#------------------------------------------------------------------------------
#$Date: 2022-09-15 03:14:55 +0300 (Thu, 15 Sep 2022) $
#$Revision: 277860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158884.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_7158884
loop_
_publ_author_name
'Zhao, Haoqiang'
'Zeng, Qi'
'yang, ji'
'Xu, Bing'
'Lei, Haimin'
'Xu, Lijin'
'Walsh, Patrick'
_publ_section_title
;
 Rhodium(I)-Catalyzed Directed Trideuteromethylation of (Hetero)arene C--H
 Bonds with CD3CO2D
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01581A
_journal_year                    2022
_chemical_formula_moiety         'C12 H9 F3 N2 O'
_chemical_formula_sum            'C12 H9 F3 N2 O'
_chemical_formula_weight         254.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-12 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.038(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.891(5)
_cell_length_b                   11.795(2)
_cell_length_c                   8.809(2)
_cell_measurement_reflns_used    2672
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.366
_cell_measurement_theta_min      2.998
_cell_volume                     2271.3(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.01
_diffrn_measured_fraction_theta_full 0.984
_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  0.0772
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10800
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         2.997
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1254 before and 0.0825 after correction. The Ratio of minimum to maximum transmission is 0.7648. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0633
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.2599
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1506
_reflns_number_total             2598
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01581a2.cif
_cod_data_source_block           mo_zhq2018100201_0m
_cod_database_code               7158884
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 F00E, C00G, F00H, F00I
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F00H, C00G, F00E, F00I
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 C00G, F00H, F00E, F00I
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Sof(F00J)=Sof(F00F)=Sof(F0AA)=1-FVAR(1)
 Sof(F00E)=Sof(F00H)=Sof(F00I)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C006(H006), C00A(H00A), C00C(H00E), C00D(H00F), C00F(H00G)
4.b Idealised Me refined as rotating group:
 C00B(H00B,H00C,H00D)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_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
O001 O 0.32274(8) 0.18202(14) 0.8319(2) 0.0441(6) Uani 1 1 d . . . . .
N002 N 0.25844(10) 0.37495(15) 0.5884(2) 0.0351(5) Uani 1 1 d . . . . .
N003 N 0.33310(10) 0.37148(14) 0.7895(2) 0.0338(5) Uani 1 1 d . . . . .
C004 C 0.22517(12) 0.37390(18) 0.8444(3) 0.0374(6) Uani 1 1 d . . . . .
H004 H 0.2359 0.3723 0.9504 0.045 Uiso 1 1 calc R . . . .
C005 C 0.26948(12) 0.37315(16) 0.7386(3) 0.0326(6) Uani 1 1 d . . . . .
C006 C 0.19980(12) 0.37656(18) 0.5385(3) 0.0374(6) Uani 1 1 d . . . . .
H006 H 0.1905 0.3765 0.4320 0.045 Uiso 1 1 calc R . . . .
C007 C 0.35664(12) 0.26561(19) 0.8388(3) 0.0372(6) Uani 1 1 d . . . . .
C008 C 0.15216(12) 0.37834(17) 0.6346(3) 0.0377(6) Uani 1 1 d . . . . .
C009 C 0.36733(12) 0.46966(19) 0.7900(3) 0.0384(6) Uani 1 1 d . . . . .
C00A C 0.16529(12) 0.37709(18) 0.7913(3) 0.0388(6) Uani 1 1 d . . . . .
H00A H 0.1332 0.3784 0.8599 0.047 Uiso 1 1 calc R . . . .
C00B C 0.33669(13) 0.5753(2) 0.7321(4) 0.0480(7) Uani 1 1 d . . . . .
H00B H 0.3217 0.5640 0.6264 0.072 Uiso 1 1 calc GR . . . .
H00C H 0.3660 0.6381 0.7373 0.072 Uiso 1 1 calc GR . . . .
H00D H 0.3022 0.5932 0.7946 0.072 Uiso 1 1 calc GR . . . .
C00C C 0.42628(13) 0.4662(2) 0.8428(4) 0.0505(8) Uani 1 1 d . . . . .
H00E H 0.4502 0.5334 0.8456 0.061 Uiso 1 1 calc R . . . .
C00D C 0.41924(13) 0.2672(2) 0.8925(3) 0.0478(7) Uani 1 1 d . . . . .
H00F H 0.4380 0.1989 0.9283 0.057 Uiso 1 1 calc R . . . .
F00E F 0.0799(3) 0.3881(10) 0.4275(6) 0.129(3) Uani 0.635(9) 1 d . U P A 1
C00F C 0.45241(14) 0.3635(2) 0.8937(4) 0.0528(8) Uani 1 1 d . . . . .
H00G H 0.4941 0.3618 0.9295 0.063 Uiso 1 1 calc R . . . .
C00G C 0.08730(14) 0.3788(2) 0.5738(4) 0.0500(7) Uani 1 1 d . U . . .
F00H F 0.0557(2) 0.2924(4) 0.6134(11) 0.106(2) Uani 0.635(9) 1 d . U P A 1
F00I F 0.05583(19) 0.4662(4) 0.6262(9) 0.0958(18) Uani 0.635(9) 1 d . U P A 1
F00J F 0.0501(3) 0.3697(17) 0.6684(9) 0.141(7) Uani 0.365(9) 1 d . . P A 2
F00F F 0.0771(6) 0.4530(10) 0.476(2) 0.139(7) Uani 0.365(9) 1 d . . P A 2
F0AA F 0.0793(4) 0.2829(8) 0.4870(16) 0.109(4) Uani 0.365(9) 1 d . . P A 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C005 N002 C006 116.6(2) . . ?
C007 N003 C005 116.07(19) . . ?
C009 N003 C005 120.37(19) . . ?
C009 N003 C007 123.6(2) . . ?
C00A C004 C005 117.6(2) . . ?
N002 C005 N003 115.5(2) . . ?
N002 C005 C004 125.0(2) . . ?
C004 C005 N003 119.5(2) . . ?
N002 C006 C008 123.0(2) . . ?
O001 C007 N003 118.9(2) . . ?
O001 C007 C00D 126.3(2) . . ?
N003 C007 C00D 114.8(2) . . ?
C006 C008 C00A 119.0(3) . . ?
C006 C008 C00G 121.1(3) . . ?
C00A C008 C00G 119.9(3) . . ?
N003 C009 C00B 117.8(2) . . ?
C00C C009 N003 119.0(2) . . ?
C00C C009 C00B 123.2(2) . . ?
C004 C00A C008 118.8(2) . . ?
C009 C00C C00F 120.2(3) . . ?
C00F C00D C007 121.4(3) . . ?
C00D C00F C00C 121.0(3) . . ?
F00E C00G C008 115.1(4) . . ?
F00E C00G F00I 103.9(5) . . ?
F00H C00G C008 114.4(3) . . ?
F00H C00G F00E 107.2(5) . . ?
F00H C00G F00I 102.9(5) . . ?
F00I C00G C008 112.2(3) . . ?
F00J C00G C008 114.7(5) . . ?
F00J C00G F00F 116.1(9) . . ?
F00J C00G F0AA 104.0(7) . . ?
F00F C00G C008 112.7(6) . . ?
F00F C00G F0AA 100.6(9) . . ?
F0AA C00G C008 106.7(4) . . ?
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
O001 C007 1.234(3) . ?
N002 C005 1.333(3) . ?
N002 C006 1.335(3) . ?
N003 C005 1.441(3) . ?
N003 C007 1.411(3) . ?
N003 C009 1.379(3) . ?
C004 C005 1.380(4) . ?
C004 C00A 1.369(4) . ?
C006 C008 1.378(4) . ?
C007 C00D 1.426(4) . ?
C008 C00A 1.395(4) . ?
C008 C00G 1.491(4) . ?
C009 C00B 1.492(4) . ?
C009 C00C 1.349(4) . ?
C00C C00F 1.402(4) . ?
C00D C00F 1.348(4) . ?
F00E C00G 1.295(6) . ?
C00G F00H 1.291(5) . ?
C00G F00I 1.336(5) . ?
C00G F00J 1.201(7) . ?
C00G F00F 1.237(8) . ?
C00G F0AA 1.371(7) . ?
