#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:42:48 +0300 (Thu, 05 May 2022) $
#$Revision: 275009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/14/7061400.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_7061400
loop_
_publ_author_name
'SD, Anwarhussaini'
'Mohitkar, Anuradha'
'Jayanty, Subbalakshmi'
_publ_section_title
;
 Unprecedented transformation from cyclized zwitterionic oxazolidine
 derivatives to corresponding non-zwitterionic aromatic amides via
 Vilsmeier reagent in a one-pot reaction: optical property and
 crystallography
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8069
_journal_page_last               8078
_journal_paper_doi               10.1039/D2NJ00591C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-07 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.9346(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.15037(8)
_cell_length_b                   15.2072(2)
_cell_length_c                   13.27838(19)
_cell_measurement_reflns_used    5124
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9560
_cell_measurement_theta_min      4.4650
_cell_volume                     1215.08(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  19.00   0.50    7.00    --    0.00  82.00 120.00   60
  2  ω     59.00  89.00   0.50    7.00    --    0.00  82.00 120.00   60
  3  ω     -6.00  19.00   0.50    7.00    --    0.00 -19.00 -90.00   50
  4  ω    -79.00 -36.00   0.50    7.00    --    0.00 -19.00 -90.00   86
  5  ω     80.00 133.00   0.50    7.00    --   95.80  45.00 -90.00  106
  6  ω    141.00 167.00   0.50    7.00    --   95.80  45.00 -90.00   52
  7  ω     86.00 125.00   0.50    7.00    --   95.80 -77.00 -60.00   78
  8  ω     45.00 112.00   0.50    7.00    --   95.80 -82.00 -90.00  134
  9  ω      7.00 123.00   0.50    7.00    --   95.80 -77.00 120.00  232
 10  ω      8.00  34.00   0.50    7.00    --   95.80 -82.00 -90.00   52
 11  ω     73.00 178.00   0.50    7.00    --   95.80  61.00 120.00  210
 12  ω     70.00 105.00   0.50    7.00    --   95.80 -82.00  90.00   70
 13  ω     86.00 179.00   0.50    7.00    --   95.80  30.00-150.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0080109000
_diffrn_orient_matrix_UB_12      -0.0991903000
_diffrn_orient_matrix_UB_13      0.0222909000
_diffrn_orient_matrix_UB_21      -0.2515172000
_diffrn_orient_matrix_UB_22      0.0067509000
_diffrn_orient_matrix_UB_23      -0.0038911000
_diffrn_orient_matrix_UB_31      -0.0470583000
_diffrn_orient_matrix_UB_32      -0.0192598000
_diffrn_orient_matrix_UB_33      -0.1164532000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6120
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.094
_diffrn_reflns_theta_min         4.476
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0332
_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)+(0.0421P)²+0.5922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2349
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj00591c2.cif
_cod_data_source_block           exp_207-jsl-11a
_cod_depositor_comments
'Adding full bibliography for 7061400--7061402.cif.'
_cod_database_code               7061400
_shelx_shelxl_version_number     2016/4
_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 99.87
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B), C14(H14A,H14B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C1(H1), C5(H5), C4(H4)
2.c 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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.740
_oxdiff_exptl_absorpt_empirical_full_min 0.550
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.07069(12) 0.57167(5) 0.10533(6) 0.01631(18) Uani 1 1 d . . . . .
O2 O -0.15230(13) 0.57975(5) 0.42644(6) 0.01864(19) Uani 1 1 d . . . . .
H2 H -0.224101 0.611075 0.457879 0.028 Uiso 1 1 calc GR . . . .
N003 N 0.10456(14) 0.55354(6) 0.27209(7) 0.0135(2) Uani 1 1 d . . . . .
N2 N 1.11712(17) 0.82824(7) 0.05800(8) 0.0224(2) Uani 1 1 d . . . . .
N1 N 1.09307(17) 0.90539(7) 0.37791(8) 0.0249(2) Uani 1 1 d . . . . .
C6 C 0.74441(17) 0.76038(7) 0.21125(8) 0.0145(2) Uani 1 1 d . . . . .
C3 C 0.37028(17) 0.65044(7) 0.20573(8) 0.0140(2) Uani 1 1 d . . . . .
C2 C 0.45088(17) 0.70419(7) 0.29162(8) 0.0146(2) Uani 1 1 d . . . . .
H2A H 0.380461 0.703624 0.347215 0.018 Uiso 1 1 calc R . . . .
C1 C 0.63251(18) 0.75753(7) 0.29429(8) 0.0150(2) Uani 1 1 d . . . . .
H1 H 0.682941 0.792474 0.351863 0.018 Uiso 1 1 calc R . . . .
C5 C 0.65861(18) 0.70768(7) 0.12426(8) 0.0153(2) Uani 1 1 d . . . . .
H5 H 0.727082 0.708786 0.068040 0.018 Uiso 1 1 calc R . . . .
C7 C 0.18306(17) 0.59211(7) 0.19879(8) 0.0136(2) Uani 1 1 d . . . . .
C4 C 0.47608(18) 0.65492(7) 0.12129(8) 0.0154(2) Uani 1 1 d . . . . .
H4 H 0.421528 0.621685 0.062724 0.018 Uiso 1 1 calc R . . . .
C13 C 0.19698(18) 0.55176(7) 0.38324(8) 0.0148(2) Uani 1 1 d . . . . .
H13A H 0.350959 0.570527 0.395719 0.018 Uiso 1 1 calc R . . . .
H13B H 0.193642 0.491882 0.408048 0.018 Uiso 1 1 calc R . . . .
C8 C 0.93632(18) 0.81532(7) 0.21514(9) 0.0158(2) Uani 1 1 d . . . . .
C11 C -0.09625(18) 0.50185(8) 0.22844(8) 0.0175(2) Uani 1 1 d . . . . .
H11A H -0.229858 0.530258 0.240375 0.021 Uiso 1 1 calc R . . . .
H11B H -0.087526 0.442768 0.256514 0.021 Uiso 1 1 calc R . . . .
C14 C 0.07012(19) 0.61056(8) 0.44287(8) 0.0175(2) Uani 1 1 d . . . . .
H14A H 0.137567 0.608727 0.515647 0.021 Uiso 1 1 calc R . . . .
H14B H 0.072998 0.670838 0.419293 0.021 Uiso 1 1 calc R . . . .
C10 C 1.03848(18) 0.82278(7) 0.12983(9) 0.0172(2) Uani 1 1 d . . . . .
C12 C -0.08826(18) 0.50138(8) 0.11459(8) 0.0175(2) Uani 1 1 d . . . . .
H12A H -0.036896 0.445055 0.094354 0.021 Uiso 1 1 calc R . . . .
H12B H -0.233476 0.513813 0.072343 0.021 Uiso 1 1 calc R . . . .
C9 C 1.02568(18) 0.86512(8) 0.30393(9) 0.0181(2) Uani 1 1 d . . . . .
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'
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
C7 O1 C12 108.59(8) . . ?
C14 O2 H2 109.5 . . ?
C7 N003 C13 128.99(9) . . ?
C7 N003 C11 110.67(9) . . ?
C13 N003 C11 120.20(9) . . ?
C1 C6 C8 121.14(10) . . ?
C5 C6 C1 117.32(10) . . ?
C5 C6 C8 121.53(10) . . ?
C2 C3 C7 123.51(10) . . ?
C2 C3 C4 118.25(10) . . ?
C4 C3 C7 118.23(10) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 C3 120.77(10) . . ?
C1 C2 H2A 119.6 . . ?
C6 C1 H1 119.3 . . ?
C2 C1 C6 121.40(10) . . ?
C2 C1 H1 119.3 . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.24(10) . . ?
C4 C5 H5 119.4 . . ?
O1 C7 C3 117.31(9) . . ?
N003 C7 O1 112.90(9) . . ?
N003 C7 C3 129.78(10) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.95(10) . . ?
C5 C4 H4 119.5 . . ?
N003 C13 H13A 109.1 . . ?
N003 C13 H13B 109.1 . . ?
N003 C13 C14 112.38(9) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C10 C8 C6 121.13(10) . . ?
C10 C8 C9 117.80(10) . . ?
C9 C8 C6 121.05(10) . . ?
N003 C11 H11A 111.5 . . ?
N003 C11 H11B 111.5 . . ?
N003 C11 C12 101.31(8) . . ?
H11A C11 H11B 109.3 . . ?
C12 C11 H11A 111.5 . . ?
C12 C11 H11B 111.5 . . ?
O2 C14 C13 108.02(9) . . ?
O2 C14 H14A 110.1 . . ?
O2 C14 H14B 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
N2 C10 C8 178.16(12) . . ?
O1 C12 C11 103.77(8) . . ?
O1 C12 H12A 111.0 . . ?
O1 C12 H12B 111.0 . . ?
C11 C12 H12A 111.0 . . ?
C11 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
N1 C9 C8 177.87(12) . . ?
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 C7 1.3265(13) . ?
O1 C12 1.4708(13) . ?
O2 H2 0.8200 . ?
O2 C14 1.4195(14) . ?
N003 C7 1.3111(14) . ?
N003 C13 1.4681(13) . ?
N003 C11 1.4775(13) . ?
N2 C10 1.1583(16) . ?
N1 C9 1.1590(16) . ?
C6 C1 1.4160(15) . ?
C6 C5 1.4153(16) . ?
C6 C8 1.4383(15) . ?
C3 C2 1.4074(15) . ?
C3 C7 1.4413(15) . ?
C3 C4 1.4095(15) . ?
C2 H2A 0.9300 . ?
C2 C1 1.3751(15) . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.3737(15) . ?
C4 H4 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5135(15) . ?
C8 C10 1.4089(16) . ?
C8 C9 1.4134(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5226(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
