#------------------------------------------------------------------------------
#$Date: 2024-01-05 13:56:28 +0100 (Fri 05 de Jan de 2024) $
#$Revision: 288699 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/97/7159751.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_7159751
loop_
_publ_author_name
'Huo, Shou-Chih'
'Indurmuddam, Ranadheer Reddy'
'Hong, Bor-Cherng'
'Lu, Chuan-Fu'
'Chien, Su-Ying'
_publ_section_title
;
 The hamburger-shape photocatalyst: thioxanthone-based chiral
 [2.2]paracyclophane for enantioselective visible-light photocatalysis of
 3-methylquinoxalin-2(1H)-one and styrenes.
;
_journal_issue                   47
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9330
_journal_page_last               9336
_journal_paper_doi               10.1039/d3ob01580g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-07-10 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.5300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7133(2)
_cell_length_b                   11.0969(3)
_cell_length_c                   17.3223(6)
_cell_measurement_reflns_used    8538
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.35
_cell_volume                     1481.23(8)
_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-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19568
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_min         2.180
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0640
_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)+(0.0747P)²+1.2808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3009
_reflns_number_total             4313
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01580g2.cif
_cod_data_source_block           ic21545
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159751
_shelx_shelxl_version_number     2019/1
_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   0.972
_shelx_estimated_absorpt_t_max   0.994
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4119(3) 0.62520(15) 0.53278(9) 0.0521(5) Uani 1 1 d . . . . .
O2 O 0.4892(2) 0.46272(13) 0.60232(9) 0.0458(4) Uani 1 1 d . . . . .
H2 H 0.513963 0.436822 0.558594 0.069 Uiso 1 1 calc R U . . .
O3 O 0.7480(3) 0.83926(18) 0.52944(11) 0.0632(5) Uani 1 1 d . . . . .
O4 O 0.8097(2) 0.66898(15) 0.59374(9) 0.0505(4) Uani 1 1 d . . . . .
C1 C 0.2765(3) 0.73026(18) 0.67486(12) 0.0365(4) Uani 1 1 d . . . . .
C2 C 0.3839(2) 0.62783(17) 0.67061(11) 0.0326(4) Uani 1 1 d . . . . .
C3 C 0.4658(3) 0.58109(17) 0.73773(11) 0.0323(4) Uani 1 1 d . . . . .
H3 H 0.540302 0.513356 0.733965 0.039 Uiso 1 1 calc R U . . .
C4 C 0.4407(3) 0.63160(17) 0.80994(12) 0.0356(4) Uani 1 1 d . . . . .
C5 C 0.3009(3) 0.7107(2) 0.81451(13) 0.0403(5) Uani 1 1 d . . . . .
H5 H 0.259517 0.731527 0.863607 0.048 Uiso 1 1 calc R U . . .
C6 C 0.2225(3) 0.75903(19) 0.74863(13) 0.0395(5) Uani 1 1 d . . . . .
H6 H 0.128635 0.813591 0.753422 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2426(3) 0.8215(2) 0.61127(14) 0.0461(5) Uani 1 1 d . . . . .
H7A H 0.139906 0.870198 0.623656 0.055 Uiso 1 1 calc R U . . .
H7B H 0.214511 0.778157 0.562369 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3996(3) 0.9088(2) 0.59877(15) 0.0513(6) Uani 1 1 d . . . . .
H8A H 0.453123 0.887992 0.549610 0.062 Uiso 1 1 calc R U . . .
H8B H 0.356059 0.992552 0.594456 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5372(3) 0.90160(18) 0.66462(14) 0.0407(5) Uani 1 1 d . . . . .
C10 C 0.6788(3) 0.82229(18) 0.66293(12) 0.0361(4) Uani 1 1 d . . . . .
C11 C 0.7517(3) 0.77372(19) 0.73148(12) 0.0366(4) Uani 1 1 d . . . . .
H11 H 0.843910 0.717310 0.729092 0.044 Uiso 1 1 calc R U . . .
C12 C 0.6915(3) 0.8065(2) 0.80312(12) 0.0400(5) Uani 1 1 d . . . . .
C13 C 0.5800(3) 0.9058(2) 0.80380(14) 0.0462(5) Uani 1 1 d . . . . .
H13 H 0.556246 0.942572 0.851713 0.055 Uiso 1 1 calc R U . . .
C14 C 0.5037(3) 0.95155(19) 0.73651(15) 0.0455(5) Uani 1 1 d . . . . .
H14 H 0.426888 1.018236 0.739076 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7169(3) 0.7240(3) 0.87189(13) 0.0508(6) Uani 1 1 d . . . . .
H15A H 0.712865 0.772479 0.919742 0.061 Uiso 1 1 calc R U . . .
H15B H 0.833566 0.686916 0.870799 0.061 Uiso 1 1 calc R U . . .
C16 C 0.5775(3) 0.6213(2) 0.87449(12) 0.0449(5) Uani 1 1 d . . . . .
H16A H 0.635957 0.542197 0.870974 0.054 Uiso 1 1 calc R U . . .
H16B H 0.520951 0.624617 0.924656 0.054 Uiso 1 1 calc R U . . .
C17 C 0.4290(3) 0.57357(18) 0.59563(12) 0.0369(4) Uani 1 1 d . . . . .
C18 C 0.7458(3) 0.7808(2) 0.58829(13) 0.0410(5) Uani 1 1 d . . . . .
C19 C 0.8811(5) 0.6216(3) 0.52547(16) 0.0673(8) Uani 1 1 d . . . . .
H19A H 0.807597 0.644888 0.480329 0.101 Uiso 1 1 calc R U . . .
H19B H 0.886352 0.533500 0.528952 0.101 Uiso 1 1 calc R U . . .
H19C H 0.998258 0.653791 0.520256 0.101 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O4 C19 115.99(19) . . ?
C6 C1 C2 115.55(19) . . ?
C6 C1 C7 117.65(19) . . ?
C2 C1 C7 125.85(19) . . ?
C3 C2 C1 120.03(17) . . ?
C3 C2 C17 117.47(17) . . ?
C1 C2 C17 122.20(18) . . ?
C4 C3 C2 121.47(18) . . ?
C3 C4 C5 116.28(19) . . ?
C3 C4 C16 121.03(19) . . ?
C5 C4 C16 121.52(19) . . ?
C6 C5 C4 120.70(19) . . ?
C5 C6 C1 122.05(19) . . ?
C1 C7 C8 113.79(18) . . ?
C9 C8 C7 112.30(19) . . ?
C14 C9 C10 116.2(2) . . ?
C14 C9 C8 119.7(2) . . ?
C10 C9 C8 122.2(2) . . ?
C11 C10 C9 120.49(19) . . ?
C11 C10 C18 118.49(18) . . ?
C9 C10 C18 120.9(2) . . ?
C12 C11 C10 121.3(2) . . ?
C11 C12 C13 116.3(2) . . ?
C11 C12 C15 120.6(2) . . ?
C13 C12 C15 122.0(2) . . ?
C14 C13 C12 121.5(2) . . ?
C13 C14 C9 121.2(2) . . ?
C12 C15 C16 113.45(18) . . ?
C4 C16 C15 112.45(18) . . ?
O1 C17 O2 122.36(19) . . ?
O1 C17 C2 124.29(18) . . ?
O2 C17 C2 113.35(18) . . ?
O3 C18 O4 122.6(2) . . ?
O3 C18 C10 125.9(2) . . ?
O4 C18 C10 111.54(18) . . ?
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 C17 1.232(3) . ?
O2 C17 1.318(2) . ?
O3 C18 1.209(3) . ?
O4 C18 1.337(3) . ?
O4 C19 1.427(3) . ?
C1 C6 1.398(3) . ?
C1 C2 1.410(3) . ?
C1 C7 1.511(3) . ?
C2 C3 1.398(3) . ?
C2 C17 1.487(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.396(3) . ?
C4 C16 1.507(3) . ?
C5 C6 1.377(3) . ?
C7 C8 1.573(4) . ?
C8 C9 1.526(3) . ?
C9 C14 1.398(3) . ?
C9 C10 1.404(3) . ?
C10 C11 1.399(3) . ?
C10 C18 1.486(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.399(3) . ?
C12 C15 1.508(3) . ?
C13 C14 1.379(4) . ?
C15 C16 1.569(4) . ?
