#------------------------------------------------------------------------------
#$Date: 2017-12-10 04:32:44 +0200 (Sun, 10 Dec 2017) $
#$Revision: 204128 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/70/1547017.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_1547017
loop_
_publ_author_name
'Qiu, Shaotong'
'Chen, Lianfen'
'Jiang, Huanfeng'
'Zhu, Shifa'
_publ_section_title
;
 CuCl/Et3N-Catalyzed Synthesis of Indanone-Fused 2-Methylene Pyrrolidines
 from Enynals and Propargylamines.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4540
_journal_page_last               4543
_journal_paper_doi               10.1021/acs.orglett.7b02121
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 109.769(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   14.4270(4)
_cell_length_b                   6.42046(13)
_cell_length_c                   17.0456(5)
_cell_measurement_reflns_used    5675
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3550
_cell_measurement_theta_min      5.3580
_cell_volume                     1485.85(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -63.00  30.00   1.00    1.00    --  -40.98  37.00 -60.00   93
  2  ω     15.00  71.00   1.00    1.00    --   40.98 -99.00 -30.00   56
  3  ω     88.00 123.00   1.00    1.00    --   40.98-169.00 -72.00   35
  4  ω     65.00 108.00   1.00    1.33    --  106.95 -94.00 -30.00   43
  5  ω     38.00 105.00   1.00    1.33    --  106.95 -94.00 -90.00   67
  6  ω     74.00 104.00   1.00    1.33    --  106.95 -94.00-180.00   30
  7  ω     39.00 132.00   1.00    1.33    --  106.95 -45.00 -60.00   93
  8  ω    106.00 177.00   1.00    1.33    --  106.95  30.00-120.00   71
  9  ω    139.00 178.00   1.00    1.33    --  106.95  61.00 -90.00   39
 10  ω    147.00 178.00   1.00    1.33    --  106.95 125.00-180.00   31
 11  ω     79.00 115.00   1.00    1.33    --  106.95  61.00 -90.00   36
 12  ω     61.00 178.00   1.00    1.33    --  106.95  15.00   0.00  117
 13  ω    115.00 142.00   1.00    1.33    --  106.95 115.00 160.00   27
 14  ω     35.00 125.00   1.00    1.33    --  106.95 -45.00 120.00   90
 15  ω     31.00  58.00   1.00    1.33    --  106.95 -94.00 -30.00   27
 16  ω     24.00 105.00   1.00    1.33    --  106.95 -94.00 120.00   81
 17  ω   -111.00 -17.00   1.00    1.00    --  -40.98 -37.00 120.00   94
 18  ω   -106.00 -30.00   1.00    1.00    --  -40.98 -57.00  30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0789883000
_diffrn_orient_matrix_UB_12      0.0301854000
_diffrn_orient_matrix_UB_13      -0.0412983000
_diffrn_orient_matrix_UB_21      0.0814607000
_diffrn_orient_matrix_UB_22      -0.0291971000
_diffrn_orient_matrix_UB_23      0.0852445000
_diffrn_orient_matrix_UB_31      -0.0000628000
_diffrn_orient_matrix_UB_32      -0.2362189000
_diffrn_orient_matrix_UB_33      -0.0158618000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9353
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.666
_diffrn_reflns_theta_min         5.374
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0394
_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)+(0.0518P)²+0.5652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2715
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b02121_si_005.cif
_cod_data_source_block           exp_218
_cod_original_cell_volume        1485.85(6)
_cod_database_code               1547017
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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.
;
_cell_oxdiff_angle_alpha         90.014(2)
_cell_oxdiff_angle_beta          109.753(3)
_cell_oxdiff_angle_gamma         90.036(2)
_cell_oxdiff_length_a            14.4259(5)
_cell_oxdiff_length_b            6.42107(17)
_cell_oxdiff_length_c            17.0436(6)
_cell_oxdiff_measurement_reflns_used 5675
_cell_oxdiff_volume              1485.85(8)
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C16(H16), C12(H12), C5(H5), C13(H13), C15(H15), C4(H4),
 C14(H14)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.589
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
O1 O 0.08703(6) 0.36907(13) 0.31328(5) 0.0184(2) Uani 1 1 d .
H1 H 0.0411 0.3971 0.2707 0.028 Uiso 1 1 calc GR
O2 O 0.06999(6) 0.96129(13) 0.31908(6) 0.0196(2) Uani 1 1 d .
H2 H 0.0793 1.0875 0.3220 0.029 Uiso 1 1 calc GR
N1 N 0.32697(7) 0.78440(17) 0.49244(6) 0.0187(2) Uani 1 1 d .
C2 C 0.18523(9) 0.59480(19) 0.51635(8) 0.0172(3) Uani 1 1 d .
C7 C 0.09959(9) 0.53372(18) 0.37236(7) 0.0156(2) Uani 1 1 d .
H7 H 0.0389 0.6163 0.3559 0.019 Uiso 1 1 calc R
C8 C 0.18648(8) 0.68253(18) 0.37916(7) 0.0154(3) Uani 1 1 d .
C007 C 0.12004(9) 0.46039(19) 0.46029(8) 0.0173(3) Uani 1 1 d .
C9 C 0.27907(9) 0.57815(19) 0.37373(8) 0.0175(3) Uani 1 1 d .
C1 C 0.22066(8) 0.76381(18) 0.47028(7) 0.0156(3) Uani 1 1 d .
H1A H 0.1901 0.8983 0.4738 0.019 Uiso 1 1 calc R
C6 C 0.07772(9) 0.2934(2) 0.48797(8) 0.0207(3) Uani 1 1 d .
H6 H 0.0338 0.2046 0.4502 0.025 Uiso 1 1 calc R
C3 C 0.20931(9) 0.5653(2) 0.60187(8) 0.0212(3) Uani 1 1 d .
H3 H 0.2524 0.6554 0.6396 0.025 Uiso 1 1 calc R
C11 C 0.38682(9) 0.89842(19) 0.55940(7) 0.0172(3) Uani 1 1 d .
C10 C 0.36316(9) 0.6138(2) 0.45446(8) 0.0186(3) Uani 1 1 d .
H10A H 0.3758 0.4906 0.4894 0.022 Uiso 1 1 calc R
H10B H 0.4229 0.6527 0.4441 0.022 Uiso 1 1 calc R
C16 C 0.34841(9) 1.0578(2) 0.59564(8) 0.0218(3) Uani 1 1 d .
H16 H 0.2809 1.0819 0.5770 0.026 Uiso 1 1 calc R
C12 C 0.48919(9) 0.8656(2) 0.59037(8) 0.0204(3) Uani 1 1 d .
H12 H 0.5167 0.7595 0.5683 0.025 Uiso 1 1 calc R
C18 C 0.15640(9) 0.85774(19) 0.31527(8) 0.0183(3) Uani 1 1 d .
H18A H 0.2099 0.9572 0.3261 0.022 Uiso 1 1 calc R
H18B H 0.1435 0.8011 0.2598 0.022 Uiso 1 1 calc R
C5 C 0.10264(10) 0.2625(2) 0.57324(9) 0.0233(3) Uani 1 1 d .
H5 H 0.0759 0.1506 0.5929 0.028 Uiso 1 1 calc R
C13 C 0.54953(9) 0.9904(2) 0.65367(8) 0.0228(3) Uani 1 1 d .
H13 H 0.6172 0.9677 0.6728 0.027 Uiso 1 1 calc R
C15 C 0.41030(10) 1.1801(2) 0.65901(8) 0.0234(3) Uani 1 1 d .
H15 H 0.3834 1.2859 0.6818 0.028 Uiso 1 1 calc R
C4 C 0.16737(10) 0.3975(2) 0.62970(8) 0.0241(3) Uani 1 1 d .
H4 H 0.1828 0.3755 0.6866 0.029 Uiso 1 1 calc R
C17 C 0.28818(10) 0.4883(2) 0.30683(9) 0.0230(3) Uani 1 1 d .
C14 C 0.51117(10) 1.1480(2) 0.68900(8) 0.0229(3) Uani 1 1 d .
H14 H 0.5520 1.2301 0.7317 0.027 Uiso 1 1 calc R
H17A H 0.3510(13) 0.434(3) 0.3060(10) 0.030(4) Uiso 1 1 d .
H17B H 0.2312(14) 0.474(3) 0.2541(12) 0.040(5) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7 O1 H1 109.5
C18 O2 H2 109.5
C11 N1 C1 124.77(10)
C11 N1 C10 123.14(10)
C10 N1 C1 108.72(9)
C007 C2 C1 110.75(10)
C007 C2 C3 120.40(12)
C3 C2 C1 128.85(11)
O1 C7 H7 108.1
O1 C7 C8 114.56(10)
O1 C7 C007 114.00(10)
C8 C7 H7 108.1
C007 C7 H7 108.1
C007 C7 C8 103.76(9)
C7 C8 C1 104.91(9)
C9 C8 C7 115.32(10)
C9 C8 C1 102.72(9)
C18 C8 C7 111.98(9)
C18 C8 C9 108.95(10)
C18 C8 C1 112.60(10)
C2 C007 C7 110.49(11)
C2 C007 C6 121.13(12)
C6 C007 C7 128.22(11)
C10 C9 C8 109.13(10)
C17 C9 C8 126.02(11)
C17 C9 C10 124.53(12)
N1 C1 C2 115.97(10)
N1 C1 C8 103.90(9)
N1 C1 H1A 111.1
C2 C1 C8 103.15(9)
C2 C1 H1A 111.1
C8 C1 H1A 111.1
C007 C6 H6 120.8
C5 C6 C007 118.46(12)
C5 C6 H6 120.8
C2 C3 H3 120.7
C2 C3 C4 118.54(12)
C4 C3 H3 120.7
N1 C11 C16 121.30(11)
N1 C11 C12 120.88(11)
C16 C11 C12 117.73(11)
N1 C10 C9 102.73(9)
N1 C10 H10A 111.2
N1 C10 H10B 111.2
C9 C10 H10A 111.2
C9 C10 H10B 111.2
H10A C10 H10B 109.1
C11 C16 H16 119.7
C15 C16 C11 120.61(12)
C15 C16 H16 119.7
C11 C12 H12 119.7
C13 C12 C11 120.54(12)
C13 C12 H12 119.7
O2 C18 C8 110.61(10)
O2 C18 H18A 109.5
O2 C18 H18B 109.5
C8 C18 H18A 109.5
C8 C18 H18B 109.5
H18A C18 H18B 108.1
C6 C5 H5 119.7
C6 C5 C4 120.67(12)
C4 C5 H5 119.7
C12 C13 H13 119.3
C14 C13 C12 121.44(12)
C14 C13 H13 119.3
C16 C15 H15 119.3
C14 C15 C16 121.46(12)
C14 C15 H15 119.3
C3 C4 H4 119.6
C5 C4 C3 120.80(12)
C5 C4 H4 119.6
C9 C17 H17A 122.0(10)
C9 C17 H17B 121.6(11)
H17A C17 H17B 116.3(14)
C13 C14 C15 118.22(12)
C13 C14 H14 120.9
C15 C14 H14 120.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1 0.8200
O1 C7 1.4287(14)
O2 H2 0.8200
O2 C18 1.4335(15)
N1 C1 1.4561(15)
N1 C11 1.3849(16)
N1 C10 1.4561(15)
C2 C007 1.3908(17)
C2 C1 1.5254(17)
C2 C3 1.3925(18)
C7 H7 0.9800
C7 C8 1.5490(16)
C7 C007 1.5020(17)
C8 C9 1.5250(16)
C8 C1 1.5524(16)
C8 C18 1.5232(16)
C007 C6 1.3929(18)
C9 C10 1.5127(16)
C9 C17 1.3235(18)
C1 H1A 0.9800
C6 H6 0.9300
C6 C5 1.3884(19)
C3 H3 0.9300
C3 C4 1.3950(19)
C11 C16 1.4028(18)
C11 C12 1.4060(17)
C10 H10A 0.9700
C10 H10B 0.9700
C16 H16 0.9300
C16 C15 1.3885(18)
C12 H12 0.9300
C12 C13 1.3887(18)
C18 H18A 0.9700
C18 H18B 0.9700
C5 H5 0.9300
C5 C4 1.393(2)
C13 H13 0.9300
C13 C14 1.3849(19)
C15 H15 0.9300
C15 C14 1.3851(19)
C4 H4 0.9300
C17 H17A 0.975(17)
C17 H17B 0.996(19)
C14 H14 0.9300
