#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:58:05 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293930 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160008.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_7160008
loop_
_publ_author_name
'Mandal, Pratap Kumar'
'Patel, Sandeep'
'Katukojvala, Sreenivas'
_publ_section_title
;
 Enal-azomethine ylides: application in the synthesis of functionalized
 pyrroles.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5734
_journal_page_last               5738
_journal_paper_doi               10.1039/d4ob00859f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H13 Cl2 N O2'
_chemical_formula_sum            'C21 H13 Cl2 N O2'
_chemical_formula_weight         383.22
_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             2022-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.776(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.445(3)
_cell_length_b                   19.168(6)
_cell_length_c                   9.550(3)
_cell_measurement_reflns_used    7856
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.35
_cell_volume                     1775.6(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_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  0.0606
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33909
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_min         2.100
_exptl_absorpt_coefficient_mu    0.382
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             784
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0484
_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)+(0.1048P)²+0.2062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3363
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00859f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7160008.cif.'
_cod_original_cell_volume        1775.7(9)
_cod_database_code               7160008
_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 C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H00C), C17(H00D), C00D(H00E), C4(H00F), C19(H00G), C18(H00J), C14(H00M),
 C10(H00N), C13(H00O), C11(H00P)
2.c :
 C1(H1)
;
_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
Cl00 Cl 0.05808(8) 0.39874(4) -0.39251(7) 0.0706(3) Uani 1 1 d . . . . .
Cl1 Cl 0.94736(7) 0.40540(5) 1.22143(7) 0.0803(3) Uani 1 1 d . . . . .
N1 N 0.50306(16) 0.33868(8) 0.50743(16) 0.0370(4) Uani 1 1 d . . . . .
O1 O 0.41128(19) 0.52418(9) 0.71163(18) 0.0605(4) Uani 1 1 d . . . . .
O2 O 0.40206(19) 0.24194(9) 0.25478(18) 0.0621(5) Uani 1 1 d . . . . .
C5 C 0.39519(19) 0.43510(10) 0.5326(2) 0.0369(4) Uani 1 1 d . . . . .
C7 C 0.3957(2) 0.35001(10) 0.3698(2) 0.0384(4) Uani 1 1 d . . . . .
C16 C 0.6150(2) 0.39520(9) 0.7571(2) 0.0366(4) Uani 1 1 d . . . . .
C3 C 0.5948(2) 0.27763(10) 0.5460(2) 0.0445(5) Uani 1 1 d . . . . .
H00A H 0.638259 0.274060 0.654800 0.053 Uiso 1 1 calc R . . . .
H00B H 0.540285 0.235805 0.509431 0.053 Uiso 1 1 calc R . . . .
C9 C 0.2814(2) 0.32980(11) 0.0870(2) 0.0407(4) Uani 1 1 d . . . . .
C6 C 0.3283(2) 0.40922(10) 0.3851(2) 0.0393(4) Uani 1 1 d . . . . .
H00C H 0.251639 0.428935 0.310886 0.047 Uiso 1 1 calc R . . . .
C17 C 0.5818(2) 0.39682(10) 0.8854(2) 0.0393(4) Uani 1 1 d . . . . .
H00D H 0.489599 0.395424 0.874750 0.047 Uiso 1 1 calc R . . . .
C00D C 0.6824(2) 0.40044(10) 1.0278(2) 0.0438(5) Uani 1 1 d . . . . .
H00E H 0.658714 0.401559 1.112535 0.053 Uiso 1 1 calc R . . . .
C4 C 0.3541(2) 0.49753(11) 0.5901(2) 0.0443(5) Uani 1 1 d . . . . .
H00F H 0.274624 0.519555 0.526067 0.053 Uiso 1 1 calc R . . . .
C19 C 0.8563(2) 0.40199(12) 0.9182(3) 0.0516(5) Uani 1 1 d . . . . .
H00G H 0.948510 0.404536 0.929648 0.062 Uiso 1 1 calc R . . . .
C12 C 0.1432(2) 0.37118(12) -0.2079(2) 0.0463(5) Uani 1 1 d . . . . .
C20 C 0.8192(2) 0.40237(11) 1.0426(2) 0.0465(5) Uani 1 1 d . . . . .
C2 C 0.7014(2) 0.28142(12) 0.4816(2) 0.0502(5) Uani 1 1 d . . . . .
C18 C 0.7537(2) 0.39776(11) 0.7760(2) 0.0454(5) Uani 1 1 d . . . . .
H00J H 0.777862 0.396600 0.691583 0.054 Uiso 1 1 calc R . . . .
C15 C 0.50630(19) 0.39039(10) 0.6055(2) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.3635(2) 0.30262(11) 0.2408(2) 0.0425(4) Uani 1 1 d . . . . .
C14 C 0.2970(2) 0.39722(11) 0.0432(2) 0.0444(5) Uani 1 1 d . . . . .
H00M H 0.353305 0.428560 0.113609 0.053 Uiso 1 1 calc R . . . .
C10 C 0.1956(2) 0.28341(12) -0.0194(2) 0.0495(5) Uani 1 1 d . . . . .
H00N H 0.185959 0.237910 0.009006 0.059 Uiso 1 1 calc R . . . .
C13 C 0.2293(2) 0.41810(12) -0.1048(2) 0.0463(5) Uani 1 1 d . . . . .
H00O H 0.241251 0.462996 -0.134801 0.056 Uiso 1 1 calc R . . . .
C11 C 0.1250(2) 0.30431(13) -0.1664(2) 0.0534(5) Uani 1 1 d . . . . .
H00P H 0.066070 0.273654 -0.236250 0.064 Uiso 1 1 calc R . . . .
C1 C 0.7871(3) 0.28504(17) 0.4317(4) 0.0771(8) Uani 1 1 d . . . . .
H1 H 0.855712 0.287945 0.391784 0.093 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'
Cl Cl 0.1484 0.1585 '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
C7 N1 C3 125.61(15) . . ?
C15 N1 C7 110.07(16) . . ?
C15 N1 C3 124.20(16) . . ?
C6 C5 C4 124.28(18) . . ?
C15 C5 C6 107.05(16) . . ?
C15 C5 C4 128.65(17) . . ?
N1 C7 C8 123.36(17) . . ?
C6 C7 N1 107.09(16) . . ?
C6 C7 C8 129.48(18) . . ?
C17 C16 C15 120.81(17) . . ?
C18 C16 C17 118.20(18) . . ?
C18 C16 C15 120.99(17) . . ?
C2 C3 N1 112.52(17) . . ?
C14 C9 C8 122.21(17) . . ?
C14 C9 C10 119.30(19) . . ?
C10 C9 C8 118.22(19) . . ?
C7 C6 C5 108.29(17) . . ?
C00D C17 C16 121.43(19) . . ?
C17 C00D C20 118.87(19) . . ?
O1 C4 C5 127.3(2) . . ?
C20 C19 C18 118.9(2) . . ?
C13 C12 Cl00 118.41(18) . . ?
C11 C12 Cl00 120.18(16) . . ?
C11 C12 C13 121.4(2) . . ?
C00D C20 Cl1 119.42(17) . . ?
C19 C20 Cl1 119.14(18) . . ?
C19 C20 C00D 121.44(19) . . ?
C1 C2 C3 179.2(3) . . ?
C19 C18 C16 121.19(19) . . ?
N1 C15 C5 107.44(16) . . ?
N1 C15 C16 122.47(16) . . ?
C5 C15 C16 130.05(16) . . ?
O2 C8 C7 122.33(18) . . ?
O2 C8 C9 119.04(17) . . ?
C7 C8 C9 118.63(18) . . ?
C13 C14 C9 120.30(19) . . ?
C11 C10 C9 120.8(2) . . ?
C14 C13 C12 119.2(2) . . ?
C12 C11 C10 118.99(19) . . ?
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
Cl00 C12 1.736(2) . ?
Cl1 C20 1.737(2) . ?
N1 C7 1.393(2) . ?
N1 C3 1.470(2) . ?
N1 C15 1.356(2) . ?
O1 C4 1.204(3) . ?
O2 C8 1.222(3) . ?
C5 C6 1.411(3) . ?
C5 C4 1.447(3) . ?
C5 C15 1.402(3) . ?
C7 C6 1.372(3) . ?
C7 C8 1.465(3) . ?
C16 C17 1.393(3) . ?
C16 C18 1.392(3) . ?
C16 C15 1.474(3) . ?
C3 C2 1.460(3) . ?
C9 C8 1.493(3) . ?
C9 C14 1.387(3) . ?
C9 C10 1.397(3) . ?
C17 C00D 1.378(3) . ?
C00D C20 1.384(3) . ?
C19 C20 1.379(3) . ?
C19 C18 1.386(3) . ?
C12 C13 1.389(3) . ?
C12 C11 1.375(3) . ?
C2 C1 1.162(4) . ?
C14 C13 1.384(3) . ?
C10 C11 1.381(3) . ?
