#------------------------------------------------------------------------------
#$Date: 2024-02-04 12:58:20 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289313 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/06/1570630.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_1570630
loop_
_publ_author_name
'Obieta, Maria'
'Urgoitia, Garazi'
'Herrero, María Teresa'
'SanMartin, Raul'
_publ_section_title
;
 Efficient iron-catalyzed direct acylation of amines with carboxylic acids
 and esters under oxygenated conditions
;
_journal_issue                   2
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              478
_journal_page_last               488
_journal_paper_doi               10.1039/D3CY01429K
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.3
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-28T12:24:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-08-23 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.23281(4)
_cell_length_b                   11.33461(9)
_cell_length_c                   22.6110(2)
_cell_measurement_reflns_used    11719
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.391
_cell_measurement_theta_min      3.877
_cell_volume                     1341.100(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -18.00   1.00    1.00    --  -42.13 -38.00   0.00   98
  2  ω   -116.00 -18.00   1.00    1.00    --  -42.13 -38.00 -60.00   98
  3  ω    -30.00  70.00   1.00    1.00    --   42.13 -57.00-120.00  100
  4  ω    -20.00  83.00   1.00    1.00    --   42.13 -99.00 150.00  103
  5  ω      2.00  98.00   1.00    1.00    --   42.13-125.00-150.00   96
  6  ω     35.00 118.00   1.00    1.00    --  107.93-125.00  60.00   83
  7  ω     80.00 158.00   1.00    1.00    --  107.93  30.00 -90.00   78
  8  ω     25.00 110.00   1.00    1.00    --  107.93 -94.00  90.00   85
  9  ω     35.00 118.00   1.00    1.00    --  107.93-125.00 -90.00   83
 10  ω     36.00 137.00   1.00    1.00    --  107.93 -61.00   0.00  101
 11  ω     32.00  69.00   1.00    1.00    --  107.93 -30.00  90.00   37
 12  ω     82.00 158.00   1.00    1.00    --  107.93  45.00 -30.00   76
 13  ω     32.00  69.00   1.00    1.00    --  107.93 -30.00 -30.00   37
 14  ω     32.00 141.00   1.00    1.00    --  107.93 -77.00  90.00  109
 15  ω     32.00  69.00   1.00    1.00    --  107.93 -30.00 -60.00   37
 16  ω     35.00 118.00   1.00    1.00    --  107.93-125.00 -30.00   83
 17  ω     32.00  69.00   1.00    1.00    --  107.93 -30.00 120.00   37
 18  ω     55.00 158.00   1.00    1.00    --  107.93  15.00 120.00  103
 19  ω     32.00  69.00   1.00    1.00    --  107.93 -30.00 150.00   37
 20  ω     36.00 137.00   1.00    1.00    --  107.93 -61.00-120.00  101
 21  ω   -118.00 -10.00   1.00    1.00    --  -42.13 -77.00 120.00  108
 22  ω   -118.00 -46.00   1.00    1.00    --  -42.13 -77.00 -90.00   72
 23  ω   -115.00 -14.00   1.00    1.00    --  -42.13 -57.00-180.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2924024
_diffrn_orient_matrix_UB_12      0.015658
_diffrn_orient_matrix_UB_13      -0.0016663
_diffrn_orient_matrix_UB_21      -0.0004995
_diffrn_orient_matrix_UB_22      -0.0298542
_diffrn_orient_matrix_UB_23      -0.066485
_diffrn_orient_matrix_UB_31      -0.0347125
_diffrn_orient_matrix_UB_32      -0.1316018
_diffrn_orient_matrix_UB_33      0.0148982
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14622
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.997
_diffrn_reflns_theta_min         4.363
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.745
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (100%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=-0.02(6).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+0.1690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2433
_reflns_number_total             2484
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cy01429k2.cif
_cod_data_source_block           a20190015_ia32ca2t150k
_cod_depositor_comments
'Adding full bibliography for 1570630--1570631.cif.'
_cod_original_cell_volume        1341.10(2)
_cod_database_code               1570630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
O1 O -0.8459(2) -0.86664(10) -0.16361(5) 0.0264(3) Uani 1 1 d . . . . .
O2 O -1.3141(2) -1.00540(9) -0.25081(5) 0.0256(3) Uani 1 1 d . . . . .
N1 N -1.2786(3) -0.86433(11) -0.15863(5) 0.0232(3) Uani 1 1 d . . . . .
H1 H -1.422301 -0.881738 -0.176858 0.028 Uiso 1 1 calc R . . . .
C1 C -1.0569(3) -0.89002(12) -0.18483(7) 0.0208(3) Uani 1 1 d . . . . .
C2 C -1.0760(3) -0.94544(13) -0.24631(7) 0.0214(3) Uani 1 1 d . . . . .
H2 H -0.934184 -1.003746 -0.251304 0.026 Uiso 1 1 calc R . . . .
C3 C -1.0500(3) -0.84992(13) -0.29312(6) 0.0198(3) Uani 1 1 d . . . . .
C4 C -0.8454(3) -0.84763(14) -0.33230(7) 0.0251(3) Uani 1 1 d . . . . .
H4 H -0.717115 -0.906767 -0.33015 0.03 Uiso 1 1 calc R . . . .
C5 C -0.8280(3) -0.75902(15) -0.37464(7) 0.0283(4) Uani 1 1 d . . . . .
H5 H -0.688045 -0.758275 -0.401388 0.034 Uiso 1 1 calc R . . . .
C6 C -1.0125(3) -0.67201(14) -0.37818(7) 0.0272(4) Uani 1 1 d . . . . .
H6 H -0.999129 -0.61143 -0.407049 0.033 Uiso 1 1 calc R . . . .
C7 C -1.2175(3) -0.67390(13) -0.33916(7) 0.0253(3) Uani 1 1 d . . . . .
H7 H -1.344756 -0.614295 -0.341279 0.03 Uiso 1 1 calc R . . . .
C8 C -1.2369(3) -0.76242(13) -0.29716(6) 0.0227(3) Uani 1 1 d . . . . .
H8 H -1.378516 -0.763577 -0.270891 0.027 Uiso 1 1 calc R . . . .
C9 C -1.3181(4) -1.08538(15) -0.29939(7) 0.0340(4) Uani 1 1 d . . . . .
H9A H -1.276015 -1.042929 -0.335871 0.051 Uiso 1 1 calc GR . . . .
H9B H -1.488785 -1.120226 -0.302958 0.051 Uiso 1 1 calc GR . . . .
H9C H -1.192192 -1.148013 -0.292765 0.051 Uiso 1 1 calc GR . . . .
C10 C -1.2894(3) -0.80810(14) -0.10051(6) 0.0252(3) Uani 1 1 d . . . . .
H10A H -1.452917 -0.764857 -0.096713 0.03 Uiso 1 1 calc R . . . .
H10B H -1.148818 -0.749982 -0.097308 0.03 Uiso 1 1 calc R . . . .
C11 C -1.2673(3) -0.89610(13) -0.05043(6) 0.0221(3) Uani 1 1 d . . . . .
C12 C -1.4497(3) -0.98455(14) -0.04442(7) 0.0276(4) Uani 1 1 d . . . . .
H12 H -1.589445 -0.987949 -0.07118 0.033 Uiso 1 1 calc R . . . .
C13 C -1.4294(4) -1.06776(15) 0.00021(7) 0.0312(4) Uani 1 1 d . . . . .
H13 H -1.553999 -1.12833 0.003636 0.037 Uiso 1 1 calc R . . . .
C14 C -1.2273(3) -1.06284(15) 0.03996(7) 0.0325(4) Uani 1 1 d . . . . .
H14 H -1.213147 -1.119828 0.070597 0.039 Uiso 1 1 calc R . . . .
C15 C -1.0471(4) -0.97447(16) 0.03460(7) 0.0321(4) Uani 1 1 d . . . . .
H15 H -0.90958 -0.970272 0.061943 0.038 Uiso 1 1 calc R . . . .
C16 C -1.0656(3) -0.89156(14) -0.01055(7) 0.0267(3) Uani 1 1 d . . . . .
H16 H -0.939793 -0.831572 -0.014132 0.032 Uiso 1 1 calc R . . . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 3 0.1085
0 0 -1 0.0763
0 0 1 0.046
-2 -6 1 0.2558
3 -3 4 0.2471
0 7 -4 0.1257
-3 4 -4 0.2918
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
C2 O2 C9 111.84(12) . . ?
C1 N1 H1 119.1 . . ?
C1 N1 C10 121.86(13) . . ?
C10 N1 H1 119.1 . . ?
O1 C1 N1 123.97(13) . . ?
O1 C1 C2 120.06(14) . . ?
N1 C1 C2 115.88(13) . . ?
O2 C2 C1 108.57(12) . . ?
O2 C2 H2 109 . . ?
O2 C2 C3 111.62(12) . . ?
C1 C2 H2 109 . . ?
C3 C2 C1 109.55(11) . . ?
C3 C2 H2 109 . . ?
C4 C3 C2 121.73(13) . . ?
C4 C3 C8 118.98(13) . . ?
C8 C3 C2 119.29(13) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.18(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.63(15) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.43(14) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.21(14) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.55(14) . . ?
C7 C8 H8 119.7 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
N1 C10 C11 112.48(12) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C12 C11 C10 119.73(14) . . ?
C16 C11 C10 121.28(14) . . ?
C16 C11 C12 118.98(14) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.63(15) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.16(16) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.48(15) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.46(16) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.29(15) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
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
O1 C1 1.2326(19) . ?
O2 C2 1.4231(18) . ?
O2 C9 1.4243(18) . ?
N1 H1 0.88 . ?
N1 C1 1.335(2) . ?
N1 C10 1.4616(18) . ?
C1 C2 1.529(2) . ?
C2 H2 1 . ?
C2 C3 1.520(2) . ?
C3 C4 1.390(2) . ?
C3 C8 1.396(2) . ?
C4 H4 0.95 . ?
C4 C5 1.390(2) . ?
C5 H5 0.95 . ?
C5 C6 1.382(2) . ?
C6 H6 0.95 . ?
C6 C7 1.389(2) . ?
C7 H7 0.95 . ?
C7 C8 1.385(2) . ?
C8 H8 0.95 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C10 C11 1.513(2) . ?
C11 C12 1.391(2) . ?
C11 C16 1.389(2) . ?
C12 H12 0.95 . ?
C12 C13 1.385(2) . ?
C13 H13 0.95 . ?
C13 C14 1.389(2) . ?
C14 H14 0.95 . ?
C14 C15 1.381(3) . ?
C15 H15 0.95 . ?
C15 C16 1.391(2) . ?
C16 H16 0.95 . ?
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 C1 C2 O2 157.01(13) . . . . ?
O1 C1 C2 C3 -80.86(17) . . . . ?
O2 C2 C3 C4 -124.16(14) . . . . ?
O2 C2 C3 C8 55.53(17) . . . . ?
N1 C1 C2 O2 -26.37(17) . . . . ?
N1 C1 C2 C3 95.76(15) . . . . ?
N1 C10 C11 C12 -60.94(19) . . . . ?
N1 C10 C11 C16 118.09(15) . . . . ?
C1 N1 C10 C11 -84.17(18) . . . . ?
C1 C2 C3 C4 115.55(15) . . . . ?
C1 C2 C3 C8 -64.76(17) . . . . ?
C2 C3 C4 C5 179.89(14) . . . . ?
C2 C3 C8 C7 179.63(13) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C3 C8 C7 -0.7(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C3 0.6(2) . . . . ?
C8 C3 C4 C5 0.2(2) . . . . ?
C9 O2 C2 C1 -163.87(12) . . . . ?
C9 O2 C2 C3 75.27(14) . . . . ?
C10 N1 C1 O1 -1.8(2) . . . . ?
C10 N1 C1 C2 -178.29(12) . . . . ?
C10 C11 C12 C13 178.35(14) . . . . ?
C10 C11 C16 C15 -179.01(14) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C11 0.7(2) . . . . ?
C16 C11 C12 C13 -0.7(2) . . . . ?
