#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:38:20 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281553 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159041.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_7159041
loop_
_publ_author_name
'Shankar, Mallepalli'
'Kumara Swamy, K. C.'
_publ_section_title
;
 Ru(II)-catalysed oxidative (4 + 2) annulation of chromene and coumarin
 carboxylic acids with alkynes/propargylic alcohols: isolation of Ru(0)
 complexes.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              195
_journal_page_last               208
_journal_paper_doi               10.1039/d2ob01890j
_journal_volume                  21
_journal_year                    2022
_chemical_formula_moiety         'C20 H15 Br O4, C Cl'
_chemical_formula_sum            'C21 H15 Br Cl O4'
_chemical_formula_weight         446.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-05-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-10-15 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.646(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4674(10)
_cell_length_b                   7.5481(5)
_cell_length_c                   16.6864(10)
_cell_measurement_reflns_used    7187
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.76
_cell_volume                     1837.3(2)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297.46
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15049
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.756
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.408
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.538
_refine_diff_density_min         -1.057
_refine_diff_density_rms         0.062
_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     246
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0462
_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)+(0.0703P)²+1.6542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2695
_reflns_number_total             3187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01890j3.cif
_cod_data_source_block           Compound5ce
_cod_depositor_comments
'Adding full bibliography for 7159040--7159044.cif.'
_cod_database_code               7159041
_shelx_shelxl_version_number     2018/3
_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_max   0.795
_shelx_estimated_absorpt_t_min   0.645
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C19(H19), C7(H7), C15(H15), C18(H18), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.28851(3) 0.68778(6) 0.00224(2) 0.0706(2) Uani 1 1 d . . . . .
O3 O 0.78562(15) 0.6328(3) 0.42070(14) 0.0484(5) Uani 1 1 d . . . . .
O1 O 0.49347(15) 0.5380(3) 0.40086(14) 0.0509(6) Uani 1 1 d . . . . .
O4 O 0.31450(16) 0.5205(4) 0.31945(16) 0.0588(6) Uani 1 1 d . . . . .
O2 O 0.76942(18) 0.6858(4) 0.54208(16) 0.0631(7) Uani 1 1 d . . . . .
C4 C 0.4984(2) 0.6085(4) 0.26208(19) 0.0397(6) Uani 1 1 d . . . . .
C3 C 0.5992(2) 0.6096(4) 0.31408(19) 0.0387(6) Uani 1 1 d . . . . .
C9 C 0.4486(2) 0.6485(4) 0.1695(2) 0.0439(7) Uani 1 1 d . . . . .
H9 H 0.478889 0.681922 0.136712 0.053 Uiso 1 1 calc R . . . .
C2 C 0.6349(2) 0.6338(4) 0.4051(2) 0.0420(7) Uani 1 1 d . . . . .
C6 C 0.3539(2) 0.5598(4) 0.2661(2) 0.0463(7) Uani 1 1 d . . . . .
C12 C 0.6603(2) 0.5764(4) 0.27481(18) 0.0374(6) Uani 1 1 d . . . . .
C5 C 0.4494(2) 0.5702(4) 0.3098(2) 0.0424(7) Uani 1 1 d . . . . .
C11 C 0.7516(2) 0.5869(4) 0.33070(19) 0.0419(7) Uani 1 1 d . . . . .
C10 C 0.7312(2) 0.6525(4) 0.4619(2) 0.0453(7) Uani 1 1 d . . . . .
C13 C 0.6255(2) 0.5111(5) 0.1791(2) 0.0475(7) Uani 1 1 d . . . . .
H13A H 0.613681 0.610429 0.139252 0.071 Uiso 1 1 calc GR . . . .
H13B H 0.569865 0.445356 0.161420 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.670781 0.435933 0.175610 0.071 Uiso 1 1 calc GR . . . .
C19 C 0.8260(2) 0.5928(5) 0.2293(2) 0.0492(8) Uani 1 1 d . . . . .
H19 H 0.775097 0.650991 0.185158 0.059 Uiso 1 1 calc R . . . .
C14 C 0.8280(2) 0.5472(4) 0.3113(2) 0.0440(7) Uani 1 1 d . . . . .
C8 C 0.3549(2) 0.6377(4) 0.1282(2) 0.0470(7) Uani 1 1 d . . . . .
C1 C 0.5738(2) 0.6436(5) 0.4488(2) 0.0522(8) Uani 1 1 d . . . . .
H1A H 0.606841 0.602256 0.510773 0.063 Uiso 1 1 calc R . . . .
H1B H 0.556112 0.765774 0.449943 0.063 Uiso 1 1 calc R . . . .
C7 C 0.3064(2) 0.5930(5) 0.1736(2) 0.0499(8) Uani 1 1 d . . . . .
H7 H 0.242769 0.585155 0.143040 0.060 Uiso 1 1 calc R . . . .
C15 C 0.9059(3) 0.4619(5) 0.3766(2) 0.0594(9) Uani 1 1 d . . . . .
H15 H 0.908917 0.431805 0.431938 0.071 Uiso 1 1 calc R . . . .
C20 C 0.2185(2) 0.5499(6) 0.2833(3) 0.0618(9) Uani 1 1 d . . . . .
H20A H 0.204217 0.668723 0.260475 0.093 Uiso 1 1 calc GR . . . .
H20B H 0.200714 0.533383 0.330068 0.093 Uiso 1 1 calc GR . . . .
H20C H 0.185887 0.467538 0.235123 0.093 Uiso 1 1 calc GR . . . .
C18 C 0.8987(3) 0.5521(6) 0.2134(3) 0.0619(9) Uani 1 1 d . . . . .
H18 H 0.896609 0.582969 0.158562 0.074 Uiso 1 1 calc R . . . .
C16 C 0.9774(3) 0.4225(7) 0.3604(3) 0.0739(12) Uani 1 1 d . . . . .
H16 H 1.028779 0.365799 0.404628 0.089 Uiso 1 1 calc R . . . .
C17 C 0.9744(3) 0.4661(7) 0.2781(3) 0.0731(12) Uani 1 1 d . . . . .
H17 H 1.023072 0.437365 0.266911 0.088 Uiso 1 1 calc R . . . .
Cl1 Cl 0.9842(4) 0.3867(4) 0.0603(2) 0.1974(15) Uani 1 1 d . . . . .
C21 C 0.9460(11) 0.512(3) -0.0123(13) 0.309(11) 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'
Br Br -0.2901 2.4595 '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'
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
C10 O3 C11 123.0(2) . . ?
C5 O1 C1 113.5(3) . . ?
C6 O4 C20 117.6(3) . . ?
C9 C4 C3 124.7(3) . . ?
C5 C4 C3 117.1(3) . . ?
C5 C4 C9 118.2(3) . . ?
C2 C3 C4 116.3(3) . . ?
C2 C3 C12 119.6(3) . . ?
C12 C3 C4 124.0(3) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 C4 119.1(3) . . ?
C8 C9 H9 120.5 . . ?
C3 C2 C10 121.7(3) . . ?
C3 C2 C1 120.7(3) . . ?
C10 C2 C1 117.6(3) . . ?
O4 C6 C5 115.9(3) . . ?
O4 C6 C7 125.0(3) . . ?
C7 C6 C5 119.1(3) . . ?
C3 C12 C13 122.1(3) . . ?
C11 C12 C3 117.3(3) . . ?
C11 C12 C13 120.2(3) . . ?
O1 C5 C4 121.3(3) . . ?
O1 C5 C6 117.3(3) . . ?
C6 C5 C4 121.5(3) . . ?
O3 C11 C14 109.5(3) . . ?
C12 C11 O3 121.6(3) . . ?
C12 C11 C14 128.9(3) . . ?
O3 C10 C2 116.1(3) . . ?
O2 C10 O3 116.9(3) . . ?
O2 C10 C2 127.0(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C14 120.4(3) . . ?
C19 C14 C11 122.2(3) . . ?
C19 C14 C15 118.3(3) . . ?
C15 C14 C11 119.5(3) . . ?
C9 C8 Br1 118.6(3) . . ?
C9 C8 C7 123.0(3) . . ?
C7 C8 Br1 118.4(2) . . ?
O1 C1 C2 110.9(3) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(4) . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C21 Cl1 C21 58.4(10) . 3_765 ?
Cl1 C21 Cl1 121.6(10) . 3_765 ?
Cl1 C21 C21 73.5(12) . 3_765 ?
C21 C21 Cl1 48.1(17) 3_765 3_765 ?
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
Br1 C8 1.904(3) . ?
O3 C11 1.381(4) . ?
O3 C10 1.367(4) . ?
O1 C5 1.369(4) . ?
O1 C1 1.429(4) . ?
O4 C6 1.355(4) . ?
O4 C20 1.424(4) . ?
O2 C10 1.211(4) . ?
C4 C3 1.473(4) . ?
C4 C9 1.405(4) . ?
C4 C5 1.401(4) . ?
C3 C2 1.363(4) . ?
C3 C12 1.455(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.370(5) . ?
C2 C10 1.428(5) . ?
C2 C1 1.493(5) . ?
C6 C5 1.396(5) . ?
C6 C7 1.391(5) . ?
C12 C11 1.355(4) . ?
C12 C13 1.508(4) . ?
C11 C14 1.469(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C14 1.395(4) . ?
C19 C18 1.376(5) . ?
C14 C15 1.397(5) . ?
C8 C7 1.374(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.357(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18 0.9300 . ?
C18 C17 1.375(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(6) . ?
C17 H17 0.9300 . ?
Cl1 C21 1.43(2) . ?
Cl1 C21 1.84(3) 3_765 ?
C21 C21 1.64(4) 3_765 ?
