#------------------------------------------------------------------------------
#$Date: 2023-07-05 12:44:54 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284899 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/92/1569214.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_1569214
loop_
_publ_author_name
'Singha, Tushar'
'Kadam, Ganesh Arjun'
'Hari, Durga Prasad'
_publ_section_title
;
 Photocatalyzed Dowd-Beckwith radical-polar crossover reaction for the
 synthesis of medium-sized carbocyclic compounds.
;
_journal_issue                   25
_journal_name_full               'Chemical science'
_journal_page_first              6930
_journal_page_last               6935
_journal_paper_doi               10.1039/d3sc01908j
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H26 O4'
_chemical_formula_sum            'C22 H26 O4'
_chemical_formula_weight         354.43
_chemical_name_common            Cycloheptanone
_chemical_name_systematic
3-phenyl-3-(2,4,6-trimethoxyphenyl)cycloheptan-1-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-05-18 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.9842(4)
_cell_length_b                   21.6573(12)
_cell_length_c                   21.6791(11)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      3.17
_cell_volume                     3748.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_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      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            94830
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.037
_diffrn_reflns_theta_max         25.037
_diffrn_reflns_theta_min         2.659
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.289
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.289
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0688
_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)+(0.0435P)²+4.9479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1459
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3113
_reflns_number_total             3315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc01908j2.cif
_cod_data_source_block           Ts_DB_119_reduced1_a
_cod_depositor_comments
'Adding full bibliography for 1569214--1569215.cif.'
_cod_database_code               1569214
_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.
;
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'
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 0.4993(2) 0.43054(8) 0.55386(8) 0.0189(4) Uani 1 1 d . . . . .
O2 O 0.6967(2) 0.55960(8) 0.72042(8) 0.0211(4) Uani 1 1 d . . . . .
O3 O 1.0098(2) 0.38711(8) 0.65349(8) 0.0171(4) Uani 1 1 d . . . . .
O4 O 1.0479(2) 0.24665(9) 0.66024(9) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.9325(3) 0.41190(11) 0.49198(11) 0.0156(5) Uani 1 1 d . . . . .
H2 H 0.982146 0.429403 0.527762 0.019 Uiso 1 1 calc R U . . .
C3 C 0.9860(3) 0.43100(12) 0.43432(11) 0.0182(6) Uani 1 1 d . . . . .
H3 H 1.070769 0.461594 0.430937 0.022 Uiso 1 1 calc R U . . .
C4 C 0.9162(3) 0.40565(12) 0.38138(12) 0.0192(6) Uani 1 1 d . . . . .
H4 H 0.952451 0.418725 0.341743 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7929(3) 0.36098(12) 0.38725(12) 0.0197(6) Uani 1 1 d . . . . .
H5 H 0.744816 0.343165 0.351327 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7388(3) 0.34198(12) 0.44521(11) 0.0179(6) Uani 1 1 d . . . . .
H6 H 0.654274 0.311290 0.448397 0.021 Uiso 1 1 calc R U . . .
C10 C 0.5860(3) 0.49657(11) 0.63680(11) 0.0151(5) Uani 1 1 d . . . . .
H10 H 0.490669 0.522300 0.631582 0.018 Uiso 1 1 calc R U . . .
C12 C 0.8457(3) 0.47323(11) 0.68803(11) 0.0134(5) Uani 1 1 d . . . . .
H12 H 0.927328 0.482991 0.718401 0.016 Uiso 1 1 calc R U . . .
C1 C 0.8070(3) 0.36737(11) 0.49866(11) 0.0138(5) Uani 1 1 d . . . . .
C7 C 0.7599(3) 0.34517(12) 0.56437(11) 0.0148(5) Uani 1 1 d . . . . .
C8 C 0.7455(3) 0.40332(11) 0.60653(11) 0.0129(5) Uani 1 1 d . . . . .
C9 C 0.6095(3) 0.44399(11) 0.59985(11) 0.0141(5) Uani 1 1 d . . . . .
C11 C 0.7056(3) 0.50977(11) 0.68094(11) 0.0146(5) Uani 1 1 d . . . . .
C13 C 0.8662(3) 0.42187(11) 0.65014(11) 0.0130(5) Uani 1 1 d . . . . .
C14 C 0.9021(3) 0.29883(11) 0.58151(11) 0.0155(5) Uani 1 1 d . . . . .
H14A H 0.892461 0.263467 0.552800 0.019 Uiso 1 1 calc R U . . .
H14B H 1.009682 0.319514 0.572072 0.019 Uiso 1 1 calc R U . . .
C15 C 0.9177(3) 0.27217(11) 0.64602(12) 0.0177(6) Uani 1 1 d . . . . .
C16 C 0.7744(3) 0.27504(12) 0.69098(12) 0.0216(6) Uani 1 1 d . . . . .
H16A H 0.756843 0.318626 0.703112 0.026 Uiso 1 1 calc R U . . .
H16B H 0.805847 0.251802 0.728561 0.026 Uiso 1 1 calc R U . . .
C17 C 0.6085(4) 0.24911(13) 0.66637(13) 0.0252(6) Uani 1 1 d . . . . .
H17A H 0.632278 0.211052 0.642632 0.030 Uiso 1 1 calc R U . . .
H17B H 0.537151 0.237450 0.701860 0.030 Uiso 1 1 calc R U . . .
C18 C 0.5107(3) 0.29345(13) 0.62534(13) 0.0227(6) Uani 1 1 d . . . . .
H18A H 0.495070 0.332747 0.647941 0.027 Uiso 1 1 calc R U . . .
H18B H 0.398211 0.275742 0.617775 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5922(3) 0.30768(12) 0.56299(12) 0.0175(6) Uani 1 1 d . . . . .
H19A H 0.510409 0.330932 0.537719 0.021 Uiso 1 1 calc R U . . .
H19B H 0.613652 0.268026 0.541696 0.021 Uiso 1 1 calc R U . . .
C20 C 0.3490(3) 0.46586(13) 0.54835(13) 0.0232(6) Uani 1 1 d . . . . .
H20A H 0.283356 0.450601 0.513322 0.035 Uiso 1 1 calc R U . . .
H20B H 0.377313 0.509381 0.541673 0.035 Uiso 1 1 calc R U . . .
H20C H 0.283089 0.461845 0.586281 0.035 Uiso 1 1 calc R U . . .
C21 C 0.5753(4) 0.60624(12) 0.70649(13) 0.0254(6) Uani 1 1 d . . . . .
H21A H 0.589286 0.641076 0.734879 0.038 Uiso 1 1 calc R U . . .
H21B H 0.462422 0.589065 0.711076 0.038 Uiso 1 1 calc R U . . .
H21C H 0.591095 0.620495 0.663984 0.038 Uiso 1 1 calc R U . . .
C22 C 1.1283(3) 0.40062(13) 0.70059(12) 0.0230(6) Uani 1 1 d . . . . .
H22A H 1.220105 0.370616 0.698834 0.034 Uiso 1 1 calc R U . . .
H22B H 1.073575 0.398233 0.740975 0.034 Uiso 1 1 calc R U . . .
H22C H 1.173017 0.442304 0.694397 0.034 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
C9 O1 C20 119.3(2) . . ?
C11 O2 C21 117.1(2) . . ?
C13 O3 C22 118.73(19) . . ?
C3 C2 C1 121.4(2) . . ?
C2 C3 C4 120.3(2) . . ?
C5 C4 C3 119.0(2) . . ?
C4 C5 C6 120.6(2) . . ?
C5 C6 C1 120.9(2) . . ?
C11 C10 C9 118.0(2) . . ?
C11 C12 C13 119.2(2) . . ?
C6 C1 C2 117.8(2) . . ?
C6 C1 C7 123.2(2) . . ?
C2 C1 C7 118.9(2) . . ?
C1 C7 C8 107.82(19) . . ?
C1 C7 C14 103.98(19) . . ?
C8 C7 C14 115.7(2) . . ?
C1 C7 C19 110.54(19) . . ?
C8 C7 C19 111.5(2) . . ?
C14 C7 C19 107.1(2) . . ?
C9 C8 C13 114.8(2) . . ?
C9 C8 C7 120.1(2) . . ?
C13 C8 C7 125.0(2) . . ?
O1 C9 C10 120.3(2) . . ?
O1 C9 C8 116.1(2) . . ?
C10 C9 C8 123.5(2) . . ?
C12 C11 O2 114.9(2) . . ?
C12 C11 C10 121.3(2) . . ?
O2 C11 C10 123.8(2) . . ?
O3 C13 C12 120.3(2) . . ?
O3 C13 C8 116.8(2) . . ?
C12 C13 C8 122.9(2) . . ?
C15 C14 C7 121.6(2) . . ?
O4 C15 C16 120.3(2) . . ?
O4 C15 C14 118.4(2) . . ?
C16 C15 C14 121.2(2) . . ?
C15 C16 C17 114.6(2) . . ?
C18 C17 C16 114.5(2) . . ?
C17 C18 C19 115.1(2) . . ?
C18 C19 C7 116.8(2) . . ?
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 C9 1.361(3) . ?
O1 C20 1.428(3) . ?
O2 C11 1.379(3) . ?
O2 C21 1.432(3) . ?
O3 C13 1.373(3) . ?
O3 C22 1.423(3) . ?
O4 C15 1.217(3) . ?
C2 C3 1.384(4) . ?
C2 C1 1.398(4) . ?
C3 C4 1.389(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.391(4) . ?
C6 C1 1.393(3) . ?
C10 C11 1.382(4) . ?
C10 C9 1.405(3) . ?
C12 C11 1.379(4) . ?
C12 C13 1.393(3) . ?
C1 C7 1.550(3) . ?
C7 C8 1.560(3) . ?
C7 C14 1.560(3) . ?
C7 C19 1.566(3) . ?
C8 C9 1.406(3) . ?
C8 C13 1.408(3) . ?
C14 C15 1.518(3) . ?
C15 C16 1.505(4) . ?
C16 C17 1.535(4) . ?
C17 C18 1.524(4) . ?
C18 C19 1.531(4) . ?
