################################################################################
#                                                                              #
#------------------------------------------------------------------------------#
#                                                                              #
#         CIF file created and formatted by CRYSCALC (ver. June 2018)          #
#                                                                              #
# Date of archive creation: 02-07-2018 at 14:11:16                             #
#                                                                              #
#------------------------------------------------------------------------------#
#                                                                              #
# Input CIF files:                                                             #
#  1. job.cif                                                                  #
#  2. import.cif                                                               #
#                                                                              #
#------------------------------------------------------------------------------#
#                                                                              #
# Date of experiment: 29 juin 2018                                             #
# Experimenter      : Thierry Roisnel                                          #
#                                                                              #
# Instrument        : D8 VENTURE Bruker AXS                                    #
# Laboratory        : CDIFX/ISCR (UMR6226 Rennes)                              #
# Sample ID         : RGYYC3x110                                               #
# Proposer          : R. Gramage-Doria [OMC/ISCR]                              #
#                                                                              #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################


data_RGYYC3X110


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

_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety              'C15 H11 N O3'
_chemical_formula_sum                 'C15 H11 N O3'
_chemical_formula_weight               253.25
_chemical_compound_source             'synthesis as described'

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

_space_group_crystal_system              monoclinic
_space_group_name_H-M_alt                'P 21/n'
_space_group_name_Hall                   '-P 2yn'
_space_group_IT_number                    14
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                         10.8718(14)
_cell_length_b                         8.0647(12)
_cell_length_c                         13.948(2)
_cell_angle_alpha                      90
_cell_angle_beta                       103.979(5)
_cell_angle_gamma                      90
_cell_volume                           1186.7(3)
_cell_formula_units_Z                 4
_cell_measurement_temperature         150(2)
_cell_measurement_reflns_used          5856                                                            
_cell_measurement_theta_min            3.0093                                                          
_cell_measurement_theta_max            27.5267                                                         
_cell_measurement_wavelength        0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#
 
_exptl_crystal_description             prism
_exptl_crystal_colour                  colourless
_exptl_crystal_size_max                 0.290
_exptl_crystal_size_mid                 0.130
_exptl_crystal_size_min                 0.080
_exptl_crystal_density_meas           ?                               
_exptl_crystal_density_diffrn         1.417                           
_exptl_crystal_density_method         ?                               
_exptl_crystal_F_000                  528                             
_exptl_special_details
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu                         0.100
_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                         0.889
_exptl_absorpt_correction_T_max                         0.992

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#
 
_diffrn_measurement_device_type        'D8 VENTURE Bruker AXS'
_diffrn_measurement_method             'rotation images'
_diffrn_detector                       '(CMOS) PHOTON 100'
_diffrn_ambient_temperature             150(2)
_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_reflns_av_r_equivalents         0.1120
_diffrn_reflns_av_uneti/neti            0.0502
_diffrn_reflns_number                   25916
_diffrn_reflns_limit_h_min              -13
_diffrn_reflns_limit_h_max              14
_diffrn_reflns_limit_k_min              -10
_diffrn_reflns_limit_k_max              10
_diffrn_reflns_limit_l_min              -18
_diffrn_reflns_limit_l_max              18
_diffrn_reflns_theta_min                2.142
_diffrn_reflns_theta_max                27.602
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_full    0.997
_diffrn_measured_fraction_theta_max     0.992
_reflns_number_total                    2739
_reflns_number_gt                       1919
_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 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2018)'

#------------------------------------------------------------------------------#
#                            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)+(0.0548P)²+0.7329P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?
_atom_sites_solution_hydrogens          mixed
_refine_ls_hydrogen_treatment           mixed
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              .
_refine_ls_number_reflns                2739
_refine_ls_number_parameters            176
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0906
_refine_ls_R_factor_gt                  0.0547
_refine_ls_wR_factor_ref                0.1349
_refine_ls_wR_factor_gt                 0.1204
_refine_ls_goodness_of_fit_ref          1.071
_refine_ls_restrained_S_all             1.071
_refine_ls_shift/su_max                 0.005
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.250
_refine_diff_density_min                -0.292
_refine_diff_density_rms                0.062

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



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

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               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
C1   C   0.4852(2)    0.2642(3)    1.11387(15)  0.0270(5)   Uani 1 1 d    .     . . . . 
H1A  H   0.439084     0.166806     1.128676     0.040       Uiso 1 1 calc R     U . . . 
H1B  H   0.440764     0.365141     1.125538     0.040       Uiso 1 1 calc R     U . . . 
H1C  H   0.571130     0.264326     1.156678     0.040       Uiso 1 1 calc R     U . . . 
C2   C   0.49213(19)  0.2585(2)    1.00708(14)  0.0194(4)   Uani 1 1 d    .     . . . . 
C3   C   0.5913(2)    0.1790(3)    0.97959(15)  0.0232(5)   Uani 1 1 d    .     . . . . 
H3   H   0.656347     0.128182     1.028645     0.028       Uiso 1 1 calc R     U . . . 
C4   C   0.59669(19)  0.1726(2)    0.88128(15)  0.0203(4)   Uani 1 1 d    .     . . . . 
H4   H   0.664610     0.116675     0.863198     0.024       Uiso 1 1 calc R     U . . . 
C5   C   0.50278(18)  0.2482(2)    0.80950(14)  0.0164(4)   Uani 1 1 d    .     . . . . 
C6   C   0.40283(18)  0.3296(2)    0.83546(14)  0.0177(4)   Uani 1 1 d    .     . . . . 
C7   C   0.39805(19)  0.3333(2)    0.93447(14)  0.0191(4)   Uani 1 1 d    .     . . . . 
H7   H   0.329537     0.387734     0.952592     0.023       Uiso 1 1 calc R     U . . . 
O9   O   0.31488(14)  0.40540(19)  0.76195(10)  0.0245(4)   Uani 1 1 d    .     . . . . 
H9   H   0.260(2)     0.462(3)     0.7870(17)   0.029       Uiso 1 1 d    .     U . . . 
N10  N   0.51020(15)  0.2475(2)    0.70855(11)  0.0164(4)   Uani 1 1 d    .     . . . . 
C10  C   0.60600(18)  0.3284(2)    0.67363(14)  0.0172(4)   Uani 1 1 d    .     . . . . 
C11  C   0.57131(18)  0.3026(2)    0.56438(14)  0.0173(4)   Uani 1 1 d    .     . . . . 
C12  C   0.63174(19)  0.3550(3)    0.49348(15)  0.0223(5)   Uani 1 1 d    .     . . . . 
H12  H   0.709174     0.414980     0.510754     0.027       Uiso 1 1 calc R     U . . . 
C13  C   0.5745(2)    0.3164(3)    0.39542(15)  0.0254(5)   Uani 1 1 d    .     . . . . 
H13  H   0.613668     0.350822     0.344772     0.030       Uiso 1 1 calc R     U . . . 
C14  C   0.4617(2)    0.2289(3)    0.37046(15)  0.0253(5)   Uani 1 1 d    .     . . . . 
H14  H   0.424150     0.205872     0.302932     0.030       Uiso 1 1 calc R     U . . . 
C15  C   0.40227(19)  0.1740(3)    0.44275(15)  0.0208(5)   Uani 1 1 d    .     . . . . 
H15  H   0.325758     0.112020     0.426065     0.025       Uiso 1 1 calc R     U . . . 
C16  C   0.45928(18)  0.2135(2)    0.53949(14)  0.0168(4)   Uani 1 1 d    .     . . . . 
C17  C   0.42043(18)  0.1746(2)    0.63173(14)  0.0174(4)   Uani 1 1 d    .     . . . . 
O18  O   0.69421(13)  0.40270(19)  0.72420(10)  0.0247(4)   Uani 1 1 d    .     . . . . 
O19  O   0.33019(13)  0.09347(18)  0.64174(10)  0.0248(4)   Uani 1 1 d    .     . . . . 



#------------------------------------------------------------------------------#
#                              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
C1   C2   1.510(3)    .           ?           
C1   H1A  0.9800      .           ?           
C1   H1B  0.9800      .           ?           
C1   H1C  0.9800      .           ?           
C2   C3   1.385(3)    .           ?           
C2   C7   1.391(3)    .           ?           
C3   C4   1.388(3)    .           ?           
C3   H3   0.9500      .           ?           
C4   C5   1.386(3)    .           ?           
C4   H4   0.9500      .           ?           
C5   C6   1.390(3)    .           ?           
C5   N10  1.430(2)    .           ?           
C6   O9   1.366(2)    .           ?           
C6   C7   1.395(3)    .           ?           
C7   H7   0.9500      .           ?           
O9   H9   0.88(3)     .           ?           
N10  C17  1.393(2)    .           ?           
N10  C10  1.412(2)    .           ?           
C10  O18  1.204(2)    .           ?           
C10  C11  1.493(3)    .           ?           
C11  C12  1.379(3)    .           ?           
C11  C16  1.384(3)    .           ?           
C12  C13  1.394(3)    .           ?           
C12  H12  0.9500      .           ?           
C13  C14  1.385(3)    .           ?           
C13  H13  0.9500      .           ?           
C14  C15  1.395(3)    .           ?           
C14  H14  0.9500      .           ?           
C15  C16  1.379(3)    .           ?           
C15  H15  0.9500      .           ?           
C16  C17  1.482(3)    .           ?           
C17  O19  1.215(2)    .           ?           

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   C1   H1A  109.5        .       .       ?       
C2   C1   H1B  109.5        .       .       ?       
H1A  C1   H1B  109.5        .       .       ?       
C2   C1   H1C  109.5        .       .       ?       
H1A  C1   H1C  109.5        .       .       ?       
H1B  C1   H1C  109.5        .       .       ?       
C3   C2   C7   118.92(18)   .       .       ?       
C3   C2   C1   120.99(19)   .       .       ?       
C7   C2   C1   120.10(19)   .       .       ?       
C2   C3   C4   120.80(19)   .       .       ?       
C2   C3   H3   119.6        .       .       ?       
C4   C3   H3   119.6        .       .       ?       
C5   C4   C3   119.86(19)   .       .       ?       
C5   C4   H4   120.1        .       .       ?       
C3   C4   H4   120.1        .       .       ?       
C4   C5   C6   120.33(18)   .       .       ?       
C4   C5   N10  120.18(17)   .       .       ?       
C6   C5   N10  119.45(17)   .       .       ?       
O9   C6   C5   117.74(17)   .       .       ?       
O9   C6   C7   123.15(18)   .       .       ?       
C5   C6   C7   119.10(18)   .       .       ?       
C2   C7   C6   120.98(18)   .       .       ?       
C2   C7   H7   119.5        .       .       ?       
C6   C7   H7   119.5        .       .       ?       
C6   O9   H9   110.4(15)    .       .       ?       
C17  N10  C10  111.58(16)   .       .       ?       
C17  N10  C5   124.28(16)   .       .       ?       
C10  N10  C5   124.06(16)   .       .       ?       
O18  C10  N10  125.28(18)   .       .       ?       
O18  C10  C11  129.52(18)   .       .       ?       
N10  C10  C11  105.19(16)   .       .       ?       
C12  C11  C16  121.46(19)   .       .       ?       
C12  C11  C10  129.96(19)   .       .       ?       
C16  C11  C10  108.57(17)   .       .       ?       
C11  C12  C13  117.26(19)   .       .       ?       
C11  C12  H12  121.4        .       .       ?       
C13  C12  H12  121.4        .       .       ?       
C14  C13  C12  121.3(2)     .       .       ?       
C14  C13  H13  119.4        .       .       ?       
C12  C13  H13  119.4        .       .       ?       
C13  C14  C15  121.13(19)   .       .       ?       
C13  C14  H14  119.4        .       .       ?       
C15  C14  H14  119.4        .       .       ?       
C16  C15  C14  117.18(19)   .       .       ?       
C16  C15  H15  121.4        .       .       ?       
C14  C15  H15  121.4        .       .       ?       
C15  C16  C11  121.71(19)   .       .       ?       
C15  C16  C17  130.21(18)   .       .       ?       
C11  C16  C17  108.07(17)   .       .       ?       
O19  C17  N10  125.03(18)   .       .       ?       
O19  C17  C16  128.41(18)   .       .       ?       
N10  C17  C16  106.55(16)   .       .       ?       

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
C7   C2   C3   C4     -0.5(3)     .       .       .       .       ?       
C1   C2   C3   C4    179.39(19)   .       .       .       .       ?       
C2   C3   C4   C5      0.7(3)     .       .       .       .       ?       
C3   C4   C5   C6     -0.3(3)     .       .       .       .       ?       
C3   C4   C5   N10   177.65(18)   .       .       .       .       ?       
C4   C5   C6   O9    178.32(18)   .       .       .       .       ?       
N10  C5   C6   O9      0.3(3)     .       .       .       .       ?       
C4   C5   C6   C7     -0.4(3)     .       .       .       .       ?       
N10  C5   C6   C7   -178.35(17)   .       .       .       .       ?       
C3   C2   C7   C6     -0.2(3)     .       .       .       .       ?       
C1   C2   C7   C6    179.92(19)   .       .       .       .       ?       
O9   C6   C7   C2   -177.97(18)   .       .       .       .       ?       
C5   C6   C7   C2      0.6(3)     .       .       .       .       ?       
C4   C5   N10  C17   118.8(2)     .       .       .       .       ?       
C6   C5   N10  C17   -63.3(3)     .       .       .       .       ?       
C4   C5   N10  C10   -64.7(2)     .       .       .       .       ?       
C6   C5   N10  C10   113.2(2)     .       .       .       .       ?       
C17  N10  C10  O18   179.20(19)   .       .       .       .       ?       
C5   N10  C10  O18     2.3(3)     .       .       .       .       ?       
C17  N10  C10  C11     0.1(2)     .       .       .       .       ?       
C5   N10  C10  C11  -176.81(16)   .       .       .       .       ?       
O18  C10  C11  C12     0.9(4)     .       .       .       .       ?       
N10  C10  C11  C12   180.0(2)     .       .       .       .       ?       
O18  C10  C11  C16  -178.0(2)     .       .       .       .       ?       
N10  C10  C11  C16     1.1(2)     .       .       .       .       ?       
C16  C11  C12  C13     0.8(3)     .       .       .       .       ?       
C10  C11  C12  C13  -178.00(19)   .       .       .       .       ?       
C11  C12  C13  C14     0.0(3)     .       .       .       .       ?       
C12  C13  C14  C15    -1.0(3)     .       .       .       .       ?       
C13  C14  C15  C16     1.3(3)     .       .       .       .       ?       
C14  C15  C16  C11    -0.6(3)     .       .       .       .       ?       
C14  C15  C16  C17   179.81(19)   .       .       .       .       ?       
C12  C11  C16  C15    -0.5(3)     .       .       .       .       ?       
C10  C11  C16  C15   178.54(17)   .       .       .       .       ?       
C12  C11  C16  C17   179.23(18)   .       .       .       .       ?       
C10  C11  C16  C17    -1.8(2)     .       .       .       .       ?       
C10  N10  C17  O19   177.81(19)   .       .       .       .       ?       
C5   N10  C17  O19    -5.3(3)     .       .       .       .       ?       
C10  N10  C17  C16    -1.1(2)     .       .       .       .       ?       
C5   N10  C17  C16   175.75(16)   .       .       .       .       ?       
C15  C16  C17  O19     2.6(4)     .       .       .       .       ?       
C11  C16  C17  O19  -177.1(2)     .       .       .       .       ?       
C15  C16  C17  N10  -178.5(2)     .       .       .       .       ?       
C11  C16  C17  N10     1.8(2)     .       .       .       .       ?       

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#===END OF CIF FILE FOR RGYYC3X110                                             #
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