#------------------------------------------------------------------------------
#$Date: 2018-05-25 14:46:31 +0300 (Fri, 25 May 2018) $
#$Revision: 207975 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/94/1549461.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1549461
loop_
_publ_author_name
'Salvati, Anna E.'
'Law, James A.'
'Liriano, Jouse'
'Frederich, Jim'
_publ_section_title
;
 Modular access to functionalized 5-8-5 ring systems via a photoinduced
 cycloisomerization reaction
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC00999F
_journal_year                    2018
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-01-11 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5881(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5568(4)
_cell_length_b                   15.0022(10)
_cell_length_c                   11.4025(7)
_cell_measurement_reflns_used    6992
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.32
_cell_measurement_theta_min      2.26
_cell_volume                     1111.80(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13557
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.349
_diffrn_reflns_theta_min         2.256
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       irregular
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.195
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.4182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2630
_reflns_number_total             2910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc00999f2.cif
_cod_data_source_block           fred28
_cod_database_code               1549461
_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. 
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2013-4
_shelx_res_file
; 
TITL fred28a in P2(1)/n 
CELL 0.71073   6.55680  15.00220  11.40250  90.0000  97.5881  90.0000 
ZERR    4.00   0.00040   0.00100   0.00070   0.0000   0.0008   0.0000 
LATT 1 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SFAC C  H  O 
UNIT 56  64  8 
L.S. 10 
ACTA 
BOND $H 
FMAP 2 
PLAN 10 
SIZE 0.195 0.222 0.423 
CONF 
TEMP -170.000 
WGHT    0.051700    0.418200 
FVAR       0.21536 
MOLE 1 
C1    1    0.664412    0.624289    0.614985    11.00000    0.02185    0.02223 = 
         0.01895    0.00044    0.00662    0.00178 
AFIX  23 
H1A   2    0.558194    0.580357    0.629979    11.00000   -1.20000 
H1B   2    0.602566    0.684593    0.609762    11.00000   -1.20000 
AFIX   0 
C2    1    0.851676    0.620181    0.712236    11.00000    0.02861    0.03693 = 
         0.01785    0.00165    0.00367    0.00817 
AFIX  23 
H2A   2    0.867303    0.559601    0.746682    11.00000   -1.20000 
H2B   2    0.835828    0.663218    0.776228    11.00000   -1.20000 
AFIX   0 
C3    1    1.040248    0.644626    0.649645    11.00000    0.02259    0.03369 = 
         0.01867   -0.00106   -0.00166    0.00354 
AFIX  23 
H3A   2    1.105393    0.700178    0.683179    11.00000   -1.20000 
H3B   2    1.143645    0.596189    0.659341    11.00000   -1.20000 
AFIX   0 
C4    1    0.956930    0.657434    0.518384    11.00000    0.01403    0.01967 = 
         0.01711   -0.00246    0.00217    0.00161 
C5    1    0.917317    0.752629    0.477472    11.00000    0.01549    0.01681 = 
         0.02412   -0.00482    0.00145   -0.00135 
AFIX  43 
H5    2    0.858465    0.797843    0.520724    11.00000   -1.20000 
AFIX   0 
C6    1    0.977580    0.762973    0.371938    11.00000    0.01618    0.01620 = 
         0.02552   -0.00173    0.00189   -0.00329 
AFIX  43 
H6    2    0.971157    0.816828    0.327776    11.00000   -1.20000 
AFIX   0 
C7    1    1.058539    0.674488    0.333388    11.00000    0.01266    0.01929 = 
         0.01993   -0.00106    0.00333   -0.00160 
AFIX  13 
H7    2    1.185971    0.683171    0.295265    11.00000   -1.20000 
AFIX   0 
C8    1    0.895522    0.626246    0.251261    11.00000    0.01410    0.01608 = 
         0.01741   -0.00111    0.00276    0.00024 
C9    1    0.924127    0.600272    0.130278    11.00000    0.01736    0.01578 = 
         0.01908    0.00011    0.00435    0.00180 
C10   1    0.734783    0.549155    0.076437    11.00000    0.02016    0.02102 = 
         0.01716   -0.00273    0.00195   -0.00010 
AFIX  23 
H10A  2    0.771293    0.487424    0.056655    11.00000   -1.20000 
H10B  2    0.668652    0.578919    0.003711    11.00000   -1.20000 
AFIX   0 
C11   1    0.591500    0.549517    0.172654    11.00000    0.01634    0.01848 = 
         0.01836   -0.00163    0.00067   -0.00257 
AFIX  23 
H11A  2    0.460298    0.579926    0.144123    11.00000   -1.20000 
H11B  2    0.561196    0.487897    0.196180    11.00000   -1.20000 
AFIX   0 
C12   1    0.708084    0.599654    0.275331    11.00000    0.01410    0.01447 = 
         0.01675   -0.00014    0.00139    0.00054 
C13   1    0.613633    0.616543    0.386522    11.00000    0.01256    0.01873 = 
         0.01871   -0.00133    0.00343   -0.00151 
AFIX  23 
H13A  2    0.492101    0.577330    0.386114    11.00000   -1.20000 
H13B  2    0.564276    0.678946    0.385207    11.00000   -1.20000 
AFIX   0 
C14   1    0.757000    0.601239    0.502279    11.00000    0.01601    0.01590 = 
         0.01735   -0.00009    0.00432    0.00070 
AFIX  13 
H14   2    0.796635    0.536836    0.506239    11.00000   -1.20000 
AFIX   0 
O1    3    1.103446    0.626463    0.443361    11.00000    0.01324    0.02226 = 
         0.01973   -0.00093    0.00226    0.00393 
O2    3    1.075039    0.617354    0.081109    11.00000    0.02333    0.02821 = 
         0.02610   -0.00365    0.01223   -0.00289 
HKLF 4 
  
REM  fred28a in P2(1)/n 
REM R1 =  0.0396 for    2630 Fo > 4sig(Fo)  and  0.0440 for all    2910 data 
REM    145 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0517      0.4168 
  
REM Highest difference peak  0.380,  deepest hole -0.213,  1-sigma level  0.045 
Q1    1   1.0053  0.7205  0.3408  11.00000  0.05    0.38 
Q2    1   0.9097  0.6195  0.1900  11.00000  0.05    0.37 
Q3    1   0.9339  0.7062  0.4994  11.00000  0.05    0.36 
Q4    1   0.9993  0.6549  0.5809  11.00000  0.05    0.34 
Q5    1   0.7095  0.6138  0.5602  11.00000  0.05    0.33 
Q6    1   0.8492  0.6307  0.5047  11.00000  0.05    0.32 
Q7    1   0.6436  0.5754  0.2222  11.00000  0.05    0.32 
Q8    1   0.6911  0.6071  0.4418  11.00000  0.05    0.32 
Q9    1   0.8216  0.5762  0.0975  11.00000  0.05    0.31 
Q10   1   0.9741  0.6459  0.2907  11.00000  0.05    0.30 
;
_shelx_res_checksum              99909
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'
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
C1 C 0.66441(16) 0.62429(7) 0.61498(9) 0.0207(2) Uani 1 1 d . .
H1A H 0.5582 0.5804 0.6300 0.025 Uiso 1 1 calc R U
H1B H 0.6026 0.6846 0.6098 0.025 Uiso 1 1 calc R U
C2 C 0.85168(18) 0.62018(9) 0.71224(10) 0.0277(3) Uani 1 1 d . .
H2A H 0.8673 0.5596 0.7467 0.033 Uiso 1 1 calc R U
H2B H 0.8358 0.6632 0.7762 0.033 Uiso 1 1 calc R U
C3 C 1.04025(17) 0.64463(8) 0.64964(10) 0.0254(2) Uani 1 1 d . .
H3A H 1.1054 0.7002 0.6832 0.030 Uiso 1 1 calc R U
H3B H 1.1436 0.5962 0.6593 0.030 Uiso 1 1 calc R U
C4 C 0.95693(14) 0.65743(7) 0.51838(8) 0.0169(2) Uani 1 1 d . .
C5 C 0.91732(15) 0.75263(7) 0.47747(9) 0.0189(2) Uani 1 1 d . .
H5 H 0.8585 0.7978 0.5207 0.023 Uiso 1 1 calc R U
C6 C 0.97758(15) 0.76297(7) 0.37194(9) 0.0194(2) Uani 1 1 d . .
H6 H 0.9712 0.8168 0.3278 0.023 Uiso 1 1 calc R U
C7 C 1.05854(15) 0.67449(7) 0.33339(9) 0.0172(2) Uani 1 1 d . .
H7 H 1.1860 0.6832 0.2953 0.021 Uiso 1 1 calc R U
C8 C 0.89552(15) 0.62625(6) 0.25126(9) 0.0158(2) Uani 1 1 d . .
C9 C 0.92413(15) 0.60027(6) 0.13028(9) 0.0172(2) Uani 1 1 d . .
C10 C 0.73478(16) 0.54915(7) 0.07644(9) 0.0195(2) Uani 1 1 d . .
H10A H 0.7713 0.4874 0.0567 0.023 Uiso 1 1 calc R U
H10B H 0.6687 0.5789 0.0037 0.023 Uiso 1 1 calc R U
C11 C 0.59150(15) 0.54952(7) 0.17265(9) 0.0179(2) Uani 1 1 d . .
H11A H 0.4603 0.5799 0.1441 0.021 Uiso 1 1 calc R U
H11B H 0.5612 0.4879 0.1962 0.021 Uiso 1 1 calc R U
C12 C 0.70808(14) 0.59965(6) 0.27533(8) 0.01516(19) Uani 1 1 d . .
C13 C 0.61363(15) 0.61654(6) 0.38652(9) 0.0165(2) Uani 1 1 d . .
H13A H 0.4921 0.5773 0.3861 0.020 Uiso 1 1 calc R U
H13B H 0.5643 0.6789 0.3852 0.020 Uiso 1 1 calc R U
C14 C 0.75700(15) 0.60124(6) 0.50228(8) 0.0162(2) Uani 1 1 d . .
H14 H 0.7966 0.5368 0.5062 0.019 Uiso 1 1 calc R U
O1 O 1.10345(11) 0.62646(5) 0.44336(6) 0.01840(17) Uani 1 1 d . .
O2 O 1.07504(13) 0.61735(5) 0.08111(7) 0.02508(19) Uani 1 1 d . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0218(5) 0.0222(5) 0.0190(5) 0.0004(4) 0.0066(4) 0.0018(4)
C2 0.0286(6) 0.0369(6) 0.0178(5) 0.0016(4) 0.0037(4) 0.0082(5)
C3 0.0226(5) 0.0337(6) 0.0187(5) -0.0011(4) -0.0017(4) 0.0035(4)
C4 0.0140(4) 0.0197(5) 0.0171(4) -0.0025(3) 0.0022(3) 0.0016(3)
C5 0.0155(4) 0.0168(4) 0.0241(5) -0.0048(4) 0.0014(4) -0.0014(3)
C6 0.0162(4) 0.0162(4) 0.0255(5) -0.0017(4) 0.0019(4) -0.0033(3)
C7 0.0127(4) 0.0193(5) 0.0199(5) -0.0011(4) 0.0033(3) -0.0016(3)
C8 0.0141(4) 0.0161(4) 0.0174(4) -0.0011(3) 0.0028(3) 0.0002(3)
C9 0.0174(4) 0.0158(4) 0.0191(5) 0.0001(3) 0.0043(4) 0.0018(3)
C10 0.0202(5) 0.0210(5) 0.0172(4) -0.0027(4) 0.0019(4) -0.0001(4)
C11 0.0163(4) 0.0185(4) 0.0184(5) -0.0016(3) 0.0007(3) -0.0026(3)
C12 0.0141(4) 0.0145(4) 0.0167(4) -0.0001(3) 0.0014(3) 0.0005(3)
C13 0.0126(4) 0.0187(4) 0.0187(5) -0.0013(3) 0.0034(3) -0.0015(3)
C14 0.0160(4) 0.0159(4) 0.0174(4) -0.0001(3) 0.0043(3) 0.0007(3)
O1 0.0132(3) 0.0223(4) 0.0197(4) -0.0009(3) 0.0023(3) 0.0039(3)
O2 0.0233(4) 0.0282(4) 0.0261(4) -0.0036(3) 0.0122(3) -0.0029(3)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C14 C1 C2 103.18(8)
C14 C1 H1A 111.1
C2 C1 H1A 111.1
C14 C1 H1B 111.1
C2 C1 H1B 111.1
H1A C1 H1B 109.1
C1 C2 C3 105.48(9)
C1 C2 H2A 110.6
C3 C2 H2A 110.6
C1 C2 H2B 110.6
C3 C2 H2B 110.6
H2A C2 H2B 108.8
C4 C3 C2 105.98(9)
C4 C3 H3A 110.5
C2 C3 H3A 110.5
C4 C3 H3B 110.5
C2 C3 H3B 110.5
H3A C3 H3B 108.7
O1 C4 C5 102.79(8)
O1 C4 C3 110.97(8)
C5 C4 C3 116.27(9)
O1 C4 C14 111.92(8)
C5 C4 C14 111.64(8)
C3 C4 C14 103.53(8)
C6 C5 C4 109.32(9)
C6 C5 H5 125.3
C4 C5 H5 125.3
C5 C6 C7 108.59(9)
C5 C6 H6 125.7
C7 C6 H6 125.7
O1 C7 C8 110.26(8)
O1 C7 C6 102.97(8)
C8 C7 C6 110.69(8)
O1 C7 H7 110.9
C8 C7 H7 110.9
C6 C7 H7 110.9
C12 C8 C9 110.12(9)
C12 C8 C7 127.06(9)
C9 C8 C7 122.81(8)
O2 C9 C8 125.75(10)
O2 C9 C10 125.90(9)
C8 C9 C10 108.34(8)
C9 C10 C11 104.72(8)
C9 C10 H10A 110.8
C11 C10 H10A 110.8
C9 C10 H10B 110.8
C11 C10 H10B 110.8
H10A C10 H10B 108.9
C12 C11 C10 105.11(8)
C12 C11 H11A 110.7
C10 C11 H11A 110.7
C12 C11 H11B 110.7
C10 C11 H11B 110.7
H11A C11 H11B 108.8
C8 C12 C13 127.36(9)
C8 C12 C11 111.67(8)
C13 C12 C11 120.95(8)
C12 C13 C14 115.25(8)
C12 C13 H13A 108.5
C14 C13 H13A 108.5
C12 C13 H13B 108.5
C14 C13 H13B 108.5
H13A C13 H13B 107.5
C1 C14 C13 115.00(8)
C1 C14 C4 101.58(8)
C13 C14 C4 115.70(8)
C1 C14 H14 108.0
C13 C14 H14 108.0
C4 C14 H14 108.0
C7 O1 C4 106.18(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C14 1.5316(13)
C1 C2 1.5432(16)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.5510(16)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5361(14)
C3 H3A 0.9900
C3 H3B 0.9900
C4 O1 1.4449(11)
C4 C5 1.5141(14)
C4 C14 1.5490(13)
C5 C6 1.3243(15)
C5 H5 0.9500
C6 C7 1.5162(14)
C6 H6 0.9500
C7 O1 1.4425(12)
C7 C8 1.5096(13)
C7 H7 1.0000
C8 C12 1.3543(13)
C8 C9 1.4691(13)
C9 O2 1.2270(13)
C9 C10 1.5182(14)
C10 C11 1.5358(14)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.5114(13)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.5042(13)
C13 C14 1.5333(14)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14 1.0000
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
C14 C1 C2 C3 28.84(11)
C1 C2 C3 C4 -2.64(12)
C2 C3 C4 O1 -144.48(9)
C2 C3 C4 C5 98.55(11)
C2 C3 C4 C14 -24.26(11)
O1 C4 C5 C6 18.05(10)
C3 C4 C5 C6 139.47(9)
C14 C4 C5 C6 -102.07(10)
C4 C5 C6 C7 1.08(11)
C5 C6 C7 O1 -19.85(10)
C5 C6 C7 C8 97.98(10)
O1 C7 C8 C12 53.48(13)
C6 C7 C8 C12 -59.79(13)
O1 C7 C8 C9 -125.64(9)
C6 C7 C8 C9 121.09(10)
C12 C8 C9 O2 177.52(10)
C7 C8 C9 O2 -3.23(16)
C12 C8 C9 C10 -2.21(11)
C7 C8 C9 C10 177.04(9)
O2 C9 C10 C11 -178.09(10)
C8 C9 C10 C11 1.63(10)
C9 C10 C11 C12 -0.58(10)
C9 C8 C12 C13 -176.91(9)
C7 C8 C12 C13 3.88(16)
C9 C8 C12 C11 1.86(11)
C7 C8 C12 C11 -177.35(9)
C10 C11 C12 C8 -0.76(11)
C10 C11 C12 C13 178.09(8)
C8 C12 C13 C14 -44.82(14)
C11 C12 C13 C14 136.52(9)
C2 C1 C14 C13 -169.41(9)
C2 C1 C14 C4 -43.68(10)
C12 C13 C14 C1 176.24(8)
C12 C13 C14 C4 58.20(11)
O1 C4 C14 C1 161.66(8)
C5 C4 C14 C1 -83.74(9)
C3 C4 C14 C1 42.08(9)
O1 C4 C14 C13 -73.07(10)
C5 C4 C14 C13 41.52(11)
C3 C4 C14 C13 167.35(8)
C8 C7 O1 C4 -87.03(9)
C6 C7 O1 C4 31.10(9)
C5 C4 O1 C7 -30.42(9)
C3 C4 O1 C7 -155.39(8)
C14 C4 O1 C7 89.51(9)