#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059421.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_7059421
loop_
_publ_author_name
'Madarasi, Packirisamy Kuzhalmozhi'
'Sivasankar, Chinnappan'
_publ_section_title
;
 Infrared spectroscopic detection of ketene formation from carbene and CO
 sources: an amide synthesis
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8718
_journal_page_last               8727
_journal_paper_doi               10.1039/C9NJ06161D
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C24 H35 N O3'
_chemical_formula_sum            'C24 H35 N O3'
_chemical_formula_weight         385.54
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-20
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2019-08-20 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.215(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2702(8)
_cell_length_b                   20.6229(13)
_cell_length_c                   10.9839(10)
_cell_measurement_reflns_used    2529
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.2936
_cell_measurement_theta_min      3.1549
_cell_volume                     2244.9(3)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 15.9821
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.8619
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -80.00  -38.00   1.0000   46.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -77.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00    6.00   1.0000   46.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -77.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -85.00  -60.00   1.0000   46.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -16.00   34.00   1.0000   46.0900
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -57.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   84.00   1.0000   46.0900
omega____ theta____ kappa____ phi______ frames
    -       19.8397   57.0000  -30.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega  -43.00   -2.00   1.0000   46.0900
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   37.0000   60.0000 41
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_UB_11      0.0426048000
_diffrn_orient_matrix_UB_12      0.0274462000
_diffrn_orient_matrix_UB_13      0.0170147000
_diffrn_orient_matrix_UB_21      0.0551108000
_diffrn_orient_matrix_UB_22      -0.0207078000
_diffrn_orient_matrix_UB_23      0.0270855000
_diffrn_orient_matrix_UB_31      0.0163965000
_diffrn_orient_matrix_UB_32      -0.0016545000
_diffrn_orient_matrix_UB_33      -0.0587266000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12603
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.36
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1407
_exptl_crystal_description       needle
_exptl_crystal_F_000             840.3857
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.4278
_refine_diff_density_min         -0.3270
_refine_diff_density_rms         0.0726
_refine_ls_d_res_high            0.7248
_refine_ls_d_res_low             6.1508
_refine_ls_goodness_of_fit_ref   1.0743
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0743
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0981P)²+0.2357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1846
_refine_ls_wR_factor_ref         0.2248
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3032
_reflns_number_total             5325
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9nj06161d2.cif
_cod_data_source_block           CS-PKM-B-132-SS
_cod_depositor_comments
;
 Adding full bibliography for 7059421.cif.

2025-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C16 H23.333 N0.667 O2'
_cod_original_formula_weight         257.03
_cod_original_formula_moiety         '0.67(C24 H35 N O3)'
_cod_original_formula_units_Z            6
_cod_database_code               7059421
_chemical_oxdiff_formula         'C18 H20 N O3'
_chemical_oxdiff_usercomment     'COLOURLESS NEEDLE, 298K, 0.8 0.16 0.08'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C12(H12a,H12b), C13(H13a,H13b), C15(H15a,H15b), C16(H16a,H16b),
 C18(H18a,H18b), C20(H20a,H20b), C21(H21a,H21b), C22(H22a,H22b), C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C23(H23), C24(H24), C1a(H1a)
2.d Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C1b(H1ba,H1bb,H1bc)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
O1 O 0.69386(17) 0.87019(7) 0.42301(18) 0.0557(5) Uani 1.000000 .
N2 N 0.86903(17) 0.68802(8) 0.55755(18) 0.0410(5) Uani 1.000000 .
O3 O 0.54273(18) 0.83852(8) 0.52556(19) 0.0637(5) Uani 1.000000 .
O4 O 0.8194(2) 0.77954(9) 0.6507(2) 0.0764(6) Uani 1.000000 .
C5 C 0.9810(2) 0.67113(10) 0.6686(2) 0.0407(5) Uani 1.000000 .
H5 H 1.0084(2) 0.62709(10) 0.6527(2) 0.0488(6) Uiso 1.000000 R
C6 C 0.6729(2) 0.75741(10) 0.4489(2) 0.0409(5) Uani 1.000000 .
H6 H 0.7034(2) 0.75758(10) 0.3715(2) 0.0490(6) Uiso 1.000000 R
C7 C 0.5578(2) 0.70933(10) 0.4330(2) 0.0430(5) Uani 1.000000 .
C8 C 0.9613(2) 0.62767(12) 0.4021(2) 0.0520(6) Uani 1.000000 .
H8a H 0.9966(2) 0.66799(12) 0.3783(2) 0.0624(7) Uiso 1.000000 R
H8b H 1.0314(2) 0.60766(12) 0.4681(2) 0.0624(7) Uiso 1.000000 R
C9 C 0.8396(2) 0.64178(10) 0.4516(2) 0.0440(5) Uani 1.000000 .
H9 H 0.7718(2) 0.66220(10) 0.3825(2) 0.0528(7) Uiso 1.000000 R
C10 C 0.7944(2) 0.74207(10) 0.5611(2) 0.0464(6) Uani 1.000000 .
C11 C 0.6272(2) 0.82606(10) 0.4716(2) 0.0451(5) Uani 1.000000 .
C12 C 0.9419(2) 0.66746(13) 0.7924(3) 0.0565(7) Uani 1.000000 .
H12a H 0.9188(2) 0.71039(13) 0.8161(3) 0.0678(8) Uiso 1.000000 R
H12b H 0.8634(2) 0.63980(13) 0.7825(3) 0.0678(8) Uiso 1.000000 R
C13 C 1.1055(2) 0.71276(12) 0.6823(3) 0.0547(6) Uani 1.000000 .
H13a H 1.1301(2) 0.71390(12) 0.6029(3) 0.0656(8) Uiso 1.000000 R
H13b H 1.0865(2) 0.75676(12) 0.7037(3) 0.0656(8) Uiso 1.000000 R
C14 C 0.4980(3) 0.68344(12) 0.3158(3) 0.0547(6) Uani 1.000000 .
H14 H 0.5297(3) 0.69492(12) 0.2468(3) 0.0657(8) Uiso 1.000000 R
C15 C 0.7776(3) 0.57916(11) 0.4841(3) 0.0569(7) Uani 1.000000 .
H15a H 0.8417(3) 0.55738(11) 0.5526(3) 0.0683(8) Uiso 1.000000 R
H15b H 0.6978(3) 0.58917(11) 0.5121(3) 0.0683(8) Uiso 1.000000 R
C16 C 1.2219(2) 0.68538(15) 0.7851(3) 0.0649(7) Uani 1.000000 .
H16a H 1.2457(2) 0.64284(15) 0.7599(3) 0.0779(9) Uiso 1.000000 R
H16b H 1.3001(2) 0.71334(15) 0.7956(3) 0.0779(9) Uiso 1.000000 R
C17 C 0.5094(3) 0.69122(13) 0.5332(3) 0.0595(7) Uani 1.000000 .
H17 H 0.5486(3) 0.70793(13) 0.6131(3) 0.0714(8) Uiso 1.000000 R
C18 C 0.8585(4) 0.52063(13) 0.3181(3) 0.0798(9) Uani 1.000000 .
H18a H 0.8288(4) 0.49485(13) 0.2420(3) 0.0958(11) Uiso 1.000000 R
H18b H 0.9248(4) 0.49553(13) 0.3792(3) 0.0958(11) Uiso 1.000000 R
C19 C 0.6659(3) 0.93852(11) 0.4426(3) 0.0614(7) Uani 1.000000 .
H19 H 0.6528(3) 0.94377(11) 0.5272(3) 0.0737(9) Uiso 1.000000 R
C20 C 1.0585(3) 0.64037(15) 0.8953(3) 0.0672(8) Uani 1.000000 .
H20a H 1.0343(3) 0.64037(15) 0.9749(3) 0.0806(9) Uiso 1.000000 R
H20b H 1.0755(3) 0.59590(15) 0.8752(3) 0.0806(9) Uiso 1.000000 R
C21 C 0.9236(3) 0.58259(13) 0.2880(3) 0.0683(8) Uani 1.000000 .
H21a H 0.8615(3) 0.60472(13) 0.2186(3) 0.0820(10) Uiso 1.000000 R
H21b H 1.0041(3) 0.57187(13) 0.2617(3) 0.0820(10) Uiso 1.000000 R
C22 C 0.7397(3) 0.53474(13) 0.3704(3) 0.0770(9) Uani 1.000000 .
H22a H 0.7050(3) 0.49430(13) 0.3943(3) 0.0924(11) Uiso 1.000000 R
H22b H 0.6687(3) 0.55484(13) 0.3054(3) 0.0924(11) Uiso 1.000000 R
C23 C 0.3913(3) 0.64053(15) 0.3001(3) 0.0757(9) Uani 1.000000 .
H23 H 0.3517(3) 0.62354(15) 0.2205(3) 0.0909(10) Uiso 1.000000 R
C24 C 0.4024(3) 0.64812(15) 0.5160(4) 0.0793(10) Uani 1.000000 .
H24 H 0.3703(3) 0.63624(15) 0.5845(4) 0.0952(12) Uiso 1.000000 R
C25 C 1.1850(3) 0.68009(16) 0.9083(3) 0.0727(8) Uani 1.000000 .
H25a H 1.2589(3) 0.66010(16) 0.9706(3) 0.0872(10) Uiso 1.000000 R
H25b H 1.1712(3) 0.72318(16) 0.9381(3) 0.0872(10) Uiso 1.000000 R
C26 C 0.5409(3) 0.95834(16) 0.3478(4) 0.0982(12) Uani 1.000000 .
H26a H 0.5522(10) 0.9523(12) 0.2646(4) 0.1473(19) Uiso 1.000000 GR
H26b H 0.4667(6) 0.9323(9) 0.3577(17) 0.1473(19) Uiso 1.000000 GR
H26c H 0.5226(15) 1.0032(4) 0.3599(16) 0.1473(19) Uiso 1.000000 GR
C1a C 0.3437(3) 0.62296(16) 0.3996(4) 0.0836(10) Uani 1.000000 .
H1a H 0.2720(3) 0.59411(16) 0.3885(4) 0.1003(12) Uiso 1.000000 R
C1b C 0.7890(3) 0.97575(14) 0.4346(4) 0.0883(11) Uani 1.000000 .
H1ba H 0.8670(5) 0.9581(8) 0.4934(18) 0.1324(16) Uiso 1.000000 GR
H1bb H 0.7999(15) 0.9725(11) 0.3506(7) 0.1324(16) Uiso 1.000000 GR
H1bc H 0.7787(12) 1.0205(3) 0.455(3) 0.1324(16) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C19 O1 C11 117.21(18) . . ?
C9 N2 C5 116.87(16) . . ?
C10 N2 C5 119.42(18) . . ?
C10 N2 C9 123.58(18) . . ?
C12 C5 N2 114.76(17) . . ?
C13 C5 N2 113.66(18) . . ?
C13 C5 C12 110.7(2) . . ?
C10 C6 C7 113.66(18) . . ?
C11 C6 C7 111.06(17) . . ?
C11 C6 C10 106.17(18) . . ?
C14 C7 C6 120.2(2) . . ?
C17 C7 C6 121.3(2) . . ?
C17 C7 C14 118.5(2) . . ?
C21 C8 C9 110.9(2) . . ?
C8 C9 N2 112.97(18) . . ?
C15 C9 N2 112.00(19) . . ?
C15 C9 C8 110.88(18) . . ?
O4 C10 N2 122.7(2) . . ?
C6 C10 N2 119.38(19) . . ?
C6 C10 O4 117.97(19) . . ?
O3 C11 O1 124.5(2) . . ?
C6 C11 O1 110.75(18) . . ?
C6 C11 O3 124.8(2) . . ?
C20 C12 C5 110.05(19) . . ?
C16 C13 C5 110.0(2) . . ?
C23 C14 C7 120.5(3) . . ?
C22 C15 C9 110.6(2) . . ?
C25 C16 C13 111.1(2) . . ?
C24 C17 C7 120.3(3) . . ?
C22 C18 C21 111.5(2) . . ?
C26 C19 O1 109.2(2) . . ?
C1b C19 O1 106.4(2) . . ?
C1b C19 C26 113.9(3) . . ?
C25 C20 C12 111.2(2) . . ?
C18 C21 C8 111.4(2) . . ?
C18 C22 C15 111.9(2) . . ?
C1a C23 C14 120.7(3) . . ?
C1a C24 C17 120.7(3) . . ?
C20 C25 C16 111.6(2) . . ?
C24 C1a C23 119.3(3) . . ?
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 C11 1.332(3) . ?
O1 C19 1.465(3) . ?
N2 C5 1.481(3) . ?
N2 C9 1.474(3) . ?
N2 C10 1.359(3) . ?
O3 C11 1.200(3) . ?
O4 C10 1.225(3) . ?
C5 C12 1.517(3) . ?
C5 C13 1.514(3) . ?
C6 C7 1.518(3) . ?
C6 C10 1.539(3) . ?
C6 C11 1.533(3) . ?
C7 C14 1.380(3) . ?
C7 C17 1.373(3) . ?
C8 C9 1.516(3) . ?
C8 C21 1.526(4) . ?
C9 C15 1.524(3) . ?
C12 C20 1.521(4) . ?
C13 C16 1.521(4) . ?
C14 C23 1.384(4) . ?
C15 C22 1.515(4) . ?
C16 C25 1.503(4) . ?
C17 C24 1.387(4) . ?
C18 C21 1.518(4) . ?
C18 C22 1.507(5) . ?
C19 C26 1.482(4) . ?
C19 C1b 1.501(4) . ?
C20 C25 1.511(4) . ?
C23 C1a 1.358(5) . ?
C24 C1a 1.365(5) . ?
