################################################################################
#                                                                              #
#------------------------------------------------------------------------------#
#                                                                              #
#         CIF file created and formatted by CRYSCALC (ver. June 2019)          #
#                                                                              #
#------------------------------------------------------------------------------#
#                                                                              #
# Date of archive creation: 14-06-2019 at 17:11:55                             #
#                                                                              #
# Input CIF files:                                                             #
#  1. job.cif                                                                  #
#  2. import.cif                                                               #
#                                                                              #
#------------------------------------------------------------------------------#
#                                                                              #
# Date of experiment: 14 juin 2019                                             #
# Experimenter      : Marie Cordier                                            #
#                                                                              #
# Instrument        : D8 VENTURE Bruker AXS                                    #
# Laboratory        : CDIFX/ISCR (UMR6226 Rennes)                              #
# CDIFX ID          : 19-xxx                                                   #
# Sample ID         : SCK121                                                   #
# Proposer          : J. Crassous [OMC/ISCR]                                   #
#                                                                              #
#------------------------------------------------------------------------------#
#                                                                              #
# Please use the following crystallographer details for CIF file deposition    #
# at CCDC or FIZ Karsruhe :                                                    #
#                                                                              #
# Crystallographer name : Marie CORDIER                                        #
# Publishing name :       Marie CORDIER                                        #
# Email adress :          marie.cordier@univ-rennes1.fr                        #
# Affiliation :           CDIFX ISCR CNRS Univ Rennes                          #
# Country :               France                                               #
# ORCID ID :              0000-0003-0917-2725                                  #
#                                                                              #
# Please use the following address for further publication:                    #
#                                                                              #
# Marie Cordier                                                                #
# Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226 #
# F-35000 Rennes, France                                                       #
#                                                                              #
################################################################################


data_SCK121

#------------------------------------------------------------------------------#
# Date of experiment: 14 juin 2019                                             #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#
 

_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety              'C27 H20 N2 O2'
_chemical_formula_sum                 'C27 H20 N2 O2'
_chemical_formula_weight               404.45
_chemical_compound_source             'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#
 

_space_group_crystal_system              monoclinic
_space_group_name_H-M_alt                'C 2/c'
_space_group_name_Hall                   '-C 2yc'
_space_group_IT_number                    15
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                         13.408(2)
_cell_length_b                         18.225(2)
_cell_length_c                         7.9041(11)
_cell_angle_alpha                      90
_cell_angle_beta                       94.302(6)
_cell_angle_gamma                      90
_cell_volume                           1926.0(4)
_cell_formula_units_Z                 4
_cell_measurement_temperature         150
_cell_measurement_reflns_used          7819                                                            
_cell_measurement_theta_min            3.0472                                                          
_cell_measurement_theta_max            27.4806                                                         
_cell_measurement_wavelength        0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#
 
_exptl_crystal_description             needle
_exptl_crystal_colour                  colourless
_exptl_crystal_size_max                 0.590
_exptl_crystal_size_mid                 0.180
_exptl_crystal_size_min                 0.075
_exptl_crystal_density_meas           ?                               
_exptl_crystal_density_diffrn         1.395                           
_exptl_crystal_density_method         ?                               
_exptl_crystal_F_000                  848                             
_exptl_special_details
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu                         0.089
_exptl_absorpt_correction_type                       multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min                         0.578
_exptl_absorpt_correction_T_max                         0.993

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#
 
_diffrn_measurement_device_type         'D8 VENTURE Bruker AXS'
_diffrn_measurement_method              'rotation images'
_diffrn_detector                        '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean        10.4167
_diffrn_ambient_temperature             150
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_probe                 x-ray
_diffrn_radiation_source                'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator         'multilayer monochromator'
_diffrn_source_current                  1.0
_diffrn_source_voltage                  50.0
_diffrn_reflns_av_r_equivalents         0.0834
_diffrn_reflns_av_uneti/neti            0.0530
_diffrn_reflns_number                   15867
_diffrn_reflns_limit_h_min              -17
_diffrn_reflns_limit_h_max              17
_diffrn_reflns_limit_k_min              -23
_diffrn_reflns_limit_k_max              21
_diffrn_reflns_limit_l_min              -10
_diffrn_reflns_limit_l_max              10
_diffrn_reflns_theta_min                3.047
_diffrn_reflns_theta_max                27.484
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_full    0.996
_diffrn_measured_fraction_theta_max     0.996
_reflns_number_total                    2216
_reflns_number_gt                       1807
_reflns_threshold_expression            >2sigma(I)
_reflns_Friedel_coverage                0.000
_reflns_Friedel_fraction_max            .
_reflns_Friedel_fraction_full           .

_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#
 
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON, A.L.Spek, Acta Cryst. 2009, D65, 148-155'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#
 
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
        'w=1/[σ²(Fo²)+(0.0912P)²+1.7207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            dual
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              .
_refine_ls_number_reflns                2216
_refine_ls_number_parameters            141
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0697
_refine_ls_R_factor_gt                  0.0572
_refine_ls_wR_factor_ref                0.1631
_refine_ls_wR_factor_gt                 0.1507
_refine_ls_goodness_of_fit_ref          1.063
_refine_ls_restrained_S_all             1.063
_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.385
_refine_diff_density_min                -0.343
_refine_diff_density_rms                0.078

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#
 
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_
    _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
O1   O   0.02742(11)  0.07333(7)   0.11153(15)  0.0334(4)   Uani 1 1 d    .     .  . . . 
N1   N   0.27584(10)  0.30399(9)   0.30019(18)  0.0279(4)   Uani 1 1 d    .     .  . . . 
C1   C   0.000000     0.03001(14)  0.250000     0.0394(7)   Uani 1 2 d    S     T  P . . 
H1A  H   0.056886    -0.001978     0.288679     0.047       Uiso 0.5        1 calc R  U  P   . . 
H1B  H  -0.056887    -0.001978     0.211323     0.047       Uiso 0.5        1 calc R  U  P   . . 
C2   C   0.09269(14)  0.13066(9)   0.1589(2)    0.0269(4)   Uani 1 1 d    .     .  . . . 
C3   C   0.19259(15)  0.12536(11)  0.1214(2)    0.0329(5)   Uani 1 1 d    .     .  . . . 
H3   H   0.215116     0.082279     0.068375     0.040       Uiso 1 1 calc R     U  . . . 
C4   C   0.25863(14)  0.18138(11)  0.1601(2)    0.0323(4)   Uani 1 1 d    .     .  . . . 
H4   H   0.326147     0.178435     0.131838     0.039       Uiso 1 1 calc R     U  . . . 
C5   C   0.22332(12)  0.24301(10)  0.2424(2)    0.0244(4)   Uani 1 1 d    .     .  . . . 
C6   C   0.12198(11)  0.24922(9)   0.28188(19)  0.0197(4)   Uani 1 1 d    .     .  . . . 
C7   C   0.05394(11)  0.19279(8)   0.23498(18)  0.0200(4)   Uani 1 1 d    .     .  . . . 
C8   C   0.21229(12)  0.34970(9)   0.3811(2)    0.0245(4)   Uani 1 1 d    .     .  . . . 
C9   C   0.23356(14)  0.41651(10)  0.4608(2)    0.0319(4)   Uani 1 1 d    .     .  . . . 
H9   H   0.298119     0.438009     0.461012     0.038       Uiso 1 1 calc R     U  . . . 
C10  C   0.15749(15)  0.45054(10)  0.5399(2)    0.0333(4)   Uani 1 1 d    .     .  . . . 
H10  H   0.170024     0.496176     0.595572     0.040       Uiso 1 1 calc R     U  . . . 
C11  C   0.06182(14)  0.41876(10)  0.5393(2)    0.0287(4)   Uani 1 1 d    .     .  . . . 
H11  H   0.011098     0.442830     0.596148     0.034       Uiso 1 1 calc R     U  . . . 
C12  C   0.04060(12)  0.35299(9)   0.4572(2)    0.0219(4)   Uani 1 1 d    .     .  . . . 
H12  H  -0.024350     0.332121     0.456661     0.026       Uiso 1 1 calc R     U  . . . 
C13  C   0.11587(11)  0.31744(8)   0.37471(19)  0.0195(3)   Uani 1 1 d    .     .  . . . 
C14  C   0.38234(13)  0.31551(13)  0.2908(3)    0.0377(5)   Uani 1 1 d    .     .  . . . 
H14A H   0.418727     0.271328     0.330149     0.057       Uiso 1 1 calc R     U  . . . 
H14B H   0.404065     0.357187     0.362728     0.057       Uiso 1 1 calc R     U  . . . 
H14C H   0.396165     0.325790     0.173111     0.057       Uiso 1 1 calc R     U  . . . 



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1   C2   1.396(2)    .           ?           
O1   C1   1.4202(19)  .           ?           
N1   C5   1.375(2)    .           ?           
N1   C8   1.382(2)    .           ?           
N1   C14  1.451(2)    .           ?           
C1   H1A  0.9900      .           ?           
C1   H1B  0.9900      .           ?           
C2   C3   1.397(3)    .           ?           
C2   C7   1.400(2)    .           ?           
C3   C4   1.371(3)    .           ?           
C3   H3   0.9500      .           ?           
C4   C5   1.398(2)    .           ?           
C4   H4   0.9500      .           ?           
C5   C6   1.421(2)    .           ?           
C6   C7   1.406(2)    .           ?           
C6   C13  1.449(2)    .           ?           
C7   C7   1.483(3)    2           ?           
C8   C9   1.391(3)    .           ?           
C8   C13  1.418(2)    .           ?           
C9   C10  1.382(3)    .           ?           
C9   H9   0.9500      .           ?           
C10  C11  1.407(3)    .           ?           
C10  H10  0.9500      .           ?           
C11  C12  1.383(2)    .           ?           
C11  H11  0.9500      .           ?           
C12  C13  1.401(2)    .           ?           
C12  H12  0.9500      .           ?           
C14  H14A 0.9800      .           ?           
C14  H14B 0.9800      .           ?           
C14  H14C 0.9800      .           ?           

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
C2   O1   C1   113.76(12)   .       .       ?       
C5   N1   C8   108.82(13)   .       .       ?       
C5   N1   C14  125.55(16)   .       .       ?       
C8   N1   C14  125.43(17)   .       .       ?       
O1   C1   O1   112.4(2)     .       2       ?       
O1   C1   H1A  109.1        .       .       ?       
O1   C1   H1A  109.1        2       .       ?       
O1   C1   H1B  109.1        .       .       ?       
O1   C1   H1B  109.1        2       .       ?       
H1A  C1   H1B  107.8        .       .       ?       
O1   C2   C3   118.91(15)   .       .       ?       
O1   C2   C7   118.36(16)   .       .       ?       
C3   C2   C7   122.66(17)   .       .       ?       
C4   C3   C2   121.00(16)   .       .       ?       
C4   C3   H3   119.5        .       .       ?       
C2   C3   H3   119.5        .       .       ?       
C3   C4   C5   117.80(16)   .       .       ?       
C3   C4   H4   121.1        .       .       ?       
C5   C4   H4   121.1        .       .       ?       
N1   C5   C4   128.38(16)   .       .       ?       
N1   C5   C6   109.69(15)   .       .       ?       
C4   C5   C6   121.92(17)   .       .       ?       
C7   C6   C5   119.73(15)   .       .       ?       
C7   C6   C13  134.50(14)   .       .       ?       
C5   C6   C13  105.71(14)   .       .       ?       
C2   C7   C6   116.77(15)   .       .       ?       
C2   C7   C7   117.81(12)   .       2       ?       
C6   C7   C7   125.38(11)   .       2       ?       
N1   C8   C9   128.67(16)   .       .       ?       
N1   C8   C13  109.01(15)   .       .       ?       
C9   C8   C13  122.32(16)   .       .       ?       
C10  C9   C8   117.68(16)   .       .       ?       
C10  C9   H9   121.2        .       .       ?       
C8   C9   H9   121.2        .       .       ?       
C9   C10  C11  121.15(17)   .       .       ?       
C9   C10  H10  119.4        .       .       ?       
C11  C10  H10  119.4        .       .       ?       
C12  C11  C10  120.91(17)   .       .       ?       
C12  C11  H11  119.5        .       .       ?       
C10  C11  H11  119.5        .       .       ?       
C11  C12  C13  119.31(15)   .       .       ?       
C11  C12  H12  120.3        .       .       ?       
C13  C12  H12  120.3        .       .       ?       
C12  C13  C8   118.60(15)   .       .       ?       
C12  C13  C6   134.63(14)   .       .       ?       
C8   C13  C6   106.73(14)   .       .       ?       
N1   C14  H14A 109.5        .       .       ?       
N1   C14  H14B 109.5        .       .       ?       
H14A C14  H14B 109.5        .       .       ?       
N1   C14  H14C 109.5        .       .       ?       
H14A C14  H14C 109.5        .       .       ?       
H14B C14  H14C 109.5        .       .       ?       

loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion_publ_flag
C2   O1   C1   O1     46.41(10)   .       .       .       2       ?       
C1   O1   C2   C3    107.27(17)   .       .       .       .       ?       
C1   O1   C2   C7    -75.71(18)   .       .       .       .       ?       
O1   C2   C3   C4    177.69(15)   .       .       .       .       ?       
C7   C2   C3   C4      0.8(3)     .       .       .       .       ?       
C2   C3   C4   C5      1.8(2)     .       .       .       .       ?       
C8   N1   C5   C4   -177.08(16)   .       .       .       .       ?       
C14  N1   C5   C4     -1.9(3)     .       .       .       .       ?       
C8   N1   C5   C6      1.53(18)   .       .       .       .       ?       
C14  N1   C5   C6    176.66(14)   .       .       .       .       ?       
C3   C4   C5   N1    176.86(15)   .       .       .       .       ?       
C3   C4   C5   C6     -1.6(2)     .       .       .       .       ?       
N1   C5   C6   C7   -179.86(13)   .       .       .       .       ?       
C4   C5   C6   C7     -1.1(2)     .       .       .       .       ?       
N1   C5   C6   C13    -2.17(17)   .       .       .       .       ?       
C4   C5   C6   C13   176.55(14)   .       .       .       .       ?       
O1   C2   C7   C6    179.62(13)   .       .       .       .       ?       
C3   C2   C7   C6     -3.5(2)     .       .       .       .       ?       
O1   C2   C7   C7      1.7(2)     .       .       .       2       ?       
C3   C2   C7   C7    178.61(16)   .       .       .       2       ?       
C5   C6   C7   C2      3.6(2)     .       .       .       .       ?       
C13  C6   C7   C2   -173.32(16)   .       .       .       .       ?       
C5   C6   C7   C7   -178.72(16)   .       .       .       2       ?       
C13  C6   C7   C7      4.4(3)     .       .       .       2       ?       
C5   N1   C8   C9    178.85(16)   .       .       .       .       ?       
C14  N1   C8   C9      3.7(3)     .       .       .       .       ?       
C5   N1   C8   C13    -0.23(18)   .       .       .       .       ?       
C14  N1   C8   C13  -175.37(14)   .       .       .       .       ?       
N1   C8   C9   C10  -177.12(16)   .       .       .       .       ?       
C13  C8   C9   C10     1.8(2)     .       .       .       .       ?       
C8   C9   C10  C11    -0.1(3)     .       .       .       .       ?       
C9   C10  C11  C12    -1.0(3)     .       .       .       .       ?       
C10  C11  C12  C13     0.5(2)     .       .       .       .       ?       
C11  C12  C13  C8      1.1(2)     .       .       .       .       ?       
C11  C12  C13  C6    178.30(16)   .       .       .       .       ?       
N1   C8   C13  C12   176.78(13)   .       .       .       .       ?       
C9   C8   C13  C12    -2.4(2)     .       .       .       .       ?       
N1   C8   C13  C6     -1.11(17)   .       .       .       .       ?       
C9   C8   C13  C6    179.74(14)   .       .       .       .       ?       
C7   C6   C13  C12     1.8(3)     .       .       .       .       ?       
C5   C6   C13  C12  -175.43(17)   .       .       .       .       ?       
C7   C6   C13  C8    179.16(16)   .       .       .       .       ?       
C5   C6   C13  C8      1.97(16)   .       .       .       .       ?       

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR SCK121                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
