#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:29:35 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225079 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/65/7156598.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_7156598
loop_
_publ_author_name
'Wang, Fang'
'Zhang, Xinying'
'He, Yan'
'Fan, Xuesen'
_publ_section_title
;
 Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the ring
 contraction and deformylative functionalization of piperidine
 derivatives.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              156
_journal_page_last               164
_journal_paper_doi               10.1039/c8ob02640h
_journal_volume                  17
_journal_year                    2018
_chemical_formula_moiety         'C10 H7 Br I N'
_chemical_formula_sum            'C10 H7 Br I N'
_chemical_formula_weight         347.98
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-02
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-02 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5281(10)
_cell_length_b                   7.7940(9)
_cell_length_c                   25.907(2)
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    294.63(10)
_cell_measurement_theta_max      27.4420
_cell_measurement_theta_min      4.0040
_cell_volume                     2125.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.63(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  33.00   1.00   10.00    --   15.98 -57.00 -60.00   84
  2  ω    -20.00  55.00   1.00   10.00    --   15.98 -99.00  30.00   75
  3  ω     34.00  89.00   1.00   10.00    --   15.98-178.00-180.00   55
  4  ω     -1.00  24.00   1.00   10.00    --   15.98  57.00  90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0172878000
_diffrn_orient_matrix_UB_12      -0.0552130000
_diffrn_orient_matrix_UB_13      -0.0206490000
_diffrn_orient_matrix_UB_21      -0.0384044000
_diffrn_orient_matrix_UB_22      0.0486129000
_diffrn_orient_matrix_UB_23      -0.0171340000
_diffrn_orient_matrix_UB_31      0.0525561000
_diffrn_orient_matrix_UB_32      0.0535412000
_diffrn_orient_matrix_UB_33      -0.0056277000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1758
_diffrn_reflns_av_unetI/netI     0.1153
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7533
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.613
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.043
_refine_diff_density_min         -3.023
_refine_diff_density_rms         0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1871
_refine_ls_number_restraints     343
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.1155
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2883
_refine_ls_wR_factor_ref         0.3252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1117
_reflns_number_total             1871
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    3d.res created by SHELXL-2014/7

TITL 3d_a.res in Pbca
REM Old TITL 3d_a.res in Pbca
REM SHELXT solution in Pbca
REM R1 0.351, Rweak 0.027, Alpha 0.061, Orientation as input
REM Formula found by SHELXT: C8 I N2 O
CELL 0.71073 10.5281 7.794 25.9072 90 90 90
ZERR 8 0.001 0.0009 0.0024 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br I N
UNIT 80 56 8 8 8
DFIX 2.13 C8 I1
SIMU 0.01 0.02 3.8
ISOR 0.01 0.02 Br1 C4 C5 C3 C2 C1 C6 N1 I1 C8 C7 C9 H7 H9 C10 H10 H6 H2 H5 H3
 
L.S. 10
PLAN  20
SIZE 0.45 0.37 0.03
list 4
fmap 2
acta
OMIT 0 50
REM <olex2.extras>
REM <HklSrc "%.\\3d.hkl">
REM </olex2.extras>
 
WGHT    0.200000
FVAR       0.21566
BR1   3    0.793699    0.537793    0.522050    11.00000    0.16956    0.08474 =
         0.04210    0.00441    0.00264    0.01326
C1    1    0.675649    0.706454    0.357940    11.00000    0.05734    0.05496 =
         0.05364   -0.00040    0.00340   -0.00006
C2    1    0.582803    0.676369    0.394575    11.00000    0.06228    0.06091 =
         0.05694   -0.00235    0.00281   -0.00021
AFIX  43
H2    2    0.497234    0.690433    0.386731    11.00000   -1.20000
AFIX   0
C3    1    0.621329    0.624244    0.443700    11.00000    0.07087    0.06149 =
         0.05621    0.00023    0.00408   -0.00088
AFIX  43
H3    2    0.561166    0.600858    0.469025    11.00000   -1.20000
AFIX   0
C4    1    0.743967    0.608249    0.454073    11.00000    0.07365    0.05867 =
         0.05530    0.00249    0.00227    0.00108
C5    1    0.833453    0.638154    0.418355    11.00000    0.06820    0.05954 =
         0.05531    0.00096    0.00139    0.00158
AFIX  43
H5    2    0.918551    0.623317    0.426886    11.00000   -1.20000
AFIX   0
C6    1    0.801506    0.690529    0.369187    11.00000    0.06032    0.05677 =
         0.05328    0.00095    0.00271    0.00086
AFIX  43
H6    2    0.863545    0.714087    0.344636    11.00000   -1.20000
AFIX   0
C7    1    0.700120    0.719996    0.260461    11.00000    0.05171    0.05064 =
         0.05022   -0.00173    0.00161    0.00136
AFIX  43
H7    2    0.772966    0.653678    0.256691    11.00000   -1.20000
AFIX   0
C8    1    0.635042    0.795575    0.222166    11.00000    0.04821    0.04945 =
         0.04580   -0.00073    0.00217   -0.00162
C9    1    0.533209    0.885353    0.242626    11.00000    0.05007    0.05038 =
         0.05340   -0.00306   -0.00025    0.00081
AFIX  43
H9    2    0.473598    0.949110    0.224353    11.00000   -1.20000
AFIX   0
C10   1    0.537424    0.861901    0.295071    11.00000    0.05219    0.05330 =
         0.05324   -0.00330    0.00338    0.00218
AFIX  43
H10   2    0.480406    0.908740    0.318591    11.00000   -1.20000
AFIX   0
I1    4    0.678714    0.776005    0.144434    11.00000    0.06092    0.07057 =
         0.05216    0.00343    0.00053   -0.00374
N1    5    0.638542    0.758833    0.307575    11.00000    0.05315    0.05194 =
         0.05325   -0.00395    0.00241   -0.00058
HKLF 4
 
REM  3d_a.res in Pbca
REM R1 =  0.1155 for    1117 Fo > 4sig(Fo)  and  0.1534 for all    1871 data
REM    118 parameters refined using    343 restraints
 
END  
     
WGHT      0.2000      0.0000 

REM Highest difference peak  2.043,  deepest hole -3.023,  1-sigma level  0.361
Q1    1   0.6797  0.9510  0.1436  11.00000  0.05    2.04
Q2    1   0.5852  0.7865  0.1449  11.00000  0.05    1.84
Q3    1   0.6778  0.6057  0.1442  11.00000  0.05    1.65
Q4    1   0.7736  0.7628  0.1457  11.00000  0.05    1.62
Q5    1   0.7110  0.5280  0.5197  11.00000  0.05    1.46
Q6    1   0.8530  0.4881  0.5215  11.00000  0.05    1.25
Q7    1   0.8143  0.6601  0.5218  11.00000  0.05    1.12
Q8    1   0.6691  0.7910  0.1825  11.00000  0.05    1.08
Q9    1   0.7528  1.0174  0.1229  11.00000  0.05    1.02
Q10   1   0.3952  0.9893  0.2808  11.00000  0.05    1.01
Q11   1   0.3991  0.9936  0.3784  11.00000  0.05    0.95
Q12   1   0.5043  0.9016  0.1452  11.00000  0.05    0.93
Q13   1   0.7593  0.5302  0.5707  11.00000  0.05    0.90
Q14   1   0.7451  0.5146  0.2167  11.00000  0.05    0.89
Q15   1   0.4037  1.0036  0.3330  11.00000  0.05    0.88
Q16   1   0.7445  0.4744  0.3408  11.00000  0.05    0.85
Q17   1   0.8065  0.5351  0.4781  11.00000  0.05    0.84
Q18   1   0.9923  0.4077  0.4714  11.00000  0.05    0.82
Q19   1   0.3963  0.5236  0.3804  11.00000  0.05    0.82
Q20   1   0.6023  1.0560  0.2208  11.00000  0.05    0.79

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.1155 for 1117 Fo > 4sig(Fo) and 0.1534 for all 10007 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 2.04, deepest hole -3.02
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1534
  REM R1_gt = 0.1155
  REM wR_ref = 0.3252
  REM GOOF = 1.043
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 10007
  REM Reflections_gt = 1117
  REM Parameters = n/a
  REM Hole = -3.02
  REM Peak = 2.04
  REM Flack = n/a

  
;
_cod_data_source_file            c8ob02640h2.cif
_cod_data_source_block           3d
_cod_depositor_comments          'Adding full bibliography for 7156598.cif.'
_cod_database_code               7156598
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 O1 N1'
_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   0.824
_shelx_estimated_absorpt_t_min   0.152
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C8-I1
 2.13 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(Br1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(N1)
\\sim Ueq, Uanis(I1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, : with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 20.177
_oxdiff_exptl_absorpt_empirical_full_min 0.231
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
Br1 Br 0.7937(3) 0.5378(3) 0.52205(8) 0.0988(10) Uani 1 1 d . U
C1 C 0.6756(13) 0.706(2) 0.3579(6) 0.055(2) Uani 1 1 d . U
C2 C 0.5828(14) 0.676(2) 0.3946(6) 0.060(2) Uani 1 1 d . U
H2 H 0.4972 0.6904 0.3867 0.072 Uiso 1 1 calc R U
C3 C 0.6213(14) 0.624(2) 0.4437(6) 0.063(2) Uani 1 1 d . U
H3 H 0.5612 0.6009 0.4690 0.075 Uiso 1 1 calc R U
C4 C 0.7440(16) 0.608(2) 0.4541(6) 0.063(2) Uani 1 1 d . U
C5 C 0.8335(14) 0.638(2) 0.4184(6) 0.061(2) Uani 1 1 d . U
H5 H 0.9186 0.6233 0.4269 0.073 Uiso 1 1 calc R U
C6 C 0.8015(14) 0.691(2) 0.3692(7) 0.057(2) Uani 1 1 d . U
H6 H 0.8635 0.7141 0.3446 0.068 Uiso 1 1 calc R U
C7 C 0.7001(13) 0.7200(18) 0.2605(7) 0.051(2) Uani 1 1 d . U
H7 H 0.7730 0.6537 0.2567 0.061 Uiso 1 1 calc R U
C8 C 0.6350(13) 0.7956(16) 0.2222(5) 0.048(2) Uani 1 1 d D U
C9 C 0.5332(11) 0.8854(18) 0.2426(6) 0.051(2) Uani 1 1 d . U
H9 H 0.4736 0.9491 0.2244 0.062 Uiso 1 1 calc R U
C10 C 0.5374(11) 0.8619(17) 0.2951(6) 0.053(2) Uani 1 1 d . U
H10 H 0.4804 0.9087 0.3186 0.063 Uiso 1 1 calc R U
I1 I 0.67871(9) 0.77601(16) 0.14443(4) 0.0612(6) Uani 1 1 d D U
N1 N 0.6385(12) 0.7588(14) 0.3076(5) 0.0528(19) Uani 1 1 d . U
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.170(2) 0.0847(15) 0.0421(14) 0.0044(10) 0.0026(12) 0.0133(14)
C1 0.057(3) 0.055(3) 0.054(4) 0.000(3) 0.003(3) 0.000(3)
C2 0.062(4) 0.061(4) 0.057(4) -0.002(3) 0.003(3) 0.000(3)
C3 0.071(4) 0.061(4) 0.056(4) 0.000(4) 0.004(4) -0.001(4)
C4 0.074(4) 0.059(4) 0.055(4) 0.002(4) 0.002(4) 0.001(4)
C5 0.068(4) 0.060(4) 0.055(4) 0.001(4) 0.001(4) 0.002(4)
C6 0.060(4) 0.057(4) 0.053(4) 0.001(4) 0.003(3) 0.001(3)
C7 0.052(3) 0.051(4) 0.050(4) -0.002(3) 0.002(3) 0.001(3)
C8 0.048(4) 0.049(4) 0.046(4) -0.001(4) 0.002(4) -0.002(4)
C9 0.050(4) 0.050(4) 0.053(4) -0.003(4) 0.000(4) 0.001(4)
C10 0.052(3) 0.053(4) 0.053(4) -0.003(4) 0.003(3) 0.002(3)
I1 0.0609(9) 0.0706(10) 0.0522(10) 0.0034(5) 0.0005(4) -0.0037(5)
N1 0.053(3) 0.052(3) 0.053(4) -0.004(3) 0.002(3) -0.001(3)
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 N1 119.0(13)
C6 C1 C2 121.7(16)
C6 C1 N1 119.3(14)
C1 C2 C3 118.0(14)
C4 C3 C2 119.7(15)
C3 C4 Br1 118.6(13)
C3 C4 C5 121.9(16)
C5 C4 Br1 119.5(12)
C4 C5 C6 121.2(15)
C1 C6 C5 117.5(15)
C8 C7 N1 108.1(12)
C7 C8 C9 109.5(13)
C7 C8 I1 125.0(10)
C9 C8 I1 125.5(10)
C10 C9 C8 106.7(12)
C9 C10 N1 109.7(13)
C7 N1 C1 127.2(12)
C10 N1 C1 126.7(13)
C10 N1 C7 106.1(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.918(17)
C1 C2 1.38(2)
C1 C6 1.362(19)
C1 N1 1.42(2)
C2 C3 1.40(2)
C3 C4 1.32(2)
C4 C5 1.34(2)
C5 C6 1.38(2)
C7 C8 1.34(2)
C7 N1 1.41(2)
C8 C9 1.386(17)
C8 I1 2.071(12)
C9 C10 1.372(19)
C10 N1 1.372(17)
