# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

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

data_P21onn
_database_code_depnum_ccdc_archive 'CCDC 1554999'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'(+-)-4-(4-bromophenyl)-2,2,7,10-tetramethyl-1,4-dihydro-2H-benzo[f]isochromene (2dA)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 Br O'
_chemical_formula_sum            'C23 H23 Br O'
_chemical_formula_weight         395.32

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 0.0000 0.0000 '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'
Br Br -0.6763 1.2805 '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                   17.0425(3)
_cell_length_b                   6.45510(10)
_cell_length_c                   17.1404(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.9170(6)
_cell_angle_gamma                90
_cell_volume                     1875.59(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      69.27

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.555
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.189
_exptl_absorpt_coefficient_mu    3.026
_shelx_estimated_absorpt_T_min   0.284
_shelx_estimated_absorpt_T_max   0.599
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4086
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω and ψ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20549
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         66.992
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3309
_reflns_number_gt                3257
_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       'APEX2 (Bruker AXS, 2004)'
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.1 (CCDC, 2013)'

_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)+(0.0360P)²+1.3958P]
 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         3309
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Br1 Br 0.03233(2) -0.03208(3) 0.11745(2) 0.02435(8) Uani 1 1 d . . . . .
O1 O 0.28385(7) -0.02084(17) 0.44591(7) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.25041(10) 0.0236(2) 0.57900(10) 0.0150(3) Uani 1 1 d . . . . .
H1A H 0.2155 -0.0989 0.5792 0.018 Uiso 1 1 calc R U . . .
H1B H 0.2743 0.0460 0.6335 0.018 Uiso 1 1 calc R U . . .
C2 C 0.31595(10) -0.0224(2) 0.52716(10) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.25124(9) 0.1713(2) 0.41838(9) 0.0136(3) Uani 1 1 d . . . . .
H3 H 0.2950 0.2654 0.4064 0.016 Uiso 1 1 calc R U . . .
C4 C 0.20291(9) 0.2786(2) 0.47670(9) 0.0130(3) Uani 1 1 d . . . . .
C5 C 0.16085(10) 0.4566(2) 0.44862(10) 0.0158(3) Uani 1 1 d . . . . .
H5 H 0.1633 0.5004 0.3960 0.019 Uiso 1 1 calc R U . . .
C6 C 0.11696(9) 0.5654(2) 0.49601(10) 0.0160(3) Uani 1 1 d . . . . .
H6 H 0.0897 0.6858 0.4763 0.019 Uiso 1 1 calc R U . . .
C7 C 0.11101(10) 0.5028(2) 0.57460(10) 0.0138(3) Uani 1 1 d . . . . .
C8 C 0.06371(9) 0.6244(3) 0.62118(10) 0.0179(3) Uani 1 1 d . . . . .
C9 C 0.05542(10) 0.5601(3) 0.69601(10) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.0241 0.6384 0.7281 0.025 Uiso 1 1 calc R U . . .
C10 C 0.09300(10) 0.3788(3) 0.72546(9) 0.0203(4) Uani 1 1 d . . . . .
H10 H 0.0850 0.3367 0.7772 0.024 Uiso 1 1 calc R U . . .
C11 C 0.14080(9) 0.2581(3) 0.68380(9) 0.0166(3) Uani 1 1 d . . . . .
C12 C 0.15231(9) 0.3204(2) 0.60462(9) 0.0138(3) Uani 1 1 d . . . . .
C13 C 0.20073(9) 0.2119(2) 0.55298(9) 0.0129(3) Uani 1 1 d . . . . .
C14 C 0.34459(10) -0.2443(3) 0.54027(10) 0.0216(4) Uani 1 1 d . . . . .
H14A H 0.3628 -0.2644 0.5959 0.032 Uiso 1 1 calc R U . . .
H14B H 0.3882 -0.2709 0.5086 0.032 Uiso 1 1 calc R U . . .
H14C H 0.3012 -0.3402 0.5248 0.032 Uiso 1 1 calc R U . . .
C15 C 0.38404(10) 0.1308(3) 0.54149(10) 0.0224(4) Uani 1 1 d . . . . .
H15A H 0.4097 0.1129 0.5949 0.034 Uiso 1 1 calc R U . . .
H15B H 0.3638 0.2725 0.5351 0.034 Uiso 1 1 calc R U . . .
H15C H 0.4224 0.1054 0.5037 0.034 Uiso 1 1 calc R U . . .
C16 C 0.20034(9) 0.1217(2) 0.34259(9) 0.0125(3) Uani 1 1 d . . . . .
C17 C 0.20015(9) 0.2459(2) 0.27623(9) 0.0158(3) Uani 1 1 d . . . . .
H17 H 0.2343 0.3624 0.2772 0.019 Uiso 1 1 calc R U . . .
C18 C 0.15071(9) 0.2019(3) 0.20849(9) 0.0173(3) Uani 1 1 d . . . . .
H18 H 0.1503 0.2880 0.1635 0.021 Uiso 1 1 calc R U . . .
C19 C 0.10215(9) 0.0299(3) 0.20804(10) 0.0157(3) Uani 1 1 d . . . . .
C20 C 0.10244(9) -0.0995(3) 0.27274(9) 0.0165(3) Uani 1 1 d . . . . .
H20 H 0.0696 -0.2186 0.2711 0.020 Uiso 1 1 calc R U . . .
C21 C 0.15160(10) -0.0517(2) 0.33974(9) 0.0148(3) Uani 1 1 d . . . . .
H21 H 0.1521 -0.1387 0.3845 0.018 Uiso 1 1 calc R U . . .
C22 C 0.02325(10) 0.8199(3) 0.58917(11) 0.0230(4) Uani 1 1 d . . . . .
H22A H 0.0626 0.9150 0.5715 0.035 Uiso 1 1 calc R U . . .
H22B H -0.0036 0.8865 0.6304 0.035 Uiso 1 1 calc R U . . .
H22C H -0.0155 0.7848 0.5449 0.035 Uiso 1 1 calc R U . . .
C23 C 0.17529(11) 0.0679(3) 0.72644(10) 0.0233(4) Uani 1 1 d . . . . .
H23A H 0.1488 0.0450 0.7738 0.035 Uiso 1 1 calc R U . . .
H23B H 0.2318 0.0889 0.7410 0.035 Uiso 1 1 calc R U . . .
H23C H 0.1675 -0.0531 0.6920 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
Br1 C19 1.8991(17) . ?
O1 C3 1.4198(18) . ?
O1 C2 1.443(2) . ?
C1 C13 1.522(2) . ?
C1 C2 1.526(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C14 1.522(2) . ?
C2 C15 1.525(2) . ?
C3 C16 1.520(2) . ?
C3 C4 1.526(2) . ?
C3 H3 1.0000 . ?
C4 C13 1.381(2) . ?
C4 C5 1.412(2) . ?
C5 C6 1.356(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.420(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.427(2) . ?
C7 C12 1.439(2) . ?
C8 C9 1.369(2) . ?
C8 C22 1.514(2) . ?
C9 C10 1.403(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.448(2) . ?
C11 C23 1.516(2) . ?
C12 C13 1.451(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.391(2) . ?
C16 C21 1.392(2) . ?
C17 C18 1.392(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(2) . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C3 O1 C2 115.05(11) . . ?
C13 C1 C2 113.79(13) . . ?
C13 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C13 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
O1 C2 C14 103.48(13) . . ?
O1 C2 C15 110.94(14) . . ?
C14 C2 C15 111.05(14) . . ?
O1 C2 C1 109.46(13) . . ?
C14 C2 C1 109.88(14) . . ?
C15 C2 C1 111.73(13) . . ?
O1 C3 C16 105.64(12) . . ?
O1 C3 C4 113.46(12) . . ?
C16 C3 C4 110.89(12) . . ?
O1 C3 H3 108.9 . . ?
C16 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C13 C4 C5 120.93(14) . . ?
C13 C4 C3 123.24(14) . . ?
C5 C4 C3 115.81(13) . . ?
C6 C5 C4 120.63(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.23(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 118.27(15) . . ?
C6 C7 C12 119.47(14) . . ?
C8 C7 C12 122.26(15) . . ?
C9 C8 C7 118.41(15) . . ?
C9 C8 C22 120.36(15) . . ?
C7 C8 C22 121.23(15) . . ?
C8 C9 C10 120.19(15) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 123.86(15) . . ?
C11 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C10 C11 C12 118.24(15) . . ?
C10 C11 C23 115.35(14) . . ?
C12 C11 C23 126.40(15) . . ?
C7 C12 C11 116.97(14) . . ?
C7 C12 C13 117.69(14) . . ?
C11 C12 C13 125.33(14) . . ?
C4 C13 C12 119.99(14) . . ?
C4 C13 C1 117.25(14) . . ?
C12 C13 C1 122.75(13) . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.92(14) . . ?
C17 C16 C3 122.06(14) . . ?
C21 C16 C3 119.02(14) . . ?
C16 C17 C18 120.99(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 118.59(15) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C20 121.69(15) . . ?
C18 C19 Br1 119.84(12) . . ?
C20 C19 Br1 118.47(12) . . ?
C21 C20 C19 118.71(15) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C16 121.07(15) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C8 C22 H22A 109.5 . . ?
C8 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C8 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 C14 178.98(13) . . . . ?
C3 O1 C2 C15 -61.87(17) . . . . ?
C3 O1 C2 C1 61.89(17) . . . . ?
C13 C1 C2 O1 -48.91(17) . . . . ?
C13 C1 C2 C14 -161.91(13) . . . . ?
C13 C1 C2 C15 74.37(17) . . . . ?
C2 O1 C3 C16 -163.29(12) . . . . ?
C2 O1 C3 C4 -41.61(17) . . . . ?
O1 C3 C4 C13 9.2(2) . . . . ?
C16 C3 C4 C13 127.87(15) . . . . ?
O1 C3 C4 C5 -172.20(13) . . . . ?
C16 C3 C4 C5 -53.49(18) . . . . ?
C13 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C5 C6 -179.02(14) . . . . ?
C4 C5 C6 C7 -0.9(2) . . . . ?
C5 C6 C7 C8 -179.91(15) . . . . ?
C5 C6 C7 C12 0.0(2) . . . . ?
C6 C7 C8 C9 177.55(15) . . . . ?
C12 C7 C8 C9 -2.4(2) . . . . ?
C6 C7 C8 C22 -2.3(2) . . . . ?
C12 C7 C8 C22 177.76(15) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C22 C8 C9 C10 179.99(16) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C9 C10 C11 C23 -179.69(16) . . . . ?
C6 C7 C12 C11 -176.91(14) . . . . ?
C8 C7 C12 C11 3.0(2) . . . . ?
C6 C7 C12 C13 2.0(2) . . . . ?
C8 C7 C12 C13 -178.11(14) . . . . ?
C10 C11 C12 C7 -1.4(2) . . . . ?
C23 C11 C12 C7 177.39(15) . . . . ?
C10 C11 C12 C13 179.78(15) . . . . ?
C23 C11 C12 C13 -1.4(3) . . . . ?
C5 C4 C13 C12 2.4(2) . . . . ?
C3 C4 C13 C12 -179.02(13) . . . . ?
C5 C4 C13 C1 -177.68(14) . . . . ?
C3 C4 C13 C1 0.9(2) . . . . ?
C7 C12 C13 C4 -3.2(2) . . . . ?
C11 C12 C13 C4 175.62(14) . . . . ?
C7 C12 C13 C1 176.93(14) . . . . ?
C11 C12 C13 C1 -4.3(2) . . . . ?
C2 C1 C13 C4 19.2(2) . . . . ?
C2 C1 C13 C12 -160.89(14) . . . . ?
O1 C3 C16 C17 -137.29(14) . . . . ?
C4 C3 C16 C17 99.38(16) . . . . ?
O1 C3 C16 C21 43.57(17) . . . . ?
C4 C3 C16 C21 -79.75(17) . . . . ?
C21 C16 C17 C18 1.7(2) . . . . ?
C3 C16 C17 C18 -177.43(14) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C20 -0.8(2) . . . . ?
C17 C18 C19 Br1 178.74(12) . . . . ?
C18 C19 C20 C21 1.4(2) . . . . ?
Br1 C19 C20 C21 -178.17(12) . . . . ?
C19 C20 C21 C16 -0.4(2) . . . . ?
C17 C16 C21 C20 -1.1(2) . . . . ?
C3 C16 C21 C20 178.04(14) . . . . ?

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_Pbca
_database_code_depnum_ccdc_archive 'CCDC 1554998'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'(2S*,4R*)-2-methyl-4-(p-tolyl)-1,4-dihydro-2H-benzo-[f]isochromene (cis-(+-)-2eD)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 O'
_chemical_formula_sum            'C21 H20 O'
_chemical_formula_weight         288.37

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 0.0000 0.0000 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   18.1842(2)
_cell_length_b                   8.95420(10)
_cell_length_c                   20.2236(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3292.91(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9703
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      64.66

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.536
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7998
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω and ψ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22603
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.864
_diffrn_reflns_theta_max         64.984
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.935
_reflns_number_total             2790
_reflns_number_gt                2308
_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       'APEX2 (Bruker AXS, 2004)'
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.1 (CCDC, 2013)'

_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)+(0.0670P)²+0.4796P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00126(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2790
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.20673(5) 0.15323(11) 0.42103(5) 0.0655(3) Uani 1 1 d . . . . .
C1 C 0.19144(8) 0.08055(17) 0.53508(8) 0.0659(4) Uani 1 1 d . . . . .
H1A H 0.1716 0.1179 0.5764 0.079 Uiso 1 1 calc R U . . .
H1B H 0.1739 -0.0209 0.5293 0.079 Uiso 1 1 calc R U . . .
C2 C 0.16287(8) 0.17527(18) 0.47921(8) 0.0687(4) Uani 1 1 d . . . . .
H2 H 0.1657 0.2806 0.4922 0.082 Uiso 1 1 calc R U . . .
C3 C 0.27960(8) 0.21016(15) 0.42974(7) 0.0579(4) Uani 1 1 d . . . . .
H3 H 0.2764 0.3186 0.4358 0.069 Uiso 1 1 calc R U . . .
C4 C 0.31549(7) 0.14352(14) 0.49056(6) 0.0518(3) Uani 1 1 d . . . . .
C5 C 0.39293(8) 0.14700(16) 0.49609(7) 0.0605(4) Uani 1 1 d . . . . .
H5 H 0.4205 0.1960 0.4640 0.073 Uiso 1 1 calc R U . . .
C6 C 0.42772(8) 0.08019(18) 0.54737(7) 0.0656(4) Uani 1 1 d . . . . .
H6 H 0.4787 0.0839 0.5500 0.079 Uiso 1 1 calc R U . . .
C7 C 0.38769(8) 0.00524(15) 0.59671(7) 0.0602(4) Uani 1 1 d . . . . .
C8 C 0.42312(11) -0.0713(2) 0.64884(9) 0.0811(5) Uani 1 1 d . . . . .
H8 H 0.4742 -0.0734 0.6505 0.097 Uiso 1 1 calc R U . . .
C9 C 0.38398(14) -0.1414(2) 0.69628(11) 0.0998(7) Uani 1 1 d . . . . .
H9 H 0.4082 -0.1910 0.7303 0.120 Uiso 1 1 calc R U . . .
C10 C 0.30754(14) -0.1396(2) 0.69442(10) 0.0996(6) Uani 1 1 d . . . . .
H10 H 0.2810 -0.1876 0.7275 0.120 Uiso 1 1 calc R U . . .
C11 C 0.27103(10) -0.0682(2) 0.64459(8) 0.0806(5) Uani 1 1 d . . . . .
H11 H 0.2199 -0.0688 0.6440 0.097 Uiso 1 1 calc R U . . .
C12 C 0.30986(8) 0.00664(15) 0.59378(7) 0.0582(4) Uani 1 1 d . . . . .
C13 C 0.27409(7) 0.07872(14) 0.53937(7) 0.0531(4) Uani 1 1 d . . . . .
C14 C 0.08454(10) 0.1389(3) 0.46077(12) 0.1041(7) Uani 1 1 d . . . . .
H14A H 0.0692 0.2022 0.4251 0.156 Uiso 1 1 calc R U . . .
H14B H 0.0532 0.1549 0.4983 0.156 Uiso 1 1 calc R U . . .
H14C H 0.0814 0.0363 0.4472 0.156 Uiso 1 1 calc R U . . .
C15 C 0.32150(8) 0.17968(15) 0.36676(7) 0.0577(4) Uani 1 1 d . . . . .
C16 C 0.33804(9) 0.03610(17) 0.34802(8) 0.0706(4) Uani 1 1 d . . . . .
H16 H 0.3231 -0.0434 0.3744 0.085 Uiso 1 1 calc R U . . .
C17 C 0.37655(10) 0.0084(2) 0.29066(8) 0.0815(5) Uani 1 1 d . . . . .
H17 H 0.3866 -0.0899 0.2789 0.098 Uiso 1 1 calc R U . . .
C18 C 0.40055(9) 0.1221(2) 0.25030(8) 0.0770(5) Uani 1 1 d . . . . .
C19 C 0.38382(11) 0.2647(2) 0.26963(9) 0.0915(6) Uani 1 1 d . . . . .
H19 H 0.3993 0.3441 0.2435 0.110 Uiso 1 1 calc R U . . .
C20 C 0.34480(10) 0.29448(19) 0.32670(9) 0.0792(5) Uani 1 1 d . . . . .
H20 H 0.3342 0.3928 0.3381 0.095 Uiso 1 1 calc R U . . .
C21 C 0.44352(11) 0.0913(3) 0.18778(9) 0.1123(8) Uani 1 1 d . . . . .
H21A H 0.4428 -0.0139 0.1786 0.168 Uiso 1 1 calc R U . . .
H21B H 0.4934 0.1237 0.1935 0.168 Uiso 1 1 calc R U . . .
H21C H 0.4216 0.1444 0.1516 0.168 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 C3 1.4307(16) . ?
O1 C2 1.4350(18) . ?
C1 C13 1.5057(19) . ?
C1 C2 1.505(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C14 1.508(2) . ?
C2 H2 0.9800 . ?
C3 C15 1.5091(19) . ?
C3 C4 1.5149(19) . ?
C3 H3 0.9800 . ?
C4 C13 1.3703(18) . ?
C4 C5 1.4130(19) . ?
C5 C6 1.354(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.413(2) . ?
C7 C12 1.416(2) . ?
C8 C9 1.349(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.416(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.4319(19) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.374(2) . ?
C15 C20 1.376(2) . ?
C16 C17 1.378(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(3) . ?
C18 C21 1.512(2) . ?
C19 C20 1.381(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C3 O1 C2 111.40(11) . . ?
C13 C1 C2 113.20(12) . . ?
C13 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
C13 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.8 . . ?
O1 C2 C1 110.25(11) . . ?
O1 C2 C14 107.00(14) . . ?
C1 C2 C14 112.94(15) . . ?
O1 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C14 C2 H2 108.9 . . ?
O1 C3 C15 107.42(11) . . ?
O1 C3 C4 111.01(11) . . ?
C15 C3 C4 113.37(11) . . ?
O1 C3 H3 108.3 . . ?
C15 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C13 C4 C5 119.99(13) . . ?
C13 C4 C3 121.00(12) . . ?
C5 C4 C3 119.00(12) . . ?
C6 C5 C4 121.09(13) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.84(13) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 121.68(15) . . ?
C6 C7 C12 118.91(13) . . ?
C8 C7 C12 119.41(14) . . ?
C9 C8 C7 121.04(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.18(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.75(18) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.98(17) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 117.64(14) . . ?
C11 C12 C13 123.00(14) . . ?
C7 C12 C13 119.34(12) . . ?
C4 C13 C12 119.66(12) . . ?
C4 C13 C1 120.15(13) . . ?
C12 C13 C1 120.18(12) . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.01(14) . . ?
C16 C15 C3 120.83(13) . . ?
C20 C15 C3 121.15(13) . . ?
C15 C16 C17 120.82(15) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 121.80(16) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 116.76(16) . . ?
C19 C18 C21 121.61(19) . . ?
C17 C18 C21 121.63(19) . . ?
C18 C19 C20 122.21(17) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C15 C20 C19 120.40(16) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 C1 -67.27(15) . . . . ?
C3 O1 C2 C14 169.55(13) . . . . ?
C13 C1 C2 O1 41.55(17) . . . . ?
C13 C1 C2 C14 161.19(14) . . . . ?
C2 O1 C3 C15 179.10(11) . . . . ?
C2 O1 C3 C4 54.64(14) . . . . ?
O1 C3 C4 C13 -19.18(17) . . . . ?
C15 C3 C4 C13 -140.20(12) . . . . ?
O1 C3 C4 C5 159.93(11) . . . . ?
C15 C3 C4 C5 38.91(17) . . . . ?
C13 C4 C5 C6 3.5(2) . . . . ?
C3 C4 C5 C6 -175.60(12) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 176.87(14) . . . . ?
C5 C6 C7 C12 -3.0(2) . . . . ?
C6 C7 C8 C9 179.25(16) . . . . ?
C12 C7 C8 C9 -0.9(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C10 C11 C12 C13 177.86(16) . . . . ?
C6 C7 C12 C11 -179.24(14) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
C6 C7 C12 C13 2.59(19) . . . . ?
C8 C7 C12 C13 -177.30(13) . . . . ?
C5 C4 C13 C12 -3.86(18) . . . . ?
C3 C4 C13 C12 175.24(11) . . . . ?
C5 C4 C13 C1 177.40(12) . . . . ?
C3 C4 C13 C1 -3.50(18) . . . . ?
C11 C12 C13 C4 -177.23(13) . . . . ?
C7 C12 C13 C4 0.84(19) . . . . ?
C11 C12 C13 C1 1.5(2) . . . . ?
C7 C12 C13 C1 179.58(12) . . . . ?
C2 C1 C13 C4 -7.74(19) . . . . ?
C2 C1 C13 C12 173.53(12) . . . . ?
O1 C3 C15 C16 -67.16(17) . . . . ?
C4 C3 C15 C16 55.86(18) . . . . ?
O1 C3 C15 C20 113.39(15) . . . . ?
C4 C3 C15 C20 -123.59(15) . . . . ?
C20 C15 C16 C17 -0.3(2) . . . . ?
C3 C15 C16 C17 -179.74(15) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C16 C17 C18 C21 179.31(17) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C21 C18 C19 C20 -179.81(17) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C3 C15 C20 C19 179.24(15) . . . . ?
C18 C19 C20 C15 0.4(3) . . . . ?

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.025

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
