#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/35/4033528.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_4033528
loop_
_publ_author_name
'Wang, Miao'
'Tang, Bo-Cheng'
'Xiang, Jia-Chen'
'Cheng, Yan'
'Wang, Zi-Xuan'
'Ma, Jin-Tian'
'Wu, Yan-Dong'
'Wu, An-Xin'
_publ_section_title
;
 C(sp³)-H Bond Functionalization of Benzo[ c]oxepines via C-O
 bond Cleavage: Formal [3+3] Synthesis of Multisubstituted Chromans.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3409
_journal_page_last               3416
_journal_paper_doi               10.1021/acs.joc.8b00126
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C25 H22 O5'
_chemical_formula_weight         402.43
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.146(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6534(11)
_cell_length_b                   20.771(3)
_cell_length_c                   11.3478(14)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    324(2)
_cell_measurement_theta_max      31.95
_cell_measurement_theta_min      2.55
_cell_volume                     2036.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      324(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13880
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0778P)²+0.4547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                3249
_reflns_number_total             3589
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00126_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033527--4033528.cif.
;
_cod_original_cell_volume        2036.6(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4033528
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.07565(16) 0.10839(7) -0.00441(12) 0.0335(3) Uani 1 1 d .
C2 C 1.1303(2) 0.14177(9) -0.09910(14) 0.0492(4) Uani 1 1 d .
H2 H 1.0654 0.1684 -0.1454 0.059 Uiso 1 1 calc R
C3 C 1.2841(2) 0.13435(11) -0.12263(17) 0.0624(5) Uani 1 1 d .
H3 H 1.3232 0.1565 -0.1858 0.075 Uiso 1 1 calc R
C4 C 1.3815(2) 0.09478(10) -0.05440(18) 0.0620(5) Uani 1 1 d .
H4 H 1.4847 0.0908 -0.0722 0.074 Uiso 1 1 calc R
C5 C 1.32769(19) 0.06132(9) 0.03925(16) 0.0517(4) Uani 1 1 d .
H5 H 1.3927 0.0345 0.0850 0.062 Uiso 1 1 calc R
C6 C 1.17268(16) 0.06886(7) 0.06366(12) 0.0359(3) Uani 1 1 d .
C7 C 1.08836(17) 0.04264(7) 0.16218(12) 0.0361(3) Uani 1 1 d .
C8 C 0.92496(16) 0.07077(6) 0.15589(11) 0.0302(3) Uani 1 1 d .
H8 H 0.8500(18) 0.0351(8) 0.1444(14) 0.036 Uiso 1 1 d .
C9 C 0.91630(15) 0.11322(6) 0.04424(11) 0.0288(3) Uani 1 1 d .
C10 C 0.89677(15) 0.10654(6) 0.27321(11) 0.0293(3) Uani 1 1 d .
H10 H 0.9494(18) 0.0798(8) 0.3356(14) 0.035 Uiso 1 1 d .
C11 C 0.72638(16) 0.10863(7) 0.30018(11) 0.0332(3) Uani 1 1 d .
C12 C 0.63980(18) 0.16440(8) 0.28493(15) 0.0460(4) Uani 1 1 d .
H12 H 0.6873 0.2014 0.2584 0.055 Uiso 1 1 calc R
C13 C 0.4845(2) 0.16652(10) 0.30810(18) 0.0597(5) Uani 1 1 d .
H13 H 0.4289 0.2046 0.2976 0.072 Uiso 1 1 calc R
C14 C 0.4132(2) 0.11192(10) 0.34678(17) 0.0593(5) Uani 1 1 d .
H14 H 0.3085 0.1126 0.3614 0.071 Uiso 1 1 calc R
C15 C 0.4980(2) 0.05635(9) 0.36367(16) 0.0552(5) Uani 1 1 d .
H15 H 0.4490 0.0197 0.3902 0.066 Uiso 1 1 calc R
C16 C 0.65465(19) 0.05327(8) 0.34240(13) 0.0426(4) Uani 1 1 d .
C17 C 0.7429(2) -0.00800(9) 0.3691(2) 0.0657(6) Uani 1 1 d .
H17A H 0.8176 -0.0007 0.4334 0.099 Uiso 1 1 calc R
H17B H 0.7951 -0.0211 0.3006 0.099 Uiso 1 1 calc R
H17C H 0.6722 -0.0411 0.3903 0.099 Uiso 1 1 calc R
C18 C 0.97469(15) 0.17146(6) 0.26874(11) 0.0286(3) Uani 1 1 d .
C19 C 0.97325(15) 0.20500(6) 0.16409(11) 0.0286(3) Uani 1 1 d .
C20 C 1.04979(16) 0.26302(6) 0.14998(12) 0.0328(3) Uani 1 1 d .
H20 H 1.0474 0.2840 0.0775 0.039 Uiso 1 1 calc R
C21 C 1.12965(16) 0.28835(6) 0.24807(12) 0.0340(3) Uani 1 1 d .
C22 C 1.13014(16) 0.25775(7) 0.35755(12) 0.0361(3) Uani 1 1 d .
H22 H 1.1816 0.2760 0.4234 0.043 Uiso 1 1 calc R
C23 C 1.05291(16) 0.19984(7) 0.36661(12) 0.0326(3) Uani 1 1 d .
C24 C 1.1169(3) 0.19260(13) 0.57289(16) 0.0825(8) Uani 1 1 d .
H24A H 1.2253 0.1991 0.5628 0.124 Uiso 1 1 calc R
H24B H 1.1041 0.1639 0.6380 0.124 Uiso 1 1 calc R
H24C H 1.0690 0.2332 0.5885 0.124 Uiso 1 1 calc R
C25 C 1.2183(3) 0.37721(9) 0.13593(16) 0.0628(5) Uani 1 1 d .
H25A H 1.2618 0.3496 0.0786 0.094 Uiso 1 1 calc R
H25B H 1.2804 0.4153 0.1457 0.094 Uiso 1 1 calc R
H25C H 1.1149 0.3890 0.1094 0.094 Uiso 1 1 calc R
O1 O 1.13809(15) 0.00659(6) 0.23849(11) 0.0590(4) Uani 1 1 d .
O2 O 0.79487(11) 0.09286(5) -0.03128(8) 0.0358(2) Uani 1 1 d D
H1O H 0.798(2) 0.1132(8) -0.0960(13) 0.043 Uiso 1 1 d D
O3 O 0.88734(11) 0.18061(4) 0.06764(8) 0.0323(2) Uani 1 1 d .
O4 O 1.21496(14) 0.34418(5) 0.24612(10) 0.0486(3) Uani 1 1 d .
O5 O 1.04698(14) 0.16558(6) 0.46902(9) 0.0463(3) Uani 1 1 d .
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
C6 C1 C2 120.63(14)
C6 C1 C9 111.91(12)
C2 C1 C9 127.28(13)
C3 C2 C1 117.93(16)
C2 C3 C4 121.49(16)
C5 C4 C3 120.79(16)
C4 C5 C6 117.94(16)
C1 C6 C5 121.23(14)
C1 C6 C7 109.47(12)
C5 C6 C7 129.19(14)
O1 C7 C6 127.05(14)
O1 C7 C8 124.31(13)
C6 C7 C8 108.60(11)
C7 C8 C9 105.08(11)
C7 C8 C10 109.32(11)
C9 C8 C10 115.29(11)
O2 C9 O3 105.99(10)
O2 C9 C1 115.39(11)
O3 C9 C1 107.49(10)
O2 C9 C8 109.55(10)
O3 C9 C8 113.76(10)
C1 C9 C8 104.89(10)
C18 C10 C11 114.86(11)
C18 C10 C8 107.85(10)
C11 C10 C8 112.63(11)
C12 C11 C16 118.78(14)
C12 C11 C10 121.45(12)
C16 C11 C10 119.77(12)
C11 C12 C13 121.80(16)
C14 C13 C12 119.49(17)
C15 C14 C13 119.42(15)
C14 C15 C16 122.13(16)
C15 C16 C11 118.35(15)
C15 C16 C17 119.48(15)
C11 C16 C17 122.14(14)
C19 C18 C23 116.93(12)
C19 C18 C10 119.88(11)
C23 C18 C10 123.18(12)
C18 C19 O3 118.42(12)
C18 C19 C20 123.85(12)
O3 C19 C20 117.71(11)
C21 C20 C19 117.27(12)
O4 C21 C20 123.58(13)
O4 C21 C22 115.03(12)
C20 C21 C22 121.39(13)
C23 C22 C21 119.00(12)
O5 C23 C22 123.87(12)
O5 C23 C18 114.63(12)
C22 C23 C18 121.49(12)
C19 O3 C9 114.04(9)
C21 O4 C25 117.12(12)
C23 O5 C24 117.95(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.380(2)
C1 C2 1.384(2)
C1 C9 1.5165(19)
C2 C3 1.381(3)
C3 C4 1.383(3)
C4 C5 1.373(3)
C5 C6 1.393(2)
C6 C7 1.473(2)
C7 O1 1.2062(18)
C7 C8 1.528(2)
C8 C9 1.5421(18)
C8 C10 1.5556(17)
C9 O2 1.3851(15)
C9 O3 1.4492(16)
C10 C18 1.5098(18)
C10 C11 1.5228(19)
C11 C12 1.385(2)
C11 C16 1.404(2)
C12 C13 1.384(2)
C13 C14 1.375(3)
C14 C15 1.375(3)
C15 C16 1.392(2)
C16 C17 1.506(3)
C18 C19 1.3762(18)
C18 C23 1.3987(19)
C19 O3 1.3848(15)
C19 C20 1.3888(19)
C20 C21 1.3817(19)
C21 O4 1.3754(17)
C21 C22 1.395(2)
C22 C23 1.383(2)
C23 O5 1.3660(17)
C24 O5 1.412(2)
C25 O4 1.428(2)
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
C6 C1 C2 C3 -0.2(2)
C9 C1 C2 C3 174.46(16)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 -0.4(3)
C2 C1 C6 C5 -0.1(2)
C9 C1 C6 C5 -175.49(13)
C2 C1 C6 C7 176.44(14)
C9 C1 C6 C7 1.02(16)
C4 C5 C6 C1 0.4(2)
C4 C5 C6 C7 -175.37(16)
C1 C6 C7 O1 -179.89(15)
C5 C6 C7 O1 -3.7(3)
C1 C6 C7 C8 -2.04(16)
C5 C6 C7 C8 174.11(15)
O1 C7 C8 C9 -179.89(14)
C6 C7 C8 C9 2.19(14)
O1 C7 C8 C10 55.83(19)
C6 C7 C8 C10 -122.09(12)
C6 C1 C9 O2 -120.25(13)
C2 C1 C9 O2 64.70(19)
C6 C1 C9 O3 121.78(12)
C2 C1 C9 O3 -53.27(18)
C6 C1 C9 C8 0.39(15)
C2 C1 C9 C8 -174.67(14)
C7 C8 C9 O2 122.87(11)
C10 C8 C9 O2 -116.72(12)
C7 C8 C9 O3 -118.73(11)
C10 C8 C9 O3 1.68(16)
C7 C8 C9 C1 -1.55(13)
C10 C8 C9 C1 118.86(12)
C7 C8 C10 C18 78.95(13)
C9 C8 C10 C18 -39.12(15)
C7 C8 C10 C11 -153.27(11)
C9 C8 C10 C11 88.66(13)
C18 C10 C11 C12 19.21(18)
C8 C10 C11 C12 -104.79(15)
C18 C10 C11 C16 -160.24(12)
C8 C10 C11 C16 75.76(16)
C16 C11 C12 C13 -1.2(2)
C10 C11 C12 C13 179.33(16)
C11 C12 C13 C14 -0.3(3)
C12 C13 C14 C15 1.1(3)
C13 C14 C15 C16 -0.3(3)
C14 C15 C16 C11 -1.3(3)
C14 C15 C16 C17 176.61(18)
C12 C11 C16 C15 2.0(2)
C10 C11 C16 C15 -178.58(13)
C12 C11 C16 C17 -175.85(16)
C10 C11 C16 C17 3.6(2)
C11 C10 C18 C19 -89.02(14)
C8 C10 C18 C19 37.47(16)
C11 C10 C18 C23 92.26(15)
C8 C10 C18 C23 -141.25(13)
C23 C18 C19 O3 -175.31(11)
C10 C18 C19 O3 5.90(18)
C23 C18 C19 C20 2.9(2)
C10 C18 C19 C20 -175.89(12)
C18 C19 C20 C21 -1.0(2)
O3 C19 C20 C21 177.26(12)
C19 C20 C21 O4 177.66(13)
C19 C20 C21 C22 -1.6(2)
O4 C21 C22 C23 -177.25(13)
C20 C21 C22 C23 2.1(2)
C21 C22 C23 O5 179.46(13)
C21 C22 C23 C18 0.0(2)
C19 C18 C23 O5 178.12(12)
C10 C18 C23 O5 -3.13(19)
C19 C18 C23 C22 -2.4(2)
C10 C18 C23 C22 176.38(12)
C18 C19 O3 C9 -49.83(15)
C20 C19 O3 C9 131.84(12)
O2 C9 O3 C19 164.15(10)
C1 C9 O3 C19 -71.95(13)
C8 C9 O3 C19 43.72(14)
C20 C21 O4 C25 0.6(2)
C22 C21 O4 C25 179.88(15)
C22 C23 O5 C24 3.5(2)
C18 C23 O5 C24 -177.02(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139096049
