#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:31:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180266 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/52/7115275.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_7115275
loop_
_publ_author_name
'Stuart Aiken'
'Kathryn Booth'
'Christopher D. Gabbutt'
'B. Mark Heron'
'Craig R. Rice'
'Azzam Charaf-Eddin'
'Denis Jacquemin'
_publ_section_title
;
 The first structural and spectroscopic characterisation of a ring-opened
 form of a 2H-naphtho[1,2-b]pyran: a novel photomerocyanine
;
_journal_name_full               Chem.Commun.
_journal_page_first              7900
_journal_paper_doi               10.1039/C4CC03435J
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C28 H24 O4'
_chemical_formula_weight         424.47
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.4847(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9087(7)
_cell_length_b                   13.6467(6)
_cell_length_c                   17.9157(7)
_cell_measurement_reflns_used    8251
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.17
_cell_measurement_theta_min      4.08
_cell_volume                     4365.1(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17375
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.163
_diffrn_reflns_theta_min         4.077
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0532
_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/[σ²(Fo²)+(0.1020P)²+2.4276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3333
_reflns_number_total             4119
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4cc03435j2.cif
_cod_data_source_block           cu_MarkCC_orange_0m
_cod_database_code               7115275
#BEGIN Tags that were not found in dictionaries:
_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   0.820
_shelx_estimated_absorpt_t_max   0.875
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
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'
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
O1 O 0.13489(8) 0.93686(11) 0.35284(7) 0.0304(3) Uani 1 1 d . .
O2 O 0.02693(8) 0.82258(11) 0.07261(7) 0.0306(4) Uani 1 1 d . .
O3 O 0.16622(8) 0.38492(12) -0.09795(8) 0.0358(4) Uani 1 1 d . .
O4 O 0.19628(8) 0.21449(12) 0.41326(9) 0.0367(4) Uani 1 1 d . .
C1 C 0.10979(10) 0.89948(15) 0.28504(10) 0.0240(4) Uani 1 1 d . .
C2 C 0.10193(10) 0.80418(14) 0.26818(10) 0.0230(4) Uani 1 1 d . .
H2 H 0.1129 0.7569 0.3064 0.028 Uiso 1 1 calc R U
C3 C 0.07705(10) 0.77081(14) 0.19317(10) 0.0218(4) Uani 1 1 d . .
C4 C 0.05452(10) 0.84549(15) 0.13542(10) 0.0238(4) Uani 1 1 d . .
C5 C 0.06629(10) 0.94969(15) 0.15613(11) 0.0247(4) Uani 1 1 d . .
C6 C 0.04911(12) 1.02240(16) 0.10290(12) 0.0322(5) Uani 1 1 d . .
H6 H 0.0315 1.0043 0.0534 0.039 Uiso 1 1 calc R U
C7 C 0.05727(13) 1.12010(17) 0.12103(13) 0.0378(5) Uani 1 1 d . .
H7 H 0.0457 1.1690 0.0842 0.045 Uiso 1 1 calc R U
C8 C 0.08263(13) 1.14671(17) 0.19360(13) 0.0371(5) Uani 1 1 d . .
H8 H 0.0875 1.2141 0.2065 0.044 Uiso 1 1 calc R U
C9 C 0.10081(11) 1.07581(16) 0.24709(12) 0.0305(5) Uani 1 1 d . .
H9 H 0.1190 1.0948 0.2962 0.037 Uiso 1 1 calc R U
C10 C 0.09268(10) 0.97656(15) 0.22937(11) 0.0243(4) Uani 1 1 d . .
C11 C 0.15236(13) 0.86881(17) 0.41190(11) 0.0346(5) Uani 1 1 d . .
H11A H 0.1081 0.8290 0.4196 0.052 Uiso 1 1 calc R U
H11B H 0.1677 0.9045 0.4580 0.052 Uiso 1 1 calc R U
H11C H 0.1933 0.8261 0.3987 0.052 Uiso 1 1 calc R U
C12 C 0.07690(10) 0.67525(15) 0.17127(10) 0.0252(4) Uani 1 1 d . .
H12 H 0.0631 0.6617 0.1200 0.030 Uiso 1 1 calc R U
C13 C 0.09584(10) 0.59326(15) 0.21927(10) 0.0256(4) Uani 1 1 d . .
H13 H 0.0945 0.6031 0.2716 0.031 Uiso 1 1 calc R U
C14 C 0.11546(10) 0.50300(15) 0.19609(10) 0.0244(4) Uani 1 1 d . .
C15 C 0.12636(10) 0.47813(15) 0.11687(10) 0.0247(4) Uani 1 1 d . .
C16 C 0.17560(11) 0.53076(15) 0.07567(11) 0.0275(4) Uani 1 1 d . .
H16 H 0.1998 0.5873 0.0970 0.033 Uiso 1 1 calc R U
C17 C 0.18996(11) 0.50170(16) 0.00364(11) 0.0291(4) Uani 1 1 d . .
H17 H 0.2245 0.5375 -0.0233 0.035 Uiso 1 1 calc R U
C18 C 0.15400(11) 0.42079(16) -0.02869(10) 0.0275(4) Uani 1 1 d . .
C19 C 0.10197(12) 0.36972(16) 0.01058(11) 0.0301(5) Uani 1 1 d . .
H19 H 0.0750 0.3162 -0.0123 0.036 Uiso 1 1 calc R U
C20 C 0.08995(11) 0.39743(15) 0.08272(11) 0.0288(4) Uani 1 1 d . .
H20 H 0.0560 0.3607 0.1098 0.035 Uiso 1 1 calc R U
C21 C 0.23390(12) 0.4142(2) -0.12894(12) 0.0411(6) Uani 1 1 d . .
H21A H 0.2322 0.4847 -0.1393 0.062 Uiso 1 1 calc R U
H21B H 0.2392 0.3782 -0.1756 0.062 Uiso 1 1 calc R U
H21C H 0.2767 0.3997 -0.0932 0.062 Uiso 1 1 calc R U
C22 C 0.13208(10) 0.42441(15) 0.25196(10) 0.0242(4) Uani 1 1 d . .
C23 C 0.19483(11) 0.36394(15) 0.24683(11) 0.0273(4) Uani 1 1 d . .
H23 H 0.2237 0.3700 0.2048 0.033 Uiso 1 1 calc R U
C24 C 0.21541(11) 0.29580(16) 0.30161(11) 0.0284(4) Uani 1 1 d . .
H24 H 0.2590 0.2570 0.2979 0.034 Uiso 1 1 calc R U
C25 C 0.17218(11) 0.28410(16) 0.36224(11) 0.0273(4) Uani 1 1 d . .
C26 C 0.10894(11) 0.34205(16) 0.36823(11) 0.0279(4) Uani 1 1 d . .
H26 H 0.0791 0.3341 0.4094 0.033 Uiso 1 1 calc R U
C27 C 0.08987(10) 0.41160(15) 0.31344(11) 0.0264(4) Uani 1 1 d . .
H27 H 0.0470 0.4515 0.3179 0.032 Uiso 1 1 calc R U
C28 C 0.15030(13) 0.1958(2) 0.47306(13) 0.0429(6) Uani 1 1 d . .
H28A H 0.1468 0.2552 0.5033 0.064 Uiso 1 1 calc R U
H28B H 0.1723 0.1428 0.5045 0.064 Uiso 1 1 calc R U
H28C H 0.1001 0.1765 0.4526 0.064 Uiso 1 1 calc R U
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C11 117.18(16)
C18 O3 C21 116.96(17)
C25 O4 C28 117.22(16)
C2 C1 O1 125.90(18)
C2 C1 C10 122.05(17)
O1 C1 C10 112.04(17)
C1 C2 C3 122.07(17)
C1 C2 H2 119.0
C3 C2 H2 119.0
C12 C3 C2 124.00(17)
C12 C3 C4 117.52(17)
C2 C3 C4 118.38(17)
O2 C4 C5 120.75(18)
O2 C4 C3 121.94(18)
C5 C4 C3 117.31(16)
C6 C5 C10 119.49(19)
C6 C5 C4 119.52(18)
C10 C5 C4 120.97(18)
C7 C6 C5 120.9(2)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 119.6(2)
C6 C7 H7 120.2
C8 C7 H7 120.2
C9 C8 C7 120.5(2)
C9 C8 H8 119.8
C7 C8 H8 119.8
C8 C9 C10 120.4(2)
C8 C9 H9 119.8
C10 C9 H9 119.8
C9 C10 C5 119.08(19)
C9 C10 C1 121.94(18)
C5 C10 C1 118.97(18)
O1 C11 H11A 109.5
O1 C11 H11B 109.5
H11A C11 H11B 109.5
O1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C3 C12 C13 125.36(18)
C3 C12 H12 117.3
C13 C12 H12 117.3
C14 C13 C12 125.43(18)
C14 C13 H13 117.3
C12 C13 H13 117.3
C13 C14 C22 119.62(17)
C13 C14 C15 123.82(18)
C22 C14 C15 116.44(17)
C16 C15 C20 117.88(18)
C16 C15 C14 121.60(18)
C20 C15 C14 120.44(17)
C15 C16 C17 120.96(19)
C15 C16 H16 119.5
C17 C16 H16 119.5
C18 C17 C16 120.12(18)
C18 C17 H17 119.9
C16 C17 H17 119.9
O3 C18 C17 124.31(19)
O3 C18 C19 116.03(19)
C17 C18 C19 119.65(18)
C20 C19 C18 119.62(19)
C20 C19 H19 120.2
C18 C19 H19 120.2
C19 C20 C15 121.67(18)
C19 C20 H20 119.2
C15 C20 H20 119.2
O3 C21 H21A 109.5
O3 C21 H21B 109.5
H21A C21 H21B 109.5
O3 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C27 C22 C23 117.67(18)
C27 C22 C14 122.12(17)
C23 C22 C14 120.08(17)
C24 C23 C22 121.34(18)
C24 C23 H23 119.3
C22 C23 H23 119.3
C23 C24 C25 119.88(18)
C23 C24 H24 120.1
C25 C24 H24 120.1
O4 C25 C24 115.89(17)
O4 C25 C26 124.07(18)
C24 C25 C26 120.03(19)
C27 C26 C25 119.36(18)
C27 C26 H26 120.3
C25 C26 H26 120.3
C26 C27 C22 121.69(18)
C26 C27 H27 119.2
C22 C27 H27 119.2
O4 C28 H28A 109.5
O4 C28 H28B 109.5
H28A C28 H28B 109.5
O4 C28 H28C 109.5
H28A C28 H28C 109.5
H28B C28 H28C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.361(2)
O1 C11 1.424(2)
O2 C4 1.233(2)
O3 C18 1.367(2)
O3 C21 1.429(3)
O4 C25 1.365(2)
O4 C28 1.424(3)
C1 C2 1.340(3)
C1 C10 1.465(3)
C2 C3 1.455(2)
C2 H2 0.9500
C3 C12 1.362(3)
C3 C4 1.486(3)
C4 C5 1.481(3)
C5 C6 1.394(3)
C5 C10 1.408(3)
C6 C7 1.377(3)
C6 H6 0.9500
C7 C8 1.391(3)
C7 H7 0.9500
C8 C9 1.383(3)
C8 H8 0.9500
C9 C10 1.396(3)
C9 H9 0.9500
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.436(3)
C12 H12 0.9500
C13 C14 1.355(3)
C13 H13 0.9500
C14 C22 1.481(3)
C14 C15 1.487(3)
C15 C16 1.393(3)
C15 C20 1.397(3)
C16 C17 1.393(3)
C16 H16 0.9500
C17 C18 1.382(3)
C17 H17 0.9500
C18 C19 1.397(3)
C19 C20 1.380(3)
C19 H19 0.9500
C20 H20 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 C27 1.395(3)
C22 C23 1.403(3)
C23 C24 1.381(3)
C23 H23 0.9500
C24 C25 1.392(3)
C24 H24 0.9500
C25 C26 1.392(3)
C26 C27 1.389(3)
C26 H26 0.9500
C27 H27 0.9500
C28 H28A 0.9800
C28 H28B 0.9800
C28 H28C 0.9800
