2,2'-Spirobis[chromene] Derivatives Chemistry and Their Relation with the Multistate System of Anthocyanins.
Moro, Artur J.; Parola, A. Jorge; Pina, Fernando; Pana, Ana-Maria; Badea, Valentin; Pausescu, Iulia; Shova, Sergiu; Cseh, Liliana; The Journal of organic chemistry 82 (2017) 5301–5309; doi:10.1021/acs.joc.7b00634

data_4037495
_publ_section_title
;
 2,2'-Spirobis[chromene] Derivatives Chemistry and Their Relation with the
 Multistate System of Anthocyanins.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5301
_journal_page_last               5309
_journal_paper_doi               10.1021/acs.joc.7b00634
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C20 H17 O3), 2(Cl O4), 1.9(H2 O)'
_chemical_formula_sum            'C40 H38 Cl2 O16'
_chemical_formula_weight         845.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3050(9)
_cell_length_b                   16.254(3)
_cell_length_c                   16.7183(19)
_cell_measurement_reflns_used    1066
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.3500
_cell_measurement_theta_min      5.2850
_cell_volume                     1985.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -8.00  20.00   1.00    2.00    --    0.00 -77.00 -30.00   28
  2  \w     10.00  81.00   1.00   10.00    --   54.00 -77.00 -30.00   71
  3  \w     39.00  59.00   1.00   30.00    --  108.00-111.00 -60.00   20
  4  \w     46.00  78.00   1.00   30.00    --  108.00 -37.00 -30.00   32
  5  \w     36.00  90.00   1.00   30.00    --  108.00 -25.00  60.00   54
  6  \w     36.00  94.00   1.00   30.00    --  108.00 -25.00   0.00   58
  7  \w     86.00 118.00   1.00   10.00    --   54.00  57.00 -60.00   32
  8  \w    101.00 135.00   1.00   30.00    --  108.00 111.00 -30.00   34
  9  \w    110.00 159.00   1.00   30.00    --  108.00 111.00   0.00   49
 10  \w     41.00  71.00   1.00   30.00    --  108.00 -37.00 120.00   30
 11  \w    -30.00  -2.00   1.00    2.00    --    0.00 125.00   1.00   28
 12  \w    -11.00  66.00   1.00   10.00    --   54.00 -37.00-150.00   77
 13  \w    -67.00 -39.00   1.00    2.00    --    0.00 -77.00 -30.00   28
 14  \w     -4.00  45.00   1.00    2.00    --    0.00  57.00 120.00   49
 15  \w    -19.00  13.00   1.00    2.00    --    0.00  57.00 -30.00   32
 16  \w     23.00  49.00   1.00    2.00    --    0.00  57.00 -30.00   26
 17  \w     34.00  86.00   1.00   10.00    --   54.00  57.00  90.00   52
 18  \w     40.00  69.00   1.00   10.00    --   54.00 -68.00 161.00   29
 19  \w     25.00 109.00   1.00   10.00    --   54.00-125.00-150.00   84
 20  \w     31.00  57.00   1.00   10.00    --   54.00-125.00  30.00   26
 21  \w     37.00 124.00   1.00   10.00    --   54.00  77.00   0.00   87
 22  \w     78.00 121.00   1.00   10.00    --   54.00  57.00 -90.00   43
 23  \w     52.00 117.00   1.00   10.00    --   54.00  57.00 120.00   65
 24  \w     92.00 141.00   1.00   30.00    --  108.00  50.00 120.00   49
 25  \w     83.00 103.00   1.00   30.00    --  108.00-111.00 150.00   20
 26  \w     75.00 163.00   1.00   30.00    --  108.00  25.00-150.00   88
 27  \w     68.00  94.00   1.00   30.00    --  108.00 -50.00 -30.00   26
 28  \w     45.00 130.00   1.00   30.00    --  108.00 -77.00  60.00   85
 29  \w     42.00  68.00   1.00   30.00    --  108.00-111.00 150.00   26
 30  \w     45.00  97.00   1.00   30.00    --  108.00-111.00  30.00   52
 31  \w     42.00  91.00   1.00   30.00    --  108.00 -91.00-150.00   49
 32  \w    109.00 135.00   1.00   30.00    --  108.00 111.00-120.00   26
 33  \w     36.00  85.00   1.00   30.00    --  108.00 -37.00-120.00   49
 34  \w     55.00  84.00   1.00   30.00    --  108.00 -37.00-180.00   29
 35  \w     68.00  94.00   1.00   30.00    --  108.00 -25.00  60.00   26
 36  \w     36.00  94.00   1.00   30.00    --  108.00 -25.00 -90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0712974000
_diffrn_orient_matrix_UB_12      -0.0744052000
_diffrn_orient_matrix_UB_13      -0.0475869000
_diffrn_orient_matrix_UB_21      -0.1127121000
_diffrn_orient_matrix_UB_22      0.0581837000
_diffrn_orient_matrix_UB_23      -0.0533866000
_diffrn_orient_matrix_UB_31      0.1633978000
_diffrn_orient_matrix_UB_32      0.0077086000
_diffrn_orient_matrix_UB_33      -0.0581121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9620
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        58.920
_diffrn_reflns_theta_max         58.920
_diffrn_reflns_theta_min         5.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 205 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1720
_refine_ls_R_factor_gt           0.0960
_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^)+(0.1115P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2311
_refine_ls_wR_factor_ref         0.3041
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1179
_reflns_number_total             2835
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00634_si_001.cif
_cod_data_source_block           shc_499_lics
_cod_database_code               4037495
_chemical_oxdiff_formula         'C30 H30 N2 O2 Cl1'
_chemical_oxdiff_usercomment     4.1
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 Cl1-O5X \\sim Cl1-O4X \\sim Cl1-O4 \\sim Cl1-O6 \\sim Cl1-O7X \\sim Cl1-O7
\\sim Cl1-O5 \\sim Cl1-O6X
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O5X) = Uanis(O5) = Uanis(O4X) = Uanis(O4) = Uanis(O7) = Uanis(O7X) =
Uanis(O6X) = Uanis(O6)
4. Others
 Fixed Sof: O4(0.5) O4X(0.5) O5(0.5) O5X(0.5) O6(0.5) O6X(0.5) O7(0.5)
 O7X(0.5) O1W(0.75) H1WA(0.75) H1WB(0.75) O2W(0.2) H2WA(0.2) H2WB(0.2)
5.a Riding coordinates:
 O1(H1), O3(H3), O1W(H1WA,H1WB), O2W(H2WA,H2WB)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C7(H7), C14(H14), C17(H17), C19(H19), C20(H20)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-09-21
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.543
_oxdiff_exptl_absorpt_empirical_full_min 0.402