#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:35:09 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257128 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038769.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_4038769
loop_
_publ_author_name
'Feberero, Claudia'
'Sedano, Carlos'
'Suárez-Pantiga, Samuel'
'López, Carlos Silva'
'Sanz, Roberto'
_publ_section_title
;
 Experimental and Computational Study of the 1,5-O → N
 Carbamoyl Snieckus-Fries-Type Rearrangement.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12561
_journal_page_last               12578
_journal_paper_doi               10.1021/acs.joc.0c01732
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C26 H28 Cl N3 O2'
_chemical_formula_sum            'C26 H28 Cl N3 O2'
_chemical_formula_weight         449.96
_chemical_name_systematic
'o-(E)-4-Chloro-2-(N,N'-di-p-tolylcarbamimidoyl)phenyl N,N-diethylcarbamate ('
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-04 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.451(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1225(6)
_cell_length_b                   12.8572(6)
_cell_length_c                   15.2915(8)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.078
_cell_measurement_theta_min      2.310
_cell_volume                     2381.2(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27631
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.104
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_min         2.190
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1245 before and 0.0621 after correction. The Ratio of minimum to maximum transmission is 0.8822. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0383
_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)+(0.0245P)²+1.5688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3729
_reflns_number_total             4212
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2001045.cif
_cod_data_source_block           mo_scan_0m_a
_cod_depositor_comments
'Adding full bibliography for 4038765--4038772.cif.'
_cod_database_code               4038769
_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.
;
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.946
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C00T(H00N,H00Q)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00O(H00O), C00P(H00P), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00R(H00D,H00K,H00M), C00U(H00R,H00T,H00U), C00V(H00V,H00W,H00X), C00W(H00Y,H,
 HA)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl01 Cl 0.95079(4) 0.92497(3) 0.37692(3) 0.03155(13) Uani 1 1 d . . . . .
O002 O 0.78488(9) 0.58756(8) 0.59484(7) 0.0189(2) Uani 1 1 d . . . . .
O003 O 0.95336(9) 0.51007(9) 0.60003(8) 0.0253(3) Uani 1 1 d . . . . .
N004 N 0.80149(12) 0.48272(10) 0.41374(9) 0.0191(3) Uani 1 1 d . . . . .
H004 H 0.8676(17) 0.4868(14) 0.4274(12) 0.023 Uiso 1 1 d R . . . .
N005 N 0.64739(11) 0.58413(10) 0.37615(9) 0.0206(3) Uani 1 1 d . . . . .
N006 N 0.79909(11) 0.42190(10) 0.63910(9) 0.0219(3) Uani 1 1 d . . . . .
C007 C 0.80781(12) 0.66296(12) 0.45357(10) 0.0174(3) Uani 1 1 d . . . . .
C008 C 0.82689(13) 0.66751(12) 0.54378(10) 0.0181(3) Uani 1 1 d . . . . .
C009 C 0.59017(13) 0.67978(12) 0.38335(10) 0.0189(3) Uani 1 1 d . . . . .
C00A C 0.85489(13) 0.50413(12) 0.61072(10) 0.0191(3) Uani 1 1 d . . . . .
C00B C 0.74485(13) 0.57455(12) 0.41144(10) 0.0173(3) Uani 1 1 d . . . . .
C00C C 0.87765(13) 0.75219(13) 0.58341(11) 0.0215(4) Uani 1 1 d . . . . .
H00C H 0.887983 0.754677 0.645313 0.026 Uiso 1 1 calc R . . . .
C00D C 0.76404(13) 0.38159(12) 0.39223(10) 0.0183(3) Uani 1 1 d . . . . .
C00E C 0.84403(13) 0.74455(12) 0.40257(11) 0.0200(3) Uani 1 1 d . . . . .
H00E H 0.831702 0.743371 0.340805 0.024 Uiso 1 1 calc R . . . .
C00F C 0.91361(14) 0.83377(13) 0.53253(11) 0.0226(4) Uani 1 1 d . . . . .
H00F H 0.948178 0.892873 0.559007 0.027 Uiso 1 1 calc R . . . .
C00G C 0.66466(14) 0.35986(13) 0.34715(10) 0.0219(4) Uani 1 1 d . . . . .
H00G H 0.616426 0.414670 0.328888 0.026 Uiso 1 1 calc R . . . .
C00H C 0.56691(14) 0.73892(13) 0.30874(11) 0.0225(4) Uani 1 1 d . . . . .
H00H H 0.595276 0.718127 0.254481 0.027 Uiso 1 1 calc R . . . .
C00I C 0.83208(14) 0.29916(13) 0.41937(11) 0.0222(4) Uani 1 1 d . . . . .
H00I H 0.899811 0.312904 0.450791 0.027 Uiso 1 1 calc R . . . .
C00J C 0.54761(14) 0.71210(13) 0.46195(11) 0.0231(4) Uani 1 1 d . . . . .
H00J H 0.563032 0.673181 0.513855 0.028 Uiso 1 1 calc R . . . .
C00K C 0.89822(14) 0.82747(12) 0.44278(11) 0.0216(4) Uani 1 1 d . . . . .
C00L C 0.63672(14) 0.25693(13) 0.32913(11) 0.0237(4) Uani 1 1 d . . . . .
H00L H 0.568699 0.242942 0.298213 0.028 Uiso 1 1 calc R . . . .
C00M C 0.67743(13) 0.41922(13) 0.63816(12) 0.0240(4) Uani 1 1 d . . . . .
H00A H 0.652546 0.345972 0.634187 0.029 Uiso 1 1 calc R . . . .
H00B H 0.647781 0.455979 0.585338 0.029 Uiso 1 1 calc R . . . .
C00N C 0.45815(14) 0.85986(13) 0.39054(11) 0.0249(4) Uani 1 1 d . . . . .
C00O C 0.50267(14) 0.82802(13) 0.31266(11) 0.0249(4) Uani 1 1 d . . . . .
H00O H 0.488864 0.868031 0.261116 0.030 Uiso 1 1 calc R . . . .
C00P C 0.48275(14) 0.80088(13) 0.46493(11) 0.0256(4) Uani 1 1 d . . . . .
H00P H 0.454493 0.821822 0.519183 0.031 Uiso 1 1 calc R . . . .
C00Q C 0.70352(14) 0.17405(13) 0.35419(11) 0.0232(4) Uani 1 1 d . . . . .
C00R C 0.63040(15) 0.46871(14) 0.71850(12) 0.0292(4) Uani 1 1 d . . . . .
H00D H 0.549605 0.465134 0.714044 0.044 Uiso 1 1 calc GR . . . .
H00K H 0.653674 0.541616 0.722387 0.044 Uiso 1 1 calc GR . . . .
H00M H 0.657532 0.431359 0.770985 0.044 Uiso 1 1 calc GR . . . .
C00S C 0.80158(14) 0.19743(13) 0.40084(11) 0.0252(4) Uani 1 1 d . . . . .
H00S H 0.848650 0.142324 0.420403 0.030 Uiso 1 1 calc R . . . .
C00T C 0.85934(15) 0.32452(14) 0.65752(13) 0.0314(4) Uani 1 1 d . . . . .
H00N H 0.939617 0.338243 0.656246 0.038 Uiso 1 1 calc R . . . .
H00Q H 0.840102 0.273593 0.610757 0.038 Uiso 1 1 calc R . . . .
C00U C 0.67216(16) 0.06328(14) 0.33170(13) 0.0333(4) Uani 1 1 d . . . . .
H00R H 0.600382 0.062474 0.299685 0.050 Uiso 1 1 calc GR . . . .
H00T H 0.667516 0.022699 0.385668 0.050 Uiso 1 1 calc GR . . . .
H00U H 0.728212 0.032779 0.295153 0.050 Uiso 1 1 calc GR . . . .
C00V C 0.83423(17) 0.27779(15) 0.74460(13) 0.0366(5) Uani 1 1 d . . . . .
H00V H 0.755750 0.259571 0.744932 0.055 Uiso 1 1 calc GR . . . .
H00W H 0.851617 0.328295 0.791174 0.055 Uiso 1 1 calc GR . . . .
H00X H 0.878957 0.215048 0.754457 0.055 Uiso 1 1 calc GR . . . .
C00W C 0.38470(17) 0.95456(15) 0.39454(14) 0.0376(5) Uani 1 1 d . . . . .
H00Y H 0.421439 1.007956 0.431072 0.056 Uiso 1 1 calc GR . . . .
H H 0.314655 0.935209 0.419820 0.056 Uiso 1 1 calc GR . . . .
HA H 0.370379 0.981929 0.335329 0.056 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C00A O002 C008 115.62(12) . . ?
C00B N004 C00D 129.36(14) . . ?
C00B N005 C009 119.66(13) . . ?
C00A N006 C00M 122.33(13) . . ?
C00A N006 C00T 118.76(14) . . ?
C00T N006 C00M 118.05(13) . . ?
C008 C007 C00B 121.22(14) . . ?
C00E C007 C008 118.82(14) . . ?
C00E C007 C00B 119.90(14) . . ?
C007 C008 O002 118.27(14) . . ?
C00C C008 O002 120.07(14) . . ?
C00C C008 C007 121.45(15) . . ?
C00H C009 N005 119.56(14) . . ?
C00H C009 C00J 118.42(15) . . ?
C00J C009 N005 121.77(15) . . ?
O003 C00A O002 121.80(14) . . ?
O003 C00A N006 127.39(15) . . ?
N006 C00A O002 110.80(13) . . ?
N004 C00B C007 113.48(13) . . ?
N005 C00B N004 123.12(14) . . ?
N005 C00B C007 123.40(14) . . ?
C008 C00C C00F 119.72(15) . . ?
C00G C00D N004 124.32(15) . . ?
C00G C00D C00I 118.92(15) . . ?
C00I C00D N004 116.76(14) . . ?
C00K C00E C007 119.21(15) . . ?
C00K C00F C00C 118.77(15) . . ?
C00D C00G C00L 119.20(16) . . ?
C00O C00H C009 120.71(15) . . ?
C00S C00I C00D 120.47(15) . . ?
C00P C00J C009 120.35(15) . . ?
C00E C00K Cl01 118.38(13) . . ?
C00F C00K Cl01 119.65(13) . . ?
C00F C00K C00E 121.95(15) . . ?
C00Q C00L C00G 122.94(15) . . ?
N006 C00M C00R 113.13(14) . . ?
C00O C00N C00W 121.53(16) . . ?
C00P C00N C00O 117.60(16) . . ?
C00P C00N C00W 120.87(16) . . ?
C00H C00O C00N 121.27(16) . . ?
C00J C00P C00N 121.63(16) . . ?
C00L C00Q C00S 116.91(15) . . ?
C00L C00Q C00U 121.67(16) . . ?
C00S C00Q C00U 121.42(16) . . ?
C00I C00S C00Q 121.54(16) . . ?
N006 C00T C00V 113.08(15) . . ?
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
Cl01 C00K 1.7454(16) . ?
O002 C008 1.3999(19) . ?
O002 C00A 1.3828(19) . ?
O003 C00A 1.214(2) . ?
N004 C00B 1.366(2) . ?
N004 C00D 1.411(2) . ?
N005 C009 1.419(2) . ?
N005 C00B 1.284(2) . ?
N006 C00A 1.337(2) . ?
N006 C00M 1.475(2) . ?
N006 C00T 1.471(2) . ?
C007 C008 1.390(2) . ?
C007 C00B 1.499(2) . ?
C007 C00E 1.389(2) . ?
C008 C00C 1.378(2) . ?
C009 C00H 1.390(2) . ?
C009 C00J 1.392(2) . ?
C00C C00F 1.387(2) . ?
C00D C00G 1.390(2) . ?
C00D C00I 1.395(2) . ?
C00E C00K 1.383(2) . ?
C00F C00K 1.379(2) . ?
C00G C00L 1.391(2) . ?
C00H C00O 1.388(2) . ?
C00I C00S 1.385(2) . ?
C00J C00P 1.388(2) . ?
C00L C00Q 1.383(2) . ?
C00M C00R 1.516(2) . ?
C00N C00O 1.390(2) . ?
C00N C00P 1.389(2) . ?
C00N C00W 1.511(2) . ?
C00Q C00S 1.393(2) . ?
C00Q C00U 1.510(2) . ?
C00T C00V 1.504(3) . ?
