#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:09:26 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236189 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/39/1553943.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_1553943
loop_
_publ_author_name
'Marin, L.'
'Guillot, R.'
'Gandon, V.'
'Schulz, E.'
'Lebœuf, D.'
_publ_section_title
;
 A diversity-oriented synthesis of cyclopenta[b]pyrroles and related
 compounds through a calcium(ii)/copper(ii) catalytic sequence
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              640
_journal_paper_doi               10.1039/C7QO00948H
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         ' 2(C41 H27 N O), C Cl2 '
_chemical_formula_sum            'C83 H54 Cl2 N2 O2'
_chemical_formula_weight         1182.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-06-13 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                105.2660(10)
_cell_angle_beta                 103.770(2)
_cell_angle_gamma                93.623(2)
_cell_formula_units_Z            1
_cell_length_a                   9.6948(2)
_cell_length_b                   10.6078(3)
_cell_length_c                   14.8224(4)
_cell_measurement_reflns_used    6643
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.76
_cell_volume                     1415.35(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.477
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.834
_refine_diff_density_min         -1.694
_refine_diff_density_rms         0.103
_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     403
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0850
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1300P)²+4.3219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2379
_refine_ls_wR_factor_ref         0.2508
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4092
_reflns_number_total             4993
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7qo00948h2.cif
_cod_data_source_block           18aq
_cod_original_cell_volume        1415.34(6)
_cod_original_formula_sum        ' C83 H54 Cl2 N2 O2 '
_cod_database_code               1553943
_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_min   0.956
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
O1 O 0.2288(3) 0.6350(2) 1.00269(18) 0.0250(6) Uani 1 1 d . . .
N1 N 0.2776(3) 0.3384(3) 0.70825(19) 0.0157(6) Uani 1 1 d . . .
C25 C 0.1060(3) 0.3621(3) 0.7926(2) 0.0155(7) Uani 1 1 d . . .
C21 C 0.1639(3) 0.2257(3) 0.3532(2) 0.0170(7) Uani 1 1 d . . .
C26 C 0.2454(3) 0.4147(3) 0.7880(2) 0.0154(7) Uani 1 1 d . . .
C35 C 0.3067(4) 0.5264(3) 0.8629(2) 0.0167(7) Uani 1 1 d . . .
C10 C 0.0821(4) 0.3327(3) 0.3586(3) 0.0190(7) Uani 1 1 d . . .
C7 C 0.3148(3) 0.3377(3) 0.5167(2) 0.0163(7) Uani 1 1 d . . .
C1 C 0.4168(3) 0.3438(3) 0.6922(2) 0.0147(7) Uani 1 1 d . . .
C36 C 0.4412(4) 0.6113(3) 0.8773(2) 0.0168(7) Uani 1 1 d . . .
C20 C 0.2836(4) 0.2295(3) 0.4320(2) 0.0174(7) Uani 1 1 d . . .
C34 C 0.2098(4) 0.5497(3) 0.9265(2) 0.0194(7) Uani 1 1 d . . .
C2 C 0.5337(4) 0.3523(3) 0.7698(2) 0.0172(7) Uani 1 1 d . . .
H2 H 0.518873 0.344824 0.828024 0.021 Uiso 1 1 calc R U .
C8 C 0.2317(4) 0.4402(3) 0.5198(2) 0.0188(7) Uani 1 1 d . . .
H8 H 0.251852 0.510964 0.575655 0.023 Uiso 1 1 calc R U .
C17 C 0.2119(4) 0.0111(3) 0.2605(3) 0.0201(7) Uani 1 1 d . . .
C24 C 0.0541(4) 0.2556(3) 0.7175(3) 0.0203(7) Uani 1 1 d . . .
H24 H -0.033969 0.204919 0.704817 0.024 Uiso 1 1 calc R U .
C4 C 0.6937(4) 0.3784(3) 0.6739(3) 0.0207(7) Uani 1 1 d . . .
H4 H 0.786409 0.392991 0.668110 0.025 Uiso 1 1 calc R U .
C3 C 0.6722(4) 0.3717(3) 0.7613(3) 0.0200(7) Uani 1 1 d . . .
H3 H 0.750060 0.380230 0.814156 0.024 Uiso 1 1 calc R U .
C9 C 0.1197(4) 0.4391(3) 0.4417(3) 0.0206(7) Uani 1 1 d . . .
H9 H 0.068735 0.510879 0.444887 0.025 Uiso 1 1 calc R U .
C22 C 0.1269(4) 0.1157(3) 0.2684(2) 0.0177(7) Uani 1 1 d . . .
C18 C 0.3326(4) 0.0177(3) 0.3401(3) 0.0209(7) Uani 1 1 d . . .
H18 H 0.388984 -0.050206 0.335445 0.025 Uiso 1 1 calc R U .
C41 C 0.4696(4) 0.6491(3) 0.7992(2) 0.0193(7) Uani 1 1 d . . .
H41 H 0.400810 0.624703 0.739894 0.023 Uiso 1 1 calc R U .
C23 C 0.1583(3) 0.2283(3) 0.6553(2) 0.0174(7) Uani 1 1 d . . .
H23 H 0.114467 0.237668 0.591068 0.021 Uiso 1 1 calc R U .
C19 C 0.3665(4) 0.1203(3) 0.4218(2) 0.0191(7) Uani 1 1 d . . .
H19 H 0.444645 0.120588 0.472366 0.023 Uiso 1 1 calc R U .
C5 C 0.5776(4) 0.3635(3) 0.5949(3) 0.0204(7) Uani 1 1 d . . .
H5 H 0.593451 0.365401 0.535736 0.025 Uiso 1 1 calc R U .
C6 C 0.4368(4) 0.3458(3) 0.6021(2) 0.0165(7) Uani 1 1 d . . .
C13 C 0.0061(4) 0.1111(4) 0.1912(3) 0.0218(8) Uani 1 1 d . . .
C11 C -0.0371(4) 0.3272(4) 0.2783(3) 0.0227(8) Uani 1 1 d . . .
H11 H -0.089734 0.397769 0.280849 0.027 Uiso 1 1 calc R U .
C27 C 0.2073(4) 0.0938(3) 0.6443(3) 0.0210(8) Uani 1 1 d . . .
C14 C -0.0292(4) 0.0016(4) 0.1093(3) 0.0261(8) Uani 1 1 d . . .
H14 H -0.110783 -0.004182 0.059520 0.031 Uiso 1 1 calc R U .
C33 C 0.0736(4) 0.4478(3) 0.8803(3) 0.0212(8) Uani 1 1 d . . .
H33A H 0.058265 0.397619 0.923937 0.025 Uiso 1 1 calc R U .
H33B H -0.010392 0.490267 0.862685 0.025 Uiso 1 1 calc R U .
C12 C -0.0745(4) 0.2209(4) 0.1988(3) 0.0248(8) Uani 1 1 d . . .
H12 H -0.153558 0.218971 0.148348 0.030 Uiso 1 1 calc R U .
C37 C 0.5448(4) 0.6518(4) 0.9659(3) 0.0236(8) Uani 1 1 d . . .
H37 H 0.526907 0.630198 1.019370 0.028 Uiso 1 1 calc R U .
C40 C 0.5987(4) 0.7225(4) 0.8088(3) 0.0239(8) Uani 1 1 d . . .
H40 H 0.615721 0.747303 0.756334 0.029 Uiso 1 1 calc R U .
C28 C 0.1809(4) 0.0042(4) 0.5530(3) 0.0252(8) Uani 1 1 d . . .
H28 H 0.135171 0.027748 0.498380 0.030 Uiso 1 1 calc R U .
C15 C 0.0559(4) -0.0980(4) 0.1016(3) 0.0254(8) Uani 1 1 d . . .
H15 H 0.032017 -0.169294 0.045915 0.030 Uiso 1 1 calc R U .
C16 C 0.1759(4) -0.0940(4) 0.1751(3) 0.0235(8) Uani 1 1 d . . .
H16 H 0.233047 -0.161263 0.167878 0.028 Uiso 1 1 calc R U .
C38 C 0.6738(4) 0.7236(4) 0.9751(3) 0.0301(9) Uani 1 1 d . . .
H38 H 0.742450 0.748954 1.034516 0.036 Uiso 1 1 calc R U .
C32 C 0.2779(5) 0.0579(4) 0.7254(3) 0.0304(9) Uani 1 1 d . . .
H32 H 0.296370 0.117525 0.786781 0.037 Uiso 1 1 calc R U .
C39 C 0.7022(4) 0.7585(4) 0.8969(3) 0.0296(9) Uani 1 1 d . . .
H39 H 0.789895 0.805748 0.903426 0.035 Uiso 1 1 calc R U .
C29 C 0.2226(5) -0.1212(4) 0.5430(3) 0.0359(10) Uani 1 1 d . . .
H29 H 0.203473 -0.181605 0.481862 0.043 Uiso 1 1 calc R U .
C31 C 0.3207(5) -0.0663(4) 0.7151(3) 0.0396(11) Uani 1 1 d . . .
H31 H 0.368467 -0.089733 0.769338 0.048 Uiso 1 1 calc R U .
C30 C 0.2919(5) -0.1552(4) 0.6237(4) 0.0396(11) Uani 1 1 d . . .
H30 H 0.319826 -0.238771 0.616801 0.048 Uiso 1 1 calc R U .
Cl1A Cl 0.406(2) -0.0707(18) 0.0287(9) 0.124(4) Uani 0.5 1 d . . P
Cl2A Cl 0.436(2) -0.0552(18) 0.0745(9) 0.124(4) Uani 0.5 1 d . . P
C100 C 0.448(2) -0.0303(18) -0.0301(19) 0.124(4) Uani 0.5 1 d . . P
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
C26 N1 C1 124.1(3) . .
C26 N1 C23 109.5(3) . .
C1 N1 C23 124.7(3) . .
C24 C25 C26 108.9(3) . .
C24 C25 C33 143.1(3) . .
C26 C25 C33 108.0(3) . .
C10 C21 C22 119.7(3) . .
C10 C21 C20 120.0(3) . .
C22 C21 C20 120.3(3) . .
N1 C26 C35 137.9(3) . .
N1 C26 C25 109.3(3) . .
C35 C26 C25 112.9(3) . .
C26 C35 C34 107.0(3) . .
C26 C35 C36 127.8(3) . .
C34 C35 C36 125.2(3) . .
C9 C10 C21 119.0(3) . .
C9 C10 C11 122.0(3) . .
C21 C10 C11 119.1(3) . .
C8 C7 C20 119.3(3) . .
C8 C7 C6 119.2(3) . .
C20 C7 C6 121.4(3) . .
C2 C1 C6 120.5(3) . .
C2 C1 N1 118.1(3) . .
C6 C1 N1 121.4(3) . .
C37 C36 C41 118.3(3) . .
C37 C36 C35 122.0(3) . .
C41 C36 C35 119.7(3) . .
C7 C20 C21 119.0(3) . .
C7 C20 C19 123.0(3) . .
C21 C20 C19 118.0(3) . .
O1 C34 C35 127.3(3) . .
O1 C34 C33 123.7(3) . .
C35 C34 C33 109.0(3) . .
C3 C2 C1 120.6(3) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C9 C8 C7 121.5(3) . .
C9 C8 H8 119.2 . .
C7 C8 H8 119.2 . .
C16 C17 C22 119.1(3) . .
C16 C17 C18 122.4(3) . .
C22 C17 C18 118.5(3) . .
C25 C24 C23 110.5(3) . .
C25 C24 H24 124.7 . .
C23 C24 H24 124.7 . .
C3 C4 C5 120.1(3) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C4 C3 C2 119.6(3) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C8 C9 C10 121.0(3) . .
C8 C9 H9 119.5 . .
C10 C9 H9 119.5 . .
C13 C22 C17 119.7(3) . .
C13 C22 C21 120.1(3) . .
C17 C22 C21 120.1(3) . .
C19 C18 C17 121.7(3) . .
C19 C18 H18 119.2 . .
C17 C18 H18 119.2 . .
C40 C41 C36 121.2(3) . .
C40 C41 H41 119.4 . .
C36 C41 H41 119.4 . .
N1 C23 C27 112.8(3) . .
N1 C23 C24 101.8(3) . .
C27 C23 C24 113.9(3) . .
N1 C23 H23 109.4 . .
C27 C23 H23 109.4 . .
C24 C23 H23 109.4 . .
C18 C19 C20 121.4(3) . .
C18 C19 H19 119.3 . .
C20 C19 H19 119.3 . .
C4 C5 C6 121.3(3) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 117.8(3) . .
C5 C6 C7 119.6(3) . .
C1 C6 C7 122.5(3) . .
C14 C13 C22 119.2(3) . .
C14 C13 C12 122.0(3) . .
C22 C13 C12 118.8(3) . .
C12 C11 C10 121.1(3) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C28 C27 C32 119.3(3) . .
C28 C27 C23 120.2(3) . .
C32 C27 C23 120.5(3) . .
C15 C14 C13 120.5(3) . .
C15 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
C25 C33 C34 102.9(3) . .
C25 C33 H33A 111.2 . .
C34 C33 H33A 111.2 . .
C25 C33 H33B 111.2 . .
C34 C33 H33B 111.2 . .
H33A C33 H33B 109.1 . .
C11 C12 C13 121.1(3) . .
C11 C12 H12 119.4 . .
C13 C12 H12 119.4 . .
C38 C37 C36 120.5(3) . .
C38 C37 H37 119.8 . .
C36 C37 H37 119.8 . .
C39 C40 C41 119.7(3) . .
C39 C40 H40 120.1 . .
C41 C40 H40 120.1 . .
C27 C28 C29 120.2(4) . .
C27 C28 H28 119.9 . .
C29 C28 H28 119.9 . .
C14 C15 C16 121.3(3) . .
C14 C15 H15 119.4 . .
C16 C15 H15 119.4 . .
C15 C16 C17 120.2(3) . .
C15 C16 H16 119.9 . .
C17 C16 H16 119.9 . .
C37 C38 C39 120.9(3) . .
C37 C38 H38 119.6 . .
C39 C38 H38 119.6 . .
C31 C32 C27 120.3(4) . .
C31 C32 H32 119.8 . .
C27 C32 H32 119.8 . .
C40 C39 C38 119.4(3) . .
C40 C39 H39 120.3 . .
C38 C39 H39 120.3 . .
C30 C29 C28 119.8(4) . .
C30 C29 H29 120.1 . .
C28 C29 H29 120.1 . .
C30 C31 C32 119.7(4) . .
C30 C31 H31 120.2 . .
C32 C31 H31 120.2 . .
C29 C30 C31 120.7(4) . .
C29 C30 H30 119.7 . .
C31 C30 H30 119.7 . .
Cl2A Cl1A C100 126(4) . .
Cl2A Cl1A C100 83(4) . 2_655
C100 Cl1A C100 44(2) . 2_655
Cl1A Cl2A C100 36(3) . .
Cl1A Cl2A C100 76(3) . 2_655
C100 Cl2A C100 40.5(14) . 2_655
C100 C100 Cl1A 91(3) 2_655 .
C100 C100 Cl2A 73(3) 2_655 .
Cl1A C100 Cl2A 18.1(16) . .
C100 C100 Cl1A 44.8(16) 2_655 2_655
Cl1A C100 Cl1A 136(2) . 2_655
Cl2A C100 Cl1A 118.1(17) . 2_655
C100 C100 Cl2A 66.1(19) 2_655 2_655
Cl1A C100 Cl2A 158(2) . 2_655
Cl2A C100 Cl2A 139.5(14) . 2_655
Cl1A C100 Cl2A 21.4(9) 2_655 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C34 1.212(4) .
N1 C26 1.361(4) .
N1 C1 1.426(4) .
N1 C23 1.493(4) .
C25 C24 1.330(5) .
C25 C26 1.454(5) .
C25 C33 1.491(5) .
C21 C10 1.421(5) .
C21 C22 1.425(5) .
C21 C20 1.427(5) .
C26 C35 1.376(5) .
C35 C34 1.471(5) .
C35 C36 1.475(5) .
C10 C9 1.388(5) .
C10 C11 1.434(5) .
C7 C8 1.391(5) .
C7 C20 1.415(5) .
C7 C6 1.492(5) .
C1 C2 1.388(5) .
C1 C6 1.399(5) .
C36 C37 1.393(5) .
C36 C41 1.399(5) .
C20 C19 1.447(5) .
C34 C33 1.543(5) .
C2 C3 1.386(5) .
C2 H2 0.9300 .
C8 C9 1.383(5) .
C8 H8 0.9300 .
C17 C16 1.401(5) .
C17 C22 1.420(5) .
C17 C18 1.434(5) .
C24 C23 1.514(5) .
C24 H24 0.9300 .
C4 C3 1.378(5) .
C4 C5 1.386(5) .
C4 H4 0.9300 .
C3 H3 0.9300 .
C9 H9 0.9300 .
C22 C13 1.417(5) .
C18 C19 1.352(5) .
C18 H18 0.9300 .
C41 C40 1.387(5) .
C41 H41 0.9300 .
C23 C27 1.513(5) .
C23 H23 0.9800 .
C19 H19 0.9300 .
C5 C6 1.399(5) .
C5 H5 0.9300 .
C13 C14 1.396(5) .
C13 C12 1.438(5) .
C11 C12 1.355(5) .
C11 H11 0.9300 .
C27 C28 1.388(5) .
C27 C32 1.393(5) .
C14 C15 1.380(6) .
C14 H14 0.9300 .
C33 H33A 0.9700 .
C33 H33B 0.9700 .
C12 H12 0.9300 .
C37 C38 1.381(5) .
C37 H37 0.9300 .
C40 C39 1.386(5) .
C40 H40 0.9300 .
C28 C29 1.395(6) .
C28 H28 0.9300 .
C15 C16 1.381(5) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C38 C39 1.387(6) .
C38 H38 0.9300 .
C32 C31 1.387(6) .
C32 H32 0.9300 .
C39 H39 0.9300 .
C29 C30 1.374(7) .
C29 H29 0.9300 .
C31 C30 1.385(7) .
C31 H31 0.9300 .
C30 H30 0.9300 .
Cl1A Cl2A 0.64(3) .
Cl1A C100 1.21(3) .
Cl1A C100 1.71(2) 2_655
Cl2A C100 1.67(3) .
Cl2A C100 1.75(3) 2_655
C100 C100 1.19(4) 2_655
