#------------------------------------------------------------------------------
#$Date: 2022-10-09 03:29:23 +0300 (Sun, 09 Oct 2022) $
#$Revision: 278504 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158918.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_7158918
loop_
_publ_author_name
'Mudulkar, Sairam'
'Kolla, Sai Teja'
'Balasubramanian, Sridhar'
'Bhimapaka, China Raju'
_publ_section_title
;
 BF3•OEt2-Catalyzed synthesis of 2,2'-spirobi-2H-1-benzopyrans from
 2H-chromenes
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01286C
_journal_year                    2022
_chemical_formula_moiety         'C21 H17 Cl O4'
_chemical_formula_sum            'C21 H17 Cl O4'
_chemical_formula_weight         368.80
_chemical_name_systematic
'Ethyl 3'-chloro-6'-methyl-2,2'-spirobi[chromene]-3-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-01 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                92.8500(10)
_cell_angle_beta                 111.8700(10)
_cell_angle_gamma                95.7020(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7937(7)
_cell_length_b                   10.0005(8)
_cell_length_c                   11.2448(9)
_cell_measurement_reflns_used    4994
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.52
_cell_volume                     909.14(13)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10400
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.378
_diffrn_reflns_theta_min         1.960
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0759P)²+0.1249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3483
_reflns_number_total             4239
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01286c2.cif
_cod_data_source_block           AZ86m
_cod_database_code               7158918
_shelx_shelxl_version_number     2014/7
_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   0.964
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.31198(17) 0.20529(13) 0.26611(13) 0.0474(3) Uani 1 1 d . . . . .
C2 C 0.56224(18) 0.25655(14) 0.46095(14) 0.0500(3) Uani 1 1 d . . . . .
C3 C 0.6526(2) 0.21732(17) 0.58053(15) 0.0598(4) Uani 1 1 d . . . . .
H3 H 0.6275 0.1322 0.6032 0.072 Uiso 1 1 calc R U . . .
C4 C 0.7811(2) 0.30758(19) 0.66570(17) 0.0724(5) Uani 1 1 d . . . . .
H4 H 0.8424 0.2827 0.7467 0.087 Uiso 1 1 calc R U . . .
C5 C 0.8200(3) 0.4335(2) 0.63279(19) 0.0807(6) Uani 1 1 d . . . . .
H5 H 0.9068 0.4930 0.6912 0.097 Uiso 1 1 calc R U . . .
C6 C 0.7303(2) 0.47110(18) 0.51346(18) 0.0731(5) Uani 1 1 d . . . . .
H6 H 0.7571 0.5560 0.4911 0.088 Uiso 1 1 calc R U . . .
C7 C 0.59941(19) 0.38313(15) 0.42550(15) 0.0551(4) Uani 1 1 d . . . . .
C8 C 0.4988(2) 0.41732(15) 0.29992(15) 0.0557(4) Uani 1 1 d . . . . .
H8 H 0.5268 0.4990 0.2724 0.067 Uiso 1 1 calc R U . . .
C9 C 0.36631(18) 0.33512(14) 0.22187(14) 0.0506(3) Uani 1 1 d . . . . .
C10 C 0.06244(17) 0.13248(14) 0.30246(13) 0.0484(3) Uani 1 1 d . . . . .
C11 C 0.03349(18) 0.01160(14) 0.22609(14) 0.0487(3) Uani 1 1 d . . . . .
C12 C 0.13516(19) -0.00707(13) 0.15223(14) 0.0501(3) Uani 1 1 d . . . . .
H12 H 0.1109 -0.0827 0.0937 0.060 Uiso 1 1 calc R U . . .
C13 C 0.26262(18) 0.08388(14) 0.16837(14) 0.0491(3) Uani 1 1 d . . . . .
C14 C -0.09275(19) -0.08586(16) 0.22488(16) 0.0584(4) Uani 1 1 d . . . . .
H14 H -0.1137 -0.1671 0.1742 0.070 Uiso 1 1 calc R U . . .
C15 C -0.1868(2) -0.06491(19) 0.29664(18) 0.0657(4) Uani 1 1 d . . . . .
C16 C -0.1557(2) 0.0570(2) 0.36974(19) 0.0707(5) Uani 1 1 d . . . . .
H16 H -0.2193 0.0729 0.4178 0.085 Uiso 1 1 calc R U . . .
C17 C -0.0321(2) 0.15632(17) 0.37332(16) 0.0617(4) Uani 1 1 d . . . . .
H17 H -0.0132 0.2380 0.4229 0.074 Uiso 1 1 calc R U . . .
C18 C 0.2555(2) 0.37293(15) 0.09595(15) 0.0550(4) Uani 1 1 d . . . . .
C19 C 0.2176(3) 0.5375(2) -0.0543(2) 0.0875(6) Uani 1 1 d . . . . .
H19A H 0.2189 0.4816 -0.1269 0.105 Uiso 1 1 calc R U . . .
H19B H 0.1042 0.5346 -0.0608 0.105 Uiso 1 1 calc R U . . .
C20 C 0.2852(4) 0.6747(3) -0.0558(3) 0.1081(9) Uani 1 1 d . . . . .
H20A H 0.2696 0.7317 0.0090 0.162 Uiso 1 1 calc R U . . .
H20B H 0.2298 0.7053 -0.1388 0.162 Uiso 1 1 calc R U . . .
H20C H 0.4011 0.6784 -0.0385 0.162 Uiso 1 1 calc R U . . .
C21 C -0.3209(3) -0.1731(3) 0.2955(3) 0.0980(7) Uani 1 1 d . . . . .
H21A H -0.3678 -0.2241 0.2128 0.147 Uiso 1 1 calc R U . . .
H21B H -0.4056 -0.1316 0.3124 0.147 Uiso 1 1 calc R U . . .
H21C H -0.2743 -0.2322 0.3607 0.147 Uiso 1 1 calc R U . . .
Cl1 Cl 0.39428(6) 0.06740(4) 0.08808(5) 0.06951(17) Uani 1 1 d . . . . .
O1 O 0.44067(13) 0.16332(10) 0.37539(10) 0.0563(3) Uani 1 1 d . . . . .
O2 O 0.12504(15) 0.31064(12) 0.02936(12) 0.0699(3) Uani 1 1 d . . . . .
O3 O 0.31760(16) 0.48739(12) 0.06558(12) 0.0763(4) Uani 1 1 d . . . . .
O4 O 0.18092(13) 0.23472(9) 0.30350(10) 0.0537(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'
Cl Cl 0.1484 0.1585 '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
O4 C1 O1 108.59(11) . . ?
O4 C1 C13 112.20(11) . . ?
O1 C1 C13 103.31(11) . . ?
O4 C1 C9 104.93(11) . . ?
O1 C1 C9 112.72(11) . . ?
C13 C1 C9 115.12(12) . . ?
O1 C2 C3 117.68(13) . . ?
O1 C2 C7 120.93(13) . . ?
C3 C2 C7 121.28(14) . . ?
C2 C3 C4 118.51(16) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.22(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 119.79(17) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.57(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.62(14) . . ?
C2 C7 C8 118.11(13) . . ?
C6 C7 C8 123.27(14) . . ?
C9 C8 C7 121.80(13) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C18 122.32(13) . . ?
C8 C9 C1 120.47(13) . . ?
C18 C9 C1 116.83(12) . . ?
C17 C10 O4 118.21(13) . . ?
C17 C10 C11 120.99(14) . . ?
O4 C10 C11 120.70(13) . . ?
C10 C11 C14 118.08(14) . . ?
C10 C11 C12 118.57(13) . . ?
C14 C11 C12 123.35(13) . . ?
C13 C12 C11 119.69(13) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C1 122.35(13) . . ?
C12 C13 Cl1 122.87(11) . . ?
C1 C13 Cl1 114.64(11) . . ?
C15 C14 C11 121.82(16) . . ?
C15 C14 H14 119.1 . . ?
C11 C14 H14 119.1 . . ?
C14 C15 C16 118.30(16) . . ?
C14 C15 C21 120.83(19) . . ?
C16 C15 C21 120.87(19) . . ?
C15 C16 C17 121.66(16) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C10 C17 C16 119.13(16) . . ?
C10 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
O2 C18 O3 123.46(14) . . ?
O2 C18 C9 124.99(14) . . ?
O3 C18 C9 111.54(13) . . ?
C20 C19 O3 108.42(18) . . ?
C20 C19 H19A 110.0 . . ?
O3 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
O3 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 O1 C1 120.66(10) . . ?
C18 O3 C19 116.81(14) . . ?
C10 O4 C1 120.31(10) . . ?
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
C1 O4 1.4170(18) . ?
C1 O1 1.4411(17) . ?
C1 C13 1.5093(19) . ?
C1 C9 1.5098(18) . ?
C2 O1 1.3726(17) . ?
C2 C3 1.383(2) . ?
C2 C7 1.390(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.439(2) . ?
C8 C9 1.334(2) . ?
C8 H8 0.9300 . ?
C9 C18 1.482(2) . ?
C10 C17 1.377(2) . ?
C10 O4 1.3817(17) . ?
C10 C11 1.392(2) . ?
C11 C14 1.398(2) . ?
C11 C12 1.447(2) . ?
C12 C13 1.321(2) . ?
C12 H12 0.9300 . ?
C13 Cl1 1.7276(15) . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 C21 1.515(3) . ?
C16 C17 1.385(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.1986(19) . ?
C18 O3 1.3336(18) . ?
C19 C20 1.444(3) . ?
C19 O3 1.454(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 176.78(15) . . . . ?
C7 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
O1 C2 C7 C6 -176.29(15) . . . . ?
C3 C2 C7 C6 -0.2(2) . . . . ?
O1 C2 C7 C8 4.5(2) . . . . ?
C3 C2 C7 C8 -179.35(15) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C5 C6 C7 C8 178.82(19) . . . . ?
C2 C7 C8 C9 4.5(2) . . . . ?
C6 C7 C8 C9 -174.57(18) . . . . ?
C7 C8 C9 C18 175.94(15) . . . . ?
C7 C8 C9 C1 3.3(2) . . . . ?
O4 C1 C9 C8 99.51(16) . . . . ?
O1 C1 C9 C8 -18.5(2) . . . . ?
C13 C1 C9 C8 -136.65(16) . . . . ?
O4 C1 C9 C18 -73.56(16) . . . . ?
O1 C1 C9 C18 168.44(13) . . . . ?
C13 C1 C9 C18 50.28(18) . . . . ?
C17 C10 C11 C14 -1.0(2) . . . . ?
O4 C10 C11 C14 -177.33(13) . . . . ?
C17 C10 C11 C12 179.09(14) . . . . ?
O4 C10 C11 C12 2.7(2) . . . . ?
C10 C11 C12 C13 6.8(2) . . . . ?
C14 C11 C12 C13 -173.19(14) . . . . ?
C11 C12 C13 C1 2.7(2) . . . . ?
C11 C12 C13 Cl1 177.98(10) . . . . ?
O4 C1 C13 C12 -20.23(19) . . . . ?
O1 C1 C13 C12 96.54(16) . . . . ?
C9 C1 C13 C12 -140.14(15) . . . . ?
O4 C1 C13 Cl1 164.16(9) . . . . ?
O1 C1 C13 Cl1 -79.07(12) . . . . ?
C9 C1 C13 Cl1 44.24(16) . . . . ?
C10 C11 C14 C15 -0.1(2) . . . . ?
C12 C11 C14 C15 179.81(15) . . . . ?
C11 C14 C15 C16 1.0(3) . . . . ?
C11 C14 C15 C21 -178.89(16) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C21 C15 C16 C17 179.08(18) . . . . ?
O4 C10 C17 C16 177.60(14) . . . . ?
C11 C10 C17 C16 1.1(2) . . . . ?
C15 C16 C17 C10 -0.2(3) . . . . ?
C8 C9 C18 O2 -170.58(17) . . . . ?
C1 C9 C18 O2 2.4(2) . . . . ?
C8 C9 C18 O3 8.5(2) . . . . ?
C1 C9 C18 O3 -178.60(13) . . . . ?
C3 C2 O1 C1 161.93(13) . . . . ?
C7 C2 O1 C1 -21.8(2) . . . . ?
O4 C1 O1 C2 -88.18(14) . . . . ?
C13 C1 O1 C2 152.54(12) . . . . ?
C9 C1 O1 C2 27.65(18) . . . . ?
O2 C18 O3 C19 0.9(3) . . . . ?
C9 C18 O3 C19 -178.14(17) . . . . ?
C20 C19 O3 C18 166.9(2) . . . . ?
C17 C10 O4 C1 161.15(13) . . . . ?
C11 C10 O4 C1 -22.39(19) . . . . ?
O1 C1 O4 C10 -83.95(14) . . . . ?
C13 C1 O4 C10 29.60(17) . . . . ?
C9 C1 O4 C10 155.29(12) . . . . ?
