#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/72/7227222.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_7227222
loop_
_publ_author_name
'Gautam, Prashant'
'Kathe, Prasad'
'Bhanage, Bhalchandra M.'
_publ_section_title
;
 Pd/C catalyzed phenoxycarbonylation using N-formylsaccharin as a CO
 surrogate in propylene carbonate, a sustainable solvent
;
_journal_issue                   3
_journal_name_full               'Green Chem.'
_journal_page_first              823
_journal_paper_doi               10.1039/C6GC03027K
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C14 H9 Br F2 O3'
_chemical_formula_sum            'C14 H9 Br F2 O3'
_chemical_formula_weight         343.12
_chemical_name_systematic        '5-bromo-2,3-difluorophenyl 4-methoxybenzoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-10-28 deposited with the CCDC.
2016-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                71.172(4)
_cell_angle_beta                 85.353(3)
_cell_angle_gamma                72.077(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6847(5)
_cell_length_b                   8.2593(7)
_cell_length_c                   12.7076(12)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.72
_cell_volume                     631.70(9)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0604
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.527
_diffrn_reflns_theta_min         2.724
_exptl_absorpt_coefficient_mu    3.282
_exptl_absorpt_correction_T_max  0.100
_exptl_absorpt_correction_T_min  0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             340
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0191P)²+0.4475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0600
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3420
_reflns_number_total             3870
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6gc03027k2.cif
_cod_data_source_block           S_44
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7227222.cif.
;
_cod_database_code               7227222
_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.
;
_shelxl_version_number           2014-3
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
Br1 Br 0.19919(3) 0.91529(2) 0.90334(2) 0.01984(6) Uani 1 1 d . .
F1 F 0.26222(16) 0.23914(13) 1.01602(9) 0.0229(2) Uani 1 1 d . .
F2 F 0.51146(16) 0.19046(13) 0.84338(9) 0.0230(2) Uani 1 1 d . .
O1 O 0.61300(18) 0.46637(16) 0.69023(9) 0.0182(2) Uani 1 1 d . .
O2 O 0.91125(19) 0.39038(18) 0.79037(10) 0.0223(3) Uani 1 1 d . .
O3 O 1.26389(18) 0.11614(15) 0.37885(9) 0.0167(2) Uani 1 1 d . .
C1 C 0.2980(2) 0.6869(2) 0.88320(13) 0.0137(3) Uani 1 1 d . .
C2 C 0.2421(2) 0.5455(2) 0.96000(13) 0.0144(3) Uani 1 1 d . .
H2 H 0.1567 0.5627 1.0213 0.017 Uiso 1 1 calc R U
C3 C 0.3140(2) 0.3796(2) 0.94464(13) 0.0154(3) Uani 1 1 d . .
C4 C 0.4410(2) 0.3533(2) 0.85637(14) 0.0155(3) Uani 1 1 d . .
C5 C 0.4955(2) 0.4959(2) 0.78147(13) 0.0149(3) Uani 1 1 d . .
C6 C 0.4241(2) 0.6656(2) 0.79321(13) 0.0144(3) Uani 1 1 d . .
H6 H 0.4602 0.7640 0.7414 0.017 Uiso 1 1 calc R U
C7 C 0.8281(2) 0.3948(2) 0.70876(13) 0.0139(3) Uani 1 1 d . .
C8 C 0.9330(2) 0.3274(2) 0.61807(12) 0.0126(3) Uani 1 1 d . .
C9 C 1.1526(2) 0.2583(2) 0.62318(13) 0.0140(3) Uani 1 1 d . .
H9 H 1.2291 0.2596 0.6826 0.017 Uiso 1 1 calc R U
C10 C 1.2585(2) 0.1881(2) 0.54223(13) 0.0149(3) Uani 1 1 d . .
H10 H 1.4075 0.1410 0.5461 0.018 Uiso 1 1 calc R U
C11 C 1.1460(2) 0.1867(2) 0.45462(13) 0.0131(3) Uani 1 1 d . .
C12 C 0.9273(2) 0.2546(2) 0.44889(13) 0.0143(3) Uani 1 1 d . .
H12 H 0.8509 0.2534 0.3895 0.017 Uiso 1 1 calc R U
C13 C 0.8221(2) 0.3242(2) 0.53117(13) 0.0141(3) Uani 1 1 d . .
H13 H 0.6730 0.3700 0.5279 0.017 Uiso 1 1 calc R U
C14 C 1.1565(3) 0.1182(2) 0.28486(14) 0.0191(3) Uani 1 1 d . .
H14A H 1.0525 0.0530 0.3108 0.029 Uiso 1 1 calc R U
H14B H 1.2584 0.0606 0.2381 0.029 Uiso 1 1 calc R U
H14C H 1.0851 0.2424 0.2415 0.029 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C7 O1 C5 115.61(12)
C11 O3 C14 117.71(12)
C2 C1 C6 122.27(14)
C2 C1 Br1 118.37(11)
C6 C1 Br1 119.36(12)
C3 C2 C1 118.08(14)
C3 C2 H2 121.0
C1 C2 H2 121.0
F1 C3 C2 120.27(14)
F1 C3 C4 118.56(14)
C2 C3 C4 121.17(15)
F2 C4 C5 120.00(14)
F2 C4 C3 120.36(15)
C5 C4 C3 119.65(14)
C4 C5 C6 120.95(14)
C4 C5 O1 117.85(14)
C6 C5 O1 121.08(14)
C5 C6 C1 117.88(14)
C5 C6 H6 121.1
C1 C6 H6 121.1
O2 C7 O1 121.92(14)
O2 C7 C8 126.52(15)
O1 C7 C8 111.56(13)
C13 C8 C9 119.50(14)
C13 C8 C7 122.55(14)
C9 C8 C7 117.90(14)
C10 C9 C8 120.31(14)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 119.85(14)
C9 C10 H10 120.1
C11 C10 H10 120.1
O3 C11 C12 124.11(14)
O3 C11 C10 115.55(13)
C12 C11 C10 120.34(14)
C13 C12 C11 119.33(14)
C13 C12 H12 120.3
C11 C12 H12 120.3
C8 C13 C12 120.66(14)
C8 C13 H13 119.7
C12 C13 H13 119.7
O3 C14 H14A 109.5
O3 C14 H14B 109.5
H14A C14 H14B 109.5
O3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.8910(15)
F1 C3 1.3437(18)
F2 C4 1.3414(18)
O1 C7 1.3836(19)
O1 C5 1.3922(18)
O2 C7 1.201(2)
O3 C11 1.3581(18)
O3 C14 1.4354(19)
C1 C2 1.390(2)
C1 C6 1.390(2)
C2 C3 1.378(2)
C2 H2 0.9500
C3 C4 1.384(2)
C4 C5 1.382(2)
C5 C6 1.388(2)
C6 H6 0.9500
C7 C8 1.474(2)
C8 C13 1.391(2)
C8 C9 1.400(2)
C9 C10 1.382(2)
C9 H9 0.9500
C10 C11 1.398(2)
C10 H10 0.9500
C11 C12 1.394(2)
C12 C13 1.392(2)
C12 H12 0.9500
C13 H13 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203056
