The rare cis-configured trisubstituted lactam products obtained by the Castagnoli-Cushman reaction in N,N-dimethylformamide
Dar'in, Dmitry; Bakulina, Olga; Nikolskaya, Sofia; Gluzdikov, Ivan; Krasavin, Mikhail; RSC Adv.  (2016) –; doi:10.1039/C6RA10249B

data_7225223
_publ_section_title
;
 The rare cis-configured trisubstituted lactam products obtained by the
 Castagnoli-Cushman reaction in N,N-dimethylformamide
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA10249B
_journal_year                    2016
_chemical_formula_moiety         'C15 H19 N O3'
_chemical_formula_sum            'C15 H19 N O3'
_chemical_formula_weight         261.31
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-18 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.352(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.6016(4)
_cell_length_b                   19.0377(7)
_cell_length_c                   11.3636(4)
_cell_measurement_reflns_used    1978
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8040
_cell_measurement_theta_min      3.2980
_cell_volume                     2681.81(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -97.00  -62.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031 -178.0000 -180.0000 35

  2 omega  -36.00  -10.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -83.0000 -164.0000 26

  3 omega  -93.00    7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031    0.0000 -180.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0150428000
_diffrn_orient_matrix_UB_12      0.0081624000
_diffrn_orient_matrix_UB_13      0.0611158000
_diffrn_orient_matrix_UB_21      0.0237965000
_diffrn_orient_matrix_UB_22      0.0313658000
_diffrn_orient_matrix_UB_23      -0.0150990000
_diffrn_orient_matrix_UB_31      -0.0493938000
_diffrn_orient_matrix_UB_32      0.0176315000
_diffrn_orient_matrix_UB_33      -0.0015233000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11740
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.698
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.294
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0479
_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/[\s^2^(Fo^2^)+(0.0588P)^2^+0.8749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4779
_reflns_number_total             6113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra10249b2.cif
_cod_data_source_block           dvd49
_cod_original_cell_volume        2681.80(16)
_cod_database_code               7225223
_chemical_oxdiff_formula         'C15 H19 N O3'
_reflns_odcompleteness_completeness 77.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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:
 C1(H1), C2(H2), C1A(H1A), C2A(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C3A(H3AB,H3AC), C4A(H4AA,H4AB),
 C7A(H7AA,H7AB)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C10A(H10A), C11A(H11A), C13A(H13A),
 C14A(H14A)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C8A(H8AA,H8AB,H8AC), C15A(H15D,H15E,H15F)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3A(H3AA)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'