#------------------------------------------------------------------------------
#$Date: 2021-12-23 23:55:04 +0100 (jue 23 de dic de 2021) $
#$Revision: 271607 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/94/7129463.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_7129463
loop_
_publ_author_name
'Ma, Ben'
'Sun, Rong-Xia'
'Yang, Jingya'
_publ_section_title
;
 Cobalt-Catalyzed Direct α-Hydroxymethylation of Amides with Methanol as
 a C1 Source
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06501G
_journal_year                    2022
_chemical_formula_moiety         'C16 H16 F N O2'
_chemical_formula_sum            'C16 H16 F N O2'
_chemical_formula_weight         273.30
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-29
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2021-09-14 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5402(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0338(3)
_cell_length_b                   11.15970(19)
_cell_length_c                   14.0652(3)
_cell_measurement_reflns_used    7217
_cell_measurement_temperature    302.01(10)
_cell_measurement_theta_max      75.5930
_cell_measurement_theta_min      3.1150
_cell_volume                     2806.17(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  68.00   0.50    0.24    --  103.99 -61.00-150.00   66
  2  ω     31.00  62.00   0.50    0.24    --  103.99 -61.00 -90.00   62
  3  ω     41.00  67.00   0.50    0.24    --  103.99 -77.00 -60.00   52
  4  ω     33.00  73.00   0.50    0.24    --  103.99 -61.00 -30.00   80
  5  ω    153.00 178.00   0.50    0.24    --  103.99  34.00  56.00   50
  6  ω     35.00 115.00   0.50    0.06    --   46.20  34.00  56.00  160
  7  ω     16.00  41.00   0.50    0.06    --   46.20 -34.00-100.00   50
  8  ω    -32.00  17.00   0.50    0.06    --  -46.20  34.00  56.00   98
  9  ω    -68.00 -29.00   0.50    0.24    -- -102.00  61.00 120.00   78
 10  ω    -69.00 -38.00   0.50    0.24    -- -102.00  61.00  30.00   62
 11  ω    -69.00 -34.00   0.50    0.24    -- -102.00  61.00  60.00   70
 12  ω    -98.00 -30.00   0.50    0.24    -- -102.00  77.00 -30.00  136
 13  ω    -65.00 -29.00   0.50    0.24    -- -102.00  61.00 150.00   72
 14  ω    -62.00 -32.00   0.50    0.24    -- -102.00  61.00-120.00   60
 15  ω    -62.00 -33.00   0.50    0.24    -- -102.00  61.00-150.00   58
 16  ω    -69.00 -29.00   0.50    0.24    -- -102.00  61.00-180.00   80
 17  ω    -40.00  25.00   0.50    0.06    --  -46.20  37.00-150.00  130
 18  ω   -175.00 -89.00   0.50    0.24    -- -102.00 -34.00-100.00  172
 19  ω   -122.00 -95.00   0.50    0.24    -- -102.00-125.00  60.00   54
 20  ω   -175.00-146.00   0.50    0.24    -- -102.00-125.00  60.00   58
 21  ω   -110.00 -34.00   0.50    0.06    --  -46.20 -34.00-100.00  152
 22  ω     72.00 106.00   0.50    0.24    --  103.99-125.00-120.00   68
 23  ω     66.00 103.00   0.50    0.24    --  103.99 -94.00 -60.00   74
 24  ω     35.00  65.00   0.50    0.24    --  103.99-125.00-120.00   60
 25  ω     39.00  67.00   0.50    0.24    --  103.99 -94.00-180.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0786042000
_diffrn_orient_matrix_UB_12      -0.0560260000
_diffrn_orient_matrix_UB_13      -0.0191966000
_diffrn_orient_matrix_UB_21      -0.0113970000
_diffrn_orient_matrix_UB_22      0.0229564000
_diffrn_orient_matrix_UB_23      0.1051213000
_diffrn_orient_matrix_UB_31      -0.0333901000
_diffrn_orient_matrix_UB_32      0.1240707000
_diffrn_orient_matrix_UB_33      -0.0280932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9716
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.694
_diffrn_reflns_theta_min         4.671
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0416
_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)+(0.0649P)²+0.8910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2552
_reflns_number_total             2801
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06501g2.cif
_cod_data_source_block           sunrongxia_0428-1_auto
_cod_original_cell_volume        2806.18(9)
_cod_database_code               7129463
_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.
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.955
_oxdiff_exptl_absorpt_empirical_full_min 0.375
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
F1 F 0.86378(6) 0.35968(12) 0.54802(11) 0.1079(5) Uani 1 1 d . . . . .
O2 O 0.62392(7) 0.77589(13) 0.24157(7) 0.0805(4) Uani 1 1 d . . . . .
H2 H 0.587183 0.741854 0.213273 0.121 Uiso 1 1 calc R U . . .
O3 O 0.49297(5) 0.64950(10) 0.36091(7) 0.0609(3) Uani 1 1 d . . . . .
N1 N 0.58046(5) 0.50827(9) 0.39737(8) 0.0499(3) Uani 1 1 d . . . . .
C1 C 0.65470(7) 0.47066(11) 0.43579(9) 0.0481(3) Uani 1 1 d . . . . .
C2 C 0.66881(9) 0.43740(13) 0.53096(10) 0.0615(4) Uani 1 1 d . . . . .
H2A H 0.630669 0.440126 0.569459 0.074 Uiso 1 1 calc R U . . .
C3 C 0.73973(10) 0.39997(16) 0.56920(13) 0.0743(5) Uani 1 1 d . . . . .
H3 H 0.749931 0.378135 0.633391 0.089 Uiso 1 1 calc R U . . .
C4 C 0.79417(9) 0.39584(14) 0.51077(14) 0.0700(4) Uani 1 1 d . . . . .
C5 C 0.78179(9) 0.42486(15) 0.41612(14) 0.0715(4) Uani 1 1 d . . . . .
H5 H 0.820023 0.419635 0.377913 0.086 Uiso 1 1 calc R U . . .
C6 C 0.71043(8) 0.46261(13) 0.37773(11) 0.0592(3) Uani 1 1 d . . . . .
H6 H 0.700432 0.482327 0.313073 0.071 Uiso 1 1 calc R U . . .
C7 C 0.52456(9) 0.41224(15) 0.38271(13) 0.0689(4) Uani 1 1 d . . . . .
H7A H 0.515675 0.380822 0.443748 0.103 Uiso 1 1 calc R U . . .
H7B H 0.542679 0.349429 0.345217 0.103 Uiso 1 1 calc R U . . .
H7C H 0.478736 0.443645 0.349591 0.103 Uiso 1 1 calc R U . . .
C8 C 0.55879(6) 0.62326(11) 0.38575(8) 0.0450(3) Uani 1 1 d . . . . .
C9 C 0.61779(6) 0.72148(11) 0.40772(9) 0.0459(3) Uani 1 1 d . . . . .
H9 H 0.667198 0.685291 0.406728 0.055 Uiso 1 1 calc R U . . .
C10 C 0.61403(6) 0.76993(11) 0.50789(9) 0.0463(3) Uani 1 1 d . . . . .
C11 C 0.66959(8) 0.74033(13) 0.58206(10) 0.0566(3) Uani 1 1 d . . . . .
H11 H 0.709667 0.693212 0.569322 0.068 Uiso 1 1 calc R U . . .
C12 C 0.66628(11) 0.77986(16) 0.67465(11) 0.0737(5) Uani 1 1 d . . . . .
H12 H 0.703715 0.758617 0.723657 0.088 Uiso 1 1 calc R U . . .
C13 C 0.60765(11) 0.85057(17) 0.69428(12) 0.0782(5) Uani 1 1 d . . . . .
H13 H 0.605323 0.877275 0.756449 0.094 Uiso 1 1 calc R U . . .
C14 C 0.55245(10) 0.88154(15) 0.62131(13) 0.0729(4) Uani 1 1 d . . . . .
H14 H 0.512974 0.929841 0.634312 0.087 Uiso 1 1 calc R U . . .
C15 C 0.55524(8) 0.84141(13) 0.52895(11) 0.0581(3) Uani 1 1 d . . . . .
H15 H 0.517401 0.862452 0.480384 0.070 Uiso 1 1 calc R U . . .
C16 C 0.60715(9) 0.81839(14) 0.33046(10) 0.0610(4) Uani 1 1 d . . . . .
H16A H 0.555759 0.846213 0.323306 0.073 Uiso 1 1 calc R U . . .
H16B H 0.639296 0.885952 0.350450 0.073 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C7 115.34(11) . . ?
C8 N1 C1 124.40(10) . . ?
C8 N1 C7 119.77(11) . . ?
C2 C1 N1 119.12(12) . . ?
C6 C1 N1 120.75(12) . . ?
C6 C1 C2 120.07(13) . . ?
C1 C2 C3 120.06(14) . . ?
C4 C3 C2 118.56(15) . . ?
F1 C4 C3 118.75(17) . . ?
F1 C4 C5 118.27(16) . . ?
C5 C4 C3 122.97(15) . . ?
C4 C5 C6 118.42(15) . . ?
C1 C6 C5 119.87(14) . . ?
O3 C8 N1 121.11(11) . . ?
O3 C8 C9 120.47(11) . . ?
N1 C8 C9 118.39(10) . . ?
C10 C9 C8 109.13(9) . . ?
C10 C9 C16 113.03(11) . . ?
C16 C9 C8 110.14(10) . . ?
C11 C10 C9 119.78(12) . . ?
C11 C10 C15 118.17(13) . . ?
C15 C10 C9 122.03(11) . . ?
C12 C11 C10 121.02(15) . . ?
C13 C12 C11 120.06(15) . . ?
C12 C13 C14 119.59(15) . . ?
C13 C14 C15 120.51(16) . . ?
C14 C15 C10 120.64(14) . . ?
O2 C16 C9 111.84(13) . . ?
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
F1 C4 1.3568(18) . ?
O2 C16 1.407(2) . ?
O3 C8 1.2279(15) . ?
N1 C1 1.4391(16) . ?
N1 C7 1.4672(16) . ?
N1 C8 1.3451(17) . ?
C1 C2 1.3803(19) . ?
C1 C6 1.3785(19) . ?
C2 C3 1.385(2) . ?
C3 C4 1.361(3) . ?
C4 C5 1.360(3) . ?
C5 C6 1.394(2) . ?
C8 C9 1.5306(16) . ?
C9 C10 1.5189(17) . ?
C9 C16 1.5273(18) . ?
C10 C11 1.3883(18) . ?
C10 C15 1.3894(19) . ?
C11 C12 1.384(2) . ?
C12 C13 1.376(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.381(2) . ?
