 C33 H33A . . 109.5 ?
C25 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C25 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichrolomethane/hexane mixed solvent'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_140324_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1031284'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        3,3diphenyl2(pyren1yl)3Hbenzo[f]chromene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H26 O'
_chemical_formula_weight         534.62

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   41.059(2)
_cell_length_b                   10.4431(6)
_cell_length_c                   13.0847(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.5570(10)
_cell_angle_gamma                90
_cell_volume                     5548.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             2240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12608
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.006
_diffrn_reflns_theta_max         24.708
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             4734
_reflns_number_gt                4098
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.0978P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4734
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_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
O1 O 0.09743(2) 1.03450(7) 0.71160(5) 0.0189(2) Uani 1 1 d . . . . .
C1 C 0.17755(3) 0.94599(11) 0.50345(8) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.08206(3) 1.31473(11) 0.53965(9) 0.0198(3) Uani 1 1 d . . . . .
C3 C 0.05179(3) 1.33317(11) 0.68673(9) 0.0221(3) Uani 1 1 d . . . . .
H3 H 0.0373 1.3793 0.7234 0.027 Uiso 1 1 calc R U . . .
C4 C 0.22990(3) 0.91200(11) 0.43453(9) 0.0216(3) Uani 1 1 d . . . . .
C5 C 0.05983(3) 1.38423(11) 0.59326(9) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.12196(3) 0.99240(11) 0.55637(8) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.18274(3) 0.76953(11) 0.38100(9) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.12086(3) 0.82966(11) 0.69627(8) 0.0177(3) Uani 1 1 d . . . . .
C9 C 0.19666(3) 0.87569(11) 0.43982(9) 0.0190(3) Uani 1 1 d . . . . .
C10 C 0.09506(3) 1.19535(11) 0.58071(9) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.13166(3) 0.80357(11) 0.44814(8) 0.0209(3) Uani 1 1 d . . . . .
H11 H 0.1097 0.7773 0.4515 0.025 Uiso 1 1 calc R U . . .
C12 C 0.15036(3) 0.73442(12) 0.38768(9) 0.0230(3) Uani 1 1 d . . . . .
H12 H 0.1410 0.6621 0.3502 0.028 Uiso 1 1 calc R U . . .
C13 C 0.22499(3) 1.08309(12) 0.55942(10) 0.0255(3) Uani 1 1 d . . . . .
H13 H 0.2346 1.1518 0.6010 0.031 Uiso 1 1 calc R U . . .
C14 C 0.02190(3) 0.88271(12) 0.44432(10) 0.0263(3) Uani 1 1 d . . . . .
H14 H 0.0137 0.8963 0.3734 0.032 Uiso 1 1 calc R U . . .
C15 C 0.14699(3) 0.86222(11) 0.77247(8) 0.0197(3) Uani 1 1 d . . . . .
H15 H 0.1517 0.9497 0.7879 0.024 Uiso 1 1 calc R U . . .
C16 C 0.08554(3) 1.14968(11) 0.67084(8) 0.0179(3) Uani 1 1 d . . . . .
C17 C 0.11779(3) 1.11656(11) 0.53311(9) 0.0199(3) Uani 1 1 d . . . . .
H17 H 0.1300 1.1540 0.4844 0.024 Uiso 1 1 calc R U . . .
C18 C 0.24917(3) 0.84103(12) 0.37200(9) 0.0250(3) Uani 1 1 d . . . . .
C19 C 0.19361(3) 1.04817(11) 0.56551(9) 0.0219(3) Uani 1 1 d . . . . .
H19 H 0.1818 1.0923 0.6120 0.026 Uiso 1 1 calc R U . . .
C20 C 0.24412(3) 1.01894(12) 0.49172(9) 0.0241(3) Uani 1 1 d . . . . .
C21 C 0.04563(3) 1.49913(12) 0.54969(9) 0.0236(3) Uani 1 1 d . . . . .
H21 H 0.0305 1.5449 0.5844 0.028 Uiso 1 1 calc R U . . .
C22 C 0.23430(3) 0.73390(12) 0.31446(10) 0.0292(3) Uani 1 1 d . . . . .
H22 H 0.2469 0.6854 0.2730 0.035 Uiso 1 1 calc R U . . .
C23 C 0.28164(3) 0.87841(14) 0.36900(10) 0.0321(3) Uani 1 1 d . . . . .
H23 H 0.2948 0.8300 0.3293 0.039 Uiso 1 1 calc R U . . .
C24 C 0.08948(3) 1.36559(12) 0.44555(10) 0.0273(3) Uani 1 1 d . . . . .
H24 H 0.1043 1.3211 0.4088 0.033 Uiso 1 1 calc R U . . .
C25 C 0.06444(3) 1.21915(12) 0.72525(8) 0.0219(3) Uani 1 1 d . . . . .
H25 H 0.0590 1.1871 0.7885 0.026 Uiso 1 1 calc R U . . .
C26 C 0.05329(3) 1.54507(12) 0.45851(10) 0.0284(3) Uani 1 1 d . . . . .
H26 H 0.0435 1.6222 0.4301 0.034 Uiso 1 1 calc R U . . .
C27 C 0.06662(3) 0.89563(11) 0.58655(9) 0.0188(3) Uani 1 1 d . . . . .
C28 C 0.27634(3) 1.05456(13) 0.48274(10) 0.0307(3) Uani 1 1 d . . . . .
H28 H 0.2857 1.1282 0.5185 0.037 Uiso 1 1 calc R U . . .
C29 C 0.05424(3) 0.91636(11) 0.48305(9) 0.0218(3) Uani 1 1 d . . . . .
H29 H 0.0679 0.9536 0.4385 0.026 Uiso 1 1 calc R U . . .
C30 C 0.14426(3) 0.91105(11) 0.50430(8) 0.0185(3) Uani 1 1 d . . . . .
C31 C 0.10142(3) 0.93565(11) 0.63440(8) 0.0176(3) Uani 1 1 d . . . . .
C32 C 0.13393(3) 0.60618(11) 0.72689(9) 0.0216(3) Uani 1 1 d . . . . .
H32 H 0.1296 0.5186 0.7105 0.026 Uiso 1 1 calc R U . . .
C33 C 0.11461(3) 0.70110(11) 0.67368(9) 0.0200(3) Uani 1 1 d . . . . .
H33 H 0.0970 0.6779 0.6214 0.024 Uiso 1 1 calc R U . . .
C34 C 0.07563(3) 1.47788(13) 0.40677(11) 0.0318(3) Uani 1 1 d . . . . .
H34 H 0.0812 1.5110 0.3440 0.038 Uiso 1 1 calc R U . . .
C35 C 0.20286(3) 0.70077(12) 0.31808(9) 0.0267(3) Uani 1 1 d . . . . .
H35 H 0.1936 0.6301 0.2781 0.032 Uiso 1 1 calc R U . . .
C36 C 0.15946(3) 0.63903(12) 0.80362(9) 0.0230(3) Uani 1 1 d . . . . .
H36 H 0.1724 0.5742 0.8409 0.028 Uiso 1 1 calc R U . . .
C37 C 0.16610(3) 0.76716(12) 0.82588(9) 0.0227(3) Uani 1 1 d . . . . .
H37 H 0.1838 0.7899 0.8780 0.027 Uiso 1 1 calc R U . . .
C38 C 0.04588(3) 0.84316(11) 0.65088(10) 0.0242(3) Uani 1 1 d . . . . .
H38 H 0.0539 0.8297 0.7220 0.029 Uiso 1 1 calc R U . . .
C39 C 0.00180(3) 0.83000(12) 0.50815(11) 0.0299(3) Uani 1 1 d . . . . .
H39 H -0.0202 0.8070 0.4813 0.036 Uiso 1 1 calc R U . . .
C40 C 0.29497(3) 0.98450(14) 0.42271(10) 0.0343(3) Uani 1 1 d . . . . .
H40 H 0.3170 1.0095 0.4185 0.041 Uiso 1 1 calc R U . . .
C41 C 0.01370(3) 0.81046(12) 0.61184(10) 0.0294(3) Uani 1 1 d . . . . .
H41 H -0.0002 0.7746 0.6562 0.035 Uiso 1 1 calc R U . . .


_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 C16 1.3755(14) . ?
O1 C31 1.4704(13) . ?
C1 C30 1.4163(16) . ?
C1 C9 1.4293(16) . ?
C1 C19 1.4400(16) . ?
C2 C24 1.4152(17) . ?
C2 C10 1.4291(16) . ?
C2 C5 1.4293(16) . ?
C3 C25 1.3653(17) . ?
C3 C5 1.4174(17) . ?
C3 H3 0.9500 . ?
C4 C20 1.4207(17) . ?
C4 C18 1.4275(17) . ?
C4 C9 1.4278(17) . ?
C5 C21 1.4162(17) . ?
C6 C17 1.3370(16) . ?
C6 C30 1.4867(16) . ?
C6 C31 1.5363(15) . ?
C7 C12 1.3940(17) . ?
C7 C9 1.4204(17) . ?
C7 C35 1.4417(16) . ?
C8 C33 1.3904(16) . ?
C8 C15 1.3937(16) . ?
C8 C31 1.5249(15) . ?
C10 C16 1.3814(16) . ?
C10 C17 1.4523(16) . ?
C11 C12 1.3851(16) . ?
C11 C30 1.3979(16) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C19 1.3527(18) . ?
C13 C20 1.4345(18) . ?
C13 H13 0.9500 . ?
C14 C39 1.3735(19) . ?
C14 C29 1.3942(17) . ?
C14 H14 0.9500 . ?
C15 C37 1.3879(16) . ?
C15 H15 0.9500 . ?
C16 C25 1.4025(16) . ?
C17 H17 0.9500 . ?
C18 C23 1.3952(19) . ?
C18 C22 1.4333(18) . ?
C19 H19 0.9500 . ?
C20 C28 1.3961(18) . ?
C21 C26 1.3653(18) . ?
C21 H21 0.9500 . ?
C22 C35 1.3442(18) . ?
C22 H22 0.9500 . ?
C23 C40 1.381(2) . ?
C23 H23 0.9500 . ?
C24 C34 1.3676(18) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C34 1.4062(19) . ?
C26 H26 0.9500 . ?
C27 C29 1.3907(17) . ?
C27 C38 1.3954(17) . ?
C27 C31 1.5305(16) . ?
C28 C40 1.384(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C32 C36 1.3826(18) . ?
C32 C33 1.3899(16) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.3878(18) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C41 1.3866(17) . ?
C38 H38 0.9500 . ?
C39 C41 1.387(2) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?

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
C16 O1 C31 114.64(8) . . ?
C30 C1 C9 119.11(10) . . ?
C30 C1 C19 123.23(10) . . ?
C9 C1 C19 117.65(10) . . ?
C24 C2 C10 122.53(11) . . ?
C24 C2 C5 118.19(11) . . ?
C10 C2 C5 119.24(10) . . ?
C25 C3 C5 121.47(10) . . ?
C25 C3 H3 119.3 . . ?
C5 C3 H3 119.3 . . ?
C20 C4 C18 119.37(11) . . ?
C20 C4 C9 120.28(11) . . ?
C18 C4 C9 120.35(11) . . ?
C21 C5 C3 122.10(11) . . ?
C21 C5 C2 119.17(11) . . ?
C3 C5 C2 118.70(11) . . ?
C17 C6 C30 121.09(10) . . ?
C17 C6 C31 117.46(10) . . ?
C30 C6 C31 121.36(10) . . ?
C12 C7 C9 118.82(10) . . ?
C12 C7 C35 122.52(11) . . ?
C9 C7 C35 118.65(11) . . ?
C33 C8 C15 119.06(11) . . ?
C33 C8 C31 121.50(10) . . ?
C15 C8 C31 119.29(10) . . ?
C7 C9 C4 119.45(10) . . ?
C7 C9 C1 120.32(11) . . ?
C4 C9 C1 120.23(11) . . ?
C16 C10 C2 119.01(10) . . ?
C16 C10 C17 116.88(10) . . ?
C2 C10 C17 124.12(10) . . ?
C12 C11 C30 121.71(11) . . ?
C12 C11 H11 119.1 . . ?
C30 C11 H11 119.1 . . ?
C11 C12 C7 120.90(11) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C19 C13 C20 121.62(11) . . ?
C19 C13 H13 119.2 . . ?
C20 C13 H13 119.2 . . ?
C39 C14 C29 120.39(12) . . ?
C39 C14 H14 119.8 . . ?
C29 C14 H14 119.8 . . ?
C37 C15 C8 120.20(11) . . ?
C37 C15 H15 119.9 . . ?
C8 C15 H15 119.9 . . ?
O1 C16 C10 120.24(10) . . ?
O1 C16 C25 117.77(10) . . ?
C10 C16 C25 121.96(11) . . ?
C6 C17 C10 121.36(10) . . ?
C6 C17 H17 119.3 . . ?
C10 C17 H17 119.3 . . ?
C23 C18 C4 118.98(12) . . ?
C23 C18 C22 122.53(12) . . ?
C4 C18 C22 118.50(11) . . ?
C13 C19 C1 121.80(11) . . ?
C13 C19 H19 119.1 . . ?
C1 C19 H19 119.1 . . ?
C28 C20 C4 119.05(11) . . ?
C28 C20 C13 122.72(12) . . ?
C4 C20 C13 118.19(11) . . ?
C26 C21 C5 121.00(11) . . ?
C26 C21 H21 119.5 . . ?
C5 C21 H21 119.5 . . ?
C35 C22 C18 121.25(11) . . ?
C35 C22 H22 119.4 . . ?
C18 C22 H22 119.4 . . ?
C40 C23 C18 121.21(12) . . ?
C40 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
C34 C24 C2 120.87(12) . . ?
C34 C24 H24 119.6 . . ?
C2 C24 H24 119.6 . . ?
C3 C25 C16 119.57(10) . . ?
C3 C25 H25 120.2 . . ?
C16 C25 H25 120.2 . . ?
C21 C26 C34 119.80(11) . . ?
C21 C26 H26 120.1 . . ?
C34 C26 H26 120.1 . . ?
C29 C27 C38 118.76(11) . . ?
C29 C27 C31 122.65(10) . . ?
C38 C27 C31 118.48(10) . . ?
C40 C28 C20 121.17(13) . . ?
C40 C28 H28 119.4 . . ?
C20 C28 H28 119.4 . . ?
C27 C29 C14 120.33(11) . . ?
C27 C29 H29 119.8 . . ?
C14 C29 H29 119.8 . . ?
C11 C30 C1 119.00(10) . . ?
C11 C30 C6 119.65(10) . . ?
C1 C30 C6 121.15(10) . . ?
O1 C31 C8 104.35(8) . . ?
O1 C31 C27 106.27(8) . . ?
C8 C31 C27 113.71(9) . . ?
O1 C31 C6 108.30(9) . . ?
C8 C31 C6 109.70(9) . . ?
C27 C31 C6 113.87(9) . . ?
C36 C32 C33 120.08(11) . . ?
C36 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C8 120.58(11) . . ?
C32 C33 H33 119.7 . . ?
C8 C33 H33 119.7 . . ?
C24 C34 C26 120.96(12) . . ?
C24 C34 H34 119.5 . . ?
C26 C34 H34 119.5 . . ?
C22 C35 C7 121.80(12) . . ?
C22 C35 H35 119.1 . . ?
C7 C35 H35 119.1 . . ?
C32 C36 C37 119.72(11) . . ?
C32 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C36 C37 C15 120.35(11) . . ?
C36 C37 H37 119.8 . . ?
C15 C37 H37 119.8 . . ?
C41 C38 C27 120.54(11) . . ?
C41 C38 H38 119.7 . . ?
C27 C38 H38 119.7 . . ?
C14 C39 C41 119.84(12) . . ?
C14 C39 H39 120.1 . . ?
C41 C39 H39 120.1 . . ?
C23 C40 C28 120.16(12) . . ?
C23 C40 H40 119.9 . . ?
C28 C40 H40 119.9 . . ?
C38 C41 C39 120.12(12) . . ?
C38 C41 H41 119.9 . . ?
C39 C41 H41 119.9 . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/ethyl acetate mixed solvent'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_140909_0m
_database_code_depnum_ccdc_archive 'CCDC 1031285'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
10bromo3(2isopropylphenyl)3(4methoxyphenyl)3Hbenzo[f]chromene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H25 Br O2'
_chemical_formula_weight         485.40

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4457(4)
_cell_length_b                   15.2032(7)
_cell_length_c                   17.4327(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.8463(6)
_cell_angle_gamma                90
_cell_volume                     2235.63(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.863
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.605
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11698
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.778
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4568
_reflns_number_gt                4216
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0309P)²+1.0960P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4568
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0619
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.004
_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
Br1 Br 0.38417(2) 1.04998(2) 0.13524(2) 0.02928(6) Uani 1 1 d . . . . .
O2 O 0.49515(12) 0.36048(6) 0.18640(6) 0.0193(2) Uani 1 1 d . . . . .
O1 O 0.21515(11) 0.70794(6) 0.04481(5) 0.01414(19) Uani 1 1 d . . . . .
C1 C 0.38362(15) 0.84567(9) 0.10788(8) 0.0157(3) Uani 1 1 d . . . . .
H1 H 0.4640 0.8875 0.1211 0.019 Uiso 1 1 calc R U . . .
C2 C 0.44126(15) 0.44360(8) 0.16942(8) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.28838(16) 1.03185(9) 0.03503(8) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.23841(15) 0.94741(9) 0.00724(8) 0.0147(3) Uani 1 1 d . . . . .
C5 C 0.14582(16) 0.94852(9) -0.06419(8) 0.0161(3) Uani 1 1 d . . . . .
C6 C 0.09274(15) 0.71934(8) 0.16858(7) 0.0138(3) Uani 1 1 d . . . . .
C7 C 0.26875(15) 0.86373(9) 0.04404(7) 0.0138(3) Uani 1 1 d . . . . .
C8 C 0.11548(16) 1.02834(10) -0.10431(8) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.0532 1.0275 -0.1512 0.023 Uiso 1 1 calc R U . . .
C9 C 0.08604(16) 0.78574(9) 0.22374(8) 0.0166(3) Uani 1 1 d . . . . .
H9 H 0.1761 0.8221 0.2340 0.020 Uiso 1 1 calc R U . . .
C10 C -0.04984(18) 0.79956(9) 0.26393(8) 0.0198(3) Uani 1 1 d . . . . .
H10 H -0.0525 0.8453 0.3010 0.024 Uiso 1 1 calc R U . . .
C11 C 0.47317(15) 0.48936(9) 0.10303(8) 0.0153(3) Uani 1 1 d . . . . .
H11 H 0.5379 0.4638 0.0660 0.018 Uiso 1 1 calc R U . . .
C12 C 0.31371(14) 0.61201(9) 0.14388(7) 0.0130(3) Uani 1 1 d . . . . .
C13 C 0.37607(15) 0.77110(9) 0.14749(8) 0.0153(3) Uani 1 1 d . . . . .
H13 H 0.4520 0.7598 0.1884 0.018 Uiso 1 1 calc R U . . .
C14 C 0.28779(16) 0.56651(9) 0.21166(8) 0.0161(3) Uani 1 1 d . . . . .
H14 H 0.2267 0.5931 0.2497 0.019 Uiso 1 1 calc R U . . .
C15 C 0.08194(16) 0.86912(9) -0.09495(8) 0.0169(3) Uani 1 1 d . . . . .
H15 H 0.0229 0.8702 -0.1428 0.020 Uiso 1 1 calc R U . . .
C16 C 0.40974(15) 0.57289(9) 0.09114(8) 0.0147(3) Uani 1 1 d . . . . .
H16 H 0.4326 0.6041 0.0458 0.018 Uiso 1 1 calc R U . . .
C17 C 0.25980(17) 1.10781(10) -0.00581(9) 0.0209(3) Uani 1 1 d . . . . .
H17 H 0.2986 1.1622 0.0143 0.025 Uiso 1 1 calc R U . . .
C18 C 0.19428(15) 0.78978(9) 0.01286(8) 0.0137(3) Uani 1 1 d . . . . .
C19 C -0.18112(17) 0.74659(10) 0.24976(8) 0.0212(3) Uani 1 1 d . . . . .
H19 H -0.2738 0.7551 0.2776 0.025 Uiso 1 1 calc R U . . .
C20 C -0.16958(17) 0.61953(11) 0.02643(9) 0.0239(3) Uani 1 1 d . . . . .
H20A H -0.2754 0.6259 0.0464 0.036 Uiso 1 1 calc R U . . .
H20B H -0.1719 0.5737 -0.0131 0.036 Uiso 1 1 calc R U . . .
H20C H -0.1372 0.6755 0.0041 0.036 Uiso 1 1 calc R U . . .
C21 C -0.17657(16) 0.68100(9) 0.19462(8) 0.0195(3) Uani 1 1 d . . . . .
H21 H -0.2676 0.6453 0.1848 0.023 Uiso 1 1 calc R U . . .
C22 C 0.34998(15) 0.48312(9) 0.22422(8) 0.0167(3) Uani 1 1 d . . . . .
H22 H 0.3303 0.4528 0.2704 0.020 Uiso 1 1 calc R U . . .
C23 C 0.17427(17) 1.10636(10) -0.07673(9) 0.0215(3) Uani 1 1 d . . . . .
H23 H 0.1574 1.1591 -0.1053 0.026 Uiso 1 1 calc R U . . .
C24 C 0.10366(15) 0.79122(9) -0.05715(8) 0.0159(3) Uani 1 1 d . . . . .
H24 H 0.0582 0.7386 -0.0778 0.019 Uiso 1 1 calc R U . . .
C25 C -0.04171(16) 0.66597(9) 0.15299(8) 0.0155(3) Uani 1 1 d . . . . .
C26 C -0.09364(18) 0.50482(10) 0.12697(10) 0.0270(3) Uani 1 1 d . . . . .
H26A H -0.0135 0.4889 0.1672 0.040 Uiso 1 1 calc R U . . .
H26B H -0.0970 0.4597 0.0868 0.040 Uiso 1 1 calc R U . . .
H26C H -0.1977 0.5089 0.1493 0.040 Uiso 1 1 calc R U . . .
C27 C 0.24783(15) 0.70412(9) 0.12807(7) 0.0134(3) Uani 1 1 d . . . . .
C28 C 0.57049(18) 0.31360(9) 0.12744(9) 0.0224(3) Uani 1 1 d . . . . .
H28A H 0.4982 0.3096 0.0818 0.034 Uiso 1 1 calc R U . . .
H28B H 0.5979 0.2543 0.1456 0.034 Uiso 1 1 calc R U . . .
H28C H 0.6671 0.3447 0.1143 0.034 Uiso 1 1 calc R U . . .
C29 C -0.05097(16) 0.59387(9) 0.09211(9) 0.0187(3) Uani 1 1 d . . . . .
H29 H 0.0560 0.5882 0.0704 0.022 Uiso 1 1 calc R U . . .


_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
Br1 C3 1.9084(14) . ?
O2 C2 1.3706(16) . ?
O2 C28 1.4262(17) . ?
O1 C18 1.3709(16) . ?
O1 C27 1.4651(15) . ?
C1 C13 1.331(2) . ?
C1 C7 1.4656(18) . ?
C1 H1 0.9500 . ?
C2 C11 1.3881(19) . ?
C2 C22 1.3933(19) . ?
C3 C17 1.372(2) . ?
C3 C4 1.4285(19) . ?
C4 C5 1.437(2) . ?
C4 C7 1.4420(18) . ?
C5 C15 1.417(2) . ?
C5 C8 1.4177(19) . ?
C6 C9 1.3973(19) . ?
C6 C25 1.4110(19) . ?
C6 C27 1.5361(18) . ?
C7 C18 1.3861(19) . ?
C8 C23 1.364(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C19 1.383(2) . ?
C10 H10 0.9500 . ?
C11 C16 1.3899(19) . ?
C11 H11 0.9500 . ?
C12 C16 1.3895(18) . ?
C12 C14 1.3958(19) . ?
C12 C27 1.5269(18) . ?
C13 C27 1.5127(18) . ?
C13 H13 0.9500 . ?
C14 C22 1.3855(19) . ?
C14 H14 0.9500 . ?
C15 C24 1.363(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C23 1.401(2) . ?
C17 H17 0.9500 . ?
C18 C24 1.4082(19) . ?
C19 C21 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C29 1.534(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C25 1.3993(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C29 1.5251(19) . ?
C26 C29 1.534(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29 1.0000 . ?

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 O2 C28 117.41(11) . . ?
C18 O1 C27 116.91(10) . . ?
C13 C1 C7 120.45(12) . . ?
C13 C1 H1 119.8 . . ?
C7 C1 H1 119.8 . . ?
O2 C2 C11 124.47(12) . . ?
O2 C2 C22 116.02(12) . . ?
C11 C2 C22 119.51(12) . . ?
C17 C3 C4 122.63(13) . . ?
C17 C3 Br1 114.15(11) . . ?
C4 C3 Br1 123.03(10) . . ?
C3 C4 C5 114.97(12) . . ?
C3 C4 C7 126.79(13) . . ?
C5 C4 C7 118.22(12) . . ?
C15 C5 C8 119.11(13) . . ?
C15 C5 C4 119.90(12) . . ?
C8 C5 C4 120.98(13) . . ?
C9 C6 C25 119.23(12) . . ?
C9 C6 C27 119.33(12) . . ?
C25 C6 C27 121.42(12) . . ?
C18 C7 C4 118.30(12) . . ?
C18 C7 C1 114.59(12) . . ?
C4 C7 C1 126.83(12) . . ?
C23 C8 C5 121.11(14) . . ?
C23 C8 H8 119.4 . . ?
C5 C8 H8 119.4 . . ?
C10 C9 C6 121.25(13) . . ?
C10 C9 H9 119.4 . . ?
C6 C9 H9 119.4 . . ?
C19 C10 C9 119.78(13) . . ?
C19 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C2 C11 C16 119.53(12) . . ?
C2 C11 H11 120.2 . . ?
C16 C11 H11 120.2 . . ?
C16 C12 C14 117.99(12) . . ?
C16 C12 C27 119.51(12) . . ?
C14 C12 C27 122.43(12) . . ?
C1 C13 C27 120.64(12) . . ?
C1 C13 H13 119.7 . . ?
C27 C13 H13 119.7 . . ?
C22 C14 C12 120.87(12) . . ?
C22 C14 H14 119.6 . . ?
C12 C14 H14 119.6 . . ?
C24 C15 C5 121.18(13) . . ?
C24 C15 H15 119.4 . . ?
C5 C15 H15 119.4 . . ?
C12 C16 C11 121.71(12) . . ?
C12 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
C3 C17 C23 120.96(14) . . ?
C3 C17 H17 119.5 . . ?
C23 C17 H17 119.5 . . ?
O1 C18 C7 122.02(12) . . ?
O1 C18 C24 114.81(12) . . ?
C7 C18 C24 122.94(12) . . ?
C10 C19 C21 119.54(13) . . ?
C10 C19 H19 120.2 . . ?
C21 C19 H19 120.2 . . ?
C29 C20 H20A 109.5 . . ?
C29 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C29 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 C25 121.88(13) . . ?
C19 C21 H21 119.1 . . ?
C25 C21 H21 119.1 . . ?
C14 C22 C2 120.30(12) . . ?
C14 C22 H22 119.9 . . ?
C2 C22 H22 119.9 . . ?
C8 C23 C17 119.18(13) . . ?
C8 C23 H23 120.4 . . ?
C17 C23 H23 120.4 . . ?
C15 C24 C18 119.13(13) . . ?
C15 C24 H24 120.4 . . ?
C18 C24 H24 120.4 . . ?
C21 C25 C6 118.31(13) . . ?
C21 C25 C29 117.60(12) . . ?
C6 C25 C29 124.07(12) . . ?
C29 C26 H26A 109.5 . . ?
C29 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C29 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O1 C27 C13 107.01(10) . . ?
O1 C27 C12 105.32(10) . . ?
C13 C27 C12 109.06(10) . . ?
O1 C27 C6 109.05(10) . . ?
C13 C27 C6 114.40(11) . . ?
C12 C27 C6 111.51(10) . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 C20 110.22(11) . . ?
C25 C29 C26 111.32(12) . . ?
C20 C29 C26 111.26(12) . . ?
C25 C29 H29 108.0 . . ?
C20 C29 H29 108.0 . . ?
C26 C29 H29 108.0 . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichrolomethane/hexane mixed solvent'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_140910_0m
_database_code_depnum_ccdc_archive 'CCDC 1031286'
_audit_update_record             
;
2014-10-28 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
3(2isopropylphenyl)3(4methoxyphenyl)3Hbenzo[f]chromene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H26 O2'
_chemical_formula_weight         406.50

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'
O O 0.0106 0.0060 '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                   8.4797(6)
_cell_length_b                   16.5725(12)
_cell_length_c                   15.9445(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.4540(9)
_cell_angle_gamma                90
_cell_volume                     2179.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11304
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.798
_diffrn_reflns_theta_max         26.301
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4419
_reflns_number_gt                3849
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0430P)²+0.8561P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4419
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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
O1 O 0.91745(9) 0.15975(5) 0.91992(5) 0.01678(18) Uani 1 1 d . . . . .
O2 O 1.27125(11) 0.07958(5) 0.62794(6) 0.0257(2) Uani 1 1 d . . . . .
C1 C 0.54854(14) 0.11302(6) 0.99664(7) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.68745(14) 0.16174(7) 0.79600(7) 0.0185(2) Uani 1 1 d . . . . .
H2 H 0.6492 0.1610 0.7351 0.022 Uiso 1 1 calc R U . . .
C3 C 0.64886(14) 0.13269(7) 0.93865(7) 0.0157(2) Uani 1 1 d . . . . .
C4 C 0.96850(13) 0.16596(7) 0.77937(7) 0.0157(2) Uani 1 1 d . . . . .
C5 C 0.61940(14) 0.10684(7) 1.08670(7) 0.0170(2) Uani 1 1 d . . . . .
C6 C 1.13683(14) 0.06231(7) 0.73922(8) 0.0196(2) Uani 1 1 d . . . . .
H6 H 1.1840 0.0101 0.7483 0.023 Uiso 1 1 calc R U . . .
C7 C 1.00097(14) 0.33055(7) 0.87769(7) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.52053(15) 0.08553(7) 1.14361(8) 0.0202(3) Uani 1 1 d . . . . .
H8 H 0.5672 0.0817 1.2037 0.024 Uiso 1 1 calc R U . . .
C9 C 0.78822(15) 0.12122(7) 1.11661(7) 0.0182(2) Uani 1 1 d . . . . .
H9 H 0.8362 0.1176 1.1766 0.022 Uiso 1 1 calc R U . . .
C10 C 0.88302(14) 0.14020(7) 1.06083(7) 0.0177(2) Uani 1 1 d . . . . .
H10 H 0.9959 0.1493 1.0819 0.021 Uiso 1 1 calc R U . . .
C11 C 0.28804(15) 0.07651(7) 1.02435(8) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.1756 0.0659 1.0034 0.026 Uiso 1 1 calc R U . . .
C12 C 0.85624(14) 0.28769(7) 0.84380(7) 0.0168(2) Uani 1 1 d . . . . .
C13 C 0.81202(14) 0.14614(7) 0.97179(7) 0.0155(2) Uani 1 1 d . . . . .
C14 C 1.16913(14) 0.11131(7) 0.67441(7) 0.0182(2) Uani 1 1 d . . . . .
C15 C 0.85481(13) 0.19519(7) 0.83457(7) 0.0162(2) Uani 1 1 d . . . . .
C16 C 0.38039(14) 0.09755(7) 0.96768(8) 0.0190(2) Uani 1 1 d . . . . .
H16 H 0.3307 0.1018 0.9080 0.023 Uiso 1 1 calc R U . . .
C17 C 0.99956(14) 0.21359(7) 0.71360(7) 0.0187(2) Uani 1 1 d . . . . .
H17 H 0.9515 0.2656 0.7041 0.022 Uiso 1 1 calc R U . . .
C18 C 1.03673(14) 0.08892(7) 0.79056(7) 0.0182(2) Uani 1 1 d . . . . .
H18 H 1.0141 0.0544 0.8339 0.022 Uiso 1 1 calc R U . . .
C19 C 0.59233(14) 0.13328(7) 0.84488(7) 0.0181(2) Uani 1 1 d . . . . .
H19 H 0.4874 0.1133 0.8187 0.022 Uiso 1 1 calc R U . . .
C20 C 0.71180(15) 0.33038(8) 0.81599(8) 0.0219(3) Uani 1 1 d . . . . .
H20 H 0.6141 0.3016 0.7941 0.026 Uiso 1 1 calc R U . . .
C21 C 0.99356(16) 0.41478(7) 0.87934(8) 0.0233(3) Uani 1 1 d . . . . .
H21 H 1.0904 0.4444 0.9010 0.028 Uiso 1 1 calc R U . . .
C22 C 0.35816(15) 0.07040(7) 1.11315(8) 0.0215(3) Uani 1 1 d . . . . .
H22 H 0.2933 0.0558 1.1520 0.026 Uiso 1 1 calc R U . . .
C23 C 0.84930(17) 0.45641(8) 0.85034(8) 0.0279(3) Uani 1 1 d . . . . .
H23 H 0.8480 0.5137 0.8516 0.033 Uiso 1 1 calc R U . . .
C24 C 1.16324(14) 0.28992(7) 0.91522(7) 0.0196(3) Uani 1 1 d . . . . .
H24 H 1.1496 0.2308 0.9031 0.024 Uiso 1 1 calc R U . . .
C25 C 1.09942(15) 0.18725(7) 0.66108(7) 0.0196(2) Uani 1 1 d . . . . .
H25 H 1.1196 0.2210 0.6166 0.024 Uiso 1 1 calc R U . . .
C26 C 1.21029(16) 0.30076(8) 1.01330(8) 0.0276(3) Uani 1 1 d . . . . .
H26A H 1.2296 0.3581 1.0271 0.041 Uiso 1 1 calc R U . . .
H26B H 1.3092 0.2700 1.0373 0.041 Uiso 1 1 calc R U . . .
H26C H 1.1222 0.2812 1.0382 0.041 Uiso 1 1 calc R U . . .
C27 C 0.70751(17) 0.41386(8) 0.81951(8) 0.0274(3) Uani 1 1 d . . . . .
H27 H 0.6076 0.4417 0.8008 0.033 Uiso 1 1 calc R U . . .
C28 C 1.29921(16) 0.32022(9) 0.87453(9) 0.0294(3) Uani 1 1 d . . . . .
H28A H 1.2695 0.3104 0.8122 0.044 Uiso 1 1 calc R U . . .
H28B H 1.3999 0.2914 0.9000 0.044 Uiso 1 1 calc R U . . .
H28C H 1.3152 0.3782 0.8854 0.044 Uiso 1 1 calc R U . . .
C29 C 1.3043(2) 0.12804(9) 0.56035(10) 0.0388(4) Uani 1 1 d . . . . .
H29A H 1.2028 0.1394 0.5181 0.058 Uiso 1 1 calc R U . . .
H29B H 1.3786 0.0992 0.5321 0.058 Uiso 1 1 calc R U . . .
H29C H 1.3541 0.1789 0.5843 0.058 Uiso 1 1 calc R U . . .


_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 C13 1.3705(13) . ?
O1 C15 1.4638(13) . ?
O2 C14 1.3689(14) . ?
O2 C29 1.4229(16) . ?
C1 C16 1.4163(16) . ?
C1 C5 1.4255(16) . ?
C1 C3 1.4320(16) . ?
C2 C19 1.3316(17) . ?
C2 C15 1.5143(16) . ?
C2 H2 0.9500 . ?
C3 C13 1.3794(16) . ?
C3 C19 1.4600(16) . ?
C4 C17 1.3858(16) . ?
C4 C18 1.3960(16) . ?
C4 C15 1.5276(15) . ?
C5 C8 1.4160(17) . ?
C5 C9 1.4198(17) . ?
C6 C18 1.3814(17) . ?
C6 C14 1.3907(17) . ?
C6 H6 0.9500 . ?
C7 C21 1.3978(17) . ?
C7 C12 1.4121(17) . ?
C7 C24 1.5238(16) . ?
C8 C22 1.3723(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3671(17) . ?
C9 H9 0.9500 . ?
C10 C13 1.4106(16) . ?
C10 H10 0.9500 . ?
C11 C16 1.3713(17) . ?
C11 C22 1.4060(18) . ?
C11 H11 0.9500 . ?
C12 C20 1.3946(16) . ?
C12 C15 1.5398(16) . ?
C14 C25 1.3857(17) . ?
C16 H16 0.9500 . ?
C17 C25 1.3923(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C27 1.3854(18) . ?
C20 H20 0.9500 . ?
C21 C23 1.3867(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C27 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C28 1.5332(17) . ?
C24 C26 1.5319(16) . ?
C24 H24 1.0000 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

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 O1 C15 118.72(8) . . ?
C14 O2 C29 116.99(10) . . ?
C16 C1 C5 118.15(11) . . ?
C16 C1 C3 122.34(10) . . ?
C5 C1 C3 119.49(10) . . ?
C19 C2 C15 122.01(10) . . ?
C19 C2 H2 119.0 . . ?
C15 C2 H2 119.0 . . ?
C13 C3 C1 118.88(10) . . ?
C13 C3 C19 116.89(10) . . ?
C1 C3 C19 124.04(10) . . ?
C17 C4 C18 118.13(11) . . ?
C17 C4 C15 120.80(10) . . ?
C18 C4 C15 120.98(10) . . ?
C8 C5 C9 121.85(11) . . ?
C8 C5 C1 119.33(11) . . ?
C9 C5 C1 118.81(10) . . ?
C18 C6 C14 120.56(11) . . ?
C18 C6 H6 119.7 . . ?
C14 C6 H6 119.7 . . ?
C21 C7 C12 118.08(11) . . ?
C21 C7 C24 118.31(11) . . ?
C12 C7 C24 123.57(10) . . ?
C22 C8 C5 120.90(11) . . ?
C22 C8 H8 119.5 . . ?
C5 C8 H8 119.5 . . ?
C10 C9 C5 121.31(11) . . ?
C10 C9 H9 119.3 . . ?
C5 C9 H9 119.3 . . ?
C9 C10 C13 119.53(11) . . ?
C9 C10 H10 120.2 . . ?
C13 C10 H10 120.2 . . ?
C16 C11 C22 120.62(11) . . ?
C16 C11 H11 119.7 . . ?
C22 C11 H11 119.7 . . ?
C20 C12 C7 119.16(11) . . ?
C20 C12 C15 119.20(11) . . ?
C7 C12 C15 121.62(10) . . ?
O1 C13 C3 122.16(10) . . ?
O1 C13 C10 115.67(10) . . ?
C3 C13 C10 121.97(11) . . ?
O2 C14 C25 124.53(11) . . ?
O2 C14 C6 115.89(10) . . ?
C25 C14 C6 119.57(11) . . ?
O1 C15 C2 109.49(9) . . ?
O1 C15 C4 105.50(8) . . ?
C2 C15 C4 107.90(9) . . ?
O1 C15 C12 108.51(9) . . ?
C2 C15 C12 112.90(9) . . ?
C4 C15 C12 112.26(9) . . ?
C11 C16 C1 121.14(11) . . ?
C11 C16 H16 119.4 . . ?
C1 C16 H16 119.4 . . ?
C4 C17 C25 121.72(11) . . ?
C4 C17 H17 119.1 . . ?
C25 C17 H17 119.1 . . ?
C6 C18 C4 120.64(11) . . ?
C6 C18 H18 119.7 . . ?
C4 C18 H18 119.7 . . ?
C2 C19 C3 120.16(11) . . ?
C2 C19 H19 119.9 . . ?
C3 C19 H19 119.9 . . ?
C27 C20 C12 121.55(12) . . ?
C27 C20 H20 119.2 . . ?
C12 C20 H20 119.2 . . ?
C23 C21 C7 122.04(12) . . ?
C23 C21 H21 119.0 . . ?
C7 C21 H21 119.0 . . ?
C8 C22 C11 119.85(11) . . ?
C8 C22 H22 120.1 . . ?
C11 C22 H22 120.1 . . ?
C27 C23 C21 119.46(12) . . ?
C27 C23 H23 120.3 . . ?
C21 C23 H23 120.3 . . ?
C7 C24 C28 112.85(10) . . ?
C7 C24 C26 110.25(10) . . ?
C28 C24 C26 110.53(10) . . ?
C7 C24 H24 107.7 . . ?
C28 C24 H24 107.7 . . ?
C26 C24 H24 107.7 . . ?
C14 C25 C17 119.34(11) . . ?
C14 C25 H25 120.3 . . ?
C17 C25 H25 120.3 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 C20 119.67(12) . . ?
C23 C27 H27 120.2 . . ?
C20 C27 H27 120.2 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichrolomethane/hexane mixed solvent'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       photochromic
