#------------------------------------------------------------------------------
#$Date: 2021-05-05 12:04:45 +0300 (Wed, 05 May 2021) $
#$Revision: 264959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157976.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_7157976
loop_
_publ_author_name
'Kumar, Pravin'
'Keshri, Santosh Kumar'
'Kapur, Manmohan'
_publ_section_title
;
 Ru(II)-Catalyzed, Cu(II)-mediated carbene migratory insertion in the
 synthesis of trisubstituted pyrroles from isoxazoles.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3428
_journal_page_last               3433
_journal_paper_doi               10.1039/d1ob00255d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-16 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.860(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2820(13)
_cell_length_b                   13.5704(9)
_cell_length_c                   10.3175(9)
_cell_measurement_reflns_used    1775
_cell_measurement_temperature    287(2)
_cell_measurement_theta_max      23.40
_cell_measurement_theta_min      2.60
_cell_volume                     1868.6(3)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      287.55
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18733
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.978
_diffrn_reflns_theta_min         2.591
_exptl_absorpt_coefficient_mu    0.073
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          .57
_exptl_crystal_size_mid          .45
_exptl_crystal_size_min          .34
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0502P)²+0.4793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2189
_reflns_number_total             4495
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00255d2.cif
_cod_data_source_block           f1_a
_cod_depositor_comments
'Adding full bibliography for 7157976--7157977.cif.'
_cod_database_code               7157976
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C004(H004), C009(H009)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00G)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
O001 O 0.29224(14) 0.40370(11) 1.13838(16) 0.0663(5) Uani 1 1 d . . . . .
N002 N 0.26369(12) 0.29382(12) 0.74286(17) 0.0434(5) Uani 1 1 d . . . . .
H002 H 0.274463 0.240496 0.705348 0.052 Uiso 1 1 calc R . . . .
C00A C 0.13960(15) 0.36390(16) 0.5242(2) 0.0438(5) Uani 1 1 d . . . . .
C00B C 0.37528(16) 0.24765(16) 0.9807(2) 0.0452(6) Uani 1 1 d . . . . .
C00C C 0.11327(16) 0.27563(17) 0.4538(2) 0.0534(6) Uani 1 1 d . . . . .
H00C H 0.134341 0.216651 0.501102 0.064 Uiso 1 1 calc R . . . .
C00D C 0.2845(2) 0.62769(17) 0.9608(2) 0.0620(7) Uani 1 1 d . . . . .
H00D H 0.319505 0.607216 0.904859 0.074 Uiso 1 1 calc R . . . .
C00E C 0.10401(17) 0.45017(18) 0.4499(2) 0.0584(7) Uani 1 1 d . . . . .
H00E H 0.119551 0.510603 0.495022 0.070 Uiso 1 1 calc R . . . .
C00F C 0.45711(19) 0.28408(19) 1.0893(3) 0.0671(8) Uani 1 1 d . . . . .
H00F H 0.471646 0.351093 1.094629 0.081 Uiso 1 1 calc R . . . .
C00G C 0.41599(19) 0.08342(18) 1.0751(3) 0.0600(7) Uani 1 1 d . . . . .
C00H C 0.1997(2) 0.5897(2) 1.1163(3) 0.0676(7) Uani 1 1 d . . . . .
H00H H 0.179168 0.544234 1.168174 0.081 Uiso 1 1 calc R . . . .
C00I C 0.05599(19) 0.2739(2) 0.3138(3) 0.0681(8) Uani 1 1 d . . . . .
H00I H 0.040046 0.213762 0.267879 0.082 Uiso 1 1 calc R . . . .
C00J C 0.02245(19) 0.3596(2) 0.2421(3) 0.0736(8) Uani 1 1 d . . . . .
H00J H -0.015934 0.357912 0.147985 0.088 Uiso 1 1 calc R . . . .
C00K C 0.04609(19) 0.4477(2) 0.3105(3) 0.0711(8) Uani 1 1 d . . . . .
H00K H 0.023037 0.506206 0.262915 0.085 Uiso 1 1 calc R . . . .
C00L C 0.2655(3) 0.7261(2) 0.9696(3) 0.0894(11) Uani 1 1 d . . . . .
H00L H 0.289248 0.772263 0.922351 0.107 Uiso 1 1 calc R . . . .
C00M C 0.4955(2) 0.1220(2) 1.1823(3) 0.0822(9) Uani 1 1 d . . . . .
H00M H 0.535581 0.080361 1.251329 0.099 Uiso 1 1 calc R . . . .
C00N C 0.2116(3) 0.7556(3) 1.0480(4) 0.1049(14) Uani 1 1 d . . . . .
H00N H 0.197376 0.822173 1.052103 0.126 Uiso 1 1 calc R . . . .
C00O C 0.5166(2) 0.2208(2) 1.1890(3) 0.0877(10) Uani 1 1 d . . . . .
H00O H 0.571423 0.245186 1.261466 0.105 Uiso 1 1 calc R . . . .
C00P C 0.1778(2) 0.6886(3) 1.1212(4) 0.0935(11) Uani 1 1 d . . . . .
H00P H 0.140415 0.709617 1.173702 0.112 Uiso 1 1 calc R . . . .
C00Q C 0.3912(2) -0.02494(19) 1.0695(3) 0.0891(10) Uani 1 1 d . . . . .
H00A H 0.349421 -0.037273 1.122848 0.134 Uiso 1 1 calc GR . . . .
H00B H 0.452017 -0.062296 1.107149 0.134 Uiso 1 1 calc GR . . . .
H00G H 0.356475 -0.044191 0.974929 0.134 Uiso 1 1 calc GR . . . .
C003 C 0.25213(17) 0.55862(16) 1.0343(2) 0.0479(6) Uani 1 1 d . . . . .
C004 C 0.20545(16) 0.44019(15) 0.7671(2) 0.0460(6) Uani 1 1 d . . . . .
H004 H 0.171801 0.500179 0.748304 0.055 Uiso 1 1 calc R . . . .
C005 C 0.27014(16) 0.40776(15) 0.9000(2) 0.0439(6) Uani 1 1 d . . . . .
C006 C 0.27528(16) 0.45206(16) 1.0312(2) 0.0465(6) Uani 1 1 d . . . . .
C007 C 0.30625(15) 0.31558(15) 0.8802(2) 0.0420(5) Uani 1 1 d . . . . .
C008 C 0.20086(16) 0.36876(15) 0.6716(2) 0.0430(5) Uani 1 1 d . . . . .
C009 C 0.35699(16) 0.14723(16) 0.9738(2) 0.0472(6) Uani 1 1 d . . . . .
H009 H 0.303906 0.121981 0.899617 0.057 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 0.0033 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'
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
C007 N002 H002 124.5 . . ?
C007 N002 C008 111.04(17) . . ?
C008 N002 H002 124.5 . . ?
C00C C00A C00E 117.5(2) . . ?
C00C C00A C008 122.4(2) . . ?
C00E C00A C008 120.1(2) . . ?
C00F C00B C007 120.3(2) . . ?
C009 C00B C00F 118.7(2) . . ?
C009 C00B C007 120.89(19) . . ?
C00A C00C H00C 119.6 . . ?
C00A C00C C00I 120.9(2) . . ?
C00I C00C H00C 119.6 . . ?
C00L C00D H00D 119.7 . . ?
C00L C00D C003 120.6(3) . . ?
C003 C00D H00D 119.7 . . ?
C00A C00E H00E 119.4 . . ?
C00K C00E C00A 121.3(2) . . ?
C00K C00E H00E 119.4 . . ?
C00B C00F H00F 120.1 . . ?
C00O C00F C00B 119.9(2) . . ?
C00O C00F H00F 120.1 . . ?
C00M C00G C00Q 121.1(2) . . ?
C00M C00G C009 118.3(2) . . ?
C009 C00G C00Q 120.6(2) . . ?
C00P C00H H00H 120.1 . . ?
C003 C00H H00H 120.1 . . ?
C003 C00H C00P 119.9(3) . . ?
C00C C00I H00I 119.6 . . ?
C00J C00I C00C 120.8(2) . . ?
C00J C00I H00I 119.6 . . ?
C00I C00J H00J 120.4 . . ?
C00K C00J C00I 119.2(2) . . ?
C00K C00J H00J 120.4 . . ?
C00E C00K H00K 119.8 . . ?
C00J C00K C00E 120.3(2) . . ?
C00J C00K H00K 119.8 . . ?
C00D C00L H00L 120.2 . . ?
C00N C00L C00D 119.6(3) . . ?
C00N C00L H00L 120.2 . . ?
C00G C00M H00M 119.4 . . ?
C00O C00M C00G 121.1(2) . . ?
C00O C00M H00M 119.4 . . ?
C00L C00N H00N 119.5 . . ?
C00L C00N C00P 121.0(3) . . ?
C00P C00N H00N 119.5 . . ?
C00F C00O H00O 119.8 . . ?
C00M C00O C00F 120.4(3) . . ?
C00M C00O H00O 119.8 . . ?
C00H C00P H00P 120.2 . . ?
C00N C00P C00H 119.5(3) . . ?
C00N C00P H00P 120.2 . . ?
C00G C00Q H00A 109.5 . . ?
C00G C00Q H00B 109.5 . . ?
C00G C00Q H00G 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00G 109.5 . . ?
H00B C00Q H00G 109.5 . . ?
C00D C003 C006 121.8(2) . . ?
C00H C003 C00D 119.3(2) . . ?
C00H C003 C006 118.9(2) . . ?
C005 C004 H004 125.6 . . ?
C008 C004 H004 125.6 . . ?
C008 C004 C005 108.86(19) . . ?
C004 C005 C006 124.6(2) . . ?
C007 C005 C004 106.44(19) . . ?
C007 C005 C006 127.3(2) . . ?
O001 C006 C003 118.2(2) . . ?
O001 C006 C005 122.8(2) . . ?
C005 C006 C003 118.9(2) . . ?
N002 C007 C00B 122.43(19) . . ?
N002 C007 C005 107.20(18) . . ?
C005 C007 C00B 130.4(2) . . ?
N002 C008 C00A 123.72(19) . . ?
C004 C008 N002 106.44(18) . . ?
C004 C008 C00A 129.8(2) . . ?
C00B C009 C00G 121.5(2) . . ?
C00B C009 H009 119.2 . . ?
C00G C009 H009 119.2 . . ?
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
O001 C006 1.234(2) . ?
N002 H002 0.8600 . ?
N002 C007 1.360(3) . ?
N002 C008 1.382(3) . ?
C00A C00C 1.382(3) . ?
C00A C00E 1.393(3) . ?
C00A C008 1.461(3) . ?
C00B C00F 1.391(3) . ?
C00B C007 1.473(3) . ?
C00B C009 1.385(3) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.383(3) . ?
C00D H00D 0.9300 . ?
C00D C00L 1.372(4) . ?
C00D C003 1.385(3) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.381(3) . ?
C00F H00F 0.9300 . ?
C00F C00O 1.377(3) . ?
C00G C00M 1.376(4) . ?
C00G C00Q 1.509(3) . ?
C00G C009 1.387(3) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.383(4) . ?
C00H C003 1.381(3) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.371(4) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.368(4) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00N 1.360(5) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.370(4) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.375(5) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00A 0.9600 . ?
C00Q H00B 0.9600 . ?
C00Q H00G 0.9600 . ?
C003 C006 1.486(3) . ?
C004 H004 0.9300 . ?
C004 C005 1.423(3) . ?
C004 C008 1.367(3) . ?
C005 C006 1.459(3) . ?
C005 C007 1.396(3) . ?
C009 H009 0.9300 . ?
